For an island that is only about four miles long and two miles wide, it is honestly wild just how much there is to see, eat, and experience in Key West. Whether you want to spend your days out on the water spotting wild dolphins, exploring remote national parks, or bar hopping down Duval Street, you will never run out of things to do on this tiny slice of paradise. Here are all my favourite must-do activities in Key West, along with a few helpful tips to make the most of your trip!
Captain’s Choice Sunset Dolphin Sail
This was hands down the best thing I did on my last trip, and I would go again in a heartbeat. It is run by Sebago Watersports and lasts approximately two and a half hours onboard a luxury catamaran. Once you board, the bar opens, and your ticket includes unlimited premium wines, sangria, and soft drinks, along with a delectable selection of appetisers including prawn cocktail, smoked fish with fried bread, and mini key lime pies. Once we left the harbour, we were all on full alert for dolphins. It was clear the captain knew exactly where the pods liked to hang out because it was maybe 20 minutes before we saw the first dorsal fin poke up out of the water. From then on, we saw dolphin after dolphin, with groups swimming and jumping together. It was magical and something that will stay with me forever. The drinks were flowing, everyone was in high spirits after the first dolphin sighting, and then the sun started to set. We had stunning views of the Key West coast, the orange sunset falling behind the horizon, and dorsal fins swimming off into the distance as we made our way back to shore. The crew was fantastic, helping to spot the dolphins, refill drinks, and keep the vibe fun and relaxed.
Visit Dry Tortugas
If you are staying in Key West for more than a couple of days, it is definitely worth adding on a trip to the Dry Tortugas, the United States’ least visited (and also coincidentally least accessible) National Park. It is located 70 miles from Key West and can only be reached by seaplane, ferry, or private boat. Seats for both the public ferry and seaplane fill up fast, especially in peak season, so do not wait until you are down on the island to book your ticket. You can even camp on the island, although spaces for that are even fewer, so you would really have to plan pretty far in advance.
The public ferry, the Yankee Freedom, departs daily at 8:00 AM from Key West. At the time of writing, tickets cost around $260 for the round-trip journey, breakfast, lunch, park entry, and the use of snorkelling equipment. Check-in begins at 6:00 AM for campers and 7:00 AM for day visitors, and honestly, the earlier you get there, the better. Boarding goes by group number (1 to 25, 26 to 50, and so on), so the lower your check-in number, the earlier you can board the boat and choose the best seat. There are a few different areas where you can pick to sit. If you suffer from motion sickness, the back of the boat on the lower level is usually your best bet, as the higher deck is going to move around more with the waves. Our crew recommended that everyone take motion sickness pills before boarding regardless of whether you usually get sick, as it was a particularly rough week weather-wise at the end of October. Breakfast and lunch are included in your ticket, and they cater for most dietary restrictions if you let them know by 9:00 AM. There are also four toilets onboard.
The ferry takes about two to two and a half hours depending on weather conditions, and once you arrive, you will have about four and a half hours to explore the national park. There is a guided tour you can join that is included in the price of your ticket, which I recommend taking so you can learn about the history of the place. You will return to Key West around 5:30 PM, so it really is an all-day event best saved for when you have a few days on the island. Alternatively, the seaplane can be booked for a half- or full-day excursion. As you can probably imagine, tickets for this are a lot more expensive than the ferry, though you could just do a half day. The flight there is only 40 minutes and offers insane views flying in. If the Maldives seaplanes seem too far out of reach, this could be your next best thing. Having flown in a seaplane in the Maldives myself, there is truly nothing like taking off and landing on the water.
While nearly every bar in Key West offers some sort of happy hour, this has probably got to be the best spot in town, as you will be gliding past Mallory Square and the harbour coastline at sunset. What better way to view the sunset than from the water? I went with Sebago Watersports and had a blast. Their sunset sail lasts about two hours, is lively and fun, and even features a live musician. They have an open bar included with your ticket featuring house white, red, and sparkling wine, along with well liquors, mixers, beers, and soft drinks, or you can upgrade to a VIP package for top-shelf liquors. During the cruise, guests are invited to mingle, walk around, enjoy the stunning coastline views, and snack on appetisers including shrimp cocktail, smoked mahi with fried bread, olive, tomato, and burrata skewers, and mini key lime pie.
This made for a fun introduction to Key West and a great way to get the lay of the land when you first arrive. The tour is just over an hour long, and trains run every half hour throughout the day. You learn a lot about the history of the island and all the funny little quirks that make Key West so unique. You are given a map, and the tour guide speaks through a microphone projected into each carriage, so you do not have to worry about sitting too far from the front. The train also makes a brief stop near the end of the trip at a gift shop, which I actually found to be the most varied and affordable souvenir store out of all the ones I visited.
