Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 692 Sailing Trips activities in North America. Sort by Popularity. - Page 8Sea to Sky Afternoon Sail
Prepare yourself for an adventure that balances the thrill of sailing Howe Sound's legendary winds with the breathtaking views of the Coastal and Tantalus mountain ranges. We will depart from the docks in Squamish (about 40 minut... More

Sea to Sky Afternoon Sail
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North America
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Superb206 reviews5
Prepare yourself for an adventure that balances the thrill of sailing Howe Sound's legendary winds w....
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

Catamaran Day Sail Shelling Excursion 42ft. Mainecat Cool Beans
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North America
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Superb139 reviews4.9
Create memories that lasts a lifetime with a day on the Gulf of Mexico sailing to a private island f....
Private Cabo 35ft cat experience Food and open bar included!
Barta is an extremely fun and comfort 36ft catamaran specifically designed to accommodate large groups of up to 20 passengers. Immerse yourself in the scenic wonders of the bay of Cabo San Lucas as Barta gracefully navigates, ensu... More
Private Tour

Private Cabo 35ft cat experience Food and open bar included!
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North America
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Superb314 reviews4.9
Barta is an extremely fun and comfort 36ft catamaran specifically designed to accommodate large grou....
Private Tour
JFarwell Sunset Wine and Cheese Yacht Sailing
Our 45' luxury sailing yacht is one of a kind on the Halifax waterfront. Our hands-on crew love to invite our guests to be involved in sailing - take the helm, hoist the sails, or sit back and enjoy the beautiful sights and wines ... More
Private Tour

JFarwell Sunset Wine and Cheese Yacht Sailing
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North America
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Superb121 reviews4.9
Our 45' luxury sailing yacht is one of a kind on the Halifax waterfront. Our hands-on crew love to i....
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
Sunset Cruise on the Scenic & Calming Chesapeake Bay
Watching the sunset over the twin beaches on the Western Shores of the Chesapeake Bay! A great way to close out a summer day with beautiful photos of the sunset. You must call 24 hours before your cruise time to see if the minimum... More
Private Tour

Sunset Cruise on the Scenic & Calming Chesapeake Bay
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North America
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Superb11 reviews4.7
Watching the sunset over the twin beaches on the Western Shores of the Chesapeake Bay! A great way t....
Private Tour
Sunset Sail from Ma'alaea Harbor
Enjoy tantalizing pupus (appetizers) and island-style music against the backdrop of a stunning sunset over the Pacific Ocean.This relaxing cruise is aboard our luxury sailing catamaran, Ocean Spirit. It’s the perfect way to ex... More
Private Tour

Sunset Sail from Ma'alaea Harbor
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North America
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Superb208 reviews4.6
Enjoy tantalizing pupus (appetizers) and island-style music against the backdrop of a stunning sunse....
Private Tour
FROM FLORIDA: Bimini Bahamas Day Trip By Fast Ferry
Take advantage of the vicinity of the Bahamas Islands during your Florida visit to experience the world's best beaches. The ocean crossing is provided with our comfortable Express-Ferry featuring restrooms, comfortable seats, air ... More
Private Tour

FROM FLORIDA: Bimini Bahamas Day Trip By Fast Ferry
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North America
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Good11 reviews3.4
Take advantage of the vicinity of the Bahamas Islands during your Florida visit to experience the wo....
Private Tour
Sunset Catamaran Sail in Cocoa Beach
Experience a Magical Sunset in Cocoa Beach! Set sail into the golden hour and enjoy a stunning evening on the serene waters of the Banana River Lagoon. Our Sunset Sail is the perfect way to relax and take in the beauty of Floridaâ... More
Private Tour

Sunset Catamaran Sail in Cocoa Beach
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North America
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Superb146 reviews5
Experience a Magical Sunset in Cocoa Beach! Set sail into the golden hour and enjoy a stunning eveni....
Private Tour
Suncoast Sailing's Sunset Sailing Experience!
Set sail aboard the iconic schooner Suncoast Horizon as we set sail in the picturesque waters of Treasure Island, Florida! You’ll set sail about an hour before sunset to give you plenty of time to catch the full range of hues p... More
Private Tour

