Florida Sailing Trips

Florida Sailing Trips

Cruises, Sailing & Water Tours See all

Only Show: Airboat Tours | Day Cruises | Dinner Cruises | Dolphin & Whale Watching | Duck Tours | Lunch Cruises | Multi-day Cruises | Night Cruises | Sailing Trips | Sunset Cruises

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Morning and Afternoon Half Day Cruise

5 star rating: Highly Recommended 10 Reviews

Don't miss one of the top things to do in Key West! Come enjoy the Florida Keys on this kayaking, snorkeling and sailing adventure. You will cruise out to the ...  Read more

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

From USD $85.99

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

Shipwreck Snorkel and Wild Dolphin Encounter

4.5 star rating: Recommended 26 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

Key West Java Cat Charter Eco Tour

Combine the best Key West activities into a 4.5-hour, eco-adventure. Escape the crowds on this catamaran sailing tour with snorkeling marine nurseries teeming ...  Read more

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

From USD $123.63

Private Sailing Trip on Biscayne Bay with Professional Photographer

5 star rating: Highly Recommended 1 Reviews

Set sail on a private 40-ft sailboat on Biscayne Bay with this charter from Miami. Choose from an afternoon or evening sail and observe the beautiful sunset ...  Read more

Location: Miami, Florida
Duration: Flexible

From USD $695.00

Lets Go Sailing Today

5 star rating: Highly Recommended 4 Reviews

A perfect way to enjoy a day is sailing on a beautiful 40 foot Beneteau sailboat on Biscayne Bay in Miami.  The most popular charter is a sunset ...  Read more

Location: Miami, Florida
Duration: Flexible

From USD $425.00

Bugeye Backcountry Eco Tour

5 star rating: Highly Recommended 1 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

Wind and Wine Sunset Sail

5 star rating: Highly Recommended 8 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

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

Key West Sail and Snorkel Day Trip from Fort Lauderdale

4.5 star rating: Recommended 2 Reviews

Whether you’re an experienced snorkeler or you want to try something new and exciting, you’ll find Key West to be the perfect destination for fun ...  Read more

Location: Fort Lauderdale, Florida
Duration: 15 hours

From USD $164.99

Catamaran Sailing Lesson or Boat Rental in Biscayne Bay

4 star rating: Recommended 2 Reviews

Sailing on a sleek catamaran is the best way to explore Miami’s beautiful Biscayne Bay. Whether you want to learn how to sail or want to rent a boat to ...  Read more

Location: Miami, Florida
Duration: Varies

From USD $16.29

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

Private Two Hour Yacht Charter in Tampa Bay

Tampa Bay Yacht Charter offers crewed yacht charters aboard the Smooth C's, a 43' Viking Motor Yacht, Coast Guard Certified for up to 20 passengers. The Smooth ...  Read more

Location: Saint Petersburg, Florida
Duration: 2 hours

From USD $944.00

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
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Only Show: Airboat Tours | Day Cruises | Dinner Cruises | Dolphin & Whale Watching | Duck Tours | Lunch Cruises | Multi-day Cruises | Night Cruises | Sailing Trips | Sunset Cruises

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