Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 766 Sailing Trips activities in North America. Sort by Popularity. - Page 6JFarwell 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
JFarwell Sunset Wine and Cheese Yacht Sailing
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North America
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Superb170 reviews4.9
Our 45' luxury sailing yacht is one of a kind on the Halifax waterfront. Our hands-on crew love to i....
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
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Hilton Hawaiian Village Turtle Snorkel with Optional Lunch
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North America
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Exellent47 reviews4.3
Swim with turtles and fish, while enjoying the crystal blue topical waters. Sail the scenic Waikiki....
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Sail on Tall Ship Windy, join us for our "Chicago Skyline Sail"
Join us for an unforgettable sail on Tall Ship Windy, Chicago's Official Tall Ship Ambassador! This is a relaxing sailing Adventure, that you will enjoy, on Lake Michigan, while enjoying the views, and the fresh air! Fun for all ... More
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Sail on Tall Ship Windy, join us for our "Chicago Skyline Sail"
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North America
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Superb27 reviews4.7
Join us for an unforgettable sail on Tall Ship Windy, Chicago's Official Tall Ship Ambassador! This ....
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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
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Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)
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North America
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Superb60 reviews4.8
Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui su....
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San Francisco Bay Sailing Cruise
Experience the beauty of San Francisco during a 1.5-hour catamaran cruise over San Francisco Bay. Sail away from bustling city and enjoy photo ops from the vantage point of the water. You’ll coast past the city skyline, the Gold... More
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San Francisco Bay Sailing Cruise
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North America
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Superb662 reviews4.9
Experience the beauty of San Francisco during a 1.5-hour catamaran cruise over San Francisco Bay. Sa....
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Windjammer Classic Sunset Sail from Camden, Maine
Maine sunsets are best appreciated from the water aboard the romantic Appledore II! This tall ship is limited to 49 passengers for an intimate sailing experience. She is a modern windjammer with luxurious accommodations and plent... More
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Windjammer Classic Sunset Sail from Camden, Maine
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North America
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Superb495 reviews4.9
Maine sunsets are best appreciated from the water aboard the romantic Appledore II! This tall ship ....
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Day's End Cocktail Sunset Sail
Drift away aboard our 65’ luxury sailing catamaran and sail into golden hour for Maui’s most scenic cocktail hour. Happy hour at sea with handcrafted drinks, vibrant music, and a relaxed-yet-refined vibe that turns every pour ... More
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Day's End Cocktail Sunset Sail
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North America
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Superb95 reviews4.7
Drift away aboard our 65’ luxury sailing catamaran and sail into golden hour for Maui’s most sce....
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Schooner Eastwind 2 Hour Day Sail in Boothbay Harbor
Sail away from it all on your two-hour voyage aboard Boothbay Harbor's schooner to relax and see the Maine coastline. Lighthouses, fishing lobstermen, wildlife, and remote islands accessible only by boat dot the seascape. Our goa... More
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Schooner Eastwind 2 Hour Day Sail in Boothbay Harbor
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North America
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Superb165 reviews4.6
Sail away from it all on your two-hour voyage aboard Boothbay Harbor's schooner to relax and see the....
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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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Superb211 reviews4.9
Our vessel "Hokulani" is a beautiful and spacious custom built sailing trimaran specifically designe....
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Sandbar, Snorkel, and Sunset Sail in Key West
This trip combines three of the most sought-after experiences in Key West into one relaxed afternoon: extended time at a shallow-water sandbar, snorkeling in clear backcountry waters, and a sunset on the water. Sailing aboard a hi... More
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Sandbar, Snorkel, and Sunset Sail in Key West
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North America
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Superb27 reviews4.7
This trip combines three of the most sought-after experiences in Key West into one relaxed afternoon....