Suncoast Sailing's Sunset Sailing Experience!
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North America
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Superb222 reviews4.9
Set sail aboard the iconic schooner Suncoast Horizon as we set sail in the picturesque waters of Tre....
Private Tour
Private Fishing Trip "All Inclusive" in Cabo San Lucas, Mexico
Embark on the most exciting fishing adventure in the crystal-clear waters of Cabo San Lucas. Our all-inclusive fishing tour offers you a unique opportunity to immerse yourself in an authentic, action-packed fishing experience, wit... More
Private Tour

Private Fishing Trip "All Inclusive" in Cabo San Lucas, Mexico
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North America
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Superb303 reviews4.7
Embark on the most exciting fishing adventure in the crystal-clear waters of Cabo San Lucas. Our all....
Private Tour
Newport Sunset Sail on Classic Sailboat
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 sailboat and see all of Newport's iconic sights from the water including histor... More
Private Tour

Newport Sunset Sail on Classic Sailboat
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North America
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Superb21 reviews4.8
Sunset sailing is one of the best evening activities to do during your stay in Newport, RI. Enjoy a ....
Private Tour
Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast
As you swim off of the coast of the world famous Waikiki beach, you’ll realize you’ve found your very own piece of paradise. Just far away enough from the bustling travelers and crowded beaches, the crystal-clear water will br... More
Private Tour

Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast
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North America
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Superb185 reviews4.9
As you swim off of the coast of the world famous Waikiki beach, you’ll realize you’ve found your....
Private Tour
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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Superb177 reviews5
Sail from Cabo San Lucas on a beautiful private 38 feet sailing boat and snorkel in tropical water....
Private Tour
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

Private Sunset Sail BYOB Dolphin/History Tours on 43ft Mystique
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North America
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Superb31 reviews5
Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charte....
Private Tour
Monterey Private 3 - 4 Hour Whale Watching Cruise
Enjoy a 3 - 4 hour sailing cruise on the Monterey Bay. This Marine Mammal and Wildlife Safari is a private guided tour and can accommodate up to 6 people. Whale sightings are NOT guaranteed. However, this tour is designed to give... More
Private Tour

Monterey Private 3 - 4 Hour Whale Watching Cruise
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North America
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Superb2 reviews5
Enjoy a 3 - 4 hour sailing cruise on the Monterey Bay. This Marine Mammal and Wildlife Safari is a p....
Private Tour
9am Turtle Canyon Snorkel Adventure
What better way to start your day than to slip into the refreshing waters of Turtle Canyon and swim with amazing green sea turtles, beautiful tropical fish, and other incredible marine life? Our snorkel guides help you feel confid... More
Private Tour

9am Turtle Canyon Snorkel Adventure
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North America
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Superb254 reviews4.9
What better way to start your day than to slip into the refreshing waters of Turtle Canyon and swim ....
Private Tour
Schooner Fame Sailing Tour
FAME is annually the #1-rated boat in Salem and the #1 outdoor activity in the entire town, per TripAdvisor. Don't miss the very best of what Salem has to offer! There's more to our town than witches! FAME is a full-scale replica... More
Private Tour

Schooner Fame Sailing Tour
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North America
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Superb528 reviews4.9
FAME is annually the #1-rated boat in Salem and the #1 outdoor activity in the entire town, per Trip....
Private Tour
Full-Day Private Sailing Cruise Puerto Vallarta with Snorkeling
Enjoy a private tour on an exclusive sailboat with a fully customizable experience through Puerto Vallarta´s Bay. You will be able to Sail, Snorkel, Swim and even Paddelboard in Los Arcos National Park, capturing beautiful views ... More
Private Tour

Full-Day Private Sailing Cruise Puerto Vallarta with Snorkeling
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North America
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Superb108 reviews4.9
Enjoy a private tour on an exclusive sailboat with a fully customizable experience through Puerto Va....
Private Tour
Miami Beach Luxury Yacht Adventure: Explore Stunning Coastline
Embark on a private yacht journey, perfect for families, couples, & adventurers seeking a unique Miami Beach experience. Connect with nature, discover new landscapes, & create lasting memories as you explore the stunning coastline... More
Private Tour

Miami Beach Luxury Yacht Adventure: Explore Stunning Coastline
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North America
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Superb23 reviews4.8
Embark on a private yacht journey, perfect for families, couples, & adventurers seeking a unique Mia....
Private Tour