The best things to do in Key West fit on an island you can bike across in 20 minutes, which is the whole charm. We work on the water here, and the same question comes up every week at the dock: with three or four days, what should we actually do?
This is our answer, with the honest notes we give friends who visit.
How this list works
We ranked these by what visitors rave about when they step off the boat, out of the bar, or off the bike. Then we grouped them by where they start, because in Key West “where” mostly means which end of Old Town you walk to. If you are still choosing where to stay, our guide to Key West’s neighborhoods will help. Within each section, the items near the top are the ones we would book first.
On the water (the reason you came)
Key West has two oceans. The Atlantic side has the reef, six miles south. The Gulf side has the backcountry, the sandbars and the dolphins. The best trips below use one or the other, and a few use both.
1. Parasailing over the harbor
Parasailing in Key West takes you up to 300 feet over the turquoise water with the whole island laid out beneath you, Old Town on one side and the reef line on the other. Takeoff and landing are from the boat deck, so nobody gets dragged through the water, and the whole trip is about an hour from the Historic Seaport. Flights start at $60 for the early-bird 9 am slot, and the morning wind is lightest. Kids from age 5 can fly with a parent.
2. Snorkeling the reef
The Florida Keys reef tract is the only living coral barrier reef in the continental United States, and the reef snorkel trip is the easiest way to see it. You sail out on a catamaran, spend an hour in the water over 15-foot coral heads with sergeant majors, parrotfish and the occasional nurse shark, and sail back with the bar open. Morning trips have the calmest water and the best visibility; the afternoon version has a bigger bar.
3. A sunset sail on a schooner
Mallory Square is where the crowd watches the sunset. The schooners are where you want to be. The Wind & Wine sunset sail puts you on a wooden schooner with eight wines, craft beer and a charcuterie spread for two hours while the sun goes down over the backcountry. It is adults-only (13 and up), it sells out in winter, and it is the single most-recommended thing on this list.
4. Dolphin watching and snorkeling with a biologist
The dolphin watch and snorkel tour heads north into the Key West National Wildlife Refuge on a small catamaran to find the resident bottlenose pods, then stops for a guided snorkel over the seagrass and sponge gardens. Groups are capped at 16, the guides are naturalists, and the operator has held the top dolphin-tour rating in Key West for years.
5. The jet ski island tour
A guided jet ski tour around Key West is 28 miles and 90 minutes, and it is the fastest way to see the entire island: the Southernmost Point from the water, the Navy base, the backcountry flats, and the harbor. You need a photo ID and, if you were born after 1987, a quick online Florida boater safety card. Each ski carries up to two riders for one price.
6. A sandbar day with the dolphins
The sandbar and dolphin trip is the local way to spend a day: a catamaran out to a waist-deep sandbar in the backcountry with floats, paddleboards and an open bar, lunch on board, then a run out to the dolphin grounds on the way home. It leaves at 11 am and gets back around 4, which lines up nicely with sunset.
7. Sail, snorkel and kayak in the backcountry
The sail, snorkel and kayak excursion is the quiet alternative to the big party boats. A schooner takes 20 or fewer people into the wildlife refuge, where you paddle through mangrove tunnels, snorkel the flats, and sail back. It is the trip we send people on who want nature instead of a bar.
8. Fort Zachary Taylor beach and shore snorkel
The best beach in Key West is inside a state park at the west end of Old Town. The water is deeper and clearer than Smathers, there is shade under the Australian pines, and the rocks off the beach have the best shore snorkeling on the island. Entry is a few dollars per person, and sunset from the point is a quieter version of Mallory Square.
9. Dry Tortugas National Park
Seventy miles west of Key West, Fort Jefferson sits on a coral island with the clearest water in Florida. The national park ferry takes about two and a half hours each way and sells out weeks ahead; the seaplane takes 40 minutes and costs several times more. Either way it is a full day and the best single day trip in the Keys. Book before you leave home.
10. Fishing: flats, reef or offshore
Key West is one of the great sportfishing towns in the world. Flats guides pole the backcountry for tarpon, permit and bonefish; reef and wreck trips fill the cooler with snapper and grouper; offshore boats run for mahi, sailfish and tuna. Charters leave from the Seaport and Stock Island. Book a half day if you have never fished before.
