Menu

Top 10 Best USA Sailing Trips

Found 430 Sailing Trips activities in USA. Sort by Popularity. - Page 2
 

Maui: Kaanapali Beach 5-hour Snorkel w/ BBQ Lunch & Open Bar

(4.6 of 10 reviews)

5-hour, two-spot snorkel is unlike any other on Ka'anapali Beach as it's aboard Ka'anapali's newest luxury custom built catamarans and includes breakfast, lunch, dessert and an open bar. This is our award-winning snorkel tour that... More

Free Cancellation
Start From $203.16
 
Maui: Kaanapali Beach 5-hour Snorkel w/ BBQ Lunch & Open Bar

Maui: Kaanapali Beach 5-hour Snorkel w/ BBQ Lunch & Open Bar

  • USA
  • Superb10 reviews4.6

5-hour, two-spot snorkel is unlike any other on Ka'anapali Beach as it's aboard Ka'anapali's newest ....

    Free Cancellation
    Start From $203.16
 
 

San Francisco Bay Cruise

(4.4 of 313 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

San Francisco Bay Cruise

  • USA
  • Exellent313 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
 
 

Waikiki Turtle Snorkel and Sail on Hawea Catamaran

(4.8 of 1,663 reviews)

Experience the best of Waikiki on a Turtle Snorkel & Sail combo aboard the Hawea Catamaran. This popular Oahu tour blends marine exploration and island relaxation in one extraordinary outing. Swim among sea turtles and tropical fi... More

Free Cancellation
Start From $89.56
 
Waikiki Turtle Snorkel and Sail on Hawea Catamaran

Waikiki Turtle Snorkel and Sail on Hawea Catamaran

  • USA
  • Superb1,663 reviews4.8

Experience the best of Waikiki on a Turtle Snorkel & Sail combo aboard the Hawea Catamaran. This pop....

    Free Cancellation
    Start From $89.56
 
 
-10% Waikiki Catamaran Snorkel Sail with Lunch: Turtles Guaranteed

Waikiki Catamaran Snorkel Sail with Lunch: Turtles Guaranteed

(4.7 of 2,112 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

Special Offer
Free Cancellation
Start From $134.95
(Saving 10% ) $149.95
 
-10% Waikiki Catamaran Snorkel Sail with Lunch: Turtles Guaranteed

Waikiki Catamaran Snorkel Sail with Lunch: Turtles Guaranteed

  • USA
  • Superb2,112 reviews4.7

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

    Special Offer
    Free Cancellation
    Start From $134.95
    (Saving 10% ) $149.95
 
 

Sunset Sail in Key West with Beverages Included

(4.9 of 920 reviews)

Key West is famous for fabulous sunsets and Floridays is famous for our spectacular uncrowded champagne sunset cruise. Our reputation for personal service and attention to detail on our sunset cruise is legendary. Being out on the... More

Free Cancellation
Start From $79.00
 
Sunset Sail in Key West with Beverages Included

Sunset Sail in Key West with Beverages Included

  • USA
  • Superb920 reviews4.9

Key West is famous for fabulous sunsets and Floridays is famous for our spectacular uncrowded champa....

    Free Cancellation
    Start From $79.00
 
 

Four Winds Molokini Snorkeling Tour from Maalaea Harbor

(4.7 of 823 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
  • Superb823 reviews4.7

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

    Free Cancellation
    Start From $202.59
 
 

Day's End Cocktail Sunset Sail

(4.7 of 72 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 $159.00
 
Day's End Cocktail Sunset Sail Likely to Sell Out

Day's End Cocktail Sunset Sail

  • USA
  • Superb72 reviews4.7

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

    Free Cancellation
    Start From $159.00
 
 

Waikiki 2-Hour Sunset Sailing Catamaran – Swim & Sail Adventure

(4.7 of 537 reviews)

There’s no better place to take a dip than the crystal-clear waters of Waikiki—and no better way to experience a Hawaiian sunset than from the ocean, with the iconic Waikiki coastline as your backdrop. As the sun begins to se... More

Special Offer
Free Cancellation
Start From $44.80
(Saving 12% ) $50.71
 
-12% Waikiki 2-Hour Sunset Sailing Catamaran – Swim & Sail Adventure Likely to Sell Out

Waikiki 2-Hour Sunset Sailing Catamaran – Swim & Sail Adventure

  • USA
  • Superb537 reviews4.7

There’s no better place to take a dip than the crystal-clear waters of Waikiki—and no better way....

