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Top 10 Best USA Sailing Trips

Found 426 Sailing Trips activities in USA. Sort by Popularity. - Page 10
 

New York Fall Foliage Sail up the Hudson River

(4.5 of 11 reviews)

Enjoy a 3.5-hour scenic sail up the Hudson River to the Palisades aboard Schooner Adirondack or Schooner America 2.0, both 1800s-style sailboats. Bordering the Hudson River north of Fort Lee, New Jersey, the Palisade Cliffs are am... More

Free Cancellation
Start From $143.27
 
New York Fall Foliage Sail up the Hudson River

New York Fall Foliage Sail up the Hudson River

  • USA
  • Exellent11 reviews4.5

Enjoy a 3.5-hour scenic sail up the Hudson River to the Palisades aboard Schooner Adirondack or Scho....

    Free Cancellation
    Start From $143.27
 
 

2hr. SUNSET Sailing Experience on San Francisco Bay

(4.9 of 35 reviews)

This sailing experience is an Interactive sunset sailing adventure on San Francisco Bay! This Sailing Experience is "interactive" which means we want you to get the full experience of sailing so you'll have an opportunity to tak... More

Free Cancellation
Start From $149.00
 
2hr. SUNSET Sailing Experience on San Francisco Bay Likely to Sell Out

2hr. SUNSET Sailing Experience on San Francisco Bay

  • USA
  • Superb35 reviews4.9

This sailing experience is an Interactive sunset sailing adventure on San Francisco Bay! This Sail....

    Free Cancellation
    Start From $149.00
 
 

Sunset and Manta Ray Snorkel Adventure

(4.9 of 872 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
  • Superb872 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
 
 

Key West Wreckers Race Aboard Schooner America 2.0

(4.9 of 15 reviews)

Join in on the annual Wreckers Race and take part in a fast pace race toward Sand Key Lighthouse aboard Schooner America 2.0! Back in the day, pirate ships from afar often ran aground on Sand Key Reef, nine miles off the southern ... More

Free Cancellation
Start From $116.10
 
Key West Wreckers Race Aboard Schooner America 2.0 Likely to Sell Out

Key West Wreckers Race Aboard Schooner America 2.0

  • USA
  • Superb15 reviews4.9

Join in on the annual Wreckers Race and take part in a fast pace race toward Sand Key Lighthouse abo....

    Free Cancellation
    Start From $116.10
 
 

Waikiki Sunset Cruise from Oahu

(4.7 of 76 reviews)

Experience a Hawaiian sunset sail aboard our 55-foot double-decker catamaran. With spacious decks and a submerged glass-bottom viewing room, you’ll have an ideal vantage point to observe marine life such as dolphins, whales, sea... More

Free Cancellation
Start From $45.00
 
Waikiki Sunset Cruise from Oahu Likely to Sell Out

Waikiki Sunset Cruise from Oahu

  • USA
  • Superb76 reviews4.7

Experience a Hawaiian sunset sail aboard our 55-foot double-decker catamaran. With spacious decks an....

    Free Cancellation
    Start From $45.00
 
 

Sunset Sailing Cruise Aboard Schooner Clearwater-Clearwater Beach

(4.9 of 279 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
  • Superb279 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
 
 

Luxury Camden Sailing Experience

(4.9 of 19 reviews)

Small groups of up to six. Two staff members to take care of you. Cushioned seating for all. Fastest boat in the harbor... More

Free Cancellation
Start From $125.00
 
Luxury Camden Sailing Experience Likely to Sell Out

Luxury Camden Sailing Experience

  • USA
  • Superb19 reviews4.9

Small groups of up to six. Two staff members to take care of you. Cushioned seating for all. Faste....

    Free Cancellation
    Start From $125.00
 
 

Waikiki Turtle Snorkeling Adventure(8am)

(5 of 135 reviews)

Discover an all-in-one Waikiki ocean adventure with our Turtle Snorkeling Tour. Cruise aboard our spacious and comfortable catamaran to Turtle Canyon, where you’ll have the opportunity to snorkel with Hawaiian green sea turtles ... More

Free Cancellation
Start From $100.00
 
Waikiki Turtle Snorkeling Adventure(8am) Likely to Sell Out

Waikiki Turtle Snorkeling Adventure(8am)

  • USA
  • Superb135 reviews5

Discover an all-in-one Waikiki ocean adventure with our Turtle Snorkeling Tour. Cruise aboard our sp....

