Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 712 Sailing Trips activities in North America. Sort by Popularity. - Page 14Sunset Cruise with the Whales from Anaeho'omalu Bay
Combine unparalleled views of the Hawaiian coastline from a stable and spacious catamaran with the biggest guests of all -- the Humpback Whales -- and you have perfect way to begin your evening in paradise! Cruise along the Kohala... More
Sunset Cruise with the Whales from Anaeho'omalu Bay
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North America
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Superb46 reviews4.8
Combine unparalleled views of the Hawaiian coastline from a stable and spacious catamaran with the b....
Deluxe private Sunset & Day Sail
Set sail on the ultimate San Diego adventure! Departing from 955 Harbor Island Drive, our thrilling voyage takes you through breathtaking waters, past iconic landmarks, and into the heart of coastal paradise. Feel the wind in your... More
Private Tour
Likely to Sell Out Deluxe private Sunset & Day Sail
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North America
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Superb2 reviews5
Set sail on the ultimate San Diego adventure! Departing from 955 Harbor Island Drive, our thrilling ....
Private Tour
Bacalar Lagoon Tour Open Bar With Pick Up
What makes our tour unique: • Multilingual captain: English, French and Spanish. • Comfortable pickup from your hotel in van. • Cold drinks and Mexican snacks during the tour. • Snorkeling and water games for children... More
Private Tour
Likely to Sell Out Bacalar Lagoon Tour Open Bar With Pick Up
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North America
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Superb78 reviews4.9
What makes our tour unique: • Multilingual captain: English, French and Spanish. • Comfortabl....
Private Tour
Polynesian Canoe Morning 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
Private Tour
Likely to Sell Out Polynesian Canoe Morning Sail
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North America
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Superb18 reviews5
Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) o....
Private Tour
Serene Private Sunset Sail on Lake Michigan - Navy Pier, Chicago
Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront. Kick back, relax, and let the US Coast Guard licensed captain treat you to stunning views of Chicago’s spectacular skyline. ... More
Private Tour
Likely to Sell Out Serene Private Sunset Sail on Lake Michigan - Navy Pier, Chicago
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North America
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Superb27 reviews5
Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefro....
Private Tour
HipHop Catamaran Party from Cancun to Isla Mujeres
Unlike other tours, we combine adventure, relaxation, and an unforgettable party vibe. Start by snorkeling in one of the Caribbean's top reefs, surrounded by vibrant marine life. Then, head to a secluded sandbank—a hidden gem pe... More
Private Tour
Likely to Sell Out HipHop Catamaran Party from Cancun to Isla Mujeres
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North America
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Very Good11 reviews4
Unlike other tours, we combine adventure, relaxation, and an unforgettable party vibe. Start by snor....
Private Tour
Likely to Sell Out
Clear Boat to Cabo Lands End, The Arch and more
Are you ready for an unforgettable experience? Come to visit the spectacular sea of Los Cabos, most uniquely, in a clear boat. You will take a tour just where the Pacific Ocean meets the Sea of Cortez, the famous Lands End. In our... More
Free Cancellation
Private Tour
(Saving 10% )
Likely to Sell Out Clear Boat to Cabo Lands End, The Arch and more
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North America
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Exellent12 reviews4.4
Are you ready for an unforgettable experience? Come to visit the spectacular sea of Los Cabos, most ....
Free Cancellation
Private Tour
(Saving 10% )
Los Cabos Catamaran Cruise with Open Bar & Light Snack
Experience Los Cabos from the best seat in the house — aboard a spacious catamaran cruising past its most iconic landmarks. Sail along the dazzling Cabo coastline to The Arch (El Arco), Lover’s Beach, and Divorce Beach, where ... More
Private Tour
Likely to Sell Out Los Cabos Catamaran Cruise with Open Bar & Light Snack
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North America
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Very Good8 reviews3.9
Experience Los Cabos from the best seat in the house — aboard a spacious catamaran cruising past i....
Private Tour
Private Sunset Catamaran Sail in Cocoa Beach
Experience a magical sunset in with Cocoa Beach Catamaran 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 bea... More
Private Tour
Likely to Sell Out Private Sunset Catamaran Sail in Cocoa Beach
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North America
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Very Good8 reviews3.9
Experience a magical sunset in with Cocoa Beach Catamaran Set sail into the golden hour and enjoy a....
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
Likely to Sell Out Private Sunset Sail BYOB Dolphin/History Tours on 43ft Mystique
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North America
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Superb42 reviews5
Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charte....
Private Tour
Whale-Watching Pirate Ship Cruise in Los Cabos
Go whale-watching in Cabo San Lucas aboard a real pirate ship called the Bucaneer Queen. Sail the Pacific Ocean and the Sea of Cortez in search of these amazing creatures. You will be accompanied by an experienced bilingual guide ... More
Private Tour
Likely to Sell Out Whale-Watching Pirate Ship Cruise in Los Cabos
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North America
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Superb98 reviews4.7
Go whale-watching in Cabo San Lucas aboard a real pirate ship called the Bucaneer Queen. Sail the Pa....
