Living through a New England winter can be tough if you don’t enjoy the cold or winter sports like skiing, snowboarding, etc. We wanted to get away but weren’t sure what to do at first. Jarrett and I already had a long trip planned for May 2026, but it seemed so far away. Jarrett threw out the idea of going to Dry Tortugas National Park, another park on our list, so we figured out the logistics and planned a quick little getaway to Key West, Florida, for February.
Our flight out of Boston was a Saturday morning. Of course, the morning we left, there was a snowstorm. We were taking the bus to Logan Airport, and luckily, we weren’t far from the bus station, because the roads were gross! Our flight was on time, but we did have to go through the deicing process first. After an interesting morning, our flight was uneventful and we landed in Key West right on time! Walking out of the airport into warm sunshine was so wonderful after weeks of brutal cold. We headed directly over to our hotel and were able to check in early. To give you an idea of the layout of island – we stayed on the very north end of the island. Duval Street is the popular tourist area downtown, which is at the south end of the island. The island is about 4 miles long and 1 mile wide, so it’s easy to get around without a vehicle. The Keys are connected by the Overseas Highway so if you do have a car, you can travel the highway to visit multiple Keys. You can also ride bikes along the bike path that hugs the highway. Since we were on the north end of Key West, we decided to walk over to Cow Key, the next island over, to grab lunch. It was a quick half-mile walk, so that was convenient! We went to a spot called Hurricane Hole, which sat right on a marina. It was so nice to be outside in the beautiful weather watching pelicans diving into the water and snacking on fish. I got a beer with my lunch – Iguana Bait Kolsch – from Florida Keys Brewing. Iguanas are invasive in the Keys, but I was still so excited whenever we saw them on our trip.
After lunch, we went back to the hotel and caught the free shuttle to downtown. We walked around a bit but the downtown area wasn’t really our vibe. We did check out First Flight Brewery – the southernmost microbrewery in the U.S.! We got a beer and a snack there. It was a really cool spot and the outside patio made it felt like you were in a jungle. Two things I have to mention about Key West: chickens and Banyan trees! Key West is known for having chickens and roosters roaming the city. I’m not sure why, but they are there and they are protected. I loved them, they were cute. They’d stroll around restaurants and shops, anywhere there was an open door, they’d go check it out. Then the Banyan trees – they are these massive, weird, stunning trees. They are not native to Florida, it sounds like they were brought over from India, but they definitely fit the vibes of the island. We saw so many around town and we loved how unique there were! After the brewery, we stopped at Books & Books, a bookstore that I later found out is owned by famous author Judy Blume! We finished up our time downtown by stopping at another brewery – Waterfront Brewery. We had their pretzel sticks, which were SO good! We also liked their beers a lot here. By this point, we were very sleepy after a long day so we got the shuttle back to the hotel and passed out.
Our second day started out in a very annoying way. We wanted to rent bikes for the duration of our trip to help us get around. There was a bike rental place on Cow Key, right near where we had lunch the day prior. However, when we checked in at the hotel, we learned they had bike rentals as well, but we’d have to visit the concierge desk when they opened at 9AM. So, Sunday morning when we woke up, we arrived at the concierge desk right at 9AM. The concierge was just logging on and told us she needed a few minutes, which was fine. We said we’d go fill up our water bottles and then come back. So, after about five minutes, we returned to the desk. The concierge said she still wasn’t ready. So, we sat on a couch right next to her desk, near the front door of the hotel lobby to wait. A few minutes passed, and then the concierge picked up some folders from her desk, didn’t say a word to us, and just walked out the door! We looked at each other like “Um…what? Where is she going!?” We were both annoyed by this point because we wanted to get bikes right away so we could go get breakfast somewhere. We had a short window of time because we did have plans in the afternoon, around lunch time. We ended up walking to the hotel next to ours to grab something quick from Starbucks and figured that by the time we got back to our hotel, maybe the concierge would be back at her desk. Well, we got back about a half hour later and she still hadn’t returned to the desk! We cut our losses and decided it made more sense going to the bike rental place on Cow Key, called WeCycle. It was super quick and easy to rent. We just got beach cruisers (that came with locks and baskets). For two bikes for three days, it was $94 total – Much cheaper than renting a car or taking Ubers around the island! Once we secured our bikes, we rode over to the grocery store near our hotel to grab a few items, like sandwich supplies and snacks. We hung out at the hotel for a little bit and ate a quick lunch before we were back on the bikes heading to our next activity.
We signed up for a snorkel tour with Captain Hooks, so we had to bike to their shop to sign our forms. They asked if we wanted to wear wet suits because the water was going to be on the cooler side, around 69º F. We both laughed and said no, because, being from New England, we are used to swimming in ocean water far colder than that! We hopped in the van with one of the workers who brought us to the marina where the boat was docked. On the tour it was Jarrett and I, a group of three women, a family of three and one solo man, who was the only scuba diver (the rest of us were snorkeling). There was also the captain of the boat, Billy, the first mate, Jennifer, and the dive instructor, Troy. We went out about 5 miles from shore to the first of two reefs that we were going to explore. The water was pretty choppy. On the boat they gave us flotation vests to wear but they had pool noodles for us to use too if we wanted. I’m not a strong swimmer at all, so I took advantage of both options. I got in the water and lasted only about two minutes. The waves were making me so nervous and I kept getting water in my mouth and just felt really panicky. I ended up getting out of the water and sitting on the boat the rest of the time. After about an hour of everyone playing in the water, we went to the next spot, which wasn’t too far away. Only the scuba divers got back in the water, while the snorkelers stayed on the boat. I wish I had gone back in, but again, I was really nervous and felt uncomfortable. Sitting on the boat waiting for the divers to return wasn’t fun though. I don’t usually have an issue on boats, but the choppiness of the waves made sitting on the boat rough – I unfortunately threw up! Even though it wasn’t a successful trip for me, I would still recommend Captain Hooks for a snorkeling tour. The guides were great and really helpful. After we got back to the snorkel shop, we grabbed our bikes, had a quick dinner at a Mediterranean place (Kennedy Café), then made our way back to the hotel to watch the Super Bowl.
