25 Best Things to Do in Key West
Key West packs more adventure per square mile than anywhere else in Florida. America's southernmost city blends Caribbean charm, water sports, legendary nightlife, and that famous laid-back attitude into one destination.
🍸 Key West Activities for Adults
Much of what Key West is known for is 21+ by design. These are the bookable options, sold by the seat. The Adults Only Sandbar Escape and Diva Royale drag show sit further down, under Food & Nightlife.
Pub crawls on foot (21+)
Comparing all six? See which Key West pub crawl to book — price basis, format, schedule, meeting point and age side by side.
Original Key West Pub Crawl — Key West Promotions
Five bars in two and a half hours, with a domestic beer or house cocktail included at each stop and a souvenir T-shirt at the end. A guide sets the route and the pace.
2.5 hours • Ages 21+, ticket required for everyone, no observer rate • 5 bars, 5 drinks included • Tue, Fri & Sat 8:00pm • Meets 424 Greene St, on foot
$39.95 per adult
Check Availability
Bone Island Haunted Pub Crawl & Ghost Tour — Key West Promotions
The cheapest way into a guided crawl here, and the one that doubles as a ghost tour — an atmospheric, storytelling-led walk between historic bars rather than a straight drinking route. Runs six nights a week, so it fits around a boat day.
2 hours • Ages 21+ • Mon–Sat 8:30pm • Old Town, on foot
$29.95 per adult
Check AvailabilityKey West Competitive Bar Crawl — Southernmost Scavenger Hunt
A scavenger-hunt format layered on top of the crawl, sponsored by Dulce Vida Tequila — teams work through challenges between bars. Afternoon and early-evening departures, which suits groups who do not want a late night.
2.5 hours • Ages 21+ • Team format • Departs 631 Greene St, on foot
$37.50 per person
Check Availability
28th Annual Lobsterfest Pub Crawl — Key West Promotions
A one-night annual event rather than a scheduled tour: up to twelve participating bars with two-for-one drink specials, a souvenir T-shirt and lanyard. It runs during Key West Lobsterfest each August, and only on that night.
One night only: Friday, August 7, 2026, 8:00pm • 4 hours • Ages 21+ • Duval Street, on foot
$25.00 per adult
Check AvailabilityIsland-hopping tiki bar crawl by van (21+)
Florida Keys Tiki Bar Crawl — Up The Keys
Not a Key West walking crawl — this one boards a custom van and island-hops to three tiki bars spread across the Lower Keys and Marathon, with happy-hour pricing at each stop. Budget the full four hours for the driving; the scenery between bars is part of it.
4 hours • Ages 21+ • By van, not on foot • Key West – Lower Keys – Marathon • Mon, Wed & Fri 2:00–6:00pm
$83.00 per adult
Check AvailabilitySunset cocktail cruises (adults only, by the seat)
Both run two hours on the same 47' catamaran and are sold by the seat rather than by the boat, so there is no charter minimum. The operator lists them as adults only. A non-alcoholic option is offered at $55 for anyone in the party who is not drinking.
Key West Cocktail Cruise, Craft Beer & Wine — Snuba of Key West
The beer-and-wine tier of the sunset cocktail cruise: all-inclusive South Florida craft beer and California wine for the two hours, with sound and lighting aboard. The cheapest per-seat way onto a drinks-included sunset boat here.
2 hours • Adults only • Craft beer & wine included • 47' catamaran • Sunset departure
$65.00 per person
Check Availability
Key West Cocktail Cruise, Craft Cocktails — Snuba of Key West
The same sunset sailing, with house specialty cocktails added to the beer and wine — three rotating craft cocktails each day, mixed from fresh ingredients rather than poured from a gun. Book this tier if the drinks are the point.
2 hours • Adults only • Craft cocktails, beer & wine included • 47' catamaran • Sunset departure
$80.00 per person
Check Availability🌊 Water Adventures
Crystal-clear water, colorful fish, sea turtles—the Florida Reef is unmissable and just minutes offshore.
Stand in waist-deep turquoise water miles from shore. Local captains know hidden sandbars where you'll feel like you discovered your own private island.
