Old Town · Historic Seaport
Key West Parasailing: Fly Over the Harbor From the Historic Seaport
Fly up to 300 feet over Key West harbor with a dry takeoff and landing from the boat deck. From $60 for the 9 am early-bird flight, year round.
Written in Key West by people who live on the water
Key West's top adventures, picked by locals
We spend our days around the Historic Seaport and out on the reef, and we know which boats guests step off raving about. These are the trips worth your one week in paradise, with real prices, what to expect, and the honest fine print.
7adventures, zero filler
★ 4.7+minimum rating of every pick
75,000+verified reviews behind the list
The list
Top-rated things to do in Key West
Ranked by what guests rave about, not by who pays the most. Every pick has thousands of reviews behind it and a crew we would send our own family out with.
Old Town · Historic Seaport
Key West Snorkeling Tour: The Rise & Reef Morning Sail to the Coral Reef
Sail out to the only living coral reef in the continental US, snorkel for an hour with gear and guides included, then sail home with the bar open. From $46.
Old Town · Front Street
Key West Sunset Sail: The Wind & Wine Schooner Cruise
Two hours on a wooden schooner with eight wines, craft beer and charcuterie while the sun drops over the backcountry. Ranked one of the top two sunset sails in North America.
Old Town · Historic Seaport
Key West Dolphin Watch & Snorkel Tour: A Biologist-Led Trip Into the Wildlife Refuge
Four hours with a naturalist guide: find the resident bottlenose pods in the wildlife refuge, then snorkel the flats. Max 16 guests, 4.9 stars, the original Key West dolphin tour since 1986.
Old Town · Front Street
Key West Jet Ski Tour: The 28-Mile Guided Island Loop
Circle the whole island in 90 minutes on a guided 28-mile loop: the Southernmost Point from the water, the backcountry flats and the harbor. From $140 per ski, two riders for one price.
Old Town · Historic Seaport
Key West Sandbar & Dolphin Trip: A Backcountry Day With Lunch and an Open Bar
Five hours in the backcountry: a waist-deep sandbar with paddleboards and floats, an open bar, lunch on board, then the resident dolphin pods on the way home. Key West's most-reviewed day on the water.
Old Town · Front Street
Key West Sail, Snorkel & Kayak Excursion: A Half Day in the Backcountry
A quiet half day on a wooden schooner into the wildlife refuge: paddle the mangrove tunnels, snorkel the flats, sail home. Twenty guests or fewer, no party, 4.9 stars.
Get your bearings
Where everything leaves from
Key West is four miles long and two miles wide, and almost every boat on this list leaves from the same half-mile of waterfront. Tap a pin to jump to that adventure.
Map data © OpenStreetMap contributors. Tap a pin to open that adventure.
ParasailingHistoric Seaport · from $60 · ★ 4.8
Reef SnorkelingHistoric Seaport · from $46 · ★ 4.8
Wind & Wine Sunset SailFront Street · from $109 · ★ 4.9
Dolphin Watch & SnorkelHistoric Seaport · from $89 · ★ 4.9
Jet Ski Island TourFront Street · from $140 · ★ 5
Sandbar & Dolphin DayHistoric Seaport · from $129 · ★ 4.8
Sail, Snorkel & KayakFront Street · from $79 · ★ 4.9
Historic Seaport
William St · Margaret St · the Bight
The working harbor at the north edge of Old Town. Parasail boats, the snorkel catamarans, the sandbar trip and the dolphin boats all check in within a two-minute walk of each other.
Seaport guide →Front Street & Mallory Square
Opal Key Marina · Hyatt Centric · Sunset Pier
The sunset end of town. The schooners sail from Opal Key Marina, the jet ski tour leaves from the Hyatt dock, and the Mallory Square sunset celebration is right there when you get back.
Front Street guide →Smathers Beach & the South Shore
S. Roosevelt Blvd · Casa Marina · the airport
The island's long public beach on the Atlantic side. A second parasail launch flies from the sand here, which saves the trip downtown if you are staying on the south side.
South shore guide →Timing matters
Key West runs all year. The water does not feel the same all year.
There is no off-season closure here like Hawaii's whale rule, but the wind, the water temperature and the crowds swing a lot between January and July. Here is how to match the trip to the month.
November to April
High season, cooler water
Dry, breezy and busy. Sunset sails are at their best, and the dolphin pods are easy to find on calm days. Snorkelers want a wetsuit top in January and February.
May to October
Flat water, warm reef
Glassy mornings, 85°F water and the clearest reef visibility of the year. The best months for parasailing, the reef snorkel and the sandbar, with afternoon storms that usually pass in an hour.
- Parasailing from $60
- Reef snorkel from $46
- Sandbar & dolphin day
Every month
Always running
Short, flexible trips that fit around weather, cruise-ship days and hangovers. Book the morning slot and keep the afternoon free for Duval.
- Jet ski island tour 90 minutes
- Parasail flight 1 hour
- Month-by-month guide
Why trust this guide
We are not a booking site pretending to be a blog
Most "things to do in Key West" lists are written by people who have never walked the docks at the Bight. We know the crews behind every company on this list, and we have been out on every trip.
7
adventures on the list. Each one is the top-rated option in its category, not a paid placement.
4.7+
minimum average rating across thousands of verified guest reviews for every operator we feature. Most are 4.8 or 4.9.
1
operator per activity. We tell you who to book instead of handing you a ten-way comparison table.
$0
extra when you book through this site. Operators pay us a referral fee, which keeps the guide free and the opinions ours.
Plan smarter
Guides from the island
October 27, 2026
Best Time to Visit Key West: Month by Month, From People Who Work on the Water
Water temperature, wind, crowds, hurricane season and prices for every month, plus which trips to book when.
October 27, 2026
25 Best Things to Do in Key West (A Local's 2026 Guide)
Our top 25 Key West adventures, grouped by where they leave from so you can plan around where you're staying.