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Top 10 Best USA Sailing Trips

Found 422 Sailing Trips activities in USA. Sort by Popularity. - Page 2
 

Four Winds Molokini Snorkeling Tour from Maalaea Harbor

(4.7 of 800 reviews)

Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beautiful coral reefs and tropical fish underneath the water, or bask in the warmth of paradise. From the experienced snorkeler to those... More

Free Cancellation
Start From $202.59
 
Four Winds Molokini Snorkeling Tour from Maalaea Harbor Likely to Sell Out

Four Winds Molokini Snorkeling Tour from Maalaea Harbor

  • USA
  • Superb800 reviews4.7

Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beauti....

    Free Cancellation
    Start From $202.59
 
 

Seattle Sunset Sail BYOB

(4.9 of 137 reviews)

Our Sunset Sail is one of the most relaxing and affordable activities in Downtown Seattle. The Sunset Sail is powered by the wind, so it is extremally Eco-Friendly. We are one of the only cruises in the area that allow you to brin... More

Free Cancellation
Start From $71.00
 
Seattle Sunset Sail BYOB Likely to Sell Out

Seattle Sunset Sail BYOB

  • USA
  • Superb137 reviews4.9

Our Sunset Sail is one of the most relaxing and affordable activities in Downtown Seattle. The Sunse....

    Free Cancellation
    Start From $71.00
 
 

Waikiki Catamaran Turtle Snorkel Sail

(4.7 of 2,095 reviews)

Welcome aboard Hawaii Nautical, you're invited to observe, learn, and experience Hawaiian Green Sea Turtles firsthand! Guests will learn about the life cycle, behaviors, and threats to the Hawaiian Sea Turtles "Honu" (Learning pr... More

Free Cancellation
Start From $109.00
 
Waikiki Catamaran Turtle Snorkel Sail Likely to Sell Out

Waikiki Catamaran Turtle Snorkel Sail

  • USA
  • Superb2,095 reviews4.7

Welcome aboard Hawaii Nautical, you're invited to observe, learn, and experience Hawaiian Green Sea ....

    Free Cancellation
    Start From $109.00
 
 

Boston Harbor Sunset Sail Tour

(4.8 of 93 reviews)

Experience a beautiful Boston Harbor sunset sail on the water and see some of the city's waterfront landmarks as the sun dips below the horizon. This elegant sailing experience will be aboard either Schooner Adirondack III or Adir... More

Free Cancellation
Start From $82.27
 
Boston Harbor Sunset Sail Tour Likely to Sell Out

Boston Harbor Sunset Sail Tour

  • USA
  • Superb93 reviews4.8

Experience a beautiful Boston Harbor sunset sail on the water and see some of the city's waterfront ....

    Free Cancellation
    Start From $82.27
 
 

Classic Tall Ship Cruise in Boston Harbor

(4.7 of 533 reviews)

Come out for a day sail adventure in Boston Harbor aboard our classic schooner, the Liberty Star. Get away from the hustle and bustle of the city streets and enjoy some quality time out on the water with unbeatable views of the ci... More

Free Cancellation
Start From $35.00
 
Classic Tall Ship Cruise in Boston Harbor Likely to Sell Out

Classic Tall Ship Cruise in Boston Harbor

  • USA
  • Superb533 reviews4.7

Come out for a day sail adventure in Boston Harbor aboard our classic schooner, the Liberty Star. Ge....

    Free Cancellation
    Start From $35.00
 
 

Deluxe Sunset & Day Sail Small Group

(5 of 175 reviews)

Experience the breathtaking beauty of San Diego Bay at sunset aboard our mono-hull sailboat, perfect for up to six passengers. Glide through calm waters as the sky transforms into a masterpiece of color. Keep an eye out for playfu... More

Free Cancellation
Start From $119.00
 
Deluxe Sunset & Day Sail Small Group Likely to Sell Out

Deluxe Sunset & Day Sail Small Group

  • USA
  • Superb175 reviews5

Experience the breathtaking beauty of San Diego Bay at sunset aboard our mono-hull sailboat, perfect....

