Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 770 Sailing Trips activities in North America. Sort by Popularity. - Page 72hr. INTERACTIVE Sailing Experience on San Francisco Bay
This is an Interactive Sailing Experience on San Francisco Bay with a maximum 6 passengers on a private yacht with a USCG licensed captain and crew where you'll sail beneath the Golden Gate Bridge, across the San Francisco waterfr... More
Likely to Sell Out 2hr. INTERACTIVE Sailing Experience on San Francisco Bay
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North America
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Superb93 reviews5
This is an Interactive Sailing Experience on San Francisco Bay with a maximum 6 passengers on a priv....
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
Likely to Sell Out Vancouver Sailing Experience on a 50 foot Sailboat
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North America
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Superb102 reviews5
I have been living aboard full time for the past 12 years, sailing the Vancouver waterways for over ....
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
Likely to Sell Out Schooner Eastwind 2 Hour Day Sail in Boothbay Harbor
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North America
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Superb126 reviews4.6
Sail away from it all on your two-hour voyage aboard Boothbay Harbor's schooner to relax and see the....
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
Likely to Sell Out Sunset Sail from Traverse City with Food, Wine & Cocktails
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North America
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Superb226 reviews4.8
Wind down and relax as our captain and crewmates teach you about our elegant schooner and share stor....
Daytime Sailing Along San Diego's Skyline
Set sail with your Captain aboard our sail yacht and see some of San Diego's finest highlights on thisfamily-friendly sailing experience. We'll set sail from Safeharbor Sunroad Marina on Harbor Island on San Diego Bay, we often s... More
Likely to Sell Out Daytime Sailing Along San Diego's Skyline
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North America
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Superb149 reviews4.9
Set sail with your Captain aboard our sail yacht and see some of San Diego's finest highlights on th....
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
Likely to Sell Out Windjammer Classic Sunset Sail from Camden, Maine
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North America
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Superb425 reviews4.9
Maine sunsets are best appreciated from the water aboard the romantic Appledore II! This tall ship ....
Small Group Key West Adult Sunset & Moët Sail & Amazing Cheeses
Avoid the crowds and Sail on Key West’s beautiful shallow waters on this Adults Only Sunset & Moët cruise, to sip Moët & Chandon champagne and indulge your palate while being washed in the colors of the Key West sunset! Incl... More
Likely to Sell Out Small Group Key West Adult Sunset & Moët Sail & Amazing Cheeses
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North America
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Superb987 reviews4.9
Avoid the crowds and Sail on Key West’s beautiful shallow waters on this Adults Only Sunset & Moë....
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
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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Superb108 reviews4.9
Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages (BYOB), take pics,....
Maui Sunset Sail
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 expe... More
Likely to Sell Out Maui Sunset Sail
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North America
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Superb218 reviews4.6
Enjoy tantalizing pupus (appetizers) and island-style music against the backdrop of a stunning sunse....
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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Superb63 reviews5
Experience the beauty of Puerto Vallarta’s stunning bay on an exclusive, half-day private sailing ....
Free Cancellation
Private Tour
(Saving 15% )
Likely to Sell Out
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
Free Cancellation
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Likely to Sell Out Private Sunset Sail BYOB Dolphin/History Tours on 43ft Mystique
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North America
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Superb48 reviews5
Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charte....
Free Cancellation
Private Tour
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Likely to Sell Out
Waikiki: Fireworks Cruise from Beach & Cocktail Open Bar | Oahu
Set sail with Waikiki’s top-rated fireworks cruise and enjoy the famous Hilton Hawaiian Village display from the best seat on Oahu—the water. Every Friday night, you’ll glide along the coastline and experience an exclusive o... More
Free Cancellation
Private Tour
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Likely to Sell Out Waikiki: Fireworks Cruise from Beach & Cocktail Open Bar | Oahu
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North America
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Superb58 reviews4.8
Set sail with Waikiki’s top-rated fireworks cruise and enjoy the famous Hilton Hawaiian Village di....
