Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 714 Sailing Trips activities in North America. Sort by Popularity. - Page 6Up to 34Pax Bachelorette Party Boat & Yacht Rental Miami
Price Includes up to 34 Pax Discover the magic of the ocean in Miami! with Dolphin Water Sport. Our +1250 reviews on Google with a 4.9 score guarantee our quality. Immerse yourself in a unique adventure as you glide through the ... More
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Up to 34Pax Bachelorette Party Boat & Yacht Rental Miami
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North America
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Superb19 reviews5
Price Includes up to 34 Pax Discover the magic of the ocean in Miami! with Dolphin Water Sport. Our....
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America's Cup 12-Meter Yacht Afternoon Sail from Hilton Head
Only on Hilton Head and only in Harbour Town can you sail aboard the real America's Cup, 12 meter, Stars & Stripes once skippered by the famous Dennis Connor. All trips take place under full sail. We only use our motor to get in a... More
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America's Cup 12-Meter Yacht Afternoon Sail from Hilton Head
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North America
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Superb579 reviews4.6
Only on Hilton Head and only in Harbour Town can you sail aboard the real America's Cup, 12 meter, S....
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Sunset Dolphin Sail Aboard the Footloose Catamaran
If you are looking to unwind before dinner or a night out on the town, come take a romantic Sunset Sail on SV Footloose, our 38 passenger catamaran, with Paradise Adventures! This breathtaking sunset sail along the Gulf of Mexico ... More
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Sunset Dolphin Sail Aboard the Footloose Catamaran
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North America
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Superb486 reviews4.8
If you are looking to unwind before dinner or a night out on the town, come take a romantic Sunset S....
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Key West Morning Snorkel Sail with Mimosas and Gourmet Breakfast
Embark on an adventure off the shores of Key West, where the turquiose waters of the Gulf of Mexico and the Atlantic Ocean meet in a symphony of beauty and tranquility. Your day begins as you board a luxurious catamaran, your vess... More
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Key West Morning Snorkel Sail with Mimosas and Gourmet Breakfast
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North America
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Superb212 reviews4.7
Embark on an adventure off the shores of Key West, where the turquiose waters of the Gulf of Mexico ....
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Premium Private 47ft Catamaran Snorkel & El Cielo (30p max)
Private 6-hour charter for up to 30 guests aboard Nemo, a spacious 47ft Nautitech catamaran, with El Cielo, guided snorkeling, fresh lunch, open bar and Marine Park fees included. Just 5–10 minutes by taxi from Cozumel’s cruis... More
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Premium Private 47ft Catamaran Snorkel & El Cielo (30p max)
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North America
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Superb26 reviews4.8
Private 6-hour charter for up to 30 guests aboard Nemo, a spacious 47ft Nautitech catamaran, with El....
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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
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Best Waikiki Sunset Cruise: BYOB Sunset Sail with Swimming
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North America
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Superb221 reviews4.9
Our vessel "Hokulani" is a beautiful and spacious custom built sailing trimaran specifically designe....
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Laguna Grill - Private Boat with on-board BBQ and Drinks Included
One of a kind in Bacalar! Cruise, swim, eat and drink in Bacalars most complete activity. Enjoy nature away from crowds while enjoying an on board BBQ.... More
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Laguna Grill - Private Boat with on-board BBQ and Drinks Included
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North America
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Superb151 reviews5
One of a kind in Bacalar! Cruise, swim, eat and drink in Bacalars most complete activity. Enjoy natu....
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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
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Likely to Sell Out Sail Biscayne Bay: An Intimate Eco-Adventure with Snorkeling
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North America
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Superb470 reviews4.9
This tour is an intimate experience, our groups are 3-5 people per boat maximum. We have two boats. ....
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Maui Premier Whale Watching Cruise - Luxury Catamaran Experience
From December through April, the waters off Maui come alive with the sights and sounds of the majestic humpback whales, and there’s no better way to witness the wonder than from the deck of our 65’ catamaran. This two-hour ex... More
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Likely to Sell Out Maui Premier Whale Watching Cruise - Luxury Catamaran Experience
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North America
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Superb89 reviews4.9
From December through April, the waters off Maui come alive with the sights and sounds of the majest....
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Sunset Sailing Cruise in Monterey Bay
Looking to impress your date or just treat yourself to something unforgettable? Our Sunset Cruise is the most popular (and most romantic!) way to experience Monterey Bay. Departing daily, 90 minutes before sunset, this dreamy 1.5-... More
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Likely to Sell Out Sunset Sailing Cruise in Monterey Bay
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North America
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Superb62 reviews4.8
Looking to impress your date or just treat yourself to something unforgettable? Our Sunset Cruise is....
