Key West Sailing Trips

Key West Sailing Trips

Cruises, Sailing & Water Tours See all

Only Show: Brunch Cruises | Catamaran Cruises | Day Cruises | Dinner Cruises | Dolphin & Whale Watching | Glass Bottom Boat Tours | Lunch Cruises | Night Cruises | Sailing Trips | Sunset Cruises

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Catamaran Eco-Adventure with Kayaking Tour and Snorkeling

5 star rating: Highly Recommended 1 Review

Combine three Key West activities on this eco-adventure by chartered catamaran. Sail to the Key West National Wildlife Refuge for a guided kayaking tour of ...  Read more

Location: Key West, Florida
Duration: 4 hours 30 minutes

From USD $123.63

Island Adventure Snorkel Kayak and Eco Tour

Discover a different side of Key West as you explore a secluded paradise in the Florida Keys backcountry on this Island Adventure. Tucked away between mangrove ...  Read more

Location: Key West, Florida
Duration: 4 hours 30 minutes

From USD $96.70

Shipwreck Snorkel and Wild Dolphin Encounter

4.5 star rating: Recommended 27 Reviews

Spend a beautiful Florida day out in the clear, blue waters off Key West. On the Key West Shipwreck Snorkel and Wild Dolphin Encounter cruise, you’ll ...  Read more

Location: Key West, Florida
Duration: 4 hours

From USD $95.59

Half-Day Cruise with Kayaking and Snorkeling

5 star rating: Highly Recommended 11 Reviews

Don't miss one of the top things to do in Key West—a half-day sailing tour where you can explore the waters of the Florida Keys. You'll cruise out to a ...  Read more

Location: Key West, Florida
Duration: 4 hours 30 minutes

From USD $85.99

Key West Tall Ship and Crawl

5 star rating: Highly Recommended 1 Review

Tall Ship sailing and off Duval Street crawling that includes a hearty progressive meal of classic Key West inspired surf and turf rations as well as plenty of ...  Read more

Location: Key West, Florida
Duration: 4 hours

From USD $116.10

Schooner Appledore Key West Cruise

4.5 star rating: Recommended 2 Reviews

Enjoy a day sail or sunset sail around Key West on the Appledore II. Stretch out and relax to the sounds of internationally renowned chanteyman Geoff Kaufman, ...  Read more

Location: Key West, Florida
Duration: 2 hours

From USD $39.00

All Inclusive Water Adventure Excursion in Key West

5 star rating: Highly Recommended 3 Reviews

This full day excursion from Key West includes all the fun things to do in the ocean - kayaking, snorkeling and sailing! You will head way back into the Key ...  Read more

Location: Key West, Florida
Duration: 6 hours 30 minutes

From USD $118.25

Hangover Cure Morning Sail

Set sail on this 2-hour sailing cruise and quickly recover from last night's fun! Enjoy the beautiful waters of Key West and relax on an authentic schooner. ...  Read more

Location: Key West, Florida
Duration: 2 hours

From USD $68.10

Private Sailing Charter on Authentic Schooner

Reserve an entire authentic schooner with this private charter! Enjoy luxurious privacy as you spend a relaxing day on the water soaking in the warm Key West ...  Read more

Location: Key West, Florida
Duration: Flexible

From USD $300.00

Schooner Summer Wind Afternoon Sail

Enjoy the beautiful waters of Key West on this 2-hour afternoon sailing cruise! Relax on an authentic schooner and spend the afternoon soaking in the warm sun ...  Read more

Location: Key West, Florida
Duration: 2 hours

From USD $68.10

Schooner Summer Wind Sunset Sail

Wind down a fun day in Key West with this 2-hour sunset sailing cruise! Relax on an authentic schooner and spend the evening surrounded by gorgeous waters and ...  Read more

Location: Key West, Florida
Duration: 2 hours

From USD $79.45

90 Min Key West Harbor Sail

This 90 minute sailing trip in Key West is the best way to experience the water with friends and/or family when time is of the essence!  The captain helps ...  Read more

Location: Key West, Florida
Duration: 90 minutes

From USD $255.38

Private Sail with Reef Eco Exploration

Trip starts out at Galleon Marina for a 4 Hour sail. You will be taken through the National Marine Sanctuary which is home to Dolphins, Loggerhead turtles and ...  Read more

Location: Key West, Florida
Duration: 4 hours

From USD $599.99

Key West Tall Ship Starlight Sail

A starry-skied sailing adventure in Key West awaits you aboard a majestic, 80-foot (24-meter) wooden tall ship! Escape to the waters just off Key West for a ...  Read more

Location: Key West, Florida
Duration: 90 minutes

From USD $48.37

Tall Ship Sunset Cruise in Key West

5 star rating: Highly Recommended 5 Reviews

Enjoy an exquisite 2-hour sunset sailing adventure in Key West aboard a stunning tall ship! Take in great views of Mallory Square, Sunset Pier, Sand Key Light ...  Read more

Location: Key West, Florida
Duration: 2 hours

From USD $74.99

Key West Schooner Sailing

5 star rating: Highly Recommended 4 Reviews

Take to the sea aboard an 1890s-style schooner from Key West and admire its beauty on the clear, calm Caribbean waters! As you sail through the turquoise ...  Read more

Location: Key West, Florida
Duration: 90 minutes

From USD $44.99

Key West Mimosa Cruise

Take off from Key West and spend a morning aboard a classic wooden Gatsby-era yacht! A fabulous way to start your day, this Key West morning mimosa cruise will ...  Read more

Location: Key West, Florida
Duration: 90 minutes

From USD $35.00

Private 90 Minute Customized Sailing Charter

Live the high life on this private chartered day sail in Key West. Set sail on your boat for a 90-minute adventure around the Florida Keys and view the city ...  Read more

Location: Key West, Florida
Duration: 90 minutes

From USD $294.99
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Only Show: Brunch Cruises | Catamaran Cruises | Day Cruises | Dinner Cruises | Dolphin & Whale Watching | Glass Bottom Boat Tours | Lunch Cruises | Night Cruises | Sailing Trips | Sunset Cruises

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