    Free Cancellation
    Start From $100.00
 
 

Sunset Dolphin Sail Aboard the Daydreams Sailboat

(5 of 45 reviews)

Your 2 hour sunset charter on our 47-foot sailboat Daydreams will include a scenic trip through Grand Lagoon and along the coast of Shell Island. Enjoy a relaxing sail in the Gulf of Mexico and look for dolphins along the way. Wit... More

Free Cancellation
Start From $106.93
 
Sunset Dolphin Sail Aboard the Daydreams Sailboat Likely to Sell Out

Sunset Dolphin Sail Aboard the Daydreams Sailboat

  • USA
  • Superb45 reviews5

Your 2 hour sunset charter on our 47-foot sailboat Daydreams will include a scenic trip through Gran....

    Free Cancellation
    Start From $106.93
 
 

Waikiki Beach Whale Watching: Catamaran Sail & Open Bar

(5 of 15 reviews)

Observe the majestic humpback whales during their migration from December to March on this 1.5-hour sail in Honolulu. Experience the beauty of Oahu's coastline while searching for dolphins and sea turtles in their natural habitat.... More

Free Cancellation
Start From $53.36
 
Waikiki Beach Whale Watching: Catamaran Sail & Open Bar Likely to Sell Out

Waikiki Beach Whale Watching: Catamaran Sail & Open Bar

  • USA
  • Superb15 reviews5

Observe the majestic humpback whales during their migration from December to March on this 1.5-hour ....

    Free Cancellation
    Start From $53.36
 
 

Fort Myers: Tiki Pub VIP Private Dolphin & Sunset Cruise

(5 of 4 reviews)

Spend the most amazing time of day in the best place to enjoy it. Our custom tiki boat has it all. Whether you want to dance, sing Tiki-Oki, slip down the on board water slide, or just relax and enjoy the sunset, this cruise will ... More

Free Cancellation
Private Tour
Start From $449.00
 
Fort Myers: Tiki Pub VIP Private Dolphin & Sunset Cruise Likely to Sell Out

Fort Myers: Tiki Pub VIP Private Dolphin & Sunset Cruise

  • USA
  • Superb4 reviews5

Spend the most amazing time of day in the best place to enjoy it. Our custom tiki boat has it all. W....

    Free Cancellation
    Private Tour
    Start From $449.00
 
 

Kona Tradewind Catamaran Day Sail

(4.8 of 51 reviews)

Experience the beauty of the Kona Coast from a new perspective aboard the Spirit of Aloha sailing catamaran. Feel the trade winds fill the sails as you glide across the water, taking in panoramic views of volcanic cliffs, sparklin... More

Free Cancellation
Private Tour
Start From $89.00
 
Kona Tradewind Catamaran Day Sail Likely to Sell Out

Kona Tradewind Catamaran Day Sail

  • USA
  • Superb51 reviews4.8

Experience the beauty of the Kona Coast from a new perspective aboard the Spirit of Aloha sailing ca....

    Free Cancellation
    Private Tour
    Start From $89.00
 
 

2 Hours Private Sailboat Charter in the San Francisco Bay

(4.8 of 22 reviews)

Imagine sailing underneath the Golden Gate Bridge on your own private yacht and seeing wildlife. Just kick back and celebrate your special event under the romance of sail. Private sailboat charters are a great way to celebrate you... More

Free Cancellation
Private Tour
Start From $695.00
 
2 Hours Private Sailboat Charter in the San Francisco Bay Likely to Sell Out

2 Hours Private Sailboat Charter in the San Francisco Bay

  • USA
  • Superb22 reviews4.8

Imagine sailing underneath the Golden Gate Bridge on your own private yacht and seeing wildlife. Jus....

    Free Cancellation
    Private Tour
    Start From $695.00
 
 

Wednesday Happy Hour Sunset Sail - Drinks Included

(5 of 8 reviews)

Aloha Wednesday Sunset Sail: Island Vibes & Relaxation on the Charleston Harbor Celebrate the spirit of the islands right here in Charleston with our Aloha Wednesday Sunset Sail. This midweek escape combines tropical charm with st... More

Free Cancellation
Private Tour
Start From $76.00
 
Wednesday Happy Hour Sunset Sail - Drinks Included Likely to Sell Out

Wednesday Happy Hour Sunset Sail - Drinks Included

  • USA
  • Superb8 reviews5

Aloha Wednesday Sunset Sail: Island Vibes & Relaxation on the Charleston Harbor Celebrate the spirit....

