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 | Lunch Cruises | Night Cruises | Sailing Trips | Sunset Cruises

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Catamaran Eco-Adventure with Kayaking Tour and Snorkeling

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

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

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

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

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

Key West Tall Ship and Crawl

Tall Ship sailing and off Duval Street crawling that includes some hearty tastings 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 star rating: Recommended 1 Review

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

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

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 | Lunch Cruises | Night Cruises | Sailing Trips | Sunset Cruises

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