Top Florida Sailing
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66 results | All Florida Tours
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45' Yacht Tour in Miami Beach
16
Enjoy the day on the water with friends & family in Miami Beach with Dolphin Water Sport
.
45 ft Sea Ray Sundancer with 2 State Rooms & 2 full bathrooms, This beautiful Sea Ray is fully equipped with excelent Bluetooth sound system, A/C, stove, microwave, refrigerator, freezer, television, and much more!
Enjoy a unique and personalized experience with our private tour!
Water, Champagne & Ice Included
4, 6 or 8 hour tours, Available for night trips.
Perfect for a day or evening out on the water, Cruise the Intracoastal and see the homes of the Rich & Famous, see some dolphins along the way, take a ride the Biscayne Bay or just chill out at one of the Sandbars where you can barbecue or relax sipping your favorite drink.
Great for Birthdays, Anniversaries or any special occasion up to 13 people.
Our US Coastguard certified captains have 10+ years experience & they're outgoing and accommodating personalities will ensure that is most enjoyable.
*Please read the inclusions & exclusions*
…More
From
$1,350.00
per group
From
$1,350.00
per group

Small-Group Key West Sunset Sail with Wine
282
Escape to the still waters off the coast of Key West on this small-group, sunset wine-tasting cruise. Enjoy the scenery and peaceful calm of a late afternoon sail on board a 65-foot schooner. Sample up to eight different wines and/or five different beers. Also included is a gourmet cheese buffet and other appetizers, like summer sausages, water crackers with brie, green apples with a honey drizzle and more. Then watch as the sun glistens and gently settles into the water, a perfect ending to a perfect cruise.
…More
From
$91.38
From
$91.38
Regularly sanitized high-traffic areas
Gear/equipment sanitized between use
Transportation vehicles regularly sanitized
Learn More

Fort Lauderdale Sailing Charter
180
Cruise along the coast of Fort Lauderdale aboard your own private 40-foot (12-meter) sailboat on this personalized excursion, ideal for couples or travelers celebrating a special occasion. Opt to cruise down the historic Fort Lauderdale New River or sail in the Atlantic Ocean, and customize your itinerary according to personal preference, choosing from activities such as sightseeing, swimming, snorkeling, or fishing.
…More
From
$150.00
Price varies by group size
From
$150.00
Price varies by group size
Hand sanitizer available to travelers and staff
Social distancing enforced throughout experience
Regularly sanitized high-traffic areas
Learn More

1-Hour Interactive Pirate Adventure Cruise in Fort Lauderdale (Family-Friendly)
727
Set sail for adventure on this exciting, interactive Pirate Adventure Cruise along Fort Lauderdale’s Intracoastal Waterway. This spirited 1-hour excursion is fun for the whole family. Help find the hidden treasure, learn to talk and dress like a pirate with face painting and temporary tattoos and fend off the attacks of rival pirates with onboard water cannons. Kids receive a pirate certificate and bag of loot to take home. This tour is great for birthday parties, group field trips or just a day of fun on the high seas.
…More
From
$23.04
From
$23.04
Face masks required for travelers in public areas
Face masks required for guides in public areas
Face masks provided for travelers
Learn More

Hobie Cat Sailing with Miami Watersports
There's no better place to experience the thrill of a sailing than in Miami. Our city is known for its protected bays, and warm tropical waters. This scenic Biscayne Bay sailing adventure is perfect for those that know how to sail, and for folks that want to learn. The bay offers a series of shallow flats which protects it from the rough seas. Price is per boat so make sure to bring your friends!
Lessons
We highly recommend adding a lesson upon arrival to help build your confidence and make sure you are starting on a strong base. Cost is per boat, you may choose to take a lessons or simply have a captain come drive the boat for you as you relax and enjoy the view!
Highlights
• Sail on your own!
• No qualifications required
• Gear available for all levels
• Lessons available
• Calm tropical water
…More
From
$86.52
per group
From
$86.52
per group

