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Top 10 Best USA Sailing Trips

Found 411 Sailing Trips activities in USA. Sort by Popularity.
 

Miami Millionaires Sightseeing Cruise

(4.3 of 1,281 reviews)

Join a sightseeing boat tour of Miami Beach and the iconic Millionaire's homes. Explore the mesmerizing beauty of Biscayne Bay, while getting an exclusive glimpse into the luxurious lifestyle of Miami's elite, with a bilingual com... More

Free Cancellation
Start From $18.00
 
Miami Millionaires Sightseeing Cruise

Miami Millionaires Sightseeing Cruise

  • USA
  • Exellent1,281 reviews4.3

Join a sightseeing boat tour of Miami Beach and the iconic Millionaire's homes. Explore the mesmeriz....

    Free Cancellation
    Start From $18.00
 
 

Deluxe Na Pali Sunset Tour on the Lucky Lady

(4.7 of 1,462 reviews)

Tour the Na Pali coast aboard a Luxury Catamaran, Lucky Lady for an afternoon that features incredible scenery topped off with a spectacular sunset. Look for dolphins, whales, and other marine critters as you sip a drink, snap som... More

Free Cancellation
Start From $222.86
 
Deluxe Na Pali Sunset Tour on the Lucky Lady

Deluxe Na Pali Sunset Tour on the Lucky Lady

  • USA
  • Superb1,462 reviews4.7

Tour the Na Pali coast aboard a Luxury Catamaran, Lucky Lady for an afternoon that features incredib....

    Free Cancellation
    Start From $222.86
 
 

Oahu Catamaran Snorkel Tour with Guaranteed Turtles

(4.9 of 1,286 reviews)

Experience one Viator's 2025 Top 20 Best Excursions in the country. This Oahu catamaran snorkel tour offers unbeatable value and family-friendly fun from Waikiki. Swim alongside Hawaiian green sea turtles and vibrant tropical fis... More

Free Cancellation
Start From $49.95
 
Oahu Catamaran Snorkel Tour with Guaranteed Turtles

Oahu Catamaran Snorkel Tour with Guaranteed Turtles

  • USA
  • Superb1,286 reviews4.9

Experience one Viator's 2025 Top 20 Best Excursions in the country. This Oahu catamaran snorkel tour....

    Free Cancellation
    Start From $49.95
 
 

Moana’s Sunset Cocktail Sail Along Oahu's Waikiki Coast

(4.9 of 2,164 reviews)

All aboard! There is no better place to be during Oahu’s magnificent golden sunsets than on our Waikiki Sunset Cruise, an unmatched experience complete with premium drinks, indescribable views, and music. As we sail alongside Oa... More

Free Cancellation
Start From $89.99
 
Moana’s Sunset Cocktail Sail Along Oahu's Waikiki Coast

Moana’s Sunset Cocktail Sail Along Oahu's Waikiki Coast

  • USA
  • Superb2,164 reviews4.9

All aboard! There is no better place to be during Oahu’s magnificent golden sunsets than on our Wa....

    Free Cancellation
    Start From $89.99
 
 

Key West Sunset Sail with Open Bar, Live Music and Hors D'oeuvres

(4.7 of 3,448 reviews)

Admire an exquisitely painted sky during this premium sunset cruise in Key West. Create fantastic memories as you set sail on one of Sebago's modern sailing catamarans while sipping sparkling wine or your favorite cocktail and fea... More

Free Cancellation
Start From $79.00
 
Key West Sunset Sail with Open Bar, Live Music and Hors D'oeuvres

Key West Sunset Sail with Open Bar, Live Music and Hors D'oeuvres

  • USA
  • Superb3,448 reviews4.7

Admire an exquisitely painted sky during this premium sunset cruise in Key West. Create fantastic me....

    Free Cancellation
    Start From $79.00
 
 

Turtles & Tacos Luxury Catamaran Snorkel

(4.8 of 88 reviews)

Laid-back, fresh, and full of fun, this mid-morning snorkel sail is all about good vibes and island flavor. Cruise aboard our spacious 65’ catamaran and snorkel alongside Hawaiian green sea turtles and colorful tropical fish at ... More

Free Cancellation
Start From $199.00
 
Turtles & Tacos Luxury Catamaran Snorkel

Turtles & Tacos Luxury Catamaran Snorkel

  • USA
  • Superb88 reviews4.8

Laid-back, fresh, and full of fun, this mid-morning snorkel sail is all about good vibes and island ....

    Free Cancellation
    Start From $199.00
 
 

Key West Signature Sunset Sail with Live Music, Open Bar & Food

(4.5 of 306 reviews)

Sunset Sip & Sail: Come see the legendary Key West Sunset on a Brand New Catamaran Sail Boat. • Open bar • Live Music • Great Appetizers Welcome aboard Key West's newest catamaran, the "Sandie Cat" as we literally... More

Free Cancellation
Start From $72.00
 
Key West Signature Sunset Sail with Live Music, Open Bar & Food

Key West Signature Sunset Sail with Live Music, Open Bar & Food

  • USA
  • Exellent306 reviews4.5

Sunset Sip & Sail: Come see the legendary Key West Sunset on a Brand New Catamaran Sail Boat. â€....

