Florida Sailing Trips
Cruises, Sailing & Water Tours See all
Only Show: Airboat Tours | Brunch Cruises | 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 or Afternoon Half-Day Cruise
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
Shipwreck Snorkel and Wild Dolphin Encounter
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
Premium Full Day Excursion in Key West
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
Key West Catamaran Eco-Adventure Including 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
Lets Go Sailing Today
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
Wind and Wine Sunset Sail
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
Key West Sail and Snorkel Day Trip from Fort Lauderdale
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
Private Sailing Trip on Biscayne Bay with Professional Photographer
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
Bugeye Backcountry Eco Tour
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
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
Catamaran Sailing Lesson or Boat Rental in Biscayne Bay
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
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
Schooner Appledore Key West Cruise
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
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
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
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
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Only Show: Airboat Tours | Brunch Cruises | Day Cruises | Dinner Cruises | Dolphin & Whale Watching | Duck Tours | Lunch Cruises | Multi-day Cruises | Night Cruises | Sailing Trips | Sunset Cruises