Unlike massive mega-aquariums that take an entire day, this historic spot offers an easy, intimate peek at the creatures native to the Florida Keys. Stepping inside feels like stepping into vintage Old Florida, as it is actually the island’s very first official tourist attraction. Its open-air roots and 1930s origins give it an old-school, nostalgic character, and it is the perfect air-conditioned spot to take a break from the midday heat while exploring. Here is my top tip if you pop in: do not just wander through on your own. Time your entry around a guided keeper talk, because that is really where the heart of the visit is. The keepers are super passionate and bring so much context to what you are looking at. The absolute highlight for me was meeting the rescue sea turtles, Rocky and Lola, and hearing their individual stories. It gives you an immediate appreciation for the rehab work happening behind the scenes for wildlife that cannot survive back in the wild.
Try Key Lime Pie
I feel like it goes without saying that you must try key lime pie on your visit to the island, as it is a true rite of passage. My favourite spots were Blue Heaven Restaurant and Kermit’s, which has a few locations throughout Key West and also serves key lime pie on a stick, chocolate-covered pie slices, and gluten-free versions, among others. If pie is not your thing, there are plenty of different variations of the flavor, from cookies to sauces, so take your pick.
Visit the Southernmost Point
This is a classic photo opportunity right at the end of Duval Street, although it does get busy during peak hours and you might have to wait your turn for a picture. If you are short on time, there is actually a mini version inside the Southernmost Point Bar nearby.
Visit the Smallest Bar in Key West
Not only is it a fun flex to say you grabbed a drink at the smallest bar in the United States, but they also make really good cocktails. Measuring just 72 square feet, it is located right on Duval Street in the heart of the action.
Visit Ernest Hemingway’s Home and Museum
While I primarily wanted to visit because of the 60 polydactyl (six-toed) cats that have claimed residence here, I was fascinated learning all about the colorful history of Ernest Hemingway’s life, and the grounds are absolutely stunning and well kept. Your entry ticket comes with a guided tour, which I highly recommend joining. It lasts about 30 minutes, and they run almost every 15 minutes throughout the day. Our tour guide was animated and full of fun facts about his life that you will not find in the history books. The tour takes you all through the house, including his writing study, and finishes outside by the pool. While it is the largest residential pool in Old Town, it was not always a pool. When one of Hemingway’s wives found out about his affair, she tore up one of his greatest prides and joys, his boxing ring, and replaced it with a pool. I could not help but laugh. There is also a great book and souvenir store on site where you can pick up six-toed cat knickknacks or a copy of one of Hemingway’s famous books.
Duval Street Crawl
It goes without saying that a trip down Duval Street needs to be on your itinerary when you visit Key West, and it is usually one of the first places people go when they arrive for the first time. The road is just over a mile long and has more than 40 bars scattered along it, along with restaurants, shops, and souvenir stores. Each spot has its own distinct vibe, and you will find live music on every corner with almost every bar hosting its own happy hour. Some notable favourites include Hog’s Breath Saloon, Sloppy Joe’s, and Irish Kevin’s. Pace yourself and stay hydrated, because it is very easy to spend all day bar hopping down this street.
Dine at Half Shell Raw Bar
This original Key West waterfront seafood restaurant was one of the highlights of my last trip and easily our best dining experience, not just for the fresh seafood, but for the whole atmosphere and service. Not only did our wonderful server, Jenna, walk through the entire menu with us and give us personalised recommendations, but she also wrote down a list of her favourite spots on the island. Be sure to make a reservation if you want one of the tables right over the water. We ordered the oyster sampler, blackened grouper, and the garlic shellfish combo, and it was all just as delicious as it sounds.
Watch the Sunset
Sunsets in Key West just hit differently, and watching them has become somewhat of a spectator sport on the island. The most popular places to watch are Mallory Square and Sunset Pier, although you will want to arrive maybe 45 minutes early to grab a good spot. If you cannot get out on the water to watch it, which is always my ultimate go-to, Elevate rooftop bar has outstanding sunset views. It is part of the Opal Key Resort, located right on top of Lolita’s (a great Mexican restaurant that should also be on your itinerary), and has rocking chairs facing straight toward the horizon. There are not many rooftop bars on the island, and not many people seemed to know about Elevate, so just arrive a little early if you want a front-row seat. The food and drinks are fantastic too.
If you want to find out more about Key West, read my Ultimate Guide to Key West
You can find out more about my stay on my “Key West” Highlights on Instagram @chase.the.rainbows.
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