Blast through mangrove channels and open water. Most trips include sandbar stops and dolphin sightings.
Paddle through natural mangrove "tunnels" in the Key West Wildlife Refuge. Spot herons, rays, and baby sharks.
Chase mahi-mahi, sailfish, and tuna. Key West is one of the top sportfishing destinations in the world.
Soar 300-500 feet above Key West for bird's-eye views of the island, reefs, and endless blue water.
Captain your own vessel to sandbars, snorkel spots, and secret beaches. No license required for most rentals.
Rise & Reef Morning Snorkel — Sunset Watersports
The reef run in item 1, on the early departure — calmer water and better visibility before the day boats arrive.
3 hours • Morning departure • Reef snorkel • Gear included
From $45.95 per adult
Check Availability
JetSki Tour (Departs From Key West) — Sunset Watersports
The backcountry jet ski run in item 3 — mangrove channels, open water and a sandbar stop, departing Key West.
1.5 hours • Guided tour • Departs Key West
From $139.95 per driver
Check Availability🌅 Sunset Experiences
Champagne, live music, and Key West's legendary sunset from the water. The most popular evening activity.
Free nightly celebration with street performers, artists, and food vendors. The crowd cheers when the sun touches the horizon.
Just you and your person on a private charter. Perfect for proposals and anniversaries.
Sunset Sip & Sail — Sunset Watersports
The catamaran sunset sail in item 8 — drinks aboard for the sunset run. Single fixed adult rate.
2 hours • Evening departure • Catamaran • Youth rate available
$69.95 per adult
Check Availability
Private Romantic Sunset Cruise — Six Fins Charter
The private romantic sunset cruise in item 10 — your group only, no other passengers. Single fixed tier for the boat.
2 hours • Whole boat • Private charter • Stock Island departure
$995 whole boat
Check Availability🐬 Nature & Wildlife
Wild bottlenose dolphins live here year-round. Morning tours have 90%+ sighting rates.
70 miles west, this remote national park has pristine beaches, incredible snorkeling, and a massive Civil War fort.
Walk through a tropical garden with 50+ butterfly species and exotic birds.
Seabreeze Dolphin Watch & Snorkel Tour — Barefoot Charters
The dolphin watching in item 11, paired with a snorkel stop. Wild bottlenose dolphins, half-day format.
4 hours • Dolphin watch + snorkel • Child and senior rates available
$99.00 per adult
Check Availability🏛️ History & Culture
See where Hemingway wrote his greatest works. Pet the famous six-toed cats.
Civil War-era fort with the best beach in Key West. Great snorkeling right off the shore.
88 steps to panoramic views of the island.
Key West has a dark history—pirates, shipwrecks, yellow fever. Evening walking tours reveal the haunted side.
The iconic marker 90 miles from Cuba. Arrive early morning to avoid lines.
🍹 Food & Nightlife
Key West's famous main drag. Sloppy Joe's, Captain Tony's, The Bull—each bar has its own character.
The official dessert of the Florida Keys. Kermit's and Blue Heaven are local favorites.
Visit waterfront tiki bars only accessible by boat. Bites, boats, and booze.
Outdoor restaurant where chickens roam free. Famous for pancakes and Key West vibes.
Tiki Bar Crawl by Water — Six Fins Charter
The tiki bar crawl by boat in item 21 — a four-hour run along the waterfront tiki bars, private to your group. This is the full crawl, not the ninety-minute happy-hour cruise.
4-hour crawl • Whole boat • Private charter • Stock Island departure
$1,295 whole boat
Check Availability
The Craft Cocktail Crawl — Key West Food Tours
The walking version of item 19 — five craft cocktails at locally-loved spots off the beaten path, with two nibbles and the history between stops. A guide handles the route, so Duval is optional.
3 hours • Ages 21+ • 5 cocktails • Old Town, on foot
Starting at $79 per person
Check AvailabilitySalty Bottom Party Boat — Salty Bottom Boat Party’s
A big-group boat for when the party is the point. Sandbars, sunsets and private events, chartered by the hour rather than sold by the seat — the practical option once a group outgrows a six-passenger charter.