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Beach Island Shelling Cruise to Keewaydin Island Tour
Enjoy a family favorite cruise aboard the Sweet Liberty, a 53' sailing catamaran, that can accommodate up to 44 passengers. Cruise along the Gordon River in Naples Bay and head out to Keewaydin Island, a 7-mile barrier island, wit... More
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Likely to Sell Out Beach Island Shelling Cruise to Keewaydin Island Tour
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North America
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Superb122 reviews4.9
Enjoy a family favorite cruise aboard the Sweet Liberty, a 53' sailing catamaran, that can accommoda....
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Private Catamaran Charter in Waikiki (1-6 Guests)
Our 48-foot catamaran has a sleek low-profile design which makes it optimal for stability out on the ocean. It has 2 large lounging nets on the front of the boat, as well as 2 small nets on the back of the boat. Not only does Hawa... More
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Likely to Sell Out Private Catamaran Charter in Waikiki (1-6 Guests)
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North America
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Superb25 reviews5
Our 48-foot catamaran has a sleek low-profile design which makes it optimal for stability out on the....
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2hr. INTERACTIVE Sailing Experience on San Francisco Bay
This is an Interactive Sailing Experience on San Francisco Bay with a maximum 6 passengers on a private yacht with a USCG licensed captain and crew where you'll sail beneath the Golden Gate Bridge, across the San Francisco waterfr... More
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Likely to Sell Out 2hr. INTERACTIVE Sailing Experience on San Francisco Bay
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North America
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Superb106 reviews5
This is an Interactive Sailing Experience on San Francisco Bay with a maximum 6 passengers on a priv....
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Private Luxury 42ft Sailing with Snorkeling in Los Cabos
Sail Cabo San Lucas aboard a luxurious 42 feet private sailing boat. Enjoy an unforgettable time Snorkeling with tropical fishes and cruise along the beautiful white beaches. Your yacht and crew will provide you with all the ameni... More
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Likely to Sell Out Private Luxury 42ft Sailing with Snorkeling in Los Cabos
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North America
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Superb130 reviews5
Sail Cabo San Lucas aboard a luxurious 42 feet private sailing boat. Enjoy an unforgettable time Sno....
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Costa Maya: Chacchoben & Bacalar sailing or Los Rápidos
Ideal for cruisers with at least 7 hours in Costa Maya. Chacchoben + Bacalar: Sailing or The Rapids Your adventure begins at Costa Maya Cruise Port, where our driver will pick you up at the agreed time. We will visit the Mayan R... More
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Likely to Sell Out Costa Maya: Chacchoben & Bacalar sailing or Los Rápidos
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North America
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Superb117 reviews4.9
Ideal for cruisers with at least 7 hours in Costa Maya. Chacchoben + Bacalar: Sailing or The Rapid....
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Sunset Cruise Tour
Kick back and relax on this beautiful 53' sailing catamaran that can accommodate up to 44 passengers. Cruise through the prestigious Port Royal neighborhood in Naples Bay and then set sail into the Gulf of Mexico to watch a breath... More
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Likely to Sell Out Sunset Cruise Tour
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North America
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Superb109 reviews4.9
Kick back and relax on this beautiful 53' sailing catamaran that can accommodate up to 44 passengers....
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Boat Ride to the Arch with Snorkeling in Cabo
This is more than a sightseeing cruise — it's a chance to see Cabo through the eyes of local marine experts. Your guide and captain are both trained biologists who share in-depth, science-backed insight into the marine life and ... More
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Likely to Sell Out Boat Ride to the Arch with Snorkeling in Cabo
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North America
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Superb194 reviews5
This is more than a sightseeing cruise — it's a chance to see Cabo through the eyes of local marin....
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Private Luxury Yacht Charters, BYOB & Dolphins
We are a family owned luxury yacht charter business. Come enjoy a BYOB day of sailing and seeing the historic sites of Charleston from the water on one of our sailboats. We offer hourly, daily, or customized tours according to you... More
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Likely to Sell Out Private Luxury Yacht Charters, BYOB & Dolphins
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North America
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Superb430 reviews5
We are a family owned luxury yacht charter business. Come enjoy a BYOB day of sailing and seeing the....
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Lahaina Maui Sea Turtle Snorkel Sail Adventure w/Lunch & Open Bar
Ready for an unforgettable day of sailing, snorkeling, island lunch, and open bar aboard our luxury sailing catamaran? Perfect for families, couples, kids, first-time snorkelers, and ocean lovers, this Lahaina adventure combines a... More
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Likely to Sell Out Lahaina Maui Sea Turtle Snorkel Sail Adventure w/Lunch & Open Bar
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North America
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Superb143 reviews5
Ready for an unforgettable day of sailing, snorkeling, island lunch, and open bar aboard our luxury ....
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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
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Likely to Sell Out 2 hour Tiki Pub Sensational Dolphin Sunset Cruise (Adults only)
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North America
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Superb156 reviews4.9
Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages (BYOB), take pics,....
Free Cancellation
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(Saving inf% )