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Top 10 Best USA Sailing Trips

Found 422 Sailing Trips activities in USA. Sort by Popularity. - Page 5
 

Newport Sunset Sail on Classic Sailboat

(4.9 of 28 reviews)

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

Start From $67.84
 
Newport Sunset Sail on Classic Sailboat

Newport Sunset Sail on Classic Sailboat

  • USA
  • Superb28 reviews4.9

Sunset sailing is one of the best evening activities to do during your stay in Newport, RI. Enjoy a ....

    Start From $67.84
 
 

Key West 2 Reef Snorkel Tour & Sunset Cruise with Beer & Wine

(4.7 of 135 reviews)

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

Free Cancellation
Start From $69.95
 
Key West 2 Reef Snorkel Tour & Sunset Cruise with Beer & Wine

Key West 2 Reef Snorkel Tour & Sunset Cruise with Beer & Wine

  • USA
  • Superb135 reviews4.7

Enjoy this 3 hour sunset combo trip. We will cruise out to Key West’s best reef location, where yo....

    Free Cancellation
    Start From $69.95
 
 

Honolulu Sunset Sail from Kewalo Harbor Including Drinks

(4.9 of 129 reviews)

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

Free Cancellation
Start From $61.50
 
Honolulu Sunset Sail from Kewalo Harbor Including Drinks

Honolulu Sunset Sail from Kewalo Harbor Including Drinks

  • USA
  • Superb129 reviews4.9

Our Sunset Sail tour is a fun and wild 90-minute sail where all drinks are complimentary! (Must be 2....

    Free Cancellation
    Start From $61.50
 
 

Schooner Eastwind 2 Hour Day Sail in Boothbay Harbor

(4.6 of 87 reviews)

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

Free Cancellation
Start From $54.95
 
Schooner Eastwind 2 Hour Day Sail in Boothbay Harbor

Schooner Eastwind 2 Hour Day Sail in Boothbay Harbor

  • USA
  • Superb87 reviews4.6

Sail away from it all on your two-hour voyage aboard Boothbay Harbor's schooner to relax and see the....

    Free Cancellation
    Start From $54.95
 
 

Private Boat Tour - Snorkeling, Star Island & Dolphin Spotting

(4.7 of 56 reviews)

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

Free Cancellation
Private Tour
Start From $65.00
 
Private Boat Tour - Snorkeling, Star Island & Dolphin Spotting Likely to Sell Out

Private Boat Tour - Snorkeling, Star Island & Dolphin Spotting

  • USA
  • Superb56 reviews4.7

DolphinWaterSport is renowned for providing exceptional experiences. With a 4.9 rate & +800 reviews ....

    Free Cancellation
    Private Tour
    Start From $65.00
 
 

Private Sailing on Beautiful Lake Michigan - Navy Pier, Chicago

(5 of 64 reviews)

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

Free Cancellation
Private Tour
Start From $507.96
 
Private Sailing on Beautiful Lake Michigan - Navy Pier, Chicago Likely to Sell Out

Private Sailing on Beautiful Lake Michigan - Navy Pier, Chicago

  • USA
  • Superb64 reviews5

Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefro....

    Free Cancellation
    Private Tour
    Start From $507.96
 
 

Private Sailing Charter on San Diego Bay

(4.9 of 34 reviews)

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

Free Cancellation
Private Tour
Start From $450.00
 
Private Sailing Charter on San Diego Bay Likely to Sell Out

Private Sailing Charter on San Diego Bay

  • USA
  • Superb34 reviews4.9

San Diego Bay is one of the most beautiful bodies of water on the West Coast of the United States. W....

    Free Cancellation
    Private Tour
    Start From $450.00
 
 

Suncoast Sailing's Sunset Sailing Experience!

(4.9 of 232 reviews)

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

Free Cancellation
Private Tour
Start From $64.99
 
Suncoast Sailing's Sunset Sailing Experience! Likely to Sell Out

Suncoast Sailing's Sunset Sailing Experience!

  • USA
  • Superb232 reviews4.9

Set sail aboard the iconic schooner Suncoast Horizon as we set sail in the picturesque waters of Tre....

    Free Cancellation
    Private Tour
    Start From $64.99
 
 

2-Hour Sunset Sail on the San Francisco Bay

(4.8 of 371 reviews)

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

Free Cancellation
Private Tour
Start From $129.00
 
2-Hour Sunset Sail on the San Francisco Bay Likely to Sell Out

2-Hour Sunset Sail on the San Francisco Bay

  • USA
  • Superb371 reviews4.8

Whether you want to kick off a fabulous date night or wrap up an enjoyable afternoon, this two-hour ....

    Free Cancellation
    Private Tour
    Start From $129.00
 
 

Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast

(4.9 of 229 reviews)

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

Free Cancellation
Private Tour
Start From $49.99
 
Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast Likely to Sell Out

Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast

  • USA
  • Superb229 reviews4.9

As you swim off of the coast of the world famous Waikiki beach, you’ll realize you’ve found your....