Key West Sunset Sail Aboard Schooner
173
Set sail on a replica of the 1851 Schooner America on a cruise from Key West. See the top sights of the city, including Fort Zachary, Mallory Square, and Sand Key Lighthouse from a unique perspective. Your cruise is accompanied by complimentary hors d’oeuvres along with alcoholic and non-alcoholic beverages. Allow yourself to truly unwind as the sun sinks into the Atlantic Ocean.
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From
$103.20
From
$103.20
Face masks required for travelers in public areas
Face masks required for guides in public areas
Hand sanitizer available to travelers and staff
Learn More

Key West Day Sail Aboard Schooner
55
Experience a slice of sailing history while soaking up fantastic Key West views on a cruise aboard the America 2.0, a replica of the schooner that won the very first America’s Cup. Relax on padded benches and teak decks as your captain navigates the island coastline past landmarks like Fort Zachary Taylor and Sand Key Light Tower, and sip unlimited drinks from the full onboard bar.
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From
$60.20
From
$60.20
Face masks required for travelers in public areas
Face masks required for guides in public areas
Hand sanitizer available to travelers and staff
Learn More

Key West Snorkel and Sunset Sail: Rum n' Reggae
118
Combine a snorkel session on North America's only living coral reef with a Key West sunset during this catamaran cruise. Listen to lively reggae beats, snorkel using the provided equipment, and watch the sunset with a rum punch in hand.
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From
$49.34
From
$49.34
Face masks required for travelers in public areas
Face masks required for guides in public areas
Face masks provided for travelers
Learn More

Key West Sail and Snorkel Trip from Miami
34
Get ready for fun in the sun on this day trip and snorkeling adventure off the coast of Key West from Miami. Ride across 32 islands from Miami to Key West, explore the island city, then sail away on board a spacious 50-foot catamaran vessel. Jump into the water off the coast for a snorkeling session above a coral reef with 600 different species of marine life. Professional snorkeling instruction provided. Relax, feel the warm sea breeze and enjoy the day. Miami hotel pickup and drop-off included.
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From
$121.27
From
$121.27
Face masks required for travelers in public areas
Face masks required for guides in public areas
Hand sanitizer available to travelers and staff
Learn More

Key West Sail and Snorkel Day Trip from Fort Lauderdale
6
Embark on a tropical adventure with this all-level snorkeling sail trip from Fort Lauderdale. Board a 50-foot (15-meter) catamaran and sail the Florida Keys’ crystal waters with expert guides who offer insight about the surrounding area. At the diving location, don your snorkeling gear and hop into the water to spot brilliantly colored coral and tropical marine life. You’ll also have plenty of independent time to explore vibrant Key West.
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From
$149.00
From
$149.00
Face masks required for travelers in public areas
Face masks required for guides in public areas
Hand sanitizer available to travelers and staff
Learn More

Key West Full-Day Power Adventure: Sailing & Watersports Package
492
Enjoy the Key West sunshine on a full-day catamaran excursion, and take part in a range of watersports, too. As you cruise around the alluring Gulf of Mexico, gaze out at the scenery and spot local marine life. Choose from a range of activities from snorkeling and kayaking to adrenaline-fuelled parasailing or Jet Skiing. Breakfast and lunch are served on board.
…More
From
$174.95
From
$174.95
Face masks required for guides in public areas
Face masks provided for travelers
Hand sanitizer available to travelers and staff
Learn More

Key West Dolphin Watch Sunset Sail with Premium Wine, and Tapas Pairings
31
Our Captain’s Choice Dolphin Watch Sunset Sail is the ultimate VIP sailing experience! Limited to an intimate number of passengers, this 3 hour sail is more like a private cruise than a group tour and is one of the top things to do in Key West.
As we leave behind the Historic Seaport, look for Key West landmarks like the legendary Mallory Square, opulent Sunset Key and historic Fort Zachary Taylor. On reaching open water, the sails are unfurled and your adventure begins as your captain tracks dolphin pods to provide you an up-close view of these elusive creatures.
With the dolphin viewing over, your cruise is just getting started! Grab a drink and relax as your captain positions the luxury catamaran for the perfect view of a famous Key West sunset.
A chef’s selection of Tapas including shrimp cocktail and tuna poke are served during the sail. Choose your favorite drinks, including boutique wines and champagne perfectly paired with our Tapas – all included in the cost of your tour!
…More
From
$79.95
From
$79.95
Face masks required for guides in public areas
Face masks provided for travelers
Hand sanitizer available to travelers and staff
Learn More

