Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 705 Sailing Trips activities in North America. Sort by Popularity. - Page 10Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure
Snorkel Turtle Canyon on the Largest Luxury Catamaran! Top Quality Gear, Certified Crew & Premium On Board Bar. When you trust Moana Sailing Co. for your snorkel adventure, you’re choosing the tour with the most professionalis... More

Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventu....
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North America
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Superb922 reviews4.7
Snorkel Turtle Canyon on the Largest Luxury Catamaran! Top Quality Gear, Certified Crew & Premium On....
Cabo San Lucas Private 38 ft Sailing Tour with Snorkeling
Sail from Cabo San Lucas on a beautiful private 38 feet sailing boat and snorkel in tropical waters alongside colorful sea life. The bilingual crew is happy to accommodate any special occasion or request. This unforgettable ex... More
Private Tour

Cabo San Lucas Private 38 ft Sailing Tour with Snorkeling
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North America
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Superb178 reviews5
Sail from Cabo San Lucas on a beautiful private 38 feet sailing boat and snorkel in tropical water....
Private Tour
2-hour Private Luxury New York City Sunset Boat Tour
Experience the breathtaking beauty of New York City as the sun sets behind the Statue of Liberty and reflects off of the city skyline on this magical 2-hour sunset cruise around lower Manhattan! Get an unobstructed view of the Man... More
Private Tour

2-hour Private Luxury New York City Sunset Boat Tour
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North America
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Superb25 reviews5
Experience the breathtaking beauty of New York City as the sun sets behind the Statue of Liberty and....
Private Tour
Ft Myers Beach 3 Hour Tiki Pub Tropical Sandbar Getaway Cruise
Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages, 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 pals on ou... More
Private Tour

Ft Myers Beach 3 Hour Tiki Pub Tropical Sandbar Getaway Cruise
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North America
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Superb19 reviews5
Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages, take pics, get so....
Private Tour
Schooner Applejack Sunset Sail Tour in Boothbay Harbor
Welcome Aboard Schooner Applejack in Boothbay Harbor; your Maine Vacation starts here! Join the Schooner crew for a sunset sail adventure on Boothbay Harbor’s oldest windjammer. Help hoist sails or take a turn at the wheel as we... More
Private Tour

Schooner Applejack Sunset Sail Tour in Boothbay Harbor
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North America
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Superb24 reviews4.9
Welcome Aboard Schooner Applejack in Boothbay Harbor; your Maine Vacation starts here! Join the Scho....
Private Tour

Polynesian Canoe Sunset Sail
Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) offering a one-of-a-kind native Hawaiian cultural and educational experience. Come sail along the beautiful Waikiki coastline and b... More
Free Cancellation
Private Tour
(Saving 10% )

Polynesian Canoe Sunset Sail
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North America
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Superb122 reviews4.9
Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) o....
Free Cancellation
Private Tour
(Saving 10% )
2 hour Tiki Pub Sensational 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

2 hour Tiki Pub Sensational Sunset Cruise (Adults only)
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North America
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Superb73 reviews4.9
Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages (BYOB), take pics,....
Private Tour
Catamaran Sail and Snorkeling Tour with Open Bar in Puerto Morelos
Join us for an unforgettable sailboat tour to the stunning Puerto Morelos Reef, a part of the Mesoamerican Barrier Reef System, the second-largest coral reef in the world! Departing daily at 9 AM and 2 PM, our adventure begins wit... More
Private Tour

Catamaran Sail and Snorkeling Tour with Open Bar in Puerto Morelo....
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North America
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Very Good10 reviews3.7
Join us for an unforgettable sailboat tour to the stunning Puerto Morelos Reef, a part of the Mesoam....
Private Tour

Small Group Key West Adult Sunset & Moët Sail & Amazing Cheeses
Avoid the crowds and Sail on Key West’s beautiful shallow waters on this Adults Only Sunset & Moët cruise, to sip Moët & Chandon champagne and indulge your palate while being washed in the colors of the Key West sunset! Incl... More
Free Cancellation
Private Tour
(Saving 10% )

Small Group Key West Adult Sunset & Moët Sail & Amazing Cheeses
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North America
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Superb912 reviews4.9
Avoid the crowds and Sail on Key West’s beautiful shallow waters on this Adults Only Sunset & Moë....
Free Cancellation
Private Tour
(Saving 10% )
Small-Group San Diego Afternoon Sailing Excursion
This three-hour adventure on a a beautiful modern-day sailboat is limited to just 6 people, allowing you a comfortable, semi-private experience (or, grab five friends and fill up the whole boat!). Sit back, relax and enjoy the com... More
Private Tour

