Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 770 Sailing Trips activities in North America. Sort by Popularity. - Page 5Riviera Maya Luxury Sunset Sailing plus Light Dinner and Open Bar
Experience the sunset like never before on this fabulous Sunset Sailing excursion. You’ll sail along the stunning coastline of the Riviera Maya aboard a luxurious catamaran, while Mother Nature prepares for her nightly performan... More
Riviera Maya Luxury Sunset Sailing plus Light Dinner and Open Bar
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North America
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Superb442 reviews4.6
Experience the sunset like never before on this fabulous Sunset Sailing excursion. You’ll sail alo....
Toronto Tall Ship Boat Cruise
This is your chance to experience Toronto's only tall ship boat cruise! Sail aboard the historic 'Tall Ship Kajama,' a traditional 165-foot, 3-masted schooner boat, and sit back and relax with a cold drink from the bar or order fr... More
Toronto Tall Ship Boat Cruise
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North America
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Exellent680 reviews4.3
This is your chance to experience Toronto's only tall ship boat cruise! Sail aboard the historic 'Ta....
Key West's Favorite Afternoon Dolphin Sail
Our afternoon dolphin watch is limited to an intimate number of passengers to optimize your views! Enjoy sailing aboard a 60' catamaran to the dolphin playground to view wild dolphins play and frolic in their natural habitat. Atla... More
Key West's Favorite Afternoon Dolphin Sail
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North America
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Superb198 reviews4.6
Our afternoon dolphin watch is limited to an intimate number of passengers to optimize your views! E....
Two Hour Coastal Sailing Cruise
What makes this tour unique is the custom experience aboard our 43-foot, 27-foot wide trimaran—one of the largest and most stable sailing vessels in Savannah. Unlike crowded tour boats, our open-deck layout offers plenty of room... More
Two Hour Coastal Sailing Cruise
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North America
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Superb61 reviews5
What makes this tour unique is the custom experience aboard our 43-foot, 27-foot wide trimaran—one....
Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)
Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui sunset begin to paint the sky. As you step aboard, you're greeted by the friendly crew who welcome you with warm aloha spirit. The c... More
Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)
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North America
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Superb54 reviews4.7
Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui su....
Newport Afternoon Sightseeing Sail on Classic Sailboat
Sail on a classic sailboat in Newport, RI, and enjoy a sightseeing sailing experience around Narragansett Bay. Pass by many iconic sights during the sail, including Newport's historic lighthouses and landmarks, bridges, mansions a... More
Likely to Sell Out Newport Afternoon Sightseeing Sail on Classic Sailboat
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North America
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Superb144 reviews4.8
Sail on a classic sailboat in Newport, RI, and enjoy a sightseeing sailing experience around Narraga....
Sunset Windjammer Cruise Along the Coast of Portland Maine
Sail with us for a two-hour Windjammer Sail on Casco Bay in Portland, Maine the perfect way to experience the beauty of the rugged coastline, complete with lighthouses, seals, and seabirds. (NOTE: This is NOT a narrated tour, bu... More
Likely to Sell Out Sunset Windjammer Cruise Along the Coast of Portland Maine
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North America
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Superb144 reviews4.8
Sail with us for a two-hour Windjammer Sail on Casco Bay in Portland, Maine the perfect way to exper....
Tall Ship Silva Sailing Cruise Ft. a Live Musician
A cruise aboard The Tall Ship Silva is the perfect way to fully appreciate a beautiful day on the Halifax Harbour. Join us on our comfortable and thoroughly impressive vessel for this relaxing afternoon outing on the water. Your j... More
Likely to Sell Out Tall Ship Silva Sailing Cruise Ft. a Live Musician
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North America
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Exellent291 reviews4.2
A cruise aboard The Tall Ship Silva is the perfect way to fully appreciate a beautiful day on the Ha....
Luxury Sunset Sail on Serendipity Catamaran in Charleston
Set sail for an unforgettable 2-hour sunset cruise on the Serendipity Catamaran, departing from Seabreeze Marina in downtown Charleston. Enjoy stunning waterfront views and local wildlife as the sun dips below the horizon. This up... More
Likely to Sell Out Luxury Sunset Sail on Serendipity Catamaran in Charleston
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North America
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Superb3 reviews5
Set sail for an unforgettable 2-hour sunset cruise on the Serendipity Catamaran, departing from Seab....