    Free Cancellation
    Private Tour
    Start From $76.00
 
 

Waikiki Friday Night Fireworks Cruise

(4.6 of 32 reviews)

Experience authentic aloha vibes with us. Our knowledgeable guides and crew are ready to share insights on local culture, marine life, and island tips. Bring your favorite beverages and join us for Waikiki's weekly fireworks displ... More

Free Cancellation
Private Tour
Start From $60.00
 
Waikiki Friday Night Fireworks Cruise Likely to Sell Out

Waikiki Friday Night Fireworks Cruise

  • USA
  • Superb32 reviews4.6

Experience authentic aloha vibes with us. Our knowledgeable guides and crew are ready to share insig....

    Free Cancellation
    Private Tour
    Start From $60.00
 
 

Sunset Sailboat Cruise on Winyah Bay

(5 of 1 review)

As the sun lowers over the bay, the water softens and the sky comes alive. This is a favorite for couples, relaxed evenings, and anyone who wants to end the day on the water. Step aboard for an unforgettable evening on the water ... More

Free Cancellation
Private Tour
Start From $145.00
 
Sunset Sailboat Cruise on Winyah Bay Likely to Sell Out

Sunset Sailboat Cruise on Winyah Bay

  • USA
  • Superb1 review5

As the sun lowers over the bay, the water softens and the sky comes alive. This is a favorite for co....

    Free Cancellation
    Private Tour
    Start From $145.00
 
 

Windjammer Classic Sunset Sail from Camden, Maine

(4.9 of 524 reviews)

Maine sunsets are best appreciated from the water aboard the romantic Appledore II! This tall ship is limited to 49 passengers for an intimate sailing experience. She is a modern windjammer with luxurious accommodations and plent... More

Free Cancellation
Private Tour
Start From $74.95
 
Windjammer Classic Sunset Sail from Camden, Maine Likely to Sell Out

Windjammer Classic Sunset Sail from Camden, Maine

  • USA
  • Superb524 reviews4.9

Maine sunsets are best appreciated from the water aboard the romantic Appledore II! This tall ship ....

    Free Cancellation
    Private Tour
    Start From $74.95
 
 

Maui Sunset Sail

(4.6 of 224 reviews)

Enjoy tantalizing pupus (appetizers) and island-style music against the backdrop of a stunning sunset over the Pacific Ocean.This relaxing cruise is aboard our luxury sailing catamaran, Ocean Spirit. It’s the perfect way to expe... More

Free Cancellation
Private Tour
Start From $137.82
 
Maui Sunset Sail Likely to Sell Out

Maui Sunset Sail

  • USA
  • Superb224 reviews4.6

Enjoy tantalizing pupus (appetizers) and island-style music against the backdrop of a stunning sunse....

    Free Cancellation
    Private Tour
    Start From $137.82
 
 

Maui Midday Whale Watch in the Humpback Sanctuary out of Maalaea

(4.9 of 104 reviews)

Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from Alaska, and although you can see them throughout Hawaii, the ‘Au ‘au channel off the coast of Maui boasts the greatest number. ... More

Free Cancellation
Private Tour
Start From $110.27
 
Maui Midday Whale Watch in the Humpback Sanctuary out of Maalaea Likely to Sell Out

Maui Midday Whale Watch in the Humpback Sanctuary out of Maalaea

  • USA
  • Superb104 reviews4.9

Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from A....

    Free Cancellation
    Private Tour
    Start From $110.27
 
 

Hilton Hawaiian Village Adventure Sail on the Spirit of Aloha

(5 of 2 reviews)

This cruise is exceptionally family-friendly, with no snorkeling or in-water activities, making it ideal for guests who want to experience the ocean without getting wet. Unlike many Waikiki beach catamarans, the Spirit of Aloha o... More

Free Cancellation
Private Tour
Start From $59.95
 
Hilton Hawaiian Village Adventure Sail on the Spirit of Aloha Likely to Sell Out

Hilton Hawaiian Village Adventure Sail on the Spirit of Aloha

  • USA
  • Superb2 reviews5

This cruise is exceptionally family-friendly, with no snorkeling or in-water activities, making it i....

    Free Cancellation
    Private Tour
    Start From $59.95
 
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