Small-Group San Diego Afternoon Sailing Excursion
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North America
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Superb514 reviews5
This three-hour adventure on a a beautiful modern-day sailboat is limited to just 6 people, allowing....
Private Tour
4-Hour St. Pete Pier to Egmont Key Experience by Ferry
From the Pier to Paradise. You’ll sail by the beautiful shorelines of St. Pete, pass under the stunning Sunshine Skyway bridge and perhaps see a dolphin or two! This is the only charter offering service from downtown St. Petersb... More
Private Tour

4-Hour St. Pete Pier to Egmont Key Experience by Ferry
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North America
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Superb298 reviews4.7
From the Pier to Paradise. You’ll sail by the beautiful shorelines of St. Pete, pass under the stu....
Private Tour
Private Sunset and Dolphin Cruise in Destin-Up to 16 Guests
Our cruise is a private tour to see Destin's sunset as you want to see it. We can look for Dolphins, or watch the sunset from classic Destin Locations Crab Island and Norriego Point. Our boat includes a full restroom, as well as a... More
Private Tour

Private Sunset and Dolphin Cruise in Destin-Up to 16 Guests
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North America
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Superb40 reviews5
Our cruise is a private tour to see Destin's sunset as you want to see it. We can look for Dolphins,....
Private Tour
Hawaiian Canoe Sailing Experience in Maui
Sail, Snorkel, and Paddle the beautiful Wailea coast in a Hawaiian Outrigger Canoe. The tour includes snorkeling with sea turtles, seasonal whale watching, and learning Hawaiian history and culture. Cold water and snorkel gear are... More
Private Tour

Hawaiian Canoe Sailing Experience in Maui
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North America
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Superb58 reviews4.8
Sail, Snorkel, and Paddle the beautiful Wailea coast in a Hawaiian Outrigger Canoe. The tour include....
Private Tour

Luxury Camden Sailing Experience
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North America
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Superb2 reviews5
Small groups of up to six. Two staff members to take care of you. Cushioned seating for all. Faste....
Private Tour
Daytime Sailing Along San Diego's Skyline
Set sail with your Captain aboard our sail yacht and see some of San Diego's finest highlights on thisfamily-friendly sailing experience. We'll set sail from Safeharbor Sunroad Marina on Harbor Island on San Diego Bay, we often s... More
Private Tour

Daytime Sailing Along San Diego's Skyline
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North America
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Superb140 reviews4.9
Set sail with your Captain aboard our sail yacht and see some of San Diego's finest highlights on th....
Private Tour
Amazing Romantic Dinner on a Spanish Galeon with Saxophone Music
Have you run out of ideas to celebrate love with your partner? Imagine reconquering your true love. In Cancun, you have an incredible opportunity to fall in love again at the rhythm of the live sax with a sunset as enchanting as t... More
Private Tour

Amazing Romantic Dinner on a Spanish Galeon with Saxophone Music
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North America
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Superb93 reviews4.6
Have you run out of ideas to celebrate love with your partner? Imagine reconquering your true love. ....
Private Tour
Cancun Adults Only Party Cruise to Isla Mujeres with Open Bar
Take a Party Cruise Adult Only from Cancun to Isla Mujeres. Make a stop to snorkel at one of the best reefs and see beautiful tropical fish. Enjoy a delicious buffet lunch on our private beach club, and then tour Isla Mujeres to s... More
Private Tour

Cancun Adults Only Party Cruise to Isla Mujeres with Open Bar
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North America
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Very Good203 reviews3.7
Take a Party Cruise Adult Only from Cancun to Isla Mujeres. Make a stop to snorkel at one of the bes....
Private Tour
Bimini or Grand Bahama Island by Ferry
Escape to the Bahamas! Get ready for an unforgettable day in the Bahamas, just off the coast of Florida! Picture this: pristine white beaches, crystal-clear turquoise waters, and tons of fun activities waiting for you. We'll pick... More
Private Tour

Bimini or Grand Bahama Island by Ferry
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North America
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Very Good13 reviews3.6
Escape to the Bahamas! Get ready for an unforgettable day in the Bahamas, just off the coast of Flor....
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

Puerto Vallarta Luxury Sailing with Premium Open bar & lunch
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North America
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Superb293 reviews4.8
Sail across Banderas Bay in luxury aboard our exclusive Leopard and Beneteau yachts, taking in breat....
Private Tour
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
Private Tour

Sunset Sail Cruise in Key West
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North America
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Superb235 reviews4.9
Sailing on the Rover is an exciting, traditional sailing experience with a Hint of Piracy! Yes - We ....
Private Tour