    Free Cancellation
    Start From $72.00
 
 

Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres

(4.9 of 1,316 reviews)

The Wind & Wine Sunset Sail offers a boutique experience unlike any other in Key West! This isn’t your typical party boat—it’s a calm, uncrowded sail aboard a historic schooner with an intimate, relaxed vibe. You’ll enjoy ... More

Free Cancellation
Start From $115.00
 
Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres Likely to Sell Out

Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres

  • USA
  • Superb1,316 reviews4.9

The Wind & Wine Sunset Sail offers a boutique experience unlike any other in Key West! This isn’t ....

    Free Cancellation
    Start From $115.00
 
 

St. Augustine Live Music Sunset Sail with Drinks Included

(4.8 of 294 reviews)

Come aboard our spacious state-of-the-art catamaran on St. Augustine's only all inclusive sunset sail! Indulge in complimentary beer, wine, soda, water, margaritas, champagne, and a snack, while enjoying live performances by some ... More

Free Cancellation
Start From $69.17
 
St. Augustine Live Music Sunset Sail with Drinks Included Likely to Sell Out

St. Augustine Live Music Sunset Sail with Drinks Included

  • USA
  • Superb294 reviews4.8

Come aboard our spacious state-of-the-art catamaran on St. Augustine's only all inclusive sunset sai....

    Free Cancellation
    Start From $69.17
 
 

Waikoloa Signature Catamaran Sunset Sail

(4.7 of 386 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
  • Superb386 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
 
 

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

(4.9 of 806 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 $54.99
 
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
  • Superb806 reviews4.9

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

    Free Cancellation
    Start From $54.99
 
 

Sunset Boat Cruise: Swim and Cruise Waikiki

(4.7 of 524 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

Free Cancellation
Start From $50.71
 
Sunset Boat Cruise: Swim and Cruise Waikiki Likely to Sell Out

Sunset Boat Cruise: Swim and Cruise Waikiki

  • USA
  • Superb524 reviews4.7

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

    Free Cancellation
    Start From $50.71
 
 

Day's End Cocktail Sunset Sail

(4.8 of 62 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
  • Superb62 reviews4.8

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

    Free Cancellation
    Start From $159.00
 
 

Sunset Sail in Key West with Beverages Included

(4.9 of 889 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 Likely to Sell Out

Sunset Sail in Key West with Beverages Included

  • USA
  • Superb889 reviews4.9

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

    Free Cancellation
    Start From $79.00
 
 

Waikiki Turtle Snorkel and Sail on Hawea Catamaran

(4.8 of 1,605 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 Likely to Sell Out

Waikiki Turtle Snorkel and Sail on Hawea Catamaran

  • USA
  • Superb1,605 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
 
 

San Francisco Bay Cruise

(4.4 of 307 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
  • Exellent307 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
 
 

Key West Schooner Sunset Sail with Bar & Hors d'oeuvres

(4.9 of 756 reviews)

Enjoy an exquisite 2-hour sunset sailing adventure aboard a stunning modern-built schooner! Take in the sights aboard Schooner America 2.0, the most elegant schooner in Key West, as you sail by Mallory Square, Sunset Pier, Sand K... More

Free Cancellation
Start From $116.10
 
Key West Schooner Sunset Sail with Bar & Hors d'oeuvres Likely to Sell Out

Key West Schooner Sunset Sail with Bar & Hors d'oeuvres

  • USA
  • Superb756 reviews4.9

Enjoy an exquisite 2-hour sunset sailing adventure aboard a stunning modern-built schooner! Take in....

    Free Cancellation
    Start From $116.10
 
 

Turtle Canyon Snorkel * Turtles guaranteed!!!

(4.7 of 1,209 reviews)

**Turtle Canyon Snorkel Adventure – Swim with Hawaiian Green Sea Turtles!****Gauranteed**** Join us for a **2-hour snorkeling adventure** at **Turtle Canyon**, one of Oahu’s top snorkeling spots! Cruise along the stunning **W... More

Free Cancellation
Start From $80.71
 
Turtle Canyon Snorkel * Turtles guaranteed!!! Likely to Sell Out

Turtle Canyon Snorkel * Turtles guaranteed!!!

  • USA
  • Superb1,209 reviews4.7

**Turtle Canyon Snorkel Adventure – Swim with Hawaiian Green Sea Turtles!****Gauranteed**** Join ....

    Free Cancellation
    Start From $80.71
 
 

Kona Catamaran Sunset Sail

(4.8 of 192 reviews)

Explore the beautiful Kona coastline from while aboard the Honi Olani, a 53-foot sailing catamaran. Catch the moment the sun slips below the horizon...you may even see the green flash. Enjoy the blue Pacific Ocean and maybe catch ... More

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

Kona Catamaran Sunset Sail

  • USA
  • Superb192 reviews4.8

Explore the beautiful Kona coastline from while aboard the Honi Olani, a 53-foot sailing catamaran. ....

    Free Cancellation
    Start From $149.00
 
 

Waikiki Sunset Cocktail Sail with Open Bar

(4.8 of 539 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
  • Superb539 reviews4.8

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

    Free Cancellation
    Start From $84.77
 
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