    Free Cancellation
    Start From $119.00
 
 

Day's End Cocktail Sunset Sail

(4.7 of 41 reviews)

Drift away aboard our 65’ luxury sailing catamaran and sail into golden hour for Maui’s most scenic cocktail hour. This isn’t a dinner cruise, it’s happy hour reimagined (a true ‘pau hana’ at sea) with handcrafted drin... More

Free Cancellation
Start From $149.00
 
Day's End Cocktail Sunset Sail Likely to Sell Out

Day's End Cocktail Sunset Sail

  • USA
  • Superb41 reviews4.7

Drift away aboard our 65’ luxury sailing catamaran and sail into golden hour for Maui’s most sce....

    Free Cancellation
    Start From $149.00
 
 

Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB

(4.9 of 698 reviews)

2025 VIATOR TOP 10 award for WATER EXPERIENCES in the UNITED STATES including the TOP SUNSET CRUISE in the US! Join us for a beautiful Hawaiian sunset!! We have been sailing the Pacific waters off of the Island of Oahu since 1985... More

Free Cancellation
Start From $64.98
 
Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB Likely to Sell Out

Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB

  • USA
  • Superb698 reviews4.9

2025 VIATOR TOP 10 award for WATER EXPERIENCES in the UNITED STATES including the TOP SUNSET CRUISE ....

    Free Cancellation
    Start From $64.98
 
 

Deluxe Sail & Snorkel to the Captain Cook Monument

(4.9 of 495 reviews)

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 adventure will begin in the turquoise waters a... More

Free Cancellation
Start From $177.73
 
Deluxe Sail & Snorkel to the Captain Cook Monument Likely to Sell Out

Deluxe Sail & Snorkel to the Captain Cook Monument

  • USA
  • Superb495 reviews4.9

Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient la....

    Free Cancellation
    Start From $177.73
 
 

San Francisco Bay Cruise

(4.4 of 278 reviews)

You haven’t fully experienced San Francisco until you’ve taken a Bay Cruise. This popular 1-hour excursion heads underneath the Golden Gate Bridge, around Alcatraz Island, past Angel Island State Park, and alongside the cit... More

Free Cancellation
Start From $39.00
 
San Francisco Bay Cruise Likely to Sell Out

San Francisco Bay Cruise

  • USA
  • Exellent278 reviews4.4

You haven’t fully experienced San Francisco until you’ve taken a Bay Cruise. This popular 1-hou....

    Free Cancellation
    Start From $39.00
 
 

Afternoon Windjammer Cruise Along the Coast of Portland Maine

(4.7 of 126 reviews)

Sail with us for a two-hour Windjammer Sail on Casco Bay in Portland, Maine — the perfect way to experience the beauty of the rugged coastline, complete with lighthouses, seals, and seabirds (NOTE: This is NOT a narrated tour,... More

Free Cancellation
Start From $67.00
 
Afternoon Windjammer Cruise Along the Coast of Portland Maine Likely to Sell Out

Afternoon Windjammer Cruise Along the Coast of Portland Maine

  • USA
  • Superb126 reviews4.7

Sail with us for a two-hour Windjammer Sail on Casco Bay in Portland, Maine — the perfect way to e....

    Free Cancellation
    Start From $67.00
 
 

Sunset Sail from Traverse City with Food, Wine & Cocktails

(4.8 of 199 reviews)

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

Free Cancellation
Start From $199.00
 
Sunset Sail from Traverse City with Food, Wine & Cocktails Likely to Sell Out

Sunset Sail from Traverse City with Food, Wine & Cocktails

  • USA
  • Superb199 reviews4.8

Wind down and relax as our captain and crewmates teach you about our elegant schooner and share stor....

    Free Cancellation
    Start From $199.00
 
 

Key West's Favorite Afternoon Dolphin Sail

(4.7 of 72 reviews)

Our afternoon dolphin watch is limited to an intimate number of passengers to optimize your views! Enjoy sailing aboard a 60' catamaran to the dolphin playground to view wild dolphins play and frolic in their natural habitat. Atla... More

Free Cancellation
Start From $59.00
 
Key West's Favorite Afternoon Dolphin Sail Likely to Sell Out

Key West's Favorite Afternoon Dolphin Sail

  • USA
  • Superb72 reviews4.7

Our afternoon dolphin watch is limited to an intimate number of passengers to optimize your views! E....

