… to Chicago

Bobby and I decided to take our first real vacation together to visit Chicago! He grew up in Illinois and lived in Chicago for several years after college and all of his closest childhood and college friends still live there (or in the area) so it was a great chance to meet the important people in his life and learn more about his life. Since it was his city and his friends, I took a step back from my normal “Type A” planning and let him arrange everything. That is pretty huge for me, y’all.

June 1, 2018 – Day 1

Our flight out was at 6:19am so we got up very, very early. I had dropped Elliott off at my dad’s house the night before so that was one less thing we had to worry about in the morning but man, we were cutting it close. Bobby had a work social the night before and was out late so it was a late night of packing and getting ready. I had looked up the weather the week before and it said the temperature all weekend would be mid-90s but when we checked Thursday night, it was saying 60s! I was NOT prepared… I packed mostly tank tops and sun dresses and it was too late to go back to my apartment to adjust. Such is life, right?

We managed to get up and out the door a little later than I was comfortable with but I had no doubt everything would work out and we would make our flight. At least, I kept telling myself that. They say you should get to the airport an hour before your boarding time but I knew with a flight that early and the fact that we were not checking bags would mean we had some flexibility. We parked the car and took a very slow, frustrating shuttle over, breezed through security, and made it to the gate with a few minutes to spare. Unfortunately, we did not have time for breakfast!

Bobby was nice enough to let me take the window seat while he braved the middle. He had to work and the guy next to him would not let him put the armrest down, so I know it was not very comfortable for him. I appreciated the window seat so much though because it allowed me to get a little nap in during the flight. As usual, I was freezing so I did my best to stay warm with what I had.


It was a smooth flight. We navigated the airport easily and purchased our train tickets for the weekend. Bobby told me a story about how he once accidentally bought 10 tickets so he stood at the ticket stands and sold them all off to make his money back. Sure enough, while we were in line, that happened to someone else. Apparently that is a common thing! Those machines were kind of wonky though so it did not surprise me too much.


We hopped on the Blue Line, headed towards the city. Our first stop: FOOD. We transferred to the Red Line and surfaced in the city. It. Was. Freezing. I got my jacket out but it was not enough. The cold and wind are not for this southern, hot-yoga-loving, gal. Luckily, Portillo’s was only a few blocks away. Bobby had told me all about them for weeks so I was excited to finally be able to try it (not to mention, we were both starving at this point). I was told they have great hot dogs but since we were going to a White Sox game in the evening, I should hold off on the Chicago hot dog. He said the best thing to get was the Italian Beef so I ordered it exactly how he loves it and it did NOT disappoint. I had never had one before and with the added mozzarella cheese and jalepenos, it was delicious. We shared some fries in an attempt to be ‘healthy’ and somehow managed to walk out of there without ordering a slice of their “famous chocolate cake.” 10/10, would recommend to a friend.

Our Airbnb host was meeting us at 11:30am so in an effort to save time, we took an Uber out to Roscoe Village. We had booked our flights weeks in advance and when we went to book our lodging, we learned that there was a huge conference of some sort going on and all of the hotels were booked and/or had an insanely high nightly rate. Luckily, Bobby managed to find an affordable Airbnb just outside of the city which worked out perfectly for us. The host gave us a quick tour of the place before heading out. Bobby needed to work and I was so exhausted so I took a 3 hour nap while he was much more productive.


I woke up (albeit, a little groggy) to get ready for our White Sox game. Bobby had coordinated with about 12 or so of his closest friends to all meet up before the game to tailgate and then go to the game as a group. I had been very, very nervous to meet everyone but also just because sometimes large group settings make me semi anxious in general. Bobby is a social, friendly guy so I knew his friends would be too… but they are important to him and he is important to me so I wanted to make a good impression and be liked. No pressure. We cleaned up and headed out the door in our Sox gear.

Unfortunately for me, the weather had not warmed up at all so our Uber took us over to a nearby North Face and I bought a little fleece. It turned out I would end up needing something a little warmer by the end of the night but for the time being, it was perfect. Bobby had packed a light jacket and was clearly so much better at braving the cold than I was.

There was a bar nextdoor, Northside Bar & Grill, so we stopped in for a quick shot of Bobby’s favorite: Jameson. Maybe a little buzz would warm me up some?!


We hopped on the train and headed towards Guaranteed Rate Field (where the White Sox play). What an interesting name, right? The area itself was a little sketchy but we were not there to tour the area, we were there to tailgate and go to the game! Some of his friends had staked out some spots in the parking lot and already had food and drinks flowing. I was still a little nervous walking up to everyone but they were so incredibly welcoming and made me feel right at home. I met his 3 best friends and a few other very close ones. Over the next couple of hours, more and more showed up and everyone was social and nice. Everyone made an effort to talk to me and ask me questions about myself (and tell me how great a guy Bob is). They were totally selling him to me but little do they know, I was already sold on him a long time ago. *awe*

The tailgate was great. In the sun I was warm and in the shade I was cold so I kept taking the jacket on and off, on and off, on and off. We snacked on chips, chicken wings, sausage, and burgers. I only had some chips and a chicken wing because I was holding out for the ‘best hot dog’ inside the stadium. I also managed to get… a little drunk in that time. We had already had a shot of Jameson before getting there but once we got there, Big James made me a vodka/soda. When that was empty, he made me another. I caught a glimpse of his bar-tending skills and he sure did have a heavy pour! No wonder I was feeling so good. The group took a round of shots, too, and I obviously could not sit out for that. When Becky and Brad showed up, she offered me a little to-go wine and I had that too. I was good to go. Becky was also nice enough to share her dual-layer jacket with me. Everyone was dressed like it was 80 degrees outside and I was shivering! I tried to not look cold but I guess they could all see it on my face and everyone was trying to keep me warm and block the wind. It was sweet.