Day three was a busy day for us. We woke up early and rode our bikes about three miles to the marina where the Yankee Freedom, the ferry that would take us to Dry Tortugas National Park, was docked. We arrived right at 7 AM and checked in. Boarding happens in numerical order of when you arrive and check in. Since we checked in right at 7 AM, we were able to board before a lot of other people and scored a seat on the upper deck of the ferry. Breakfast was provided on board (bagels and cream cheese, fruit, coffee, tea, etc.). The ferry ride was a little over two hours long. During the ride, the park ranger would pop on over the loud speaker and point out different things, like landmarks and protected areas. Once we arrived at the park, the park ranger offered a 45-minute tour of the first level of Fort Jefferson, the large historical fort on the island, or you could do your own self-guided tour of all three levels, which is what we did. We started by visiting the tiny park store and then explored the fort. The roof level was really interesting with multiple cannons and little hidden passageways. The water around the island was stunning, I couldn’t get over how bright blue it was.
After we explored the fort, we headed back to the boat to grab lunch, which was included with our tickets. They had large sub sandwiches, some snacks and beverages. We quickly ate on the dock and then grabbed snorkeling gear (also included in the ticket price). We snorkeled at South Beach around the moat walls. The water was calm and shallow; it was nice being able to ease my way into it and feel more comfortable. I was still a little nervous to swim further out, but I did have more fun snorkeling at the park than I did on the tour. However, I wish we had done the park snorkeling first, because I think I would’ve felt more comfortable on the snorkeling tour after getting a little practice in first. After we finished swimming, we walked out to Bush Key to see the Magnificent Frigatebird colony. This part of the island actually closes February through September for nesting season, so we were lucky to be able to check it out before the closure started. The ferry left the park at 3 PM for the long ride back to Key West. For people who wanted to camp overnight, they have few campsites available on the island, but they book out far in advance so plan ahead! When we got back to the marina, we biked back to the hotel, making a pit stop at The Stoned Crab for dinner. I got the yellow tail snapper, which was a new fish for me – it was pretty good!
We had to return our bikes on the afternoon of day four, so we wanted to spend as much time using them as possible. We started the day biking along the east side of the island and watching sunrise along the seawall. It was so beautiful – cloudy, but very dramatic. After watching sunrise, we continued on our bikes down to Higgs Beach. The bike ride was so nice. You are allowed to bike on the sidewalks in Key West, but while a lot of them are narrow, the ones along the outer edge of the island are very wide, making for a pleasant ride. Once we got to Higgs, we locked up our bikes and walked to the Southernmost Point of the Continental United States. There is a large concrete buoy that you can take pictures with. By going first thing in the morning, we were able to get pictures without having to wait in line. From there we walked over to Moondog Café to get breakfast. I had a delicious breakfast sandwich and a watermelon mimosa. It was such a nice morning sitting out on the patio people-watching. Before we left the café, we grabbed some to-go pastries to have for breakfast the next morning. We walked back to our bikes and then had a leisurely ride back to the hotel.
We spent a few hours lounging by the pool before returning our bikes to WeCycle. From there, we walked over to Lazy Dog Adventures, a kayaking and paddleboard rental company right next to Hurricane Hole, where we had lunch the first day. We rented kayaks and explored Cow Key Marina and got to paddle through mangroves, which I loved doing! I could’ve spent hours floating around in the mangrove tunnels! I was hoping to see a manatee or nurse shark or something, but we only saw birds, an iguana and some fish. After a few hours on the water, we had dinner again at Hurricane Hole since it was right next door, then headed back to the hotel for the night.
The next day we got up early again and walked back to seawall on the east side of the island for another sunrise. It wasn’t as dramatic as the day before but it was still beautiful and peaceful. We ate our breakfast pastries from Moondog Café and watched the birds hunting in the shallow water. Afterwards, we walked back to the hotel to pack, only to find out our flight was delayed. We spent some more time at the hotel before taking a Lyft to the airport, where, unfortunately, we found out we were delayed again. We had a lot of waiting around and when we got back to New England, we had arrived in the tail end of another snow storm. We got home later than anticipated but luckily the car wasn’t covered with too much snow and we didn’t need to dig it out of the parking spot.
It was really nice getting to escape the cold for a few days and to feel the sun again. I can see why people love going to Key West. I’d love to go back but rent a car to drive along the overseas highway and check out some of the other Keys. Getting out on the water with a kayak or paddleboard is really the way to go. I can’t recommend it enough. Have you been to Key West?
📍I acknowledge the lands mentioned in this post are the ancestral lands of the Taíno, Calusa, Seminole and Mascogo people.
The Adventures of Suze 
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