Key West Premium Sunset Sail aboard Schooner with Hors D'oeuvres and Full Bar
182
Enjoy the sunset from the water on this Key West cruise aboard a classic schooner. As you stand on the deck of the tall ship, pass by sights such as Mallory Square with its Sunset Celebration and the Navy Mole, where big ships dock. Hors d'oeuvres and unlimited drinks are included onboard. Take your pick of beer, wine, sparkling wine, cocktails, soda, and homemade tropical sangria.
…More
From
$79.95
From
$79.95
Face masks required for travelers in public areas
Face masks required for guides in public areas
Hand sanitizer available to travelers and staff
Learn More

Key West Schooner Backcountry Eco-Tour: Sail, Snorkel & Kayak
77
Explore the patch reefs, mangrove islands, and waterways of Key West on a 6-hour cruise and snorkeling tour aboard a wooden sailing schooner. Take a hand at the wheel on your way across the Gulf of Mexico, kayak through the mangroves, then snorkel through patch reefs and sponge gardens. This 6-hour tour includes breakfast, lunch, and access to an open bar on the return sail to Key West.
…More
From
$109.95
From
$109.95
Face masks required for travelers in public areas
Face masks required for guides in public areas
Hand sanitizer available to travelers and staff
Learn More

Key West Full-Day Island T'ing Eco-Tour: Sail, Kayak and Dolphin Watch
367
Enjoy a day of fun in the sun on the Island T’ing adventure off the coast of Key West. Sail away from the island city of Key West to the beautiful blue waters of the Gulf of Mexico on a large catamaran. Hop in a kayak and enjoy a paddle around a natural stand of mangrove. Look for dolphins, stingrays, sea turtles, manatees and more on this full-day adventure. A full breakfast and buffet lunch, plus beer, wine, soft drinks and homemade sangria are included.
…More
From
$124.95
From
$124.95
Face masks required for guides in public areas
Face masks provided for travelers
Hand sanitizer available to travelers and staff
Learn More

Key West Sunset Champagne Catamaran Cruise
280
Experience a sunset you’ll never forget on this 2-hour catamaran cruise in Key West. Sip on your choice of wine, champagne, beer or sangria as you watch the sun go down over the water. As you sail you’ll catch glimpses of the island and marvel at the views from the turquoise water. Cocktails are also available at a cash bar on board.
…More
From
$49.95
From
$49.95
Face masks required for guides in public areas
Face masks provided for travelers
Hand sanitizer available to travelers and staff
Learn More

Key West Sunset Sail with Full Bar, Live Music & Hors D'oeuvres
867
Watch the sun set and the moon rise off the coast of Key West on this sunset cruise. Enjoy the scenery and peaceful calm of a late afternoon sail aboard a 70-foot catamaran with plenty of deck space to stretch out and enjoy the breathtaking view. Then watch a legendary Key West sunset as the sun glistens and gently settles into the water. Hearty appetizers plus champagne, wine, full liquor bar, ice-cold beer and soft drinks are included.
…More
From
$69.95
From
$69.95
Face masks required for guides in public areas
Face masks provided for travelers
Hand sanitizer available to travelers and staff
Learn More

4 Hours Private Charter On A 62' Azimut Fly Bridge Luxury Yacht
Bring your party to South Beach and take a 4-hour private charter along the beautiful scenery of Biscayne Bay. The amazing 62' Azimut yacht will comfortably carry you and 12 friends and family for an unforgettable party cruise. Bring your own food and alcohol and enjoy the luxuries of a yacht for eating, drinking and dancing to amazing music. Choose your own departure between 10am to 6pm and enjoy the Miami and Miami Beach waterways.
…More
From
$3,750.00
per group
From
$3,750.00
per group