We made our way inside the stadium and as promised, our first stop was to order the hot dogs. James (not Big James, there are 2!), Bobby, and I found a booth and I ordered one the same way they did as to fully experience the greatness. Two natives would know more than I would! I skipped ordering a drink and chose water instead; I know my limits. Everyone had kind of gone their own way so we made our way to our seats. The hot dog was amazing and I spilled mustard on my jeans (not surprising). Everyone spent the next maybe 30 minutes coming and going, eating and drinks, and “watching” the game. (Note: I do not think anyone actually watched the game.). A few guys had gone to the bar below the stadium so after it got too cold, the rest of us joined them. It was much warmer out of the wind so I was glad to be down there. They drank and we all socialized until the game was over. This group was a hoot. I really enjoyed talking to everyone and getting to know them and hear stories about Bobby.

Just before the game ended, half the group (who lived outside of the city and who had driven to the game), took off. The rest of us decided to head out to Old Town to go to a bar. As we left the game, fireworks started (the White Sox surprisingly won 7-3)! It does not matter how old you are, fireworks are always nice. We waited at the train with everyone else and managed to grab some seats once on board. They were all reminiscing on old memories and sharing stories so it was difficult for me to keep up and know what was going on but Becky, the only other girl there the whole night, was very good at pausing and catching me up to help keep me in the loop. Girl power.


By the time we made it to Old Town, I had sobered up a bit and was back to feeling like a popsicle. My teeth were chattering, loudly. I do not know how everyone was managing with just a lightweight jacket. Becky shared one of her layers with me again which helped but by that point, I could not stop the chattering. It was so embarrassing.


Andy chose the bar for us, a place called Benchmark. I prefer a more dive-y place but it was a fun time. It was packed and it was loud but Andy knew everyone it seemed and had drinks ordered for everyone in matter of seconds. Impressive. I got a glass of wine and we went to the upstairs section and grabbed some tables. Over the next who-knows-how-long, we all went from drunk to dRuNk. Everyone probably had at least 2 drinks and Bobby bought a round of shots so things were getting dicey. I got to witness Bobby’s amazing dance moves and the whole group was making me laugh. Me being me, I started getting hungry and asking if we were getting food. Brad started a food countdown but when he got to the 3 minute mark, Bobby randomly decided it was time for us to head out. Looking back, that was probably a good call. It was definitely time to go.

He and I made our way through the crowds to the streets. I did not know enough about the trains to navigate our way home so I thought it would be best to just take an Uber home. That turned out to be way more difficult than I thought because I had no idea what the address of the Airbnb was! It was a struggle getting but I eventually found the place in my own email’s Trash folder and we were in a car shortly after. Whew. Bobby instantly fell asleep. After only 3 hours of sleep the night before, no nap on the plane, no nap before the game, and then a night out… I was surprised he had made it as long as he had. It was impressive. The Uber driver was chatty and I barely remember what we talked about and before we knew it, we were home. Bobby and I both had a set of keys, thankfully, and after a brief struggle between the door and me, we made it inside. We both fell asleep the moment our heads hit the pillows. Out.

June 2, 2018 – Day 2

As you probably could imagine, we slept in late. We needed it. When we finally got going for the day, we made our way back to Old Town to have brunch at Happy Camper. Thankfully it was much warmer outside. This place was pretty cool, very trendy, very hipster. It is a pizza place but since we were going to go to a real Chicago pizza place later, we shared a pulled-pork brunch dish and mozzarella sticks (which, to our surprise, were not fried cheese… but instead bread with cheese on a top and a side of marinara). We ate, had a morning drink, and watched Tiger Woods play golf. I had been hungry but after we started eating and drinking, my stomach was kind of achy. I have never been good at being hungover!

By this point, it was mid-afternoon. We decided to start our walking tour and made our way over to Navy Pier. We walked past the Trump Tower, walked along the river, and explored parts of the city even he had not been to yet. I loved strolling through the city, aimlessly wandering, hand in hand together. We people watched and just enjoyed each other’s company.

Eventually, we made it to Navy Pier and walked along it. It was warming up and the sun was starting to come out so it was nice. Lake Michigan was amazing; it really did look like an ocean, just going on and on forever into the distance. The Pier had several fun activities, restaurants, and all sorts of things to do on it. We opted out of those things in favor of just walking and soaking in the sights and people watching. There was an indoor section that we decided to go in and inside was the most beautiful 6-foot tall atrium. It was Bobby’s decision to go inside initially so I credit him for that great find! On our way out, Bobby came THISCLOSE to being pooped on by a bird. It literally landed mere centimeters in front of him. Thankfully, he dodged that bullet!

We had made our way back the front so we decided it was time to head out. We cut through Jane Addams Memorial Park and walked down Lake Shore Drive along the water. Our plan was to grab a drink at the Hancock Tower then maybe meet up with some of his friends again but we were both feeling a little exhausted from the night before that we decided to just keep it the two of us for the time being and check-in with his friends the next day. I struggled with helping make that decision because while I loved the idea of it just being us for the day, I did not want to be the type of girlfriend who held him back from seeing his friends the one time he was in town. It all ended up working out though.

