Things to do in Key West
Key West Snorkeling Tour21 optionsFishing Tour Key West7 optionsBoat Tour Key West39 optionsKey West Kayaking Tour13 optionsCatamaran Cruises10 optionsSunset Cruises16 optionsEco Tour Key West9 optionsFood Tour Key West12 optionsKey West Airport Shuttle5 optionsKey West Walking Tour14 optionsDolphin Watching Tour Key West9 options
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Key West: Jimmy Buffett Walking Tour & Key Lime PieYou walk 90 minutes through Old Key West with a local guide, stopping at the bars, studios, and restaurants where Jimmy Buffett played and ate over five decades. You get key lime pie, a drink, and the actual geography of how his songs came to life. No driving, no waiting—just walking and listening, and you end the afternoon at a real saloon instead of a tour office.Is it for me?Pick this if you want to understand Key West through the one person whose music defined it, without arranging your own route or timing—the guide does the navigation and the storytelling, and the pie and drink are already paid for.
Key West Old Town: Food Tour with 5 Tastings & Cuban CuisineYou walk through Key West's Old Town with a local guide, stopping for five tastings that move from iced coffee and conch fritters through Cuban specialties to Key lime pie and a surprise final dish. The guide shares the island's real history—maritime, cultural, human—while you eat your way through the neighborhood. Plan for two to three hours of walking in comfortable shoes, and contact ahead if you have dietary restrictions.Is it for me?Book this if you want to taste Key West's real food culture without planning five separate stops yourself—the guide knows where to go and the restaurants expect you, which means no hunting for lunch and no guessing whether a place is worth the wait.
Key West: Sunset Sail Cruise on Schooner Jolly II RoverYou’ll join a small group aboard Key West’s famous schooner for a true sunset sail cruise—helping raise sails, steering if you want, firing real cannons (seriously!), and gliding past mansions and historic forts with snacks and water included. The sea breeze and those changing colors will probably stay with you longer than you expect.
Key West Schooner Sunset Sail & Open BarYou board at Key West Historic Seaport and spend two hours sailing into the Gulf on a traditional schooner. The full open bar runs the whole time — cocktails, wine, beer, and champagne included for adults. You watch the sunset from the deck with no stops or detours, just the boat, the water, and the sky changing color. The guide is English-speaking, and kids and non-drinkers are welcome too.Is it for me?Book this if you want to see a Key West sunset without arranging your own boat or worrying about drink prices — the schooner and the bar are both included, which means you show up at the seaport and the rest is handled.
Key West: Bahama Village & Hemingway Walking TourYou’ll wander Key West’s Bahama Village with a local guide who knows every story behind those pastel streets. Step inside Hemingway’s house (watch for cats), climb the old lighthouse for wild island views, and pause outside legendary bars where music spills onto the sidewalk. It’s not just facts—it’s laughter, salt air, and small surprises that linger long after your walk ends.
Key West: Sailing & Snorkeling Tour with Craft DrinksYou’ll sail from Key West on a small-group yacht toward North America’s only living coral reef, guided by locals who know every current and color change. Expect instruction if you need it, time to snorkel among bright fish (and maybe turtles), plus drinks like craft beer or margaritas after your swim. It’s relaxed but vivid—the kind of trip you’ll remember when you catch yourself daydreaming weeks later.
Key West Parasailing: 8-15 Min Flight & Seaport ViewsYou'll spend 8 to 15 minutes airborne over the Key West Seaport, with up to an hour total on a licensed, insured parasail boat. The crew handles all the gear and timing; you just fly and look. Optional toe-dip in the water and photo packages are available on the boat.Is it for me?Best for anyone who wants to see Key West from above without arranging their own boat or worrying about safety details—the licensed crew and 36 years of local experience mean you just show up and fly.
Florida Keys: Marathon Sunset Cruise & Seven Mile BridgeYou’ll watch the sky shift over Seven Mile Bridge on this Marathon sunset cruise, sipping champagne as you glide through Boot Key Harbor with music playing softly. Expect local stories from your guide, snacks along the way, and time to just soak up those Florida Keys colors before heading back.
Key West: Speedboat Snorkel & Mud Keys Sandbar TourYou captain your own speedboat through the Florida Keys National Marine Sanctuary, spotting dolphins, manatees, and ospreys along the way, then snorkel at Mud Key Sandbar in shallow, clear water. Small groups (max two adults per boat) mean no crowds, and the guide leads but doesn't control your route. Arrive one hour early with a passed boaters safety certificate—Florida law requires it if you were born after January 1, 1988.Is it for me?Right for travelers who want to steer their own boat and avoid the crowds of standard snorkel tours—the small group size and hands-on driving experience are what make the backcountry feel like your own discovery instead of a scheduled stop.
Key West: Night Kayak Tour Luminous Lagoon with LED KayaksYou’ll paddle through Key West’s luminous lagoon in a clear LED-lit kayak with a local guide leading you deep into mangrove tunnels after dark. Watch marine life glow beneath your feet, listen to nighttime sounds, and catch those rare silent moments on the water—an evening that lingers long after you’re back on shore.
Key West: Afternoon Dolphin Sail on 60' CatamaranYou board a 60-foot catamaran at Key West's Historic Seaport and spend an afternoon watching wild Atlantic bottlenose dolphins in their natural habitat. Small groups mean you're not elbowing for space at the rail. Beer, wine, and soft drinks are included. The boat handles the sailing while you watch for pods jumping and playing in the shallow water — no early start, no rushing, just time on the water with a real chance to see dolphins doing what they do.Is it for me?A good fit if you want to watch wild dolphins without the early start or the crowds — the small-group format and afternoon timing are what make both possible. Plan for a couple of hours on the water, which is exactly what lets you relax instead of rushing between stops.