Free Cancellation
Private Tour
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Likely to Sell Out
1-Hour Interactive Pirate Cruise (arrive 30 minutes early)
Prepare for high seas adventure on this fully interactive, family-friendly, 1-Hour Pirate Adventure Cruise (check in is a half hour before the sail time) along Florida’s Intracoastal Waterway that’s fun for the whole family! T... More
Free Cancellation
Private Tour
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Likely to Sell Out 1-Hour Interactive Pirate Cruise (arrive 30 minutes early)
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North America
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Superb1,516 reviews4.9
Prepare for high seas adventure on this fully interactive, family-friendly, 1-Hour Pirate Adventure ....
Free Cancellation
Private Tour
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Likely to Sell Out
Premium Private Catamaran Sail, Snorkel & "El Cielo" Charter
Sail in style aboard Cozumel’s largest and most spacious catamaran—a 47ft Nautitech—on an unforgettable journey to the famous El Cielo sandbar! Just 5–10 minutes by taxi from any cruise terminal or downtown, enjoy award-wi... More
Free Cancellation
Private Tour
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Likely to Sell Out Premium Private Catamaran Sail, Snorkel & "El Cielo" Charter
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North America
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Superb23 reviews4.8
Sail in style aboard Cozumel’s largest and most spacious catamaran—a 47ft Nautitech—on an unfo....
Free Cancellation
Private Tour
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Likely to Sell Out
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
Free Cancellation
Private Tour
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Likely to Sell Out Sail on Tall Ship Windy, join us for our "Chicago Skyline Sail"
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North America
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Superb21 reviews4.8
Join us for an unforgettable sail on Tall Ship Windy, Chicago's Official Tall Ship Ambassador! This ....
Free Cancellation
Private Tour
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Likely to Sell Out
Puerto Vallarta Luxury Sailing with Premium Open bar & lunch
Sail across Banderas Bay in luxury aboard our exclusive Leopard and Beneteau yachts, taking in breathtaking views of Puerto Vallarta’s coastline and the majestic Sierra Madre mountains. This small-group experience offers a perfe... More
Free Cancellation
Private Tour
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Likely to Sell Out Puerto Vallarta Luxury Sailing with Premium Open bar & lunch
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North America
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Superb312 reviews4.8
Sail across Banderas Bay in luxury aboard our exclusive Leopard and Beneteau yachts, taking in breat....
Free Cancellation
Private Tour
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Likely to Sell Out
Sail & Splash Excursion in Ft. Lauderdale
Come sail and play in Fort Lauderdale’s “Aquatic Playground” on this unforgettable excursion aboard our state of the art catamaran, the Spirit of Lauderdale. Enjoy one of the best cruise Ft Lauderdale has to offer . Sit back... More
Free Cancellation
Private Tour
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Likely to Sell Out Sail & Splash Excursion in Ft. Lauderdale
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North America
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Superb278 reviews4.8
Come sail and play in Fort Lauderdale’s “Aquatic Playground” on this unforgettable excursion a....
Free Cancellation
Private Tour
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Likely to Sell Out
Paragon Lahaina Sunset Sail
Join us aboard our flagship sailing catamaran, Paragon, for an unforgettable Maui sunset sail from Lahaina Harbor. Enjoy the afternoon hours at sea in the glassy, miraculous ‘au’au Channel is like floating inside an infinite ... More
Free Cancellation
Private Tour
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Likely to Sell Out Paragon Lahaina Sunset Sail
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North America
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Superb9 reviews4.6
Join us aboard our flagship sailing catamaran, Paragon, for an unforgettable Maui sunset sail from L....
Free Cancellation
Private Tour
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Likely to Sell Out
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
Free Cancellation
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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Superb731 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
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
Free Cancellation
Private Tour
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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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Superb963 reviews4.7
Snorkel Turtle Canyon on the Largest Luxury Catamaran! Top Quality Gear, Certified Crew & Premium On....
Free Cancellation
Private Tour
(Saving inf% )