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Escape from the Rock! Cruise around Alcatraz
Embark on a 90-minute cruise along the San Francisco waterfront, under the Golden Gate Bridge and past Angel Island State Park before circling Alcatraz Island for an in-depth view of the prison. Take in the sights and sounds of ... More
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Escape from the Rock! Cruise around Alcatraz
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North America
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Exellent162 reviews4.2
Embark on a 90-minute cruise along the San Francisco waterfront, under the Golden Gate Bridge and ....
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Waikiki Sunset Cruise from Oahu
Experience a Hawaiian sunset sail aboard our 55-foot double-decker catamaran. With spacious decks and a submerged glass-bottom viewing room, you’ll have an ideal vantage point to observe marine life such as dolphins, whales, sea... More
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Waikiki Sunset Cruise from Oahu
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North America
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Superb72 reviews4.7
Experience a Hawaiian sunset sail aboard our 55-foot double-decker catamaran. With spacious decks an....
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Sunset Sail from Traverse City with Food, Wine & Cocktails
Wind down and relax as our captain and crewmates teach you about our elegant schooner and share stories about the history of the lands, people, and waters of the Grand Traverse Bay area. Enjoy complimentary locally sourced food, w... More
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Sunset Sail from Traverse City with Food, Wine & Cocktails
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North America
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Superb245 reviews4.8
Wind down and relax as our captain and crewmates teach you about our elegant schooner and share stor....
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Cabo San Lucas Luxury Sailing Yacht and Dinner with a Chef
Sail into the sunset on board Tu Enamorado, a beautifully crafted sailing yacht of unsurpassed quality, comfort, and performance. Live the yachting lifestyle, walk barefoot on the deck, feel the sun and breeze on your face, dance ... More
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Cabo San Lucas Luxury Sailing Yacht and Dinner with a Chef
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North America
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Exellent308 reviews4.5
Sail into the sunset on board Tu Enamorado, a beautifully crafted sailing yacht of unsurpassed quali....
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Likely to Sell Out
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
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Likely to Sell Out Cabo San Lucas Sunset Sailing Shared Cruise
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North America
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Superb818 reviews4.9
Enjoy a 2-hour sunset cruise aboard a beautiful luxury sailing boat. Admire the sights illuminated ....
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Likely to Sell Out
Riviera 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
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Likely to Sell Out Riviera Maya Luxury Sunset Sailing plus Light Dinner and Open Bar
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North America
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Exellent454 reviews4.5
Experience the sunset like never before on this fabulous Sunset Sailing excursion. You’ll sail alo....
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Likely to Sell Out
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
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Private Tour
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Likely to Sell Out Private Fishing Trip "All Inclusive" in Cabo San Lucas, Mexico
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North America
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Superb526 reviews4.8
Embark on the most exciting fishing adventure in the crystal-clear waters of Cabo San Lucas. Our all....
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Private Tour
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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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Private Tour
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Likely to Sell Out Premium Private 47ft Catamaran Snorkel & El Cielo (30p max)
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North America
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Superb25 reviews4.8
Private 6-hour charter for up to 30 guests aboard Nemo, a spacious 47ft Nautitech catamaran, with El....
Free Cancellation
Private Tour
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Likely to Sell Out
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
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Private Tour
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Likely to Sell Out Small-Group San Diego Afternoon Sailing Excursion
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North America
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Superb563 reviews4.9
This three-hour adventure on a a beautiful modern-day sailboat is limited to just 6 people, allowing....
Free Cancellation
Private Tour
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Likely to Sell Out
Private Sailing Charter with Captain, BYOB
Embark on an exclusive sailing adventure on board "Esprit de Joy," tailor-made for groups of up to 6 guests for a 2.5-hour charter embracing Charleston's scenic Harbor. The golden hour of sunset is our prime booking time, offering... More
Free Cancellation
Private Tour
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Likely to Sell Out Private Sailing Charter with Captain, BYOB
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North America
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Superb91 reviews5
Embark on an exclusive sailing adventure on board "Esprit de Joy," tailor-made for groups of up to 6....
Free Cancellation
Private Tour
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