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Top 10 Best USA Sailing Trips

Found 452 Sailing Trips activities in USA. Sort by Popularity. - Page 6
 

America's Cup 12-Meter Yacht Afternoon Sail from Hilton Head

(4.6 of 553 reviews)

Only on Hilton Head and only in Harbour Town can you sail aboard the real America's Cup, 12 meter, Stars & Stripes once skippered by the famous Dennis Connor. All trips take place under full sail. We only use our motor to get in a... More

Free Cancellation
Start From $55.00
 
America's Cup 12-Meter Yacht Afternoon Sail from Hilton Head

America's Cup 12-Meter Yacht Afternoon Sail from Hilton Head

  • USA
  • Superb553 reviews4.6

Only on Hilton Head and only in Harbour Town can you sail aboard the real America's Cup, 12 meter, S....

    Free Cancellation
    Start From $55.00
 
 

2-Hour Oahu Sunset Catamaran Sail

(4.8 of 134 reviews)

Relax, sit back and delight in our 2-hour sunset sailing cruise on a gorgeous, 53' foot catamaran from the beautiful Ko Olina Marina on Oahu. Sip a cocktail and enjoy warm wind in your hair as you scan for dolphins and listen for ... More

Free Cancellation
Start From $130.00
 
2-Hour Oahu Sunset Catamaran Sail

2-Hour Oahu Sunset Catamaran Sail

  • USA
  • Superb134 reviews4.8

Relax, sit back and delight in our 2-hour sunset sailing cruise on a gorgeous, 53' foot catamaran fr....

    Free Cancellation
    Start From $130.00
 
 

Windjammer Classic Day Sail from Camden, Maine

(4.8 of 428 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
Start From $59.95
 
Windjammer Classic Day Sail from Camden, Maine

Windjammer Classic Day Sail from Camden, Maine

  • USA
  • Superb428 reviews4.8

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

    Free Cancellation
    Start From $59.95
 
 

Ft Myers Beach 2 Hour Tiki Pub Fun in the Sun Dolphin Cruise

(4.9 of 113 reviews)

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

Free Cancellation
Start From $59.95
 
Ft Myers Beach 2 Hour Tiki Pub Fun in the Sun Dolphin Cruise Likely to Sell Out

Ft Myers Beach 2 Hour Tiki Pub Fun in the Sun Dolphin Cruise

  • USA
  • Superb113 reviews4.9

Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages (BYOB), take pics,....

    Free Cancellation
    Start From $59.95
 
 

Classic Key West Schooner Sunset Sail with Full Open Bar

(4.9 of 250 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
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
  • Superb250 reviews4.9

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

    Free Cancellation
    Start From $109.00
 
 

Luxury Sunset Sail on Serendipity Catamaran in Charleston

(5 of 12 reviews)

Set sail for an unforgettable 2-hour sunset cruise on the Serendipity Catamaran, departing from Seabreeze Marina in downtown Charleston. Enjoy stunning waterfront views and local wildlife as the sun dips below the horizon. This up... More

Free Cancellation
Start From $150.00
 
Luxury Sunset Sail on Serendipity Catamaran in Charleston Likely to Sell Out

Luxury Sunset Sail on Serendipity Catamaran in Charleston

  • USA
  • Superb12 reviews5

Set sail for an unforgettable 2-hour sunset cruise on the Serendipity Catamaran, departing from Seab....

    Free Cancellation
    Start From $150.00
 
 

Key West Reef Snorkel & Sail Adventure

(4.7 of 562 reviews)

Join us for a snorkel adventure to the only living coral reef in North America. We have several fantastic reefs to choose from on both the north and south sides of Key West, each offering a unique experience. It’s about an hour ... More

Free Cancellation
Start From $79.00
 
Key West Reef Snorkel & Sail Adventure Likely to Sell Out

Key West Reef Snorkel & Sail Adventure

  • USA
  • Superb562 reviews4.7

Join us for a snorkel adventure to the only living coral reef in North America. We have several fant....

    Free Cancellation
    Start From $79.00
 
 

Casco Bay Morning Windjammer Sail

(4.9 of 30 reviews)

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

Free Cancellation
Start From $61.00
 
Casco Bay Morning Windjammer Sail Likely to Sell Out

Casco Bay Morning Windjammer Sail

  • USA
  • Superb30 reviews4.9

Sail with us for a two-hour morning Windjammer Sail on Casco Bay in Portland, Maine. This is the per....

    Free Cancellation
    Start From $61.00
 
 

New York City Sailboat Day Cruise to the Statue of Liberty

(4.9 of 163 reviews)

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

Free Cancellation
Start From $60.08
 
New York City Sailboat Day Cruise to the Statue of Liberty Likely to Sell Out

New York City Sailboat Day Cruise to the Statue of Liberty

  • USA
  • Superb163 reviews4.9

Experience New York by water aboard Schooner Adirondack, an 80-foot, 2-masted schooner inspired by t....

    Free Cancellation
    Start From $60.08
 
 

Waikiki Sunset Cocktail Cruise - Hilton Hawaiian Village

(4.4 of 35 reviews)

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

Free Cancellation
Start From $119.95
 
Waikiki Sunset Cocktail Cruise - Hilton Hawaiian Village Likely to Sell Out

Waikiki Sunset Cocktail Cruise - Hilton Hawaiian Village

  • USA
  • Exellent35 reviews4.4

Explore the Waikiki coastline aboard the new Spirit of Aloha, a 65-foot sailing catamaran custom-bui....