    Free Cancellation
    Private Tour
    Start From $49.99
 
 

Classic Key West Schooner Sunset Sail with Full Open Bar

(5 of 170 reviews)

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

Free Cancellation
Private Tour
Start From $109.00
 
Classic Key West Schooner Sunset Sail with Full Open Bar Likely to Sell Out

Classic Key West Schooner Sunset Sail with Full Open Bar

  • USA
  • Superb170 reviews5

There's no better way to savor the magic of a Key West sunset than aboard a majestic schooner, compl....

    Free Cancellation
    Private Tour
    Start From $109.00
 
 

Day Sails and Sunset tours on Schooner Surprise in Camden Maine

(4.9 of 27 reviews)

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

Free Cancellation
Private Tour
Start From $70.00
 
Day Sails and Sunset tours on Schooner Surprise in Camden Maine Likely to Sell Out

Day Sails and Sunset tours on Schooner Surprise in Camden Maine

  • USA
  • Superb27 reviews4.9

Sail on board the only historic day sailing schooner out of Camden Maine. We carry 18 passengers at ....

    Free Cancellation
    Private Tour
    Start From $70.00
 
 

Luxury Sailing Tour of San Diego's Bay and Coastal Waterways

(4.9 of 194 reviews)

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

Free Cancellation
Private Tour
Start From $119.00
 
Luxury Sailing Tour of San Diego's Bay and Coastal Waterways Likely to Sell Out

Luxury Sailing Tour of San Diego's Bay and Coastal Waterways

  • USA
  • Superb194 reviews4.9

This is an engaging and unique, small group tour, of San Diego's beautiful bay and coastal waterways....

    Free Cancellation
    Private Tour
    Start From $119.00
 
 

Catamaran Day Sail Shelling Excursion 42ft. Mainecat Cool Beans

(4.9 of 147 reviews)

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

Free Cancellation
Private Tour
Start From $73.00
 
Catamaran Day Sail Shelling Excursion 42ft. Mainecat Cool Beans Likely to Sell Out

Catamaran Day Sail Shelling Excursion 42ft. Mainecat Cool Beans

  • USA
  • Superb147 reviews4.9

Create memories that lasts a lifetime with a day on the Gulf of Mexico sailing to a private island f....

    Free Cancellation
    Private Tour
    Start From $73.00
 
 

Newport Sightseeing Day Sailing Experience on Schooner Adirondack

(4.9 of 41 reviews)

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

Free Cancellation
Private Tour
Start From $57.24
 
Newport Sightseeing Day Sailing Experience on Schooner Adirondack Likely to Sell Out

Newport Sightseeing Day Sailing Experience on Schooner Adirondack

  • USA
  • Superb41 reviews4.9

See Newport, Rhode Island from the water on an exciting sunset sail around Newport Harbor on Schoone....

    Free Cancellation
    Private Tour
    Start From $57.24
 
 

Sunset Catamaran Sail in Cocoa Beach

(5 of 154 reviews)

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

Free Cancellation
Private Tour
Start From $55.37
 
Sunset Catamaran Sail in Cocoa Beach Likely to Sell Out

Sunset Catamaran Sail in Cocoa Beach

  • USA
  • Superb154 reviews5

Experience a Magical Sunset in Cocoa Beach! Set sail into the golden hour and enjoy a stunning eveni....

    Free Cancellation
    Private Tour
    Start From $55.37
 
 

Afternoon Sail & Snorkel to the Captain Cook Monument

(4.9 of 233 reviews)

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

Free Cancellation
Private Tour
Start From $136.19
 
Afternoon Sail & Snorkel to the Captain Cook Monument Likely to Sell Out

Afternoon Sail & Snorkel to the Captain Cook Monument

  • USA
  • Superb233 reviews4.9

A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathtakin....

    Free Cancellation
    Private Tour
    Start From $136.19
 
 

New York City Sunset Jazz Sail aboard Clipper City

(4.4 of 102 reviews)

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

Free Cancellation
Private Tour
Start From $112.00
 
New York City Sunset Jazz Sail aboard Clipper City Likely to Sell Out

New York City Sunset Jazz Sail aboard Clipper City

  • USA
  • Exellent102 reviews4.4

Watch night fall on the city as the sun sets behind the Statue of Liberty from the unbeatable vantag....

    Free Cancellation
    Private Tour
    Start From $112.00
 
 

Windjammer Classic Day Sail from Camden, Maine

(4.7 of 374 reviews)

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

Free Cancellation
Private Tour
Start From $59.95
 
Windjammer Classic Day Sail from Camden, Maine Likely to Sell Out

Windjammer Classic Day Sail from Camden, Maine

  • USA
  • Superb374 reviews4.7

See the best of Camden while sailing Maine’s magnificent rocky coast on the elegant Appledore I....

    Free Cancellation
    Private Tour
    Start From $59.95
 
 

Sunset Sailing Cruise in Monterey Bay

(4.8 of 20 reviews)

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

Free Cancellation
Private Tour
Start From $95.00
 
Sunset Sailing Cruise in Monterey Bay Likely to Sell Out

Sunset Sailing Cruise in Monterey Bay

  • USA
  • Superb20 reviews4.8

Looking to impress your date or just treat yourself to something unforgettable? Our Sunset Cruise is....

    Free Cancellation
    Private Tour
    Start From $95.00
 
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