Florida Sailing Trips

Florida Sailing Trips

Cruises, Sailing & Water Tours See all

Only Show: Airboat Tours | Brunch Cruises | Catamaran Cruises | Day Cruises | Dinner Cruises | Dolphin & Whale Watching | Duck Tours | Glass Bottom Boat Tours | Lunch Cruises | Multi-day 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

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

Private Sailing Charter in Miami

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 cruise. ...  Read more

Location: Miami, Florida
Duration: Flexible

From USD $425.00

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

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 in the ocean. ...  Read more

Location: Fort Lauderdale, Florida
Duration: 15 hours

From USD $149.00

Private Sailing Trip on Biscayne Bay with Professional Photographer

5 star rating: Highly Recommended 1 Review

Set sail on a private 40-ft sailboat for 4 hours on Biscayne Bay with this charter from Miami. Choose from a morning, afternoon or evening sail and enjoy a ...  Read more

Location: Miami, Florida
Duration: 4 hours

From USD $595.00

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

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 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

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

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

Key West Sail Under the Stars

Unwind under the stars on this 2-hour nighttime sailing cruise! Relax on an authentic schooner and bask in the moonlight as you sail through the crystal clear ...  Read more

Location: Key West, Florida
Duration: 2 hours

From USD $73.78

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

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

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

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

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