Key West: Schooner America 2.0 Sailing Tour & 2 DrinksYou board the America 2.0 at the ticket booth after a 30-minute check-in, then spend 1.5 hours sailing past Fort Zachary Taylor, Sunset Pier, and Sand Key Light Tower with two included drinks in hand. The captain works the coast close enough to see the sights clearly but far enough out to feel like you're actually on the water. Kids sail free on afternoon departures, and the boat operates in all weather unless unsafe.Is it for me?This works well if you want to see Key West's waterfront landmarks without arranging your own boat or timing a sunset perfectly — the fixed 1.5-hour route covers the main sights, and the two included drinks let you settle in instead of managing a tab.
Key West: Reef Snorkel & Sunset Cruise with Beer & WineYou board the Miss Valyn in late afternoon, snorkel at two Key West reefs with all equipment provided, then cruise back into the sunset with unlimited beer, wine, and champagne. The trip takes three hours total and suits all swimming levels—if you skip the water, the bar keeps you occupied. Check in 30 minutes early and plan to be back before evening.Is it for me?Pick this if you want snorkeling and a sunset view in one afternoon without hunting for two separate activities—the boat does both, and the drinks keep the second half relaxed.
Key West: Kayak, Snorkel & Morning Sail Eco TourYou’ll start your day sailing from Key West’s Historic Seaport on a roomy catamaran, kayak through quiet mangrove islands with a local guide, then snorkel clear waters over Sand Key Reef. Fresh organic snacks are served onboard. Expect laughter, salty breezes, and moments you’ll keep replaying long after you’ve rinsed off the salt.
Key West: Double Dip Snorkel Tour with Two Reef StopsYou’ll jump straight into Key West’s living coral reef at two different spots—no waiting around—with all your gear sorted by friendly guides. There’s time to relax with drinks after swimming among curious fish and textured corals. It’s easygoing even if things don’t go perfectly—and those underwater colors will stick with you long after you dry off.
Key West Morning Snorkel Sail & Gourmet BreakfastYou board a catamaran in Key West, sail to a reef selected that morning based on conditions, snorkel among coral and tropical fish with provided gear, then return to the boat for gourmet croissants and unlimited mimosas while watching for dolphins on the way back. The whole experience takes roughly four to five hours, and you don't arrange transport, equipment or timing yourself.Is it for me?Book this if you want to snorkel the Keys reef without renting a boat or figuring out where to go—the crew picks the spot that morning, which is what makes the difference between a crowded tourist reef and one where you actually see fish.
Key West: Mini Catamaran Eco Tour & Mangrove IslandsYou pilot your own two-person CraigCat through Key West's mangrove channels, pristine sandbars, and secluded backcountry islands with a local guide leading up to four boats. The tour includes life jackets, a cooler, and wildlife spotting opportunities — dolphins, manatees, herons, and sea turtles depending on season. Small group size and your control of the boat mean you explore at your own pace instead of following a schedule.Is it for me?Book this if you want to explore Key West's backcountry on your own terms rather than as a passenger on a crowded boat — steering your own CraigCat through shallow mangrove channels and hidden islands is what makes the difference between watching nature and moving through it.
Key West Sandbar Safari Tiki Boat: Beach Games FunA 3.5-hour sandbar cruise from Key West Historic Seaport aboard the Lazy Lady tiki boat, with a live English-speaking guide, soda, beer and wine included. You anchor at a secluded sandbar in shallow waters where you wade, swim, collect shells and play beach games with floaties and watermats provided. Infants sit on an adult's lap; the tour suits all fitness levels.Is it for me?If you land in Key West with a free afternoon and want to be in the water without renting a car or booking a guided tour of the town, a tiki boat to a sandbar gives you the shallow water and the games without the planning—the boat, the guide, the drinks and the gear all show up so you just wade in.
Key West Sunset Cruise: BYOB Tiki Bar Boat for Up to 6A 2-hour sunset cruise on a custom tiki bar boat in Key West harbor for up to 6 guests, where you bring your own alcohol and snacks while a USCG-certified captain points out landmarks, wildlife and the famous sunset. The boat departs 75 minutes before sunset and includes ice, cups, a blender, a walk-in bathroom and a live edge tiki bar under a thatch roof.Is it for me?Small groups and couples looking to celebrate the Key West sunset without the crowds on shore — the boat holds up to 6, so it stays intimate, and you control the drinks and the music.
Key West Ghost Hunting Tour: Fort East Martello & Robert DollVIP Robert the Doll After Dark is a two-hour ghost-hunting tour in Key West's Fort East Martello Museum, where you spend the first hour guided through the haunted Civil War fort and meet the infamous Robert the Doll, then hunt ghosts solo for an hour with K-2 meters, spirit boxes, dowsing rods and trigger objects in the after-hours Yellow Fever hospital wing. The tour is led by a live English-speaking guide and takes place in low-light conditions; visibly intoxicated guests are not admitted.Is it for me?Walk the dark halls of Fort East Martello with authentic ghost-hunting equipment and meet Robert, Key West's infamous haunted doll—the only ghost tour on the island where you actively engage spirits instead of just observing.