Key West Wild Dolphin Sail and Shallow-Water Snorkel
158
Take a half-day sailing adventure off the coast of Key West, Florida and observe wildlife. Sail away from the island city of Key West to the beautiful blue waters off the coast on a large catamaran. See dolphins swimming and jumping alongside the boat, then jump in for an easy shallow-water snorkel above a coral reef, shipwreck, or sponge garden, all supporting over 600 species of marine life. Relax, feel the warm sea breeze and enjoy light snacks and a variety of refreshing beverages on board the boat.
…More
From
$97.91
From
$97.91
Hand sanitizer available to travelers and staff
Regularly sanitized high-traffic areas
Gear/equipment sanitized between use
Learn More

Adults only Champagne Celebration Sunset Cruise from Key West
267
Escape to the still waters off the coast of Key West on this adults-only sunset champagne cruise. Enjoy the peaceful calm of a late afternoon sail on a comfortable catamaran limited to just 14 passengers. Enjoy house champagne, red or white wine, ice-cold beer, a soft drink or bottled spring water, and a gourmet cheese buffet. Then watch as the sun glistens and gently settles into the water, a perfect ending to a perfect cruise.
…More
From
$81.40
From
$81.40
Hand sanitizer available to travelers and staff
Regularly sanitized high-traffic areas
Gear/equipment sanitized between use
Learn More

3 Hour Private Sunset Sailboat Tour for up to 4 Complimentary beverages, snacks
1
**Price listed is per boat, so you will only need to select one adult for your booking of a maximum of 4 people.
Sailing on the protected waters of Biscayne Bay aboard a prestine 40 foot Beneteau sailboat. This offers you a spectacular experience on the water with views of the Skyline of Miami, as well as the island of Key Biscayne and beautiful open water views of the sunset over Biscayne Bay. Being that it is a protected body of water, it is easy to relax on our foredeck with comfortable cushioned seating sipping a glass of your complimentary favorite beverage. If you forget to bring your camera, don't worry, Captain Bill and crew will be happy to take many incredible photos of you and the sunset and the surrounding sights for lasting memories.
…More
From
$615.00
per group
From
$615.00
per group
Face masks required for travelers in public areas
Hand sanitizer available to travelers and staff
Social distancing enforced throughout experience
Learn More

Private Sailing Charter in Miami for up to Four Guests
66
Enjoy a private sailing trip on a 40 foot Beneteau sailboat. Customize your own trip with Captain Bill, who's always game to give an impromptu sailing lesson to adventurous passengers—you can even take the helm or help work a wench. Or, just sit back, relax, and take in the sights. Choose a northern or southern route to highlight Miami classics like the skyline, MIllionaire's Row, and the magnificent Vizcaya estate.
…More
From
$450.00
per group
From
$450.00
per group
Face masks required for travelers in public areas
Hand sanitizer available to travelers and staff
Social distancing enforced throughout experience
Learn More

Private Sailing on Classic Yacht Charter in Key West
Setting sail from stock island provides quick access to the south side of key west and open Atlantic waters that allow unobstructed views of our key west sunset. Schooner Metani is offered for no more than 6 passengers allowing ample space and comfort.
…More
From
$695.00
per group
From
$695.00
per group
Hand sanitizer available to travelers and staff
Regularly sanitized high-traffic areas
Gear/equipment sanitized between use
Learn More

Sail Charter Tour Aboard Star of Orion
19
Since 2009, we offer the cleanest, safest, and best maintained modern sailing vessel. Multiple daily sails that include a quarter day and sunset sail aboard a real sailboat. Visit our website for more options and availability.
Owned and operated by a husband and wife, we immediately reduce the "Creepy Captain and Crew" factor and make for a relaxed and comfortable experience for all guests. Our vessel looks like new due to our rigorous daily maintenance. You'll feel a sense of pride sailing aboard our vessel as we depart Salty Sam's Marina heading for the Gulf of Mexico. We will pass the shrimp boat fleet and beautiful homes on the way to the Gulf. Once out of the marked channel, we raise our sails and shut the motor off. Wildlife such as dolphins, sea turtles, manatee, and various birds can appear at anytime. If the wind allows, we will sail towards the Sanibel lighthouse or along the shores of Fort Myers Beach. Book 6 seats for a private tour. Welcome aboard!
…More
From
$77.00
From
$77.00
Hand sanitizer available to travelers and staff
Regularly sanitized high-traffic areas
Gear/equipment sanitized between use
Learn More