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.
Top-rated Key West adventures
Seven trips, ranked by what guests rave about. Filter by the kind of day you want or by where the boat leaves from. Prices are "from" rates before tax and booking fees.
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.
How we rank
We only list one operator per activity, and it has to be the one we would send our own family out with. We weigh verified review scores (every pick is 4.7 stars or better across thousands of reviews, and most are 4.8 or 4.9), the crew's safety record and Coast Guard inspections, how the trip actually feels on the water, and value for what is included. We update prices and seasons every few weeks. If an operator slips, it comes off the list.