Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 769 Sailing Trips activities in North America. Sort by Popularity. - Page 7JFarwell Adventure Yacht Sailing in the Halifax Harbour
Halifax's only wind powered sailing experience! This 45' Oceanis Beneteau handles beautifully on the water, and offers a great introduction to sailing. Guests are encouraged to be as hands on with the sailing process as they would... More
JFarwell Adventure Yacht Sailing in the Halifax Harbour
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North America
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Superb151 reviews5
Halifax's only wind powered sailing experience! This 45' Oceanis Beneteau handles beautifully on the....
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
Waikiki Sunset Cruise from Oahu
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North America
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Superb66 reviews4.7
Experience a Hawaiian sunset sail aboard our 55-foot double-decker catamaran. With spacious decks an....
Private Sailing on Beautiful 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 Private Sailing on Beautiful Lake Michigan - Navy Pier, Chicago
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North America
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Superb70 reviews5
Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefro....
Private Tour
Waikiki Turtle Snorkeling Tour 6 Activities + & Sunset Cruise
Our sunset turtle snorkeling tour delivers a unique all-in-one Waikiki ocean experience, combining adventure, relaxation, and unforgettable views in one trip. We reach Turtle Canyon quickly, giving you more time in the water to s... More
Private Tour
Likely to Sell Out Waikiki Turtle Snorkeling Tour 6 Activities + & Sunset Cruise
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North America
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Superb14 reviews5
Our sunset turtle snorkeling tour delivers a unique all-in-one Waikiki ocean experience, combining a....
Private Tour
Classic Key West Schooner Sunset Sail with Full Open Bar
There's no better way to savor the magic of a Key West sunset than aboard a majestic schooner, complete with a full open bar. This enchanting journey blends the timeless elegance of traditional sailing with the lively spirit of Ke... More
Private Tour
Likely to Sell Out Classic Key West Schooner Sunset Sail with Full Open Bar
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North America
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Superb249 reviews4.9
There's no better way to savor the magic of a Key West sunset than aboard a majestic schooner, compl....
Private Tour
San Diego Harbor Cruise on the Largest Catamaran in San Diego
Enjoy a San Diego harbor cruise on San Diego's largest and newest catamaran yacht. We provide our guests with a unique way to splash by all of the amazing San Diego harbor monuments while enjoying the smooth sailing of San Diego's... More
Private Tour
Likely to Sell Out San Diego Harbor Cruise on the Largest Catamaran in San Diego
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North America
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Superb47 reviews4.9
Enjoy a San Diego harbor cruise on San Diego's largest and newest catamaran yacht. We provide our gu....
Private Tour
Likely to Sell Out
Half Day Private Sailing Cruise Puerto Vallarta with Snorkeling
Experience the beauty of Puerto Vallarta’s stunning bay on an exclusive, half-day private sailing cruise. Explore los arcos area while savoring fresh guacamole and a selection of delicious snacks. This personalized sailing expe... More
Free Cancellation
Private Tour
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Likely to Sell Out Half Day Private Sailing Cruise Puerto Vallarta with Snorkeling
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North America
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Superb65 reviews5
Experience the beauty of Puerto Vallarta’s stunning bay on an exclusive, half-day private sailing ....
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Private Tour
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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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Exellent450 reviews4.5
Experience the sunset like never before on this fabulous Sunset Sailing excursion. You’ll sail alo....
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Sunset Dolphin Sail Aboard the Privateer Catamaran
If you are looking to unwind before dinner or a night out on the town, come take a romantic Sunset Sail on the SV Privateer, our 78-passenger catamaran, with Paradise Adventures! This breathtaking sunset sail along the Gulf of Mex... More
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Private Tour
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Likely to Sell Out Sunset Dolphin Sail Aboard the Privateer Catamaran
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North America
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Superb739 reviews4.8
If you are looking to unwind before dinner or a night out on the town, come take a romantic Sunset S....
Free Cancellation
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Ft Myers Beach 2 Hour Tiki Pub Fun in the Sun Dolphin Cruise
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
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Likely to Sell Out Ft Myers Beach 2 Hour Tiki Pub Fun in the Sun Dolphin Cruise
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North America
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Superb113 reviews4.9
Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages (BYOB), take pics,....
Free Cancellation
Private Tour
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Likely to Sell Out
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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Likely to Sell Out Schooner Eastwind 2 Hour Day Sail in Boothbay Harbor
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North America
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Superb139 reviews4.6
Sail away from it all on your two-hour voyage aboard Boothbay Harbor's schooner to relax and see the....