    Free Cancellation
    Start From $59.00
 
 

Panama City Beach Sunset Catamaran Sail on The Privateer

(4.8 of 656 reviews)

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
Start From $45.00
 
Panama City Beach Sunset Catamaran Sail on The Privateer Likely to Sell Out

Panama City Beach Sunset Catamaran Sail on The Privateer

  • USA
  • Superb656 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
    Start From $45.00
 
 

Sunset Sail on a Small Charming Hawaiian Catamaran Maalaea Harbor

(4.8 of 65 reviews)

Experience the resilience and spirit of Maui aboard the Winona, a vessel that bravely survived the Lahaina harbor wildfires, moored outside of the harbor breakwall. Now operating from Ma'alaea Harbor, we invite you to join our cap... More

Free Cancellation
Start From $119.00
 
Sunset Sail on a Small Charming Hawaiian Catamaran Maalaea Harbor Likely to Sell Out

Sunset Sail on a Small Charming Hawaiian Catamaran Maalaea Harbor

  • USA
  • Superb65 reviews4.8

Experience the resilience and spirit of Maui aboard the Winona, a vessel that bravely survived the L....

    Free Cancellation
    Start From $119.00
 
 

Sunset Sail Along the San Diego Skyline

(4.9 of 565 reviews)

Enjoy an evening sailing under the sunset on a relaxing sailing cruise with a unique perspective on San Diego that you can only get from the water.  Our San Diego Bay Sunset Sailing Cruises provide an up-close and personal view o... More

Free Cancellation
Start From $115.00
 
Sunset Sail Along the San Diego Skyline Likely to Sell Out

Sunset Sail Along the San Diego Skyline

  • USA
  • Superb565 reviews4.9

Enjoy an evening sailing under the sunset on a relaxing sailing cruise with a unique perspective on ....

    Free Cancellation
    Start From $115.00
 
 

Sunset Catamaran Cruise in Ft. Lauderdale

(4.8 of 672 reviews)

A perfect way to end the day, with a relaxing sail upon the Atlantic Ocean. Imagine taking in the breathtaking views of FT. Lauderdale beach as the sun slips slowly behind the lights of the city. This evening cruise calls for sun ... More

Free Cancellation
Start From $99.00
 
Sunset Catamaran Cruise in Ft. Lauderdale Likely to Sell Out

Sunset Catamaran Cruise in Ft. Lauderdale

  • USA
  • Superb672 reviews4.8

A perfect way to end the day, with a relaxing sail upon the Atlantic Ocean. Imagine taking in the br....

    Free Cancellation
    Start From $99.00
 
 

Waikoloa Signature Catamaran Sunset Sail

(4.7 of 351 reviews)

Explore the Waikoloa and Kohala-Kona coastline aboard The Spirit of Aloha, a 54-foot sailing catamaran. Catch the moment the sun slips below the horizon. You may even see the green flash. Board from Anaehoomalu Bay (A-Bay) to sail... More

Free Cancellation
Start From $149.00
 
Waikoloa Signature Catamaran Sunset Sail Likely to Sell Out

Waikoloa Signature Catamaran Sunset Sail

  • USA
  • Superb351 reviews4.7

Explore the Waikoloa and Kohala-Kona coastline aboard The Spirit of Aloha, a 54-foot sailing catamar....

    Free Cancellation
    Start From $149.00
 
 

Afternoon Sail & Snorkel to the Captain Cook Monument

(4.9 of 692 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 a... More

Free Cancellation
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
  • Superb692 reviews4.9

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

    Free Cancellation
    Start From $136.19
 
 

Private Luxury Yacht Charters, BYOB & Dolphins

(5 of 379 reviews)

We are a family owned luxury yacht charter business. Come enjoy a BYOB day of sailing and seeing the historic sites of Charleston from the water on one of our sailboats. We offer hourly, daily, or customized tours according to you... More

Free Cancellation
Private Tour
Start From $499.00
 
Private Luxury Yacht Charters, BYOB & Dolphins Likely to Sell Out

Private Luxury Yacht Charters, BYOB & Dolphins

  • USA
  • Superb379 reviews5

We are a family owned luxury yacht charter business. Come enjoy a BYOB day of sailing and seeing the....

    Free Cancellation
    Private Tour
    Start From $499.00
 
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