    Free Cancellation
    Start From $119.95
 
 

San Diego Harbor Cruise on the Largest Catamaran in San Diego

(4.9 of 47 reviews)

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

Free Cancellation
Start From $55.00
 
San Diego Harbor Cruise on the Largest Catamaran in San Diego Likely to Sell Out

San Diego Harbor Cruise on the Largest Catamaran in San Diego

  • USA
  • Superb47 reviews4.9

Enjoy a San Diego harbor cruise on San Diego's largest and newest catamaran yacht. We provide our gu....

    Free Cancellation
    Start From $55.00
 
 

Schooner Eastwind 2 Hour Day Sail in Boothbay Harbor

(4.6 of 141 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 Likely to Sell Out

Schooner Eastwind 2 Hour Day Sail in Boothbay Harbor

  • USA
  • Superb141 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
 
 

Akialoa Mā’alaea Sunset Sail

(4.7 of 15 reviews)

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

Free Cancellation
Start From $108.11
 
Akialoa Mā’alaea Sunset Sail Likely to Sell Out

Akialoa Mā’alaea Sunset Sail

  • USA
  • Superb15 reviews4.7

Witness the stunning sunsets of Maui from the comfort of a luxury sailing catamaran. The Akialoa Sun....

    Free Cancellation
    Start From $108.11
 
 

Key West: Sunset Sail + Reef Snorkel & Sandbar

(5 of 41 reviews)

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

Free Cancellation
Start From $143.05
 
Key West: Sunset Sail + Reef Snorkel & Sandbar Likely to Sell Out

Key West: Sunset Sail + Reef Snorkel & Sandbar

  • USA
  • Superb41 reviews5

Reef Snorkel + Sandbar & Sunset Sail • Summer Only with Small Groups on an Honest Eco Tour. Wh....

    Free Cancellation
    Start From $143.05
 
 

Sunset Sailing Cruise in Monterey Bay

(4.8 of 53 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
Start From $95.00
 
Sunset Sailing Cruise in Monterey Bay Likely to Sell Out

Sunset Sailing Cruise in Monterey Bay

  • USA
  • Superb53 reviews4.8

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

    Free Cancellation
    Start From $95.00
 
 

Top Rated San Diego Sunset Sail Classic Yacht 6 Guests

(4.9 of 351 reviews)

Skip the crowded tour boats. Liberty carries just six guests and that changes everything. Sail San Diego Bay aboard a classic 41-ft Friendship sloop with Captain Phil, a USCG-licensed captain with 55 years of sailing experience. ... More

Free Cancellation
Start From $125.00
 
Top Rated San Diego Sunset Sail Classic Yacht 6 Guests Likely to Sell Out

Top Rated San Diego Sunset Sail Classic Yacht 6 Guests

  • USA
  • Superb351 reviews4.9

Skip the crowded tour boats. Liberty carries just six guests and that changes everything. Sail San ....

    Free Cancellation
    Start From $125.00
 
 

Sunset Sailing Cruise Aboard Schooner Clearwater-Clearwater Beach

(4.9 of 268 reviews)

Whether you are a seasoned sailor or if this is your first time sailing, the Schooner Clearwater will be a memorable visit!!! ;) *Children under age 5-not permitted to sail. *Not Suitable for Guests with mobility issues. *Partic... More

Free Cancellation
Start From $80.00
 
Sunset Sailing Cruise Aboard Schooner Clearwater-Clearwater Beach Likely to Sell Out

Sunset Sailing Cruise Aboard Schooner Clearwater-Clearwater Beach

  • USA
  • Superb268 reviews4.9

Whether you are a seasoned sailor or if this is your first time sailing, the Schooner Clearwater wil....

    Free Cancellation
    Start From $80.00
 
 

America's Cup Evening Sailing Adventure Newport, RI

(4.9 of 42 reviews)

Get on board for the best hands-on sailing experience Newport, RI has to offer. A 2 hour sail around Narragansett Bay passed many iconic sights including New York Yacht Club, Ida Lewis Light, Fort Adams, Eisenhower House, Hammersm... More

Free Cancellation
Start From $125.00
 
America's Cup Evening Sailing Adventure Newport, RI Likely to Sell Out

America's Cup Evening Sailing Adventure Newport, RI

  • USA
  • Superb42 reviews4.9

Get on board for the best hands-on sailing experience Newport, RI has to offer. A 2 hour sail around....

    Free Cancellation
    Start From $125.00
 
 

Sunset and Manta Ray Snorkel Adventure

(4.9 of 866 reviews)

Our most popular tour!  Watch a legendary Kona sunset from our spacious 50’ catamaran as you sail the Kona coast, followed by the adventure of a lifetime - snorkeling with the majestic manta rays!  Upon arriving, receive an in... More

Free Cancellation
Start From $154.51
 
Sunset and Manta Ray Snorkel Adventure Likely to Sell Out

Sunset and Manta Ray Snorkel Adventure

  • USA
  • Superb866 reviews4.9

Our most popular tour!  Watch a legendary Kona sunset from our spacious 50’ catamaran as you sail....

    Free Cancellation
    Start From $154.51
 
 

Waikoloa Catamaran Snorkel Sail Including Lunch

(4.6 of 109 reviews)

Set sail from Anaeho‘omalu Bay on a 3-hour snorkel and cruise adventure along Waikoloa’s beautiful Kohala Coast. Aboard the spacious Spirit of Aloha catamaran, enjoy a smooth, comfortable ride to one of the region’s best sno... More

Free Cancellation
Start From $189.00
 
Waikoloa Catamaran Snorkel Sail Including Lunch Likely to Sell Out

Waikoloa Catamaran Snorkel Sail Including Lunch

  • USA
  • Superb109 reviews4.6

Set sail from Anaeho‘omalu Bay on a 3-hour snorkel and cruise adventure along Waikoloa’s beautif....

    Free Cancellation
    Start From $189.00
 
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