Our walk continued through Lake Shore Park, past the Museum of Contemporary Art (we did not stop inside), and then over to the Signature Room at the 95th in the Hancock Tower where we enjoyed very expensive but very delicious drinks. The elevator took us up and we exited in the restaurant. From there, we wanted to see the view so we went to the windows instead of going upstairs to the bar and we were politely told to go directly upstairs (e.g. we got scolded in a nice way). We sat at the bar and socialized for a bit. The views were tough because it was a bit cloudy but they were still amazing. I ordered a Rose Sangria which quite possibly could have been the tastiest drink I had ever had in my life and Bobby got his favorite: an Old Fashioned. My stomach actually started to feel better after that drink so maybe it was a bit magical, too.

Our next stop was the Water Tower Place (a large, indoor vertical mall). We stopped inside the mall and went to a few different floors just to look around. I ended up buying a pair of shorts at Express before we left. It was a completely different style of mall than I had ever seen so it was cool to see, but at the end of the day it was just a mall so how much time could we actually spend there? Both of us were children though and put our hands in the water fountain as we went down the escalator. The water looked so perfect… we just had to touch it!

We passed the Historic Water Tower, one of the few buildings to survive The Chicago Fire. As we would pass things or through our conversations, we constantly kept saying to each other, “let’s look that up later” and learning about The Chicago Fire was one of them. Bobby was mostly sure he knew the whole story but he wanted a knowledge check.


By this point, it was getting late and close to dinner time. We headed toward Giordano’s, his favorite pizza place, but made a quick pit-stop at Jake Melnick’s Corner Tap for a shot or Malort first. Bobby and all of his friends had talked about Malort and how awful it was but because taking a shot of it apparently made you a “real Chicagoan” so I did not have a choice. Bobby ordered a shot for both of us (that was nice that he was willing to torture himself with me) and immediately the bartender laughed. GREAT. Great first sign. He brought the drinks over and asked what the occasion was. Another bartender heard Bobby say it was my first time having it and asked if she could watch me take it! Bobby even wanted to record a video of my “Malort face” as I took it. Just HOW BAD was this stuff? The bartender brought me a small class of Coke to help “wash it down” too and a glass of water. I was genuinely scared of what I was just about to drink but I was no wuss and took it like a champ. Bobby ended up not getting video (whew) but apparently I did not make a “Malort face” so it would not have been an exciting video anyhow. Anyway, the shot was complete garbage. It was not a burning shot or initially bad, it went down easily. The “gotcha” was the most foul, horrendous, lingering after-taste. Oh my gosh, it was awful. I do not drink soda and I drank that Coke just to help wash the taste out of my mouth. What in the hell was that stuff? Instead of adding it to the list of things to look up later, I immediately googled it to learn about the poison I just digested. Was I going to die? Was this a trap?! It turned out it was not poison and I was not going to die but you can read about it here. I was a real Chicagoan now! Bobby downed his shot and told me he was proud of me. The things we do for love.


Now, it was definitely time for dinner. Not only were we hungry but we needed to get that bitter taste out of our mouths immediately. Giordano’s was across the street so thankfully we did not have a long ways to go. The place was really cool with a fun environment. Bobby is so picky about his pizza in Houston (which makes sense if you come from a place known for pizza) so I was very much looking forward to finally trying his beloved Giordano’s. Last time I was in the city, I tried Gino’s East which apparently is not as good but hey, how could I have known that? We ordered right away because it takes 45-60 minutes to make the pizza. We also ordered a cocktail to cap off the evening.

While we waited, we discussed the components of pizza, the big pizza debate of Chicago (which is better: Lou’s or Giordano’s), and the bizarre couple next to us. When the pizza arrived, it looked so amazing. The couple next to us laughed at us for taking a picture of it and taking a boomerang of the “cheese pull.” Rude. We could have been MUCH more touristy if you ask me but that is fine, at least we entertained them. Finally, we dove in and it did not disappoint. Wow. That was some truly amazing pizza. I understood why it was his favorite and could agree that nothing in Houston compared. The closest thing would be Star Pizza, which we often frequented back home. But even then… Star Pizza had nothing on Giordano’s. It was well worth the wait! We each had 2 slices and took the last 2 home with us, knowing we would enjoy the leftovers later.

Our bellies full, we started to head home. Bobby surprised me and suggested we go back to Portillo’s to try the famous chocolate cake. YES! We got on the train then realized we had actually already been near Portillo’s so after a quick turnaround on the train, we arrived. We ordered a piece but waited until we were home to eat it. On our way home, we finally looked up everything on our “let’s look that up later” list. I love that we both share the need to look up and learn more about things we do not know.

We made it home and devoured that cake in a matter of seconds. Yep, it was just as delicious as they advertised and as it looked. Even Bobby, someone who does not prefer chocolate, admitted it was great. I loved it.


It had a been a long day with a lot of walking so we called it a night and tried to watch a movie. The Airbnb did not have cable and the local channels had nothing on. Netflix was not working. Everything was broken! Just then, it started to rain. We fell asleep to the sound of the thunderstorm, a perfect way to end the day.

June 3, 2018 – Day 3

We got a little bit of an earlier start as to fit in as much stuff as we could for our last day. We split a breakfast at Wishbone, a cute restaurant nearby that the Airbnb host had recommended to us on the first day. It was a great breakfast but we did not want to get too full so we could enjoy a nice lunch in town.

