Key West Sailing Trips

Key West Sailing Trips

Cruises, Sailing & Water Tours See all

Only Show: Day Cruises | Dinner Cruises | Dolphin & Whale Watching | Night Cruises | Sailing Trips | Sunset Cruises

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Morning or Afternoon Half-Day Cruise

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

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

Premium Full Day 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

Key West Java Cat Charter Eco Tour

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

Wind and Wine Sunset Sail

5 star rating: Highly Recommended 10 Reviews

Cruise into the sunset with wines from all around the world, Import and Domestic beers and Hors d'euvres. This cruise is great for a romantic evening or just ...  Read more

Location: Key West, Florida
Duration: 2 hours

From USD $86.00

Bugeye Backcountry Eco Tour

5 star rating: Highly Recommended 2 Reviews

Set sail aboard our classically-styled schooner as she departs the Historic Key West Seaport for a full day of sailing and exploration through the ...  Read more

Location: Key West, Florida
Duration: 6 hours

From USD $99.99

Private Sunset sail in Key West

Sunset sailing trips in Key West should be romantic with friends and/or family, and that's why we only offer private sunset sails. Our beautiful sail boat is ...  Read more

Location: Key West, Florida
Duration: 2 hours

From USD $350.00

Private Half Day Sails In Key West

Sailing trips in Key West should be romantic with friends and/or family, and that's why this private sail offers exactly that.  This beautiful sail boat is ...  Read more

Location: Key West, Florida
Duration: 4 hours

From USD $350.00

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

Day Sail in Key West by Private 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 ...  Read more

Location: Key West, Florida
Duration: Flexible

From USD $294.99

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
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Only Show: Day Cruises | Dinner Cruises | Dolphin & Whale Watching | Night Cruises | Sailing Trips | Sunset Cruises

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