My Favorite Things to Do in Key West
Hey, babe! Planning a Key West vacation can be overwhelming because there are so many things to choose from. These are experiences I have personally tried, trust, and recommend to my own friends, family, and followers.
I live and work here, and I would not put anything on this page just because somebody gave me a booking link. These are places and experiences I genuinely believe can make your Key West vacation better.
Water Adventures
Special Event
Race World Offshore Key West World Championship
Watch the Powerboat Races From the Water
Race Days: November 4, 6 & 8, 2026
Race World Offshore returns to Key West for its 2026 World Championship, and there may be no better place to experience the Key West powerboat races than from the water. Fury Water Adventures operates premier viewing boats positioned just outside the race course near Turns 2 and 3, putting you about as close to the racing action as spectator vessels are allowed.
Spend the day aboard a spacious Fury catamaran as some of the fastest offshore powerboats in the world roar past you at more than 100 mph. Instead of trying to catch a glimpse from shore, you'll be out on the water where you can see, hear, and feel the racing.
This is approximately an eight-hour experience. Check-in is at 7:45 AM, with departure around 8:30 AM and return around 4:30 PM. Breakfast, lunch, snacks, and beverages are included — lunch features fried chicken along with pinwheels, snacks, vegetables, antipasti, hummus, and cookies. Included drinks cover water, sodas, mimosas, beer, wine, and champagne. Additional full-liquor drinks are available for purchase with drink tickets.
Shawn's Take
If you're coming to Key West for the Key West World Championship Powerboat Races, this is the way I'd want to see them. Watching from shore is one thing. Being out on the water near the turns and hearing those boats come screaming toward you is a completely different experience.
You get an entire day on the water, some of the closest spectator views of the race, breakfast, fried chicken for lunch, and drinks while you watch. For me, that beats standing behind a crowd trying to see what's happening out on the course.
Water Adventures
Ultimate Adventure H2.0
The Biggest Adventure Day in Key West
If your family wants to do everything while you are in Key West, this is the trip. The Ultimate Adventure H2.0 is the only all-day adventure in Key West that combines snorkeling at the coral reef, parasailing, Jet Skis, a banana boat ride, and the largest state-certified ocean water park in Key West.
Breakfast, lunch, snacks, refreshments, and alcoholic beverages after the water activities are also included.
Shawn's Take
This is the trip I recommend when someone tells me they only have a few days in Key West and want to experience as much as possible. Instead of booking several activities separately, you can knock out nearly every major Key West water adventure in one full day.
It is especially great for families, groups, teenagers, and anyone who wants a full day of nonstop fun. You will sleep well that night. I promise you that.
Backcountry Sandbar Adventure
Island Adventure
Go Farther West Than the Rest
The Island Adventure travels approximately 12 miles west of Key West to the beautiful backcountry near Woman Key. The trip includes time at a remote sandbar, a guided kayak tour through the mangroves, standup paddleboards, Sunchill floating loungers, and plenty of time to enjoy the clear, shallow water.
A picnic lunch, soft drinks, water, beer, wine, champagne, and High Noon hard seltzers are also included.
Shawn's Take
This is one of my favorite ways to show visitors the natural side of the Florida Keys. You get away from the crowds and see an area most people visiting Key West never experience.
You can kayak through the mangroves, try a paddleboard, or spend your time floating on a Sunchill with a cold drink. There is no wrong way to enjoy this trip.
I recommend it for couples, families, groups, and anyone who wants a more relaxed day on the water without sacrificing the activities.
Sunset Cruise
Commotion on the Ocean
Key West's Live Music Sunset Cruise
Commotion on the Ocean is the only sunset cruise in Key West with a full three-piece live band performing onboard.
Guests can enjoy live music, appetizers, beer, wine, champagne, margaritas, and mixed drinks while sailing into the Gulf of Mexico for a Key West sunset.
It is part sunset cruise, part live concert, and one of the most entertaining ways to finish a day in Key West.
Shawn's Take
Key West has plenty of sunset cruises, but this one has an energy all its own. The full live band makes a huge difference.
It is lively and fun without feeling like a wild party boat. I recommend it for couples, groups of friends, birthdays, celebrations, and anyone who wants more than a quiet ride around the harbor.
You get the Key West sunset, live music, food, drinks, and a great atmosphere all in one trip.
Water Adventures
Spencer's Boatyard
Rent Your Own Boat in Key West
Want to be your own captain for the day? Spencer's Boatyard gives you the option to rent your own boat and experience the waters around Key West at your own pace. It's a great option for visitors who would rather create their own day on the water instead of joining a scheduled tour.
Shawn's Take
I love the organized trips around Key West, but sometimes you just want your own boat and your own schedule. If you're comfortable operating a boat and want the freedom to explore Key West's waters on your own, Spencer's Boatyard gives you that option.
Take your time, enjoy the water, and make the day your own.
Land Adventures
Explore the Island
Key West Golf Cart Rentals
Explore Key West at Your Own Pace
A golf cart is one of the easiest and most enjoyable ways to explore Key West. Use it to visit Old Town, the Historic Seaport, the Southernmost Point, Fort Zachary Taylor, Smathers Beach, restaurants, shops, and attractions across the island.
Rental sizes and availability may vary depending on the date and the number of guests.
Shawn's Take
Key West may only be a few miles wide, but the attractions, beaches, restaurants, and historic sites are spread all over the island.
A golf cart gives you the freedom to explore on your own schedule, carry your beach bags and souvenirs, and enjoy the island breeze instead of spending your vacation walking in the heat.
I especially recommend one for families, groups, guests staying outside Old Town, and anyone who wants to see more of the island without wearing out their flip-flops.
Historic Tours of America
Explore the History of Key West
There is a lot more to Key West than beaches and sunsets. Historic Tours of America offers some of the best ways to explore the island's history, architecture, characters, and stories. Whether you want to ride through Old Town, visit one of Key West's iconic museums, or learn more about the people who shaped the island, these are experiences I'm happy to recommend.
Old Town Trolley Tours
One of the easiest and most enjoyable ways to see a lot of Key West while learning the stories behind the island. Ride through Old Town with live narration, get your bearings, and discover places you may want to come back and explore later.
Opens all available Historic Tours of America Key West experiences.
Conch Tour Train
A true Key West classic. The Conch Tour Train has been showing visitors around the island for generations and is a fun way to hear the history, see the landmarks, and experience Old Town without walking the entire route.
Opens all available Historic Tours of America Key West experiences.
Harry S. Truman Little White House
Step inside one of Key West's most important historic homes. President Harry S. Truman spent significant time here during his presidency, and the property offers a fascinating look at both presidential history and Key West's past.
Opens all available Historic Tours of America Key West experiences.
Key West Aquarium
One of Key West's longest-running attractions and a great stop for families. Learn about the marine life found around the Florida Keys and get a closer look at some of the animals that call these waters home.
Opens all available Historic Tours of America Key West experiences.
Key West Shipwreck Treasure Museum
Discover the days when shipwreck salvaging helped make Key West one of the wealthiest cities in America. This museum combines artifacts, storytelling, and incredible views from the observation tower.
Opens all available Historic Tours of America Key West experiences.
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