    Special Offer
    Free Cancellation
    Start From $44.80
    (Saving 12% ) $50.71
 
 

Key West Sunset Sail: Dolphin Watching, Wine, and Tapas

(4.6 of 713 reviews)

Our Captain’s Choice Dolphin Watch Sunset Sail is the ultimate VIP sailing experience! Limited to an intimate number of passengers, this 2.5 hour sail is more like a private cruise than a group tour and is one of the top things ... More

Free Cancellation
Start From $89.00
 
Key West Sunset Sail: Dolphin Watching, Wine, and Tapas Likely to Sell Out

Key West Sunset Sail: Dolphin Watching, Wine, and Tapas

  • USA
  • Superb713 reviews4.6

Our Captain’s Choice Dolphin Watch Sunset Sail is the ultimate VIP sailing experience! Limited to ....

    Free Cancellation
    Start From $89.00
 
 

Waikiki Sunset Cocktail Sail with Open Bar

(4.7 of 557 reviews)

Experience Waikiki’s favorite sunset sail, perfect for social adventurers and party seekers. This lively evening cruise invites solo travelers and groups alike to unwind with unlimited drinks—including Maui Brewing beers, wine... More

Free Cancellation
Start From $84.77
 
Waikiki Sunset Cocktail Sail with Open Bar Likely to Sell Out

Waikiki Sunset Cocktail Sail with Open Bar

  • USA
  • Superb557 reviews4.7

Experience Waikiki’s favorite sunset sail, perfect for social adventurers and party seekers. This ....

    Free Cancellation
    Start From $84.77
 
 

St. Augustine Live Music Cruise with Drinks and Sunset Option

(4.8 of 328 reviews)

**45' Corinthian Power Catamaran will be operating this tour from January 13th - March 1st 2026.** Sailing Catamaran tours will resume on March 2nd. Come aboard our spacious state-of-the-art catamaran on St. Augustine's only all ... More

Free Cancellation
Start From $69.17
 
St. Augustine Live Music Cruise with Drinks and Sunset Option Likely to Sell Out

St. Augustine Live Music Cruise with Drinks and Sunset Option

  • USA
  • Superb328 reviews4.8

**45' Corinthian Power Catamaran will be operating this tour from January 13th - March 1st 2026.** S....

    Free Cancellation
    Start From $69.17
 
 

Luxury Catamaran Whale Watch

(4.9 of 74 reviews)

From December through April, the waters off Maui come alive with the sights and sounds of the majestic humpback whales, and there’s no better way to witness the wonder than from the deck of our 65’ catamaran. This two-hour ex... More

Free Cancellation
Start From $119.00
 
Luxury Catamaran Whale Watch Likely to Sell Out

Luxury Catamaran Whale Watch

  • USA
  • Superb74 reviews4.9

From December through April, the waters off Maui come alive with the sights and sounds of the majest....

    Free Cancellation
    Start From $119.00
 
 

Kauai’s Na Pali Coast Snorkel and Sail Tour

(4.8 of 546 reviews)

Set sail for a once-in-a-lifetime adventure along Kauai’s iconic Na Pali Coast. This five-hour catamaran journey combines spectacular sightseeing, exciting snorkeling, and all-inclusive comfort, making it the top choice for fami... More

Free Cancellation
Start From $292.48
 
Kauai’s Na Pali Coast Snorkel and Sail Tour Likely to Sell Out

Kauai’s Na Pali Coast Snorkel and Sail Tour

  • USA
  • Superb546 reviews4.8

Set sail for a once-in-a-lifetime adventure along Kauai’s iconic Na Pali Coast. This five-hour cat....

    Free Cancellation
    Start From $292.48
 
 

Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbor

(4.5 of 622 reviews)

Meet us at Aquarium Wharf near Concord St. and Calhoun St. in Charleston SC as you experience historic Charleston Harbor aboard our classic 84-foot Tall Ship for a unique sailing experience. There is no better way to witness all o... More

Free Cancellation
Start From $45.00
 
Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbor Likely to Sell Out

Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbo....

