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Top 10 Best USA Sailing Trips

Found 450 Sailing Trips activities in USA. Sort by Popularity. - Page 8
 

Akialoa Mā’alaea Sunset Sail

(4.7 of 13 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

Akialoa Mā’alaea Sunset Sail

  • USA
  • Superb13 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
 
 

4-Hour Fort Lauderdale Sailing Charter

(4.9 of 319 reviews)

Enjoy some time on the water with this 4-Hour Half Day Sailing Charter located in Fort Lauderdale. Your sail is entirely customizable, and travelers have the option(PRIVATE CRUISES) to use their time docked or sailing out to sea. ... More

Free Cancellation
Start From $148.00
 
4-Hour Fort Lauderdale Sailing Charter

4-Hour Fort Lauderdale Sailing Charter

  • USA
  • Superb319 reviews4.9

Enjoy some time on the water with this 4-Hour Half Day Sailing Charter located in Fort Lauderdale. Y....

    Free Cancellation
    Start From $148.00
 
 

Private Sailing Charter on San Diego Bay

(4.9 of 45 reviews)

San Diego Bay is one of the most beautiful bodies of water on the West Coast of the United States. Why not enjoy this natural wonder aboard a beautiful sailing yacht with a knowledgeable and friendly Captain? This private charter... More

Free Cancellation
Private Tour
Start From $475.00
 
Private Sailing Charter on San Diego Bay Likely to Sell Out

Private Sailing Charter on San Diego Bay

  • USA
  • Superb45 reviews4.9

San Diego Bay is one of the most beautiful bodies of water on the West Coast of the United States. W....

    Free Cancellation
    Private Tour
    Start From $475.00
 
 

3 Hours Ultimate Watersports Excursion in Miami

(4.9 of 45 reviews)

All-Inclusive Catamaran Adventure in Miami: 3 Hours of Adrenaline and Party! Board your comfortable and stable Catamaran for an unforgettable all-inclusive water experience. Highlights: - Extreme Watersports: Feel the thrill wi... More

Free Cancellation
Private Tour
Start From $139.00
 
3 Hours Ultimate Watersports Excursion in Miami Likely to Sell Out

3 Hours Ultimate Watersports Excursion in Miami

  • USA
  • Superb45 reviews4.9

All-Inclusive Catamaran Adventure in Miami: 3 Hours of Adrenaline and Party! Board your comfortable....

    Free Cancellation
    Private Tour
    Start From $139.00
 
 

New York City Sunset Sail to the Statue of Liberty

(4.8 of 69 reviews)

Experience a sunset from New York Harbor and enjoy sweeping views of Manhattan's skyline, parts of Brooklyn and Jersey City from Schooner America. This classic sailboat is 