Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 755 Sailing Trips activities in North America. Sort by Popularity. - Page 6Newport Sunset Sail on Schooner Adirondack
Join us aboard a classic sailboat for a 1.5-hour sunset sail in Newport! Sunset sailing is one of the best evening activities to do during your stay in Newport, RI. Enjoy a relaxing sail around Narragansett Bay on a classic sailbo... More
Likely to Sell Out Newport Sunset Sail on Schooner Adirondack
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North America
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Superb80 reviews4.9
Join us aboard a classic sailboat for a 1.5-hour sunset sail in Newport! Sunset sailing is one of th....
Sunset Sail Cruise in Key West
Sailing on the Rover is an exciting, traditional sailing experience with a Hint of Piracy! Yes - We have cannons! Come sail on Key West's most photographed ship! The Schooner Jolly II Rover is the only squared rigged, topsail scho... More
Likely to Sell Out Sunset Sail Cruise in Key West
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North America
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Superb276 reviews4.9
Sailing on the Rover is an exciting, traditional sailing experience with a Hint of Piracy! Yes - We ....
Private Sunset Sail BYOB Dolphin/History Tours on 43ft Mystique
Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charter company in Charleston's history. #1 activity on Tripadvisor for over 12 years, our sailing yachts are the highest quality and op... More
Private Tour
Likely to Sell Out Private Sunset Sail BYOB Dolphin/History Tours on 43ft Mystique
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North America
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Superb44 reviews5
Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charte....
Private Tour
Best Waikiki Sunset Cruise:BYOB Sunset Sail with Swimming
Our vessel "Hokulani" is a beautiful and spacious custom built sailing trimaran specifically designed for a comfortable ride in Hawaiian waters. What makes Hokulani unique from every other tour boat operating in Waikiki, is that s... More
Private Tour
Likely to Sell Out Best Waikiki Sunset Cruise:BYOB Sunset Sail with Swimming
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North America
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Superb197 reviews4.9
Our vessel "Hokulani" is a beautiful and spacious custom built sailing trimaran specifically designe....
Private Tour
Catamaran Day Sail Shelling Excursion 42ft. Mainecat Cool Beans
Create memories that lasts a lifetime with a day on the Gulf of Mexico sailing to a private island for some swimming and shelling (weather permitting) while taking in the sun and spectacular views. Our beautifully, well appointed ... More
Private Tour
Likely to Sell Out Catamaran Day Sail Shelling Excursion 42ft. Mainecat Cool Beans
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North America
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Superb178 reviews4.9
Create memories that lasts a lifetime with a day on the Gulf of Mexico sailing to a private island f....
Private Tour
1-Hour Interactive Pirate Cruise (arrive 30 minutes early)
Prepare for high seas adventure on this fully interactive, family-friendly, 1-Hour Pirate Adventure Cruise (check in is a half hour before the sail time) along Florida’s Intracoastal Waterway that’s fun for the whole family! T... More
Private Tour
Likely to Sell Out 1-Hour Interactive Pirate Cruise (arrive 30 minutes early)
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North America
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Superb1,506 reviews4.9
Prepare for high seas adventure on this fully interactive, family-friendly, 1-Hour Pirate Adventure ....
Private Tour
Private Sailing Charter with Captain, BYOB
Embark on an exclusive sailing adventure on board "Esprit de Joy," tailor-made for groups of up to 6 guests for a 2.5-hour charter embracing Charleston's scenic Harbor. The golden hour of sunset is our prime booking time, offering... More
Private Tour
Likely to Sell Out Private Sailing Charter with Captain, BYOB
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North America
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Superb69 reviews5
Embark on an exclusive sailing adventure on board "Esprit de Joy," tailor-made for groups of up to 6....
Private Tour
Afternoon Sail & Snorkel to the Captain Cook Monument
A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient lava flows. As you arrive at the "World Famous Captain Cook Monument" your snorkeling adve... More
Private Tour
Likely to Sell Out Afternoon Sail & Snorkel to the Captain Cook Monument
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North America
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Superb250 reviews4.9
A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathtakin....
Private Tour
Waikiki Sunset Cruise from Oahu
Experience a Hawaiian sunset sail aboard our 55-foot double-decker catamaran. With spacious decks and a submerged glass-bottom viewing room, you’ll have an ideal vantage point to observe marine life such as dolphins, whales, sea... More
Private Tour
Likely to Sell Out Waikiki Sunset Cruise from Oahu
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North America
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Superb53 reviews4.8
Experience a Hawaiian sunset sail aboard our 55-foot double-decker catamaran. With spacious decks an....
Private Tour
2 hour Tiki Pub Sensational Dolphin Sunset Cruise (Adults only)
Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages (BYOB), take pics, get some sun, make friends, play party games and have a blast! With a cozy capacity for 25, choose between mingling with new pal... More
Private Tour
Likely to Sell Out 2 hour Tiki Pub Sensational Dolphin Sunset Cruise (Adults only)
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North America
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Superb124 reviews4.9
Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages (BYOB), take pics,....
