Sailing Trips in USA
Top 10 Best USA Sailing Trips
Found 422 Sailing Trips activities in USA. Sort by Popularity. - Page 5Newport Sunset Sail on Classic Sailboat
Sunset sailing is one of the best evening activities to do during your stay in Newport, RI. Enjoy a relaxing sail around Narragansett Bay on a classic sailboat and see all of Newport's iconic sights from the water including histor... More

Newport Sunset Sail on Classic Sailboat
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USA
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Superb28 reviews4.9
Sunset sailing is one of the best evening activities to do during your stay in Newport, RI. Enjoy a ....
Key West 2 Reef Snorkel Tour & Sunset Cruise with Beer & Wine
Enjoy this 3 hour sunset combo trip. We will cruise out to Key West’s best reef location, where you are welcome to jump in and enjoy an evening snorkel. If you do not feel like getting in the water, no worries, the bar is open! ... More

Key West 2 Reef Snorkel Tour & Sunset Cruise with Beer & Wine
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USA
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Superb135 reviews4.7
Enjoy this 3 hour sunset combo trip. We will cruise out to Key West’s best reef location, where yo....
Honolulu Sunset Sail from Kewalo Harbor Including Drinks
Our Sunset Sail tour is a fun and wild 90-minute sail where all drinks are complimentary! (Must be 21+ with valid ID to consume alcoholic beverages). Sail the south shore from Kaka'ako Waterfront to Waikiki, with beautiful views o... More

Honolulu Sunset Sail from Kewalo Harbor Including Drinks
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USA
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Superb129 reviews4.9
Our Sunset Sail tour is a fun and wild 90-minute sail where all drinks are complimentary! (Must be 2....
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

Schooner Eastwind 2 Hour Day Sail in Boothbay Harbor
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USA
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Superb87 reviews4.6
Sail away from it all on your two-hour voyage aboard Boothbay Harbor's schooner to relax and see the....
Private Boat Tour - Snorkeling, Star Island & Dolphin Spotting
DolphinWaterSport is renowned for providing exceptional experiences. With a 4.9 rate & +800 reviews on Google. What you will get: Nature Immersion: Encounter dolphins, turtles, manatees, and more as you explore Miami's waters Cel... More
Private Tour

Private Boat Tour - Snorkeling, Star Island & Dolphin Spotting
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USA
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Superb56 reviews4.7
DolphinWaterSport is renowned for providing exceptional experiences. With a 4.9 rate & +800 reviews ....
Private Tour
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

Private Sailing on Beautiful Lake Michigan - Navy Pier, Chicago
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USA
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Superb64 reviews5
Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefro....
Private Tour
Private Sailing Charter on San Diego Bay
San Diego Bay is one of the most beautiful bodies of water on the West Coast of the United States. Why not enjoy this natural wonder aboard a beautiful sailing yacht with a knowledgeable and friendly Captain? This private charterÂ... More
Private Tour

Private Sailing Charter on San Diego Bay
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USA
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Superb34 reviews4.9
San Diego Bay is one of the most beautiful bodies of water on the West Coast of the United States. W....
Private Tour
Suncoast Sailing's Sunset Sailing Experience!
Set sail aboard the iconic schooner Suncoast Horizon as we set sail in the picturesque waters of Treasure Island, Florida! You’ll set sail about an hour before sunset to give you plenty of time to catch the full range of hues p... More
Private Tour

Suncoast Sailing's Sunset Sailing Experience!
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USA
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Superb232 reviews4.9
Set sail aboard the iconic schooner Suncoast Horizon as we set sail in the picturesque waters of Tre....
Private Tour
2-Hour Sunset Sail on the San Francisco Bay
Whether you want to kick off a fabulous date night or wrap up an enjoyable afternoon, this two-hour sunset sail is just the ticket. Step aboard the gorgeous traditional vessel to take in the sights at the most bewitching time of d... More
Private Tour

2-Hour Sunset Sail on the San Francisco Bay
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USA
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Superb371 reviews4.8
Whether you want to kick off a fabulous date night or wrap up an enjoyable afternoon, this two-hour ....
Private Tour
Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast
As you swim off of the coast of the world famous Waikiki beach, you’ll realize you’ve found your very own piece of paradise. Just far away enough from the bustling travelers and crowded beaches, the crystal-clear water will br... More
Private Tour

Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast
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USA
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Superb229 reviews4.9
As you swim off of the coast of the world famous Waikiki beach, you’ll realize you’ve found your....
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

Classic Key West Schooner Sunset Sail with Full Open Bar
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USA
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Superb170 reviews5
There's no better way to savor the magic of a Key West sunset than aboard a majestic schooner, compl....
Private Tour
Day Sails and Sunset tours on Schooner Surprise in Camden Maine
Sail on board the only historic day sailing schooner out of Camden Maine. We carry 18 passengers at most and have cushioned seating on board for all. Experienced crew will point out wild life, tell you history of our area and show... More
Private Tour

Day Sails and Sunset tours on Schooner Surprise in Camden Maine
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USA
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Superb27 reviews4.9
Sail on board the only historic day sailing schooner out of Camden Maine. We carry 18 passengers at ....
Private Tour
Luxury Sailing Tour of San Diego's Bay and Coastal Waterways
This is an engaging and unique, small group tour, of San Diego's beautiful bay and coastal waterways. You'll be on a beautiful Catalina 34' Sailboat enjoying the fresh air and best that San Diego has to offer. On your adventure yo... More
Private Tour

Luxury Sailing Tour of San Diego's Bay and Coastal Waterways
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USA
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Superb194 reviews4.9
This is an engaging and unique, small group tour, of San Diego's beautiful bay and coastal waterways....
Private Tour
Catamaran Day Sail Shelling Excursion 42ft. Mainecat Cool Beans
Create memories that lasts a lifetime with a day on the Gulf of Mexico sailing to a private island for some swimming and shelling (weather permitting) while taking in the sun and spectacular views. Our beautifully, well appointed ... More
Private Tour

Catamaran Day Sail Shelling Excursion 42ft. Mainecat Cool Beans
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USA
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Superb147 reviews4.9
Create memories that lasts a lifetime with a day on the Gulf of Mexico sailing to a private island f....
Private Tour
Newport Sightseeing Day Sailing Experience on Schooner Adirondack
See Newport, Rhode Island from the water on an exciting sunset sail around Newport Harbor on Schooner Adirondack. You'll pass by many iconic sights, bridges, lighthouses and more during this 1.5-hour experience!... More
Private Tour

Newport Sightseeing Day Sailing Experience on Schooner Adirondack
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USA
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Superb41 reviews4.9
See Newport, Rhode Island from the water on an exciting sunset sail around Newport Harbor on Schoone....
Private Tour
Sunset Catamaran Sail in Cocoa Beach
Experience a Magical Sunset in Cocoa Beach! 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 beauty of Floridaâ... More
Private Tour

Sunset Catamaran Sail in Cocoa Beach
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USA
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Superb154 reviews5
Experience a Magical Sunset in Cocoa Beach! Set sail into the golden hour and enjoy a stunning eveni....
Private Tour
Afternoon Sail & Snorkel to the Captain Cook Monument
A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient lava flows. As you arrive at the "World Famous Captain Cook Monument" your snorkeling adve... More
Private Tour

Afternoon Sail & Snorkel to the Captain Cook Monument
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USA
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Superb233 reviews4.9
A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathtakin....
Private Tour
New York City Sunset Jazz Sail aboard Clipper City
Watch night fall on the city as the sun sets behind the Statue of Liberty from the unbeatable vantage point of the harbor. Order a drink from our full bar as we raise canvas and leave Manhattan behind as the melodies of live jazz ... More
Private Tour

New York City Sunset Jazz Sail aboard Clipper City
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USA
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Exellent102 reviews4.4
Watch night fall on the city as the sun sets behind the Statue of Liberty from the unbeatable vantag....
Private Tour
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
Private Tour

Windjammer Classic Day Sail from Camden, Maine
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USA
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Superb374 reviews4.7
See the best of Camden while sailing Maine’s magnificent rocky coast on the elegant Appledore I....
Private Tour
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
Private Tour

Sunset Sailing Cruise in Monterey Bay
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USA
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Superb20 reviews4.8
Looking to impress your date or just treat yourself to something unforgettable? Our Sunset Cruise is....
Private Tour