After breakfast, we walked over to where Bobby’s old stomping grounds. He pointed out all of his old hangouts and important places along the way. That was probably my favorite part of the trip as I really enjoyed seeing him in his element and hearing more stories about when he lived there. We arrived at his old house: The Bro-lagio. You could tell he was happy to be back in the area. He took a few pictures out front and we continued on. I loved looking at all the different houses and brownstones. We were constantly looking up the prices of ones for sale and talked about which ones we liked and did not like. It would be a different way to live but I can appreciate the appeal of it. My favorite thing were all of the trees arching over the streets; it made for a beautiful walk.

We made our way down Clark Street through Wrigleyville and past Wrigley Field. I was not allowed to take a picture in front of it because “we are White Sox fans” but that was fine, I did not care either way. It was a great little area though! He told me all about how much it had changed since he lived there and we explored the area a bit. Although, is it exploring when he knows where everything is? The weather was perfect, in the mid-70s, so it was nice to walk around.


Our next stop was the Willis Tower to be tourists and visit the Skydeck. They said it would be about 2 hours and they were not wrong; our total time there from start to finish was just barely over 2 hours. The line to the top was short but the line to take photos instead the Skydeck was insane. In line, it was revealed that I had already been up there before and if I had, then why would I do it again? *oops* I did feel bad for dragging him up there but you cannot argue with a great view of the city from every direction and a cute Skydeck picture together, right? Again, the things we do for love! It was a long, miserable wait but we survived and I appreciated him for being a trooper and doing that with me. It was great people watching, if anything. Of course I had to buy the professional photos, too.



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It was early afternoon and because of our light breakfast, we were starved. We made our way back to Old Town to meet up with his friends Brad and Becky again. Everyone met at The Rabbit Hole where Bobby and I grabbed a quick bite to eat. We all enjoyed some drinks, of course. Bobby ordered a “mystery beer and shot” which was kind of fun. The place was cute; the windows were open to the outside so it was nice to have the sun on us and there were table-top games (that we did not end up playing).

Afterward, we started our afternoon bar hop. Our first stop was Declan’s Irish Pub where everyone got Jameson and I got a lemon drop martini because I do not like whiskey. We hung out there for a bit, again a half indoor/half outdoor place. I liked how all the restaurants and bars were able to “open up” to the outside when it was a nice day. I know they cannot do that when it is freezing outside but on a nice day like it was, what a great option to have!

Next up was The Fireplace Inn where we all had “Huge Ass” vodka lemonades; their popular item. Those were very delicious but large and strong! Uh oh. It was nice to sit outside and hear all about their time working together in Chicago and more stories. Unfortunately, we were sitting in the shade so we made our way to a sunnier location.


I did not catch the name of our 4th place but there, I had my first Irish Car Bomb! We made a huge mess on the table when we dropped our shots but we were outside so it was fine. We also ordered cheese curds because I had said they sounded gross but they all called me on it and said I only made that accusation because of the word “curd.” Busted. We ordered them and they were fantastic. Y’all got me.

Our last stop was Woodie’s Flat where Becky and I finally contributed and bought a round fireball shots. The waitress asked me if we wanted a sparkler with it and I obviously said yes. No one knew though so it was a surprise to everyone when they came out with sparklers!

The sun was going to be going down soon and I wanted to be a tourist one more time an visit The Bean so we all said our goodbyes and parted ways. I had heard so much about them and loved getting to know them more. They were very kind to me and I appreciated how welcoming and inclusive they were. It was a great afternoon but the one thing I learned from it was that I cannot drink as much as a Chicagoan! I cannot speak for Bobby but I was preeeetty buzzed by that point.

We went to Cloud Gate (the Bean) and took some touristy photos. I had been there once before but it really is a great piece with the reflection of the surrounding buildings and whatnot. It was a beautiful night and a gorgeous sunset. I somehow managed to grab some kind of awesome snapshots of the skyline.

We had strangers take some photos for us and hung around the area for a little bit. We enjoyed one last drink at Park Grill and watched Game 2 of the NBA finals. I had a frozen something (no idea what) and from what I remember, it was good. It was the drink that pushed me over my limit and getting home was kind of rough. The bumpiness of the train was making me feel nauseated!

We made it home and instantly heated up the leftover Giordano’s. Not shockingly, the microwave did not work so our drunk patience was tested with having to wait on the oven. There were only 2 slices and it was definitely not enough; I think we both could have eaten at least one more slice. It was probably best that we did not have more though after how much we had ate and drank all weekend.

June 4, 2018 – Day 4

Our last day in Chicago was much more relaxed. Our flight was not until the evening so I slept in while Bobby got up and worked a little bit. We cleaned up, got ready to go home, and packed before the Airbnb host came by around 11:30am to pick up the keys. We made our way to the Brown Line one last time (the Paulina stop had been our nightmare all trip because the train always took forever). Our train pass was expired so we bought a one-way to the airport and made our way. It was quite the ride out there! I did not remember it being that long on the way but to be fair, we did stop for lunch on the way in and then used an Uber. We eventually made it to the airport.

Before our trip, we both registered for TSA-Pre Check. Our approval and travel ID did not come in time for our trip to Chicago but we had both received our official emails the day before so we were able to utilize our new fancy Pre-Check for the first time! Talk about a time saver. It was great to breeze through security.

We split chips/queso and a buffalo chicken sandwich at Chili’s before getting in line to board our flight. Our timing for that flight was perfect and made me much more comfortable than our one the other day. It was great to not rush or feel anxious. Bobby went to get us water and then we boarded swiftly, this time I took the middle seat. Teamwork.