Private Tour
Cabo San Lucas Small-Group Whale Watching Tour: Hear the Whales
Your whale watching tour in Cabo San Lucas will become magical with the help of professional-grade hydrophones. If whales are communicating, you may be lucky to get the rare opportunity to hear the whale songs live! Our RABEN (Me... More
Private Tour
Likely to Sell Out Cabo San Lucas Small-Group Whale Watching Tour: Hear the Whales
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North America
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Superb14 reviews4.9
Your whale watching tour in Cabo San Lucas will become magical with the help of professional-grade h....
Private Tour
Southwest Florida Sunset Sail
SWFL sunsets are the best, and there is no better place to watch them than from the deck of our 36ft. Sailing Catamaran, "Copacetic". The sunset hours are a magical time to be out on the water. With the winds calm, the sun turns g... More
Private Tour
Likely to Sell Out Southwest Florida Sunset Sail
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North America
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Superb494 reviews4.9
SWFL sunsets are the best, and there is no better place to watch them than from the deck of our 36ft....
Private Tour
Luxury Sunset Sailing Cruise in Cancun with Light Dinner and Open Bar
*Step into luxury when you board one of our fully-equipped sailboats. *Receive a friendly greeting from our crew who will provide you with unmatched service throughout the excursion. *Take a moment for a photo opportunity with y... More
Private Tour
Likely to Sell Out Luxury Sunset Sailing Cruise in Cancun with Light Dinner and Open....
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North America
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Exellent85 reviews4.5
*Step into luxury when you board one of our fully-equipped sailboats. *Receive a friendly greeting ....
Private Tour
Full-Day Luxurious Catamaran Adventure - Cancún to Isla Mujeres
Discover Isla Mujeres in our luxury 45-foot catamaran over the beautiful Caribbean Sea, enjoying a delicious drink and the entertainment from the crew. Unique and quality service is our priority. We are sure that you will love all... More
Private Tour
Likely to Sell Out Full-Day Luxurious Catamaran Adventure - Cancún to Isla Mujeres
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North America
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Exellent305 reviews4.4
Discover Isla Mujeres in our luxury 45-foot catamaran over the beautiful Caribbean Sea, enjoying a d....
Private Tour
Key West Reef Snorkel & Sail Adventure
Join us for a snorkel adventure to the only living coral reef in North America. We have several fantastic reefs to choose from on both the north and south sides of Key West, each offering a unique experience. It’s about an hour ... More
Private Tour
Likely to Sell Out Key West Reef Snorkel & Sail Adventure
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North America
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Superb548 reviews4.7
Join us for a snorkel adventure to the only living coral reef in North America. We have several fant....
Private Tour
Puerto Vallarta Luxury Sailing with Premium Open bar & lunch
Sail across Banderas Bay in luxury aboard our exclusive Leopard and Beneteau yachts, taking in breathtaking views of Puerto Vallarta’s coastline and the majestic Sierra Madre mountains. This small-group experience offers a perfe... More
Private Tour
Likely to Sell Out Puerto Vallarta Luxury Sailing with Premium Open bar & lunch
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North America
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Superb308 reviews4.8
Sail across Banderas Bay in luxury aboard our exclusive Leopard and Beneteau yachts, taking in breat....
Private Tour
Oahu: 3 Hours - Kane‘ohe Sandbar Splash and Snorkeling Adventure
Discover an unforgettable side of O‘ahu most visitors never experience! Our Kāneʻohe Sandbar Splash & Snorkeling Adventure takes you beyond Waikiki to the serene waters of Kāneʻohe Bay, framed by the dramatic Ko‘olau mount... More
Private Tour
Likely to Sell Out Oahu: 3 Hours - Kane‘ohe Sandbar Splash and Snorkeling Adventur....
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North America
Discover an unforgettable side of O‘ahu most visitors never experience! Our Kāneʻohe Sandbar Spl....
Private Tour
Sail Biscayne Bay: An Intimate Eco-Adventure with Snorkeling
This tour is an intimate experience, our groups are 3-5 people per boat maximum. We have two boats. We have been sailing the Biscayne Bay for over 15 years, just for the fun of it. We started this eco-tour in 2018 to share the ama... More
Private Tour
Likely to Sell Out Sail Biscayne Bay: An Intimate Eco-Adventure with Snorkeling
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North America
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Superb453 reviews4.9
This tour is an intimate experience, our groups are 3-5 people per boat maximum. We have two boats. ....
Private Tour
Suncoast Sailing's Sunset Sailing Experience!
Step aboard Suncoast Horizon, a real working schooner and experience what sailing is actually supposed to feel like. No roaring engines. No canned tour script. Just wind in the sails, salt in the air, and the kind of quiet glide ... More
Private Tour
Likely to Sell Out Suncoast Sailing's Sunset Sailing Experience!
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North America
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Superb267 reviews4.9
Step aboard Suncoast Horizon, a real working schooner and experience what sailing is actually suppos....
Private Tour
Your Private Miami Yacht Charter with Music and Fun
Ready for the party of a lifetime? Step aboard our luxurious Yacht Tour in Miami Beach and celebrate like never before. This VIP experience is designed for fun, style, and unforgettable memories with your group. Adventure Highlig... More
Private Tour
Likely to Sell Out Your Private Miami Yacht Charter with Music and Fun
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North America
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Superb65 reviews4.6
Ready for the party of a lifetime? Step aboard our luxurious Yacht Tour in Miami Beach and celebrate....
Private Tour