Private Tour
Private Sunset Sail for Two
Experience intimacy while sailing along the San Diego Bay. Leave your worries behind as you cruise along the vibrant waterfront and marvel at the cityscape. Create a memory of a lifetime while sailing past Downtown, Point Loma, an... More
Private Tour
Likely to Sell Out Private Sunset Sail for Two
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North America
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Superb5 reviews5
Experience intimacy while sailing along the San Diego Bay. Leave your worries behind as you cruise a....
Private Tour
Key West Christmas Cruise with Live Band and Drinks
Join us for a family-friendly holiday sail aboard Schooner America 2.0 decorated with festive Christmas lights! Sing along to your favorite Christmas music with our live band and celebrate the holidays and Christmas in Key West. E... More
Private Tour
Likely to Sell Out Key West Christmas Cruise with Live Band and Drinks
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North America
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Superb3 reviews5
Join us for a family-friendly holiday sail aboard Schooner America 2.0 decorated with festive Christ....
Private Tour
Vancouver Sailing Experience on a 50 foot Sailboat
I have been living aboard full time for the past 12 years, sailing the Vancouver waterways for over 45 years. I have raced competitively for 20 of those, have extensive sailing and local knowledge, 12 years experience volunteering... More
Private Tour
Likely to Sell Out Vancouver Sailing Experience on a 50 foot Sailboat
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North America
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Superb100 reviews5
I have been living aboard full time for the past 12 years, sailing the Vancouver waterways for over ....
Private Tour
Likely to Sell Out
12pm 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
Free Cancellation
Private Tour
(Saving 15% )
Likely to Sell Out 12pm Turtle Canyon Snorkel Adventure
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North America
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Superb300 reviews4.8
What better way to start your day than to slip into the refreshing waters of Turtle Canyon and swim ....
Free Cancellation
Private Tour
(Saving 15% )
Private boat for 6 hours with snorkeling & beaches in Puerto Vallarta
Sail on a private trip aboard our 26-foot boat. Ideal for up to 8 passengers. We are sure that with us you will know the best part of our beautiful bay of Puerto Vallarta. Do not miss the opportunity we offer you to make this rese... More
Private Tour
Likely to Sell Out Private boat for 6 hours with snorkeling & beaches in Puerto Vall....
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North America
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Superb2 reviews5
Sail on a private trip aboard our 26-foot boat. Ideal for up to 8 passengers. We are sure that with ....
Private Tour
Cancun: 4-Hour All Inclusive Luxury Yacht – 50' Cranchi
An incredible 4 hours experience in an exclusive yacht, tasting exquisite dishes and enjoying a day just for you and your family. You can visit different exclusive places... More
Private Tour
Likely to Sell Out Cancun: 4-Hour All Inclusive Luxury Yacht – 50' Cranchi
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North America
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Superb30 reviews5
An incredible 4 hours experience in an exclusive yacht, tasting exquisite dishes and enjoying a day ....
Private Tour
Private Family Catamaran From Isla Mujeres
Enjoy our “Lite Sailing Charters” Sail through the wonderful Bay of Isla Mujeres! Why invest all day when you can do it in less time? Affordable Private Catamaran, avoid crowded vessels Half-day fun catamaran, with a guided sn... More
Private Tour
Likely to Sell Out Private Family Catamaran From Isla Mujeres
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North America
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Superb1 review5
Enjoy our “Lite Sailing Charters” Sail through the wonderful Bay of Isla Mujeres! Why invest all....
Private Tour
Diamond Head Sunset Sail
Hawaii’s Best Sunset Cruise is the experience you don’t want to miss. Our Diamond Head Sunset Sail features a two hour cruise aboard a private luxury yacht. Immerse yourself in a gorgeous Hawaiian sunset the only way, from the... More
Private Tour
Likely to Sell Out Diamond Head Sunset Sail
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North America
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Superb15 reviews4.7
Hawaii’s Best Sunset Cruise is the experience you don’t want to miss. Our Diamond Head Sunset Sa....
Private Tour
Private Luxury Sunset Sail on the 50ft Sailing Yacht Fate BYOB
Sail the Charleston Harbor, see dolphins, amazing sunsets or even participate in real sailing yacht regattas. Fate is not only the most demanded but also the largest and nicest sailing yacht available for Charter in Charleston, kn... More
Private Tour
Likely to Sell Out Private Luxury Sunset Sail on the 50ft Sailing Yacht Fate BYOB
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North America
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Superb55 reviews4.9
Sail the Charleston Harbor, see dolphins, amazing sunsets or even participate in real sailing yacht ....
Private Tour