Cabo San Lucas Sunset Sailing Shared Cruise
Enjoy a 2-hour sunset cruise aboard a beautiful luxury sailing boat. Admire the sights illuminated at night, and see the wonderful sunset contrasting with Cabo San Lucas amazing waters. This is a family-friendly tour and includes... More
Likely to Sell Out Cabo San Lucas Sunset Sailing Shared Cruise
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North America
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Superb811 reviews4.9
Enjoy a 2-hour sunset cruise aboard a beautiful luxury sailing boat. Admire the sights illuminated ....
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
Likely to Sell Out Key West Reef Snorkel & Sail Adventure
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North America
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Superb557 reviews4.7
Join us for a snorkel adventure to the only living coral reef in North America. We have several fant....
Portland Tall Ship Cruise on Casco Bay
What better way to see the delights of Portland than from the sea in one of the famous schooner tall ships. Join us for this mid morning cruise that will make your visit to Portland live long in the memory.... More
Likely to Sell Out Portland Tall Ship Cruise on Casco Bay
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North America
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Superb236 reviews4.6
What better way to see the delights of Portland than from the sea in one of the famous schooner tall....
Snorkel Sail Adventure off Ka'anapali Beach, Maui
While snorkeling along West Maui’s coastline, experience warm waters abundant with sea life. You will see a variety of tropical fish, and if you’re lucky, an endangered Hawaiian Green Sea turtle called a ‘Honu’. A hot buff... More
Likely to Sell Out Snorkel Sail Adventure off Ka'anapali Beach, Maui
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North America
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Superb39 reviews4.9
While snorkeling along West Maui’s coastline, experience warm waters abundant with sea life. You w....
Seattle's Original Sunset Sail (Est. 1984) - 70ft Boat - BYOB
Our Sunset Sail is one of the most relaxing and affordable activities in Downtown Seattle. The Sunset Sail is powered by the wind, so it is extremally Eco-Friendly. We are one of the only cruises in the area that allow you to brin... More
Likely to Sell Out Seattle's Original Sunset Sail (Est. 1984) - 70ft Boat - BYOB
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North America
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Superb195 reviews4.9
Our Sunset Sail is one of the most relaxing and affordable activities in Downtown Seattle. The Sunse....
Puerto Vallarta, Luxury Sunset Sailing
Sail into one of Puerto Vallarta's stunning sunsets aboard our luxurious French sailboats or catamarans. Relax and unwind as you enjoy delicious appetizers, a premium open bar, and top-tier service from our attentive crew. This i... More
Likely to Sell Out Puerto Vallarta, Luxury Sunset Sailing
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North America
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Superb439 reviews4.6
Sail into one of Puerto Vallarta's stunning sunsets aboard our luxurious French sailboats or catamar....
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
Likely to Sell Out 4-Hour St. Pete Pier to Egmont Key Experience by Ferry
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North America
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Superb326 reviews4.7
From the Pier to Paradise. You’ll sail by the beautiful shorelines of St. Pete, pass under the stu....
Hilton Hawaiian Village Turtle Snorkel with Optional Lunch
Swim with turtles and fish, while enjoying the crystal blue topical waters. Sail the scenic Waikiki coastline and snorkel at Turtle Canyon. Our eco-conscious cruise lets you see whales (December through March), fish, even green s... More
Likely to Sell Out Hilton Hawaiian Village Turtle Snorkel with Optional Lunch
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North America
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Exellent41 reviews4.5
Swim with turtles and fish, while enjoying the crystal blue topical waters. Sail the scenic Waikiki....
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
Likely to Sell Out Sunset Dolphin Sail Aboard the Footloose Catamaran
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North America
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Superb467 reviews4.8
If you are looking to unwind before dinner or a night out on the town, come take a romantic Sunset S....
Small-Group San Diego Sunset Sailing Excursion
Set sail from San Diego on this small-group sailing tour on a sunset sail on the open ocean. This three-hour adventure on a Catalina sailboat is limited to six (6) guests allowing you a comfortable, semi-private experience (or, pu... More
Likely to Sell Out Small-Group San Diego Sunset Sailing Excursion
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North America
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Superb617 reviews4.9
Set sail from San Diego on this small-group sailing tour on a sunset sail on the open ocean. This th....
El Cielo Snorkel by Private Boat
- Private and comfortable vessels - Snorkel at world famous reefs - Spectacular marine life and coral formations - Stop over at a secluded pristine white sandy beach away from the crowds - Taste a delicious fish ceviche and co... More
Private Tour
Likely to Sell Out El Cielo Snorkel by Private Boat
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North America
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Superb358 reviews4.8
- Private and comfortable vessels - Snorkel at world famous reefs - Spectacular marine life and co....
Private Tour