Florida · Guided Tours
Key West Tours & Things to Do — 2026
Island sunsets and laid-back tropical charm at America's southernmost point
Photo: Frank Eiffert / Unsplash
Expert-Curated Selection · Only the Highest-Rated Experiences · By the Award-Winning USA Guided Tours Team
Key West Ghost & Haunted Tours
Key West is an old wreckers' and sailors' town at the end of the road, and after dark it leans all the way into its ghost stories — the island is regularly ranked among the most haunted places in the country. The tours work the historic core: the lantern-lit lanes off Duval, the 19th-century houses and their sea-captain histories, the old cemetery, and the island's most famous resident, Robert the Doll, the reputedly cursed sailor's doll now kept at the Fort East Martello museum. Most are small-group walking tours, with narrated ghost-trolley versions that cover more ground. The guide makes the tour, so read recent reviews before you book, and note these run year-round and book up around Halloween and Fantasy Fest.
Key West Snorkeling & Reef Tours
Key West sits beside the only living coral barrier reef in the continental United States, six or seven miles offshore, and snorkeling it is the signature thing to do here. Catamaran and boat trips run out to the reef and the shallows around it, where the warm, clear water and the coral make for some of the easiest, most rewarding snorkeling in the country — good for first-timers and strong swimmers alike. Half-day reef trips are the standard, and many pair the snorkel with a sail or add gear, drinks, and a second stop. Bring reef-safe sunscreen; morning trips usually have the calmest water and the best visibility.
Key West: Reef Snorkeling with Drinks and Sunset Option
4.4 · 535+ GetYourGuide reviews
From $34.95Book on GetYourGuide →
Curated August 2026
Photo: KaroGraphix Photography / Unsplash
Key West Glass-Bottom, Dolphin & Sandbar Tours
For the reef and the wildlife without getting in the water — or for a half-day on the flats — this is the family cluster, and it holds the easiest wins in Key West. Glass-bottom boat tours run out to the reef with the coral and the fish framed under your feet, the dry way to see what the snorkelers do. Dolphin-watch trips head into the backcountry and the Gulf side to find the island's resident wild dolphins, often pairing the watch with a snorkel stop on the way back. And sandbar trips anchor on the shallow, waist-deep flats off the island for a few hours of swimming and wading in impossibly clear water. Jet-ski and parasailing round out the watersports for the more active. Most run morning and afternoon; the calmer morning water is best for the glass-bottom and dolphin trips.
Key West Sunset Sails & Boat Cruises
The Key West sunset is an institution — Mallory Square throws a nightly party for it — and the best seat in the house is on the water. Sunset sails leave the harbor in the late afternoon and work the Gulf side as the sky goes, from quiet schooner sails with wine and hors d'oeuvres to livelier catamaran and tiki-boat cruises with a bar and music. Daytime sightseeing cruises circle the island and the harbor if you'd rather see it in the sun. These book up fast in high season and around Fantasy Fest, so reserve the sunset departures ahead — and aim to board 30 minutes before the posted sailing time.
Key West Kayak & Eco Tours
The quieter side of the water is in the backcountry — the mangrove creeks and shallow flats north of the island that make up the edge of the Florida Keys wilderness. Guided kayak and eco tours paddle the mangrove tunnels and grass flats, where the guide points out the wading birds, rays, sea turtles, the occasional manatee, and the nursery of marine life the mangroves shelter. Some launch from the island; others run as a boat-plus-kayak combo that carries you out to the backcountry first. These are calm, small-group, and naturalist-led — the antidote to the party boats — and they're best in the morning when the water is glassy and the wildlife is up.
Key West Trolley, Train & Sightseeing Tours
Old Town Key West is compact, but the narrated loop tours are the fast way to get the lay of the island and the history behind it — the wrecking and cigar-making days, the writers and presidents, the Conch Republic. Hop-on-hop-off trolleys and the open-air tour trains run a continuous circuit of the landmarks, from the Southernmost Point and the Hemingway house to Mallory Square and the harbor, so you can ride the full narrated loop or hop off at what catches your eye. It's the practical first move for a day-tripper or a first-timer, and an easy way to cover the island before settling in on foot. Tickets are usually good all day.
Key West Food & Drink Tours
Key West's food is its own thing — conch fritters, fresh pink shrimp and hogfish, Cuban mix sandwiches and strong Cuban coffee, and a slice of key lime pie that the island claims as its birthplace. A guided food tour is the fastest way through it, walking Old Town to sample across a handful of kitchens with the history and the island characters filled in between stops. The drink side is a genuine draw too — this is Hemingway's town and a famous bar-crawl island, and guided historic-pub walks trace the watering holes and their stories. Tours run midday and early evening and are small-group, so book weekends ahead.
Key West Walking & Bike Tours
Old Town is flat, walkable, and made for a bike, and the self-powered tours are the way to get under the island's skin. Guided walking tours trace the historic district on foot — the gingerbread conch houses and sea-captains' mansions, the Truman Little White House, the cigar-era streets and the literary history — at the pace the town wants to be seen. Bike tours cover more of the island on the flat, quiet lanes, from the Southernmost Point to the beaches and the back streets the trolleys skip. Both are low-key, low-cost, and easy to book; go in the morning or late afternoon to beat the midday heat.