Old Town and Duval Street
11. Mallory Square Sunset Celebration
Every evening, two hours before sunset, Mallory Square fills with jugglers, cat acts, conch fritter stands and a crowd that applauds when the sun hits the water. It is touristy and it is also genuinely fun. Go once, then watch the next sunset from a schooner.
12. The Hemingway Home and its cats
The house on Whitehead Street where Hemingway wrote most of his best work, with the six-toed cats still in residence. The guided tour is short and good. Go early before the cruise-ship crowds.
13. Duval Street, done right
Duval runs a mile from the Gulf to the Atlantic. The north end is the bars (Sloppy Joe’s, the Green Parrot a block over, the Bull and Whistle). The south end is quieter, with galleries and the Butterfly Conservatory. The Duval Crawl is a rite of passage; the locals’ version starts late and ends at the Green Parrot.
14. The Southernmost Point buoy
The painted concrete buoy at Whitehead and South is 90 miles from Cuba and has a line for photos all day. Go at 7 am for no line and good light, then walk to the Southernmost Beach Cafe for breakfast on the sand.
15. Key West Lighthouse and the Custom House
Climb the 88 steps of the 1848 lighthouse for the best view over Old Town’s tin roofs, then walk down to the Custom House museum near Mallory Square for the island’s history, from wrecking fortunes to the Navy to Jimmy Buffett.
16. Bike the island
Key West is flat, small and mostly 25 mph. Rent a cruiser for a day, ride the Atlantic side along South Roosevelt to Smathers, loop back through the Casa Marina neighborhood, and you have seen more of the island than most visitors ever do.
17. The Key West Cemetery
Nineteen acres of above-ground tombs in the middle of Old Town, with famous epitaphs (“I told you I was sick”), roosters and iguanas. Free, self-guided, and best in the morning before it gets hot.
18. Conch fritters, key lime pie and a Cuban mix
The food is a thing to do. Order conch fritters at the Seaport, a Cuban mix sandwich from a window on White Street, and key lime pie from at least two places so you can argue about which is better. Stock Island fish houses do the freshest hogfish.
Day trips and a little further afield
19. Bahia Honda State Park
Forty minutes up the Overseas Highway, Bahia Honda has the best natural beaches in the Keys and the old railroad bridge for photos. Pair it with a stop at the Blue Hole on Big Pine Key to see Key deer.
20. Kayak or paddleboard the mangroves
If the guided trips are booked, rent a kayak at the Seaport or on Stock Island and paddle the mangrove channels on your own. Mornings are calm; afternoons get a breeze from the southeast.
21. Scuba diving the Vandenberg
The 524-foot USNS Vandenberg was sunk in 2009 as an artificial reef, seven miles off Key West in 140 feet of water. For certified divers it is the signature dive in the Keys. Dive shops run it daily from Stock Island and the Seaport.
22. Sunset at Fort Zach or the Edge of the World
Two quieter sunset spots: the point at Fort Zachary Taylor, and the rooftop bars along the Seaport. Both beat the Mallory Square crowd once you have done it once.
23. Key West Aquarium and Eco-Discovery Center
The small aquarium at Mallory Square is good for kids, with a shark feeding and touch tanks. The free Florida Keys Eco-Discovery Center near Fort Zach explains the reef and the backcountry better than any brochure.
24. Fantasy Fest, Hemingway Days and the rest of the calendar
Key West runs on festivals: Fantasy Fest in late October, Hemingway Days in July, the Conch Republic celebration in April, the powerboat races in November. Hotels double in price and the tours sell out. Check the calendar before you book, both to join in and to avoid.
25. Do nothing at the pool
Key West is a place to slow down. One day with no plan, a pool, a book and a 4 pm walk to the Seaport for a drink is a day well spent. The tours will still be there tomorrow.
A three-day plan that works
- Day one: Parasail or the reef snorkel in the morning from the Seaport, lunch on the Harbor Walk, Hemingway House in the afternoon, Mallory Square at sunset.
- Day two: Sandbar and dolphin day from 11 to 4, then straight onto the Wind & Wine sunset sail from Opal Key, dinner late on Duval.
- Day three: Jet ski tour at 9:30, Fort Zach beach for the afternoon, Southernmost Point at golden hour, key lime pie.
For how the months differ, read the best time to visit Key West. For prices, restrictions and booking for every trip above, see the full list of top-rated Key West adventures.
Written by Key West locals who spend their days on the water. How we make money.