Free Cancellation
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Likely to Sell Out
Akialoa Mā’alaea Sunset Sail
Witness the stunning sunsets of Maui from the comfort of a luxury sailing catamaran. The Akialoa Sunset Sail offers a two-hour journey through the picturesque inter-island channel, showcasing the beauty of Maui, Lāna‘i, and Kah... More
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Likely to Sell Out Akialoa Mā’alaea Sunset Sail
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North America
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Superb15 reviews4.7
Witness the stunning sunsets of Maui from the comfort of a luxury sailing catamaran. The Akialoa Sun....
Free Cancellation
Private Tour
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Likely to Sell Out
Moana’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
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Likely to Sell Out Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventu....
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North America
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Superb967 reviews4.7
Snorkel Turtle Canyon on the Largest Luxury Catamaran! Top Quality Gear, Certified Crew & Premium On....
Free Cancellation
Private Tour
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Likely to Sell Out
New York City Sailboat Day Cruise to the Statue of Liberty
Experience New York by water aboard Schooner Adirondack, an 80-foot, 2-masted schooner inspired by the pilot schooners of the 1890s. Sit back and relax as the crew raises sail and the boat effortlessly glides along the Hudson Rive... More
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Likely to Sell Out New York City Sailboat Day Cruise to the Statue of Liberty
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North America
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Superb163 reviews4.9
Experience New York by water aboard Schooner Adirondack, an 80-foot, 2-masted schooner inspired by t....
Free Cancellation
Private Tour
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Windjammer Classic Day Sail from Camden, Maine
See the best of Camden while sailing Maine’s magnificent rocky coast on the elegant Appledore II! Feel like an adventurer from the 19th century while enjoying state-of-the-art accommodations on a modern windjammer. With wide ... More
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Likely to Sell Out Windjammer Classic Day Sail from Camden, Maine
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North America
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Superb426 reviews4.8
See the best of Camden while sailing Maine’s magnificent rocky coast on the elegant Appledore I....
Free Cancellation
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Waikiki Sunset Cocktail Cruise - Hilton Hawaiian Village
Explore the Waikiki coastline aboard the new Spirit of Aloha, a 65-foot sailing catamaran custom-built for the Hilton Hawaiian Village Waikiki Beach Resort. See the island like never before as you set sail from the only pier in W... More
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Likely to Sell Out Waikiki Sunset Cocktail Cruise - Hilton Hawaiian Village
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North America
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Exellent34 reviews4.5
Explore the Waikiki coastline aboard the new Spirit of Aloha, a 65-foot sailing catamaran custom-bui....
Free Cancellation
Private Tour
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Likely to Sell Out
Key West: Sunset Sail + Reef Snorkel & Sandbar
Reef Snorkel + Sandbar & Sunset Sail • Summer Only with Small Groups on an Honest Eco Tour. What Makes this Eco Tour different? • Guided Snorkeling Your mate hops in the water with you and points out animals and shows yo... More
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Likely to Sell Out Key West: Sunset Sail + Reef Snorkel & Sandbar
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North America
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Superb40 reviews5
Reef Snorkel + Sandbar & Sunset Sail • Summer Only with Small Groups on an Honest Eco Tour. Wh....
Free Cancellation
Private Tour
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Likely to Sell Out
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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Private Tour
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Likely to Sell Out Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)
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North America
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Superb59 reviews4.8
Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui su....
Free Cancellation
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Sunset Sailing Cruise in Monterey Bay
Looking to impress your date or just treat yourself to something unforgettable? Our Sunset Cruise is the most popular (and most romantic!) way to experience Monterey Bay. Departing daily, 90 minutes before sunset, this dreamy 1.5-... More
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Likely to Sell Out Sunset Sailing Cruise in Monterey Bay
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North America
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Superb52 reviews4.8
Looking to impress your date or just treat yourself to something unforgettable? Our Sunset Cruise is....
Free Cancellation
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Wrightsville Beach Day Sail Private Catamaran Charter
On this 4hr private charter, you will work with your captain to plan your perfect itinerary of islands and local spots. Upon anchoring, the crew will dinghy you around wherever you'd like to go! The boat is fully equipped with ai... More
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Likely to Sell Out Wrightsville Beach Day Sail Private Catamaran Charter
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North America
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Superb1 review5
On this 4hr private charter, you will work with your captain to plan your perfect itinerary of islan....
Free Cancellation
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