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
Sort
Marathon FL: Sandbar Cruise & Water Sports with DrinksYou’ll step onto a boat in Marathon FL and let go of schedules for four hours—swimming at the sandbar, trying paddleboards or kayaks if you want, snacking as you float under the sun. Friendly crew keeps things easy with drinks and laughs. It’s relaxed fun—the kind where you remember how saltwater feels on your skin long after you’re home.
Key West: Smathers Beach Parasailing with State-of-the-Art BoatsYou’ll meet a laid-back local crew at Smathers Beach in Key West before soaring high above turquoise water on a parasailing ride. Feel the rush of wind and silence as you float overhead, maybe dipping your toes in the ocean if you ask. All gear is included, plus options for photos or bringing your own camera—memories that might stick with you longer than you expect.
Key West Historic Schooner Sunset Cruise: Champagne ToastThe When And If is a historic wooden schooner commissioned by General George Patton in 1939, sailing out of Key West Historic Seaport for a two-hour evening cruise through the Florida Keys National Marine Sanctuary. You board 15 minutes before departure at E dock in front of the Waterfront Brewery, then sail past Mallory Square and the offshore estates while watching for dolphins, sea turtles and marine birds. Champagne and a sunset toast are included, and you can take the wheel and help raise the sails under the captain's guidance if you want to.Is it for me?The crew handles all the sailing if you want to watch and toast—but if you've ever wanted to actually steer a wooden schooner at sunset, this is the boat and the moment to do it.
Key West sandbar boat tour: Private tiki bar cruiseA private boat tour from Key West for up to 6 passengers that takes you to a backcountry sandbar chosen by your USCG-certified captain based on conditions that day. The boat includes ice, cups, a blender and a Bluetooth soundbar; you bring your own drinks and snacks. The 4-hour cruise runs daily from noon to 4 pm and passes through the Great Heron National Wildlife Refuge, where you might see dolphins, turtles, rays, egrets and herons before anchoring at the sandbar to swim and snorkel.Is it for me?Your captain picks the sandbar based on weather and tides, so you're never stuck in one spot—and you control the music, drinks, and pace with your group.
Key West: Small-Group Walking Tour to Southernmost PointYou’ll wander Key West’s lively streets with a local guide, starting at Kino Sandals and ending at the famous Southernmost Point marker. Along the way you’ll hear wild shipwreck tales, peek at Hemingway’s cats, and catch those little details—like coconut oil or distant gulls—that make this island feel alive beneath your feet.
Key West Kayak Rental: Mangrove Tunnels & Marine WildlifeYou get a 2-hour self-guided paddle through Key West's mangrove creeks and shallow sea grass beds, with all equipment, a map and a pre-paddle lesson included. The operator briefs you on the best wildlife-spotting routes before you launch, then you explore on your own at your own pace, looking for fish, rays, sharks and manatees in water clear enough to see the bottom. Everything you need is provided — kayak, paddle, life vest — and the rental includes access to onsite facilities like restrooms and a restaurant for before or after.Is it for me?This works well if you want to explore on your own schedule without a guide's pace or fixed stops — the 2-hour window and self-guided format mean you can linger over wildlife or cover more distance depending on what interests you, and the calm shallow water keeps the paddling manageable for most swimmers.
Key West Dolphin & Snorkeling Tour: Small Group, 95% SightingsYou board a 25-foot boat with a maximum of five other people and a USCG-licensed captain who has worked these waters for two decades. The tour includes snorkeling equipment, a visit to sandbars where you can wade in turquoise water, and a 95% track record of dolphin sightings. You get fresh water showers, onboard refreshments, and free parking at the marina — all the logistics handled so you just show up and get in the water.Is it for me?Book this if you want to see dolphins without the crowds and logistics of a larger tour — the six-person limit and the captains' two decades of local knowledge are what make the 95% sighting rate and the sandbar stops possible in a single morning or afternoon.
Florida Keys: Bahia Honda, Key Deer & 7-Mile Bridge Day TripYou’ll ride across legendary bridges with salty air in your hair, walk beaches at Bahia Honda where two oceans meet, spot wild Key Deer up close on Big Pine Key, and maybe catch an alligator’s eye at Blue Hole—all with a local guide who brings stories to life. Expect moments you’ll want to tell friends about later.
Key West Deep Sea Fishing: Marlin & Offshore CharterYou spend a full day offshore with Captain Russ McKinley, a 30-year veteran, on a 50-foot fishing boat rigged with live bait, a fighting chair, and navigational electronics. The boat holds up to six anglers and runs 18 miles out for Marlin, Sailfish, Tuna, Mahi Mahi, and reef fish. Bottled water is included, and the boat has restrooms, a kitchen, and AC for comfort between bites.Is it for me?Right for anglers who want a real offshore boat and an experienced captain, not a crowded party charter. Plan for a full day on the water—that's what gets you 18 miles out where the Marlin run.
Key West Schooner Sail & Full Bar: 2-Hour Tall ShipYou board at the Key West Historic Seaport, help the crew raise the sails on a traditional tall ship, and take a turn steering. The two-hour sail includes a full open bar, water, and guidance from an English-speaking crew member. No stops, no transfers — just the boat, the water, and the thing you came for.Is it for me?Book this if you want to actually do something on the water rather than watch from a seat — the hands-on part is what makes the difference, and the bar means you can relax between turns at the wheel.