WiFi on the plane was not working so Bobby could not work and instead, we worked on the in-flight magazine crossword puzzle. I had actually never done one for-real so he was teaching me and we were helping each other. I knew how they worked but it there are definitely tricks to filling it out. Afterward, I lent him my Sudoku book and taught him how to play it. What a bunch of nerds: doing crosswords and playing Sudoku the whole flight. I loved every second of it. When we landed, we stopped to buy me an easy crossword puzzle book and him an easy Sudoku book (flashforward: we both use our books just about every night now). Bobby also surprised me with a cookie he bought for us when he went to get the water. My hero.

We picked up the car and headed to my dad’s house to pick up Elliott. I always appreciate my dad and Suzette taking care of Elliott while I am away. He loves it there and I can trust he is loved in return.

Bobby and I decided to start the Keto diet after our trip so to finish off a weekend of poor eating and have one last carb-loaded meal, we stopped for Pei Wei on the way home. Worth it.

I had been told it is important to be able to travel well with your partner so I was so thankful that we had a fun, successful trip. There were moments I wish we had (or I had known of) more of a plan instead of winging it but I trusted him and it always worked out. We never ran out of things to talk about and I loved getting to see where is was from, meet his friends, and share the city with him. For some reason, I had always been a fan of Chicago and it did not let me down. My first time (and only ever time before) to the city was just for part of one day so to be able to experience it in its entirety with someone who knows it so well was perfect. I was worried about the weather but after the freezing Friday night, it warmed up and it was just as I hoped it would be. Everything was!

Thank you, Bobby, for taking me and inviting me to share in that part of your life! It was a wonderful trip and hopefully our first of many. 2018-06-08 16_22_18-🤟 I Love You Hand Sign Emoji

Until next time,



… to Turks & Caicos

Alright, busted. This post is coming nearly 3 months after-the-fact but better late than never, right?

At the end of March, Steven (one of my very dear friends from high school and college who now lives in NYC) and I took our first trip together to the island of Turks and Caicos. It was right after my birthday and just before his so it was somewhat of a “let’s go somewhere tropical” and “let’s celebrate our birthdays” trip! We deserved it.

March 22, 2018 – Day 1

The trip started off with an insanely early wake-up call. Steven was lucky enough to catch a direct flight from NYC to T&C but I had to go through Miami first. We timed it so we would both land in T&C within about an hour of each other which just meant I had to get an earlier start with a 6am flight out of Houston. My dad did not want to drive me to the airport at that ungodly hour (can you blame him?) so I caught an Uber. However, my dad’s neighborhood is gated and the Uber could not get in so my dad still had to wake up and drive me to the firehouse across the street to meet the Uber. Oops. Thanks, dad!

The Uber driver was an interesting, chatty lady who almost made me feel bad for needing an Uber at 4:30am. The hell? I made the mistake of thinking my flight was ‘international’ so we went to the wrong terminal at first but we had plenty of time to correct ourselves. Of course the flight to Miami would not be international; I blame lack of sleep for that error.

I was not checking a bag and security lines were short at that hour so it was a smooth check-in. I stopped at Starbucks for a Bacon Gouda sandwich (a tasty breakfast my boyfriend, Bobby, introduced me too a few weeks prior that had become a little addiction). No coffee for this gal… I slept the entire plane ride.

The Miami airport was something else. I had to walk/ride to what felt like the other side of Florida to get to my next terminal. It was a ridiculous amount of long halls, several escalators, and 2 trams. Luckily, I had enough time but it was cutting it close! I slept about half the plane ride this time and enjoyed the extra leg room I paid for. Worth it. I could have done without all of the babies crying but such is life.

If you recall, Steven and I were supposed to land around the same time. I was nervous we would not be able to find each other. He had broken his phone the night before after a nasty slip on ice outside his apartment (good ol’ NYC blizzards) so he had no way to contact me or I him. Well, that turned out to be a non-issue. The T&C airport was SMALL. So. Very. Small. I was not allowed to wait inside so I went outside and waited for him. I saw Rico, our driver to our Airbnb, holding a sign for Steven so I paired up with him and we waited. About an hour later, Steven came hobbling out (he also sprained his ankle pretty badly during the slip). I had picked him up a sturdy ankle brace before I left so he strapped in and we kept our fingers crossed it was not broken.

Rico was so nice and pleasant as he took us to the Airbnb, Kokomo Botanical Resort. It was a beautiful villa, about 5-10 minutes away from the resort area/ocean. We were greeted by Gabriella (the owner) and a handful of butlers who gave us warm towels to wipe our faces, a welcome drink, and a quick tour of the area. It was such a lovely space with 2 rooms and just perfect for what we needed! We received our villa keys, laughed at the option to buy a $30 bath pack when the place did not have a bathtub, and decided our first stop would be the grocery store.

We could not pick up our Vespa (our chosen method of transportation for the trip) until the next morning so we walked to the nearby grocery store, Graceway, to stock up for the week. I felt so bad for Steven because I knew his ankle was killing him through the crazy paths but he was a trooper and pressed on.

I had not eaten since Starbucks minus the free snacks on the plane and by this point it was 5pm, so I was starving. I made some guacamole and the two of us devoured it. Being stranded at the villa for the evening, we relaxed pool-side, enjoyed the hot tub, and drank (they have a local Rum, Bambarra, that became our mixer of choice). A lot. As the sun disappeared, we shifted to one of the many the cabanas and kept drinking and listening to music. Eventually, we made tacos, then returned to the cabana for our own Taylor Swift karaoke. The weather was so amazing and we had such a fun, drunken time staring at the stars. Because of our long day of travel, we were out by 10:30pm.