  • USA
  • Exellent622 reviews4.5

Meet us at Aquarium Wharf near Concord St. and Calhoun St. in Charleston SC as you experience histor....

    Free Cancellation
    Start From $45.00
 
 

Sunset Sail Along the San Diego Skyline

(4.9 of 605 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 $109.00
 
Sunset Sail Along the San Diego Skyline Likely to Sell Out

Sunset Sail Along the San Diego Skyline

  • USA
  • Superb605 reviews4.9

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

    Free Cancellation
    Start From $109.00
 
 

Key West Sunset Sail Aboard Legendary Schooner Appledore

(5 of 281 reviews)

Experience sailing Key West on a majestic 2-masted schooner, just like adventurers from the 19th century, while enjoying the luxurious state-of-the-art accommodations of a modern passenger schooner. Her decks are spacious and comf... More

Free Cancellation
Start From $89.00
 
Key West Sunset Sail Aboard Legendary Schooner Appledore Likely to Sell Out

Key West Sunset Sail Aboard Legendary Schooner Appledore

  • USA
  • Superb281 reviews5

Experience sailing Key West on a majestic 2-masted schooner, just like adventurers from the 19th cen....

    Free Cancellation
    Start From $89.00
 
 

Waikoloa Signature Catamaran Sunset Sail

(4.7 of 399 reviews)

End your day in paradise with a relaxing sunset cruise along Waikoloa’s beautiful Kohala Coast. Departing from Anaeho‘omalu Bay, the Spirit of Aloha catamaran offers a smooth, comfortable ride with panoramic views of Mauna Kea... More

Free Cancellation
Start From $159.00
 
Waikoloa Signature Catamaran Sunset Sail Likely to Sell Out

Waikoloa Signature Catamaran Sunset Sail

  • USA
  • Superb399 reviews4.7

End your day in paradise with a relaxing sunset cruise along Waikoloa’s beautiful Kohala Coast. De....

    Free Cancellation
    Start From $159.00
 
 

2.5-Hour Small-Group Catamaran Sail with Drinks

(4.9 of 230 reviews)

Experience the ultimate San Diego sailing adventure with a spacious catamaran cruise, offering your choice of a relaxing daytime sail or a breathtaking sunset sail. Designed for comfort and stability, these modern catamarans featu... More

Free Cancellation
Start From $119.00
 
2.5-Hour Small-Group Catamaran Sail with Drinks Likely to Sell Out

2.5-Hour Small-Group Catamaran Sail with Drinks

  • USA
  • Superb230 reviews4.9

Experience the ultimate San Diego sailing adventure with a spacious catamaran cruise, offering your ....

    Free Cancellation
    Start From $119.00
 
 

Small-Group San Diego Sunset Sailing Excursion

(4.9 of 597 reviews)

Set sail from San Diego on this small-group sailing tour on a sunset sail on the open ocean. This three-hour adventure on a Catalina sailboat is limited to six (6) guests allowing you a comfortable, semi-private experience (or, pu... More

Free Cancellation
Start From $127.00
 
Small-Group San Diego Sunset Sailing Excursion Likely to Sell Out

Small-Group San Diego Sunset Sailing Excursion

  • USA
  • Superb597 reviews4.9

Set sail from San Diego on this small-group sailing tour on a sunset sail on the open ocean. This th....

    Free Cancellation
    Start From $127.00
 
 

Southwest Florida Sunset Sail

(4.9 of 483 reviews)

SWFL sunsets are the best, and there is no better place to watch them than from the deck of our 36ft. Sailing Catamaran, "Copacetic". The sunset hours are a magical time to be out on the water. With the winds calm, the sun turns g... More

Free Cancellation
Start From $70.00
 
Southwest Florida Sunset Sail Likely to Sell Out

Southwest Florida Sunset Sail

  • USA
  • Superb483 reviews4.9

SWFL sunsets are the best, and there is no better place to watch them than from the deck of our 36ft....

    Free Cancellation
    Start From $70.00
 
1 2 3 4 5
Booking.com
Booking.com
Booking.com