Key West: Hemingway Food & Walking Tour with Pie StopsYou’ll follow Hemingway’s real-life trail in Key West—see where he wrote, ate, fished, and drank—with a local guide who brings every stop alive. Taste bean salad with mango poppy dressing, enjoy lunch and that sharp-sweet key lime pie. Expect laughter, stories you won’t read in any guidebook, and moments that stick with you long after you leave.
Key West: Schooner Sail, Snorkel & Kayak BackcountryYou board at the historic seaport, sail out under canvas to the Wildlife Refuge, then split your time kayaking and snorkeling in shallow mangrove waters with a professional guide. Lunch, drinks, and equipment are included, and you're back by early afternoon. The climb back aboard uses a ladder, so you need moderate fitness and comfort with that step.Is it for me?Book this if you want to see the backcountry wildlife and mangrove islands without arranging your own boat or gear — the schooner, guides, lunch, and drinks are all handled, and the five-hour window fits a half-day without eating into the rest of your Key West time.
Key West Ghost Hunt: Haunted Locations & EquipmentYou arrive at a microbrewery, get trained on ghost hunting gear, then walk Old Town Key West with a local expert who knows the haunted history. The tour ends with exclusive access into a former Masonic temple where you use the equipment yourself. Nightly departures, ages 16 and up only.Is it for me?Book this if you want to actually use ghost hunting gear instead of just hearing about it, and you're comfortable walking Old Town Key West at night with a group that knows the local haunted history.
Key West Jet Ski Tour: 28-mile island ride with sandbar stopA guided jet ski tour around Key West covers 28 miles of coastline in 90 minutes, with stops at the Southernmost Point, Boca Chica Sandbar, and the Florida Keys Wildlife Sanctuary. The morning departure is the first trip out on the water and costs less than later tours. Jet skis, fuel, gear, and a second rider are included; drivers and riders can switch at stops so both get time at the helm.Is it for me?The early start—you're on the water before most visitors finish breakfast—is what keeps the price down and the water calm. If you want to ride jet skis without paying full rate and prefer a morning departure, this tour delivers both.
Florida Keys self-guided audio tour: Drive at your own paceA self-guided audio driving tour of the Florida Keys that plays commentary automatically based on your GPS location as you drive the Overseas Highway. Download the tour to your phone once and use it forever with no expiry date; you control the pace, choose which stops to visit, and can tour offline without cell service. Suggested itineraries cover half-day, full-day or multi-day routes, and one purchase works for everyone in the vehicle.Is it for me?Choose this if you're driving the Overseas Highway and want audio commentary that plays only at each stop—you control the pace, so you can linger at beaches or rush through viewpoints without a guide or group waiting.
Key West 2-Hour Jet Ski Island Tour: 28-Mile Full LapA two-hour guided jet ski tour around Key West on a Yamaha WaveRunner VX, covering a full 28-mile island lap with an experienced local guide who adjusts the route based on weather, tides, and marine traffic. The tour includes fuel, neoprene shorts, and safety equipment; riders follow the guide through backcountry channels, open water, and coastal stretches, with stops at the Southernmost Point, wildlife areas within the Florida Keys National Marine Sanctuary, and sandbars when conditions allow. First-time and experienced riders are welcome, and you can book a shared tour or a private group of up to six jet skis.Is it for me?Book a shared tour if you want to ride with other groups and keep the cost down, or choose a private group of up to six jet skis if you prefer to stay with people you know. The full two-hour lap gives you roughly 30 minutes more riding time than shorter tours, so pick this one if you want a complete island circuit instead of a partial route.
Key West: Tiki Cocktail Class & Rum Tasting on Duval StYou’ll shake up classic tiki cocktails right in Key West’s lively center, learn surprising bits of history from local bartenders, taste rich rums, and even try lighting your own drink on fire (don’t worry — they’ll help). Expect laughter, hands-on mixing, and flavors that stick with you long after you leave.
Key Largo to Key West Self-Guided Driving Tour: 7 Mile BridgeA self-guided audio driving tour covers 100 miles from Key Largo to Key West, with GPS-triggered audio stories, route maps and scenic stops included. Download the app before you go, and the tour works offline using your phone's GPS. One purchase covers everyone in your car; start anytime and pause for photos, hikes or meals whenever you want.Is it for me?Choose this tour if you want to explore the Keys on your own schedule without a guide or a group. The self-guided format and offline GPS mean you drive at your own pace, stop whenever something catches your eye, and don't depend on a tour bus or a set departure time — ideal for a first-time visit where you want flexibility, or a return trip where you already know what you want to see.
Key West: Private Inshore Fishing Charter & Sandbar EscapeYou’ll head out from Key West on a private fishing charter with everything ready—rods, reels, live bait, even bottled water. Try your luck at catching snappers or maybe spot sharks gliding by as your guide shares local tips. Pause at a sandbar for some sun and easy conversation before cruising back in salty air you won’t forget.
Key West Pedicab Tour: Old Town History with Private GuideA private pedicab tour of Key West's Old Town and Historic District where your guide drives while you sit on a spacious tiki bike and learn the island's history, culture and folklore. The tour passes four key sites—the cemetery with its ghost stories and first settlers, the historic seaport harbor, Ernest Hemingway's home, and the Mel Fisher Maritime Museum—over 2.5 hours. Your own private guide and driver means the pace and stops are yours to set, and bottled water is included.Is it for me?Book this if you want to cover Key West's main historic sites and stories without walking or joining a group—the private pedicab means your guide sets the pace around what you want to hear, and you stay comfortable and shaded the whole way.