March 23, 2018 – Day 2

I was up by 7:30am and just hung out in bed and talked to Bobby for a bit. I missed him so much already. He was in Florida for a wedding at the time and it was our first time since we had started dating that we had been apart. *cue the awes*

Eventually, I got up and got ready for the day. Rico took us to pick up our vespa and tried to talk us out of renting it the entire time. He said it was going to rain and we’d be miserable (thank you for the Rico Weather Report, but it never rained that day). We pressed on. We picked up our single vespa and had decided I would be our driver for the trip. Everyone was required to go through a mini training on how to drive the thing so I attempted that and to say I was bad at it would be the biggest understatement of all time. I was NOT a natural. Needless to say, Steven drove the whole trip while I hung on for my dear life and navigated us around.

Our first stop was Coral Gardens. It is said to have great corals for snorkeling. It was our first glimpse of the amazingly blue water and gorgeous beaches T&C has to offer so it was pretty exciting. We lounged on the beach and soaked up the sun for a little bit. The water looked so nice but was kind of cold! We did not book an official snorkeling tour but instead, brought our own gear and were going to attempt it ourselves. I had never snorkeled before so I was nervous but eventually just went for it. Steven attempted it but his ankle was bothering him too much so he did not make it long. So, there I was in the cold water, not knowing how to snorkel and getting water everywhere. Eventually I learned that the trick was to be CALM. Breathe normally. Do not panic. That is general life advice, right? Anyway, I eventually got the hang of it. I brought an underwater camera but the battery was dead (of course) so I did not get to take pictures but I did enjoy getting up close and personal with the fish. I expected to see beautiful, colorful reefs but that was not the case. The views were just… okay. I had never seen anything like it before so it was better than nothing but definitely not what I expected. I did like having a cute little blue and yellow fish be about a foot from my face. That was cool.

We relaxed at the beach for a little longer then decided to head home, drop off our gear, download the offline maps for T&C so we could navigate around, and get a drink. My hair was SO tangled and gross from the water, vespa helmet, and wind. It was a nightmare.

Steven found a great place a little farther South called Bugaloo’s. This became our place! We LOVED this place. It was quite a vespa ride to get there (about 20 minutes, I guessed, and very bumpy at the end when we had to off-road a little bit), but it was so worth it. We also experienced our first (and last) vespa ‘crash’ as we fell over when we tried to slow down/turn/park. We both managed to hop off before it fell but Steven hopped off on his bad ankle, only aggravating it more. The restaurant and the beach it was on were beyond beautiful, the best beach we had seen so far. The environment there was great. Steven was a little quiet; I could tell he was hurting and frustrated that his ankle was holding him back from having the trip he wanted to have. He perked up though and we had a fun time. The place had a fun entertainer guy who played music, sang, and interacted with the crowd. “Conch” was the popular item on the menu and apparently popular for T&C so we decided to try it. It was just okay; nothing to get excited about. A little chewy. Bugaloo’s was also where I realized I was starting to develop a nice sunburn. I applied sunscreen at the beach but it never crossed my mind that sitting on the back of a vespa still meant I was in the sun… so the tops of my arms, legs, and of course my shoulders were starting to get a nice pink. I applied more sunscreen!

After a nice lunch and a few drinks, we decided to go explore some areas on the map the vespa rental place had provided us. She had pointed out some good places to go and one seemed nearby so we headed that direction. (Side note: this was the same lady who told us that “everyone has vespas” in T&C and I swear, I did not see one other person on a vespa the entire trip.) We followed my GPS to Taylor Bay Beach, one we heard was really nice. Unfortunately for us, my GPS did not care if the suggested roads were paved or not… so we did QUITE A BIT of off-roading. At one point, right before the roads got really bad, a guy in a truck that was parked nearby honked at us, probably trying to tell us to not go that way. Us being us, we went anyway. I did tell Steven we should turn around (the “roads” were so bumpy) but it made more sense to keep going and hope it get better. The area it took us through was a tad shady and that is putting it nicely. I actually felt slightly uncomfortable and tried not to entertain the voice in my head telling me that was how we were going to get kidnapped and die. I did not want to be on the news.

Eventually, we made it back to paved roads and ended up in a surprisingly nice area. Everywhere we tried to turn to get to the beaches, including Taylor Bay Beach, was blocked off and marked as “private.” What we could see was beautiful, though. Even so, the I learned that island itself was complete garbage. We passed a lot of half-built houses, abandoned lots, trash everywhere, etc. Whenever a house WAS finished, it was incredibly nice! Wherever there was water, gorgeous. Everywhere in between? Yikes. (We later learned that the island was recovering from some serious damage from Hurricane Irma and Hurricane Maria.)

Our map had Chalk Sound View as a good place to visit so we kept driving to find it. There were so many times I said we should turn around or that we had gone too far (we were going AWAY from the villa into more and more remote areas) but Steven had a feeling we were close. He was right and we found the place. It was worth it, of course. Basically, it was a long narrow road to the edge of a cliff. Nothing indicated it was a “place to visit.” The view faced inland so the water we saw was more of a bay than the ocean but it was huge and amazing. We saw a truck coming down the small path to the ledge and got a little apprehensive (were we in trouble?? were we about to get murdered?) but they just said they saw us heading down there and wanted to come offer to take our picture. That was nice!