Things to Do in Key West
Beyond the guided tours, Key West packs the only living coral barrier reef in the continental US, a nightly sunset celebration, a walkable Old Town of conch houses and Hemingway history, a famous Duval Street bar scene, and one of the most haunted reputations in the country into one small island at the end of the road. Here is how to make the most of a trip — from the reef and the backcountry to Old Town, the food, and the ghosts.
The Reef & the Water
Key West's headline is the water — the only living coral barrier reef in the continental US, a few miles offshore, best seen on a half-day snorkel or catamaran trip, or dry on a glass-bottom boat. Beyond the reef, dolphin-watch and sandbar trips work the backcountry flats, kayak and eco tours paddle the mangroves, and the nightly sunset sail is a Key West institution. Farther out, the Dry Tortugas and Fort Jefferson make a full-day trip by the Yankee Freedom ferry or seaplane, booked directly with the operator.
Old Town, Duval & Hemingway
The compact historic district is the other half of Key West — Duval Street, the gingerbread conch houses, the Southernmost Point, and the Ernest Hemingway Home with its six-toed cats (a self-ticketed attraction you book at the door). A narrated trolley or tour-train loop is the quick way to orient; a walking or bike tour is the way to slow down. Cap it with a food tour through the conch fritters, Cuban coffee, and key lime pie.
Ghosts & After Dark
Key West is one of the most haunted towns in the country, and the after-dark walking and trolley tours have real material — the sea-captains' houses, the old cemetery, and Robert the Doll, the reputedly cursed doll kept at the Fort East Martello museum. Duval Street is the other nightlife, a famous bar-crawl strip, and the historic-pub walks trace Hemingway's watering holes and their stories.
Trolley, walk, or pub crawl? Which Key West ghost tour is worth it →
Best Time to Visit
Winter and spring (December–April) are peak — warm, dry, and the calmest, clearest water for the reef, but the busiest and priciest. Late spring and early summer are quieter with good water before the summer heat and afternoon storms. Fall is hurricane season and the quietest, though October's Fantasy Fest fills the island. Ghost tours run year-round; reef and sunset trips are best on the calmer mornings and clear evenings, and high-season departures book up ahead.
Key West Travel Guides
- Weighing your options in Key West? The Best Ghost Tour in Key West: Which One Is Actually Worth It
Frequently Asked Questions
What's the best tour to do in Key West?
For most visitors it's a reef snorkeling trip — Key West sits beside the only living coral barrier reef in the continental US, and a half-day catamaran or boat trip out to it is the signature experience. Close behind is a sunset sail, a Key West institution best seen from the water, and an after-dark ghost tour of Old Town, since the island is one of the most haunted in the country. If you'd rather stay dry, a glass-bottom boat shows you the reef from above, and a trolley or tour-train loop is the easy way to see the whole island in a few hours.
How do I see the coral reef in Key West?
Two main ways. To get in the water, a half-day snorkeling trip runs out to the reef six or seven miles offshore, where the warm, clear, shallow water makes it easy for first-timers and strong swimmers alike; many trips pair the snorkel with a sail or add gear and drinks. To stay dry, a glass-bottom boat runs the same reef with the coral and fish framed under your feet. Morning trips usually have the calmest water and best visibility, and reef-safe sunscreen is the rule out there.
What are Key West ghost tours like?
They're small-group and story-driven, working the historic core after dark on foot or by narrated trolley — the lantern-lit lanes off Duval, the 19th-century sea-captains' houses, the old cemetery, and the island's famous Robert the Doll, the reputedly cursed sailor's doll now kept at the Fort East Martello museum. Key West has a genuine haunted reputation, so there's real island history under the stories. Because the guide makes the tour, read recent reviews before booking; they run year-round and are busiest around Halloween and Fantasy Fest.
How do I get around Old Town Key West?
Old Town is compact and flat, so you have easy options. A hop-on-hop-off trolley or an open-air tour-train loop narrates the island's history and links the landmarks — the Southernmost Point, the Hemingway home, Mallory Square — and the ticket is usually good all day. To go at your own pace, Old Town is one of the most walkable and bike-friendly towns anywhere, and a guided walking or bike tour gets you into the conch houses and back streets the loops skip.
Can I visit the Dry Tortugas or the Hemingway Home?
Both, but you book them directly. The Dry Tortugas and Fort Jefferson are a full-day trip about 70 miles west, reached by the official Yankee Freedom ferry or by seaplane — reserve with the operator well ahead, as space is limited. The Ernest Hemingway Home is a self-ticketed attraction in Old Town that you pay for at the door; a walking or trolley tour will take you past it and supply the history, but the house admission is its own. We don't resell either — they're operator-direct.
Curated by Darko Marsalek · Updated
Booking links may be affiliate links; we may earn a commission at no cost to you.