2–8 hours • Up to 36 passengers • Whole boat • Palm Ave departure
Check Availability
Adults Only Sandbar Escape — Brightwild Adventures
A four-hour sandbar trip run for adults only, so the boat stays quiet in the way a family departure cannot. Lunch is included. Useful if you want the sandbar without the school-holiday crowd.
4-hour trip • Adults only • Lunch included • Key West departure
Check Availability
Diva Royale — Drag Queen Show Key West
A weekly drag dinner show on Petronia Street, and a long-standing fixture of the bachelorette and bachelor party circuit here. Fixed showtimes, so it slots around a boat day rather than competing with one.
Fri & Sat 7:00pm • Sun 1:30pm • 422 Petronia St • Seated show
Starting at $40.51 per person
Check Availability💰 Free Activities
Free nightly entertainment with incredible sunset views.
Historic Key West Cemetery has quirky tombstones ("I Told You I Was Sick") and beautiful old trees.
Key West's largest beach. Free access, calm water, rentals available.
Arriving by cruise ship
Cruise ships dock in Key West for roughly 8–12 hours, and the clock is the whole problem. Most passengers get 6–8 hours ashore once boarding buffers are subtracted, so a tour has to depart soon after docking and return with room to spare. The tours that work are 3–4 hours with morning departures; anything longer eats the entire call. Expect crowds too — when a ship is in, popular departures run at 50–100+ passengers against a normal 30–40.
Three ways to book. Through the cruise line, shore excursions are convenient and the ship guarantees your return. At the port, operators keep kiosks and you can walk up on arrival — cheaper and more flexible, though your first choice may be gone. Booking online in advance is the middle path and the one most passengers do best with: same direct pricing, confirmation in hand before you sail.
If your tour runs late. Tell the operator and the marina staff immediately, then call the ship’s customer service line — the number is on your boarding material. Reputable operators know the ship schedule, build in buffer, and have contingency plans. Ships do not leave early under normal circumstances. In a genuine worst case you are responsible for reaching the next port yourself, which is expensive and complicated, and it is the reason to pick an operator with a clear return guarantee rather than the cheapest departure.
Ships don’t leave early in normal circumstances. But have a backup plan: get your tour operator’s phone number and the ship’s customer service number. If significantly delayed, contact the ship immediately. Reputable tour operators know the ship schedule and build in buffer time.
Both have merit. Duval Street walking tour is free and cultural. Water tours are experiences you can’t replicate. For first-time cruise passengers: do a water tour. For return visitors: explore on foot.
Not typically. Cruise line pre-booked excursions are group tours. But you can book a private charter directly if your port time allows (6+ hours). Confirm departure/return times with the ship before committing.
Inform the tour operator and marina staff immediately. Use your ship’s customer service number to alert them. Most reputable tour operators have contingency plans. In worst case, you’re responsible for your own transportation to the next port (expensive and complicated). This is why choosing a tour with solid return guarantees is critical.
Morning Dolphin & Snorkel Combo — Sunset Watersports
A three-hour morning departure — the shape that fits a cruise call, with time to spare before boarding closes.
3 hours • Morning departure • Dolphin watch + snorkel • Youth rate available
From $64.95 per adult
Check AvailabilityGetting on the water
Two experiences define a Key West day on the water. A sandbar trip is the signature one — captains anchor over shallow turquoise flats miles from shore, where you can stand waist-deep, swim, and watch for dolphins. A tiki boat is the other local staple: a floating bar you cruise the harbor on. One thing to know up front — Key West tiki boats price two ways: per-person seats from $59.95, or a private whole-boat charter from $300.
For the sandbar options, see which sandbar trip to book. For tiki, here's the tiki boat cost and what's included.
Sandbar & Dolphin Adventure — Sunset Watersports
From $129.95 per adult (from $89.95 youth) · priced per person · shallow flats, calm water, swimming
Check Availability
Happy Hour & a Half Tiki Bar Boat Cruise — Key West Promotions
$300 private charter, whole boat — not per person · your group only
Check Availability