We were not there long because despite how beautiful it was, it was just a cliff ledge with nothing to do and no where to go. As we were leaving, a couple we had seen at Bugaloo’s earlier (and who turned around at the area of the road where the truck honked at us to turn around), pulled up. I guess they were looking for the same place as us! They were in a car but they did not brave the bumpy roads and shady area like us. Probably smart. I offered to take their picture for them and then we headed back, this time on the main roads the entire time.

I felt like we had been on that vespa… forever. I could tell my skin was frying, my legs were hurting from holding on, and my back was hurting (no back support). I am sure Steven was feeling it too! It was so windy and of course being on the vespa just made it windier. My sunglasses were lifesavers; I do not know how Steven drove without a pair. I thought we should head back home but Steven wanted to go North this time up the main highway so we went that way. He was getting more confident with his driving skills but I was still scared to be on the dang thing (I mentally renamed it a ‘death-spa’). As we went more and more North, I started to get anxiety about not knowing where we were or flying off the back of the vespa. It was getting darker and the areas were a little scary. I had not come to T&C to get kidnapped or disappear on the island, no thank you. I desperately wanted to turn around but I also did not want to be a wet blanket and who knew if we would actually find something cool? So, I mostly kept quiet! Eventually, I pointed out to Steven that the map did not have any ‘landmarks’ or ‘activities’ or anything to do up North so we were headed no where. He agreed and we turned around.

We had passed a bar called da Conch Shack and it was on our itinerary to visit the next day so we decided to go there next before going back to the villa (which was far at this point). A stray dog welcomed us and fell in love with Steven. Stray dogs always make me sad. It was cold in the shade, nice in the sun, and windy as all hell so we only stayed for a quick drink before heading home. Plus, most of the restaurant was on sand and it was very difficult for Steven to walk on sand with his hurt ankle. We decided to maybe come back another night for dinner and their live music.

We made a quick stop at the grocery store for some essentials (sunscreen, aloe, cookies, and wine) and were home by 5pm. I was burnt. Everything hurt. I could feel the heat radiating off of me. I fell asleep on the couch for about an hour while Steven was at the pool. Then I fell asleep again. And again. Steven made guacamole and I tried to have a drink but the only thing that sounded good was water. I was definitely not drinking enough water.

The rest of the evening was spent just lounging and snacking. We went through all the pictures we had taken (I tossed the cover up I had worn all day, that thing was so unflattering in pictures), listened to music, and rested. We were both in bed and out by 10pm. The sun really took it out of us! There was a roach on my blinds before bed (yuck) and I missed Bobby. We texted a lot but during the day we were both out and about and distracted but at night, I always missed him just a bit more!

March 24, 2018 – Day 3

We both slept in. We needed it. We made a big breakfast at the villa before heading out for the day. Since we had gone West the day before, we decided to go East and explore what that side of the island had to offer. Apparently, it had a lot! We found the very nice side of town and the tourist area. The resorts were beautiful but some of those houses there… wow. They were all different styles and very, very fancy. It was so weird to see those houses compared to other areas of the island we had visited. Talk about an income gap.


A lot of the beaches were still private but we did eventually find one, it just did not have a great place to lounge.

We kept going and ended up at Sunset Beach for a couple of hours. It was so nice to rest and do nothing for a bit except soak up the sun and watch the water. I loved that beach!

After awhile, we got hungry and after a quick stop to pick up some souvenirs, we went back to the villa to get some snacks. We had all those groceries, we might as well eat them instead of going out! It was nice to be out of the sun for a bit, too. We thought about visiting the private beach the villa had access to (about 5 minutes away) but decided against it and went to the store for more wine instead. Our villa had a cute patio so we enjoyed wine on the patio before getting dressed up for our “formal dinner” night.

Steven had a very detailed itinerary planned for us with a restaurant already picked out but since we had not done most of the things on it (because of his ankle) we decided to go back to our beloved Bugaloo’s for birthday dinner. Steven picked out this dress for me and insisted I get it – I loved it so much! I felt very beautiful in it.

We loved Bugaloo’s the first time but at night it was even more amazing. There was a completely different vibe going on but not necessarily a party vibe either. The place was lit up with string lights and the entertainment guy was a little more chill. The tide had receded a bit, too, which gave us great access to the boat we could not reach earlier. We intentionally arrived there just as the sun went down so we could have nice sunset pictures. Everyone watched us take about 1,000 photos and one guy (who took one of us together) even said he and his wife thought we were on our honeymoon. We laughed!

Steven had ordered a bottle of wine for us and when we ran out, I ordered another while Steven was in the bathroom. He came back and then informed me the bottle was $60! We also ate a LOT: Conch salad (yes, we attempted the conch again, it needed chips though), corn fritters (yum), and drilled shrimp. We drank and ate and had a fun time. I danced alone on the dance floor; I blame the alcohol. $300 later, we called it a night. (PS – we did not realize until the last day that in T&C, tip is already on the check so we had tipped generously, too!). After the sun went down, it had gotten rather cold and windy so it was definitely time to go.

At the villa, I tried to have a drink and be social but I was beyond tired. The hot tub was hurting my sunburn so I did not last long and went to sleep. It had been a slow, relaxing day but I was exhausted. I think Steven stayed up for awhile longer.

March 25, 2018 – Day 4

I slept in, hard. I normally cannot sleep in like that but vacation me was completely capable. Eventually I got up and cleaned the villa up for a little bit. Our “butler” at the villa would clean up for us once a day but we tended to make it messy again quickly. We got a slow start which was nice.

Our first adventure for the day was a massage. I knew we had massages booked but did not know where they would be so I called Jason (one of the butlers) on the villa phone (they had given us a cell phone with only the butlers’ and Rico’s numbers) to find out because I was getting nervous we would be late. Steven was still sleeping and I did not want to miss the massages! Luckily, they were local at the villa pool, just a 30 second walk from our front door. It was a grrrrrreat, hour-long massage and totally needed. My sunburn hurt a little bit but it was so nice and relaxing. Plus, the weather in T&C was always great so it being outside was a nice touch.


Our villa was being cleaned when our massages were finished so we sat in the cabana for a little bit, completely spaced out in a massage coma. When we were allowed back in our room, Steven made fish tacos, we snacked on plantain chips (we were addicted to those the whole time), and then we went to the villa’s private beach nearby.

The beach had chairs and umbrellas for us so we got cozy and hung out there for about 3 hours. We both slept on and off the whole time. The sun was blocked by clouds which kept it cooler out so every now and then, I would use a towel as a blanket. Seesh. I looked around and was not alone though; several people were doing the same thing. It was nice to be in the shade after all the sun we had gotten but I do not like being cold! We had our music playing and brought our own rum drinks so it was just a nice, chill afternoon.

We went back to the room and cleaned up for dinner. We decided to have dinner at Shark Bite, a little place on the water. I loved it there! There was a beautiful sunset over Turtle Cove that we were lucky enough to see. I had a delicious hamburger (I was so done with conch). We reminisced over our trip and just enjoyed our last evening on the island. Steven and I had never taken a trip together and I think we were both excited but nervous about it; you never know how 2 people will get along on a trip like this. We both agreed it was very successful and would do it again! I liked the vibe of the place a lot so we hung out there for awhile.

We took one last stop at the grocery store on the way home and then relaxed on our patio. Bobby and I had obviously talked the entire trip but only in text but now that he was home from his own trip, we were finally able to video chat. It was great to actually see his face again and hear his voice! Did I mention that I had missed him?

March 26, 2018 – Day 5

We had to drop the vespa off early so we got up, packed, cleaned up a bit, and returned the vespa. Rico had to pick us up and take us home; we did not know it was the last time we would see him! We had a last big breakfast, with delicious rice, to fill us up before our long day of travel (or for me, at least until Miami). Steven went to go swim for a bit until our taxi was ready to take us to the airport but I did not want to get sweaty again so I finished packing and relaxed inside until it was time to leave.

Rico was supposed to get us but I guess had another trip so he sent an insane man to pick us up. This guy was a nut job. He was kind of rude, on the phone a lot, and an aggressive driver. He picked up 2 other guys from another area who were also going to the airport and together we survived the drive.

It was the same small, shady airport but this time I got to see the departures area. What a mess. Steven had to check his luggage so I went ahead through security. It took no time at all to get through everything, even with the ridiculous people who behave as if they have never been through an airport before. When the security guy is telling you to take your laptop out, he means take your laptop out! The guy literally asked, “do I have to take both laptops out?” Oh my gosh, yes. People.

For some reason I had lost the ability to send text messages that day. Messages were not leaving my phone at all and it was stressing me out. I wanted to be able to tell Bobby and my family I was on my way. To kill time, I started outlining my blog. At one point, an American Airlines representative came over to talk to me and checked my boarding pass. It was odd.

I waited for Steven to come through security but never saw him. We did not get an official goodbye but that was probably better anyhow as neither of like awkward, sentimental goodbyes. I did see him as I was in line to board my plane but at that point, it did not make sense. He was probably just as fine with that as I was, which is one of the reasons we get along so well!

It was a short flight to Miami and I played Sudoku on my phone the whole time.

I was supposed to have a 4 hour layover but my flight landed SO early and I flew through customs so I tried to catch an earlier flight so I could get home to see Bobby earlier. My original flight was expected to land in Houston around 9pm and I did not want to wait that long. I literally ran to the gate (remember all those halls and escalators?). I made it to the gate in time but there were already people on the standby list so I was SOL. Thus began my 4 hour wait. I slowly made my way back to my original gate area to grab a bite to eat. I bought headphones only to learn after I ripped the box open that my phone did not have a headphone port anymore. Of course! I found an outlet, ate my pizza, and charged my phone while I played more Sudoku.


My gate changed approximately 400 times without me even knowing. I was not getting any notifications and they were not making announcements, probably because it was still so early before the actual flight time. Luckily, my text messaging was working and Bobby was sending me updates on where to go. I had to go back to the ANOTHER side of the airport. That side was so much nicer and had better food options; I should have waited to eat! The layover went by very fast and before I knew it, I was on the plane home.

The last flight was great. I had an in-seat screen and was suddenly thankful for the headphones I had purchased and deemed useless earlier. Bobby had sent me a code for WiFi on the plane so we had messaged back and forth a little bit about my arrival time, trying to coordinate him picking me up. I finally watched the movie Coco (and cried like a baby during it).


When I landed, Bobby was there in my car, with Elliott, to pick me up! It was a great trip but I was so happy to be home.

Steven and I spent a lot of time putting together our “lewks” for the trip (outfits) and planning a schedule. We had the most detailed itinerary I had ever seen in my life. We did not wear half of our outfits and did not do almost anything on the itinerary but it was such a fun trip! I am lucky to have a friend like him and to have stayed in touch so well after college while living in different cities! I hope we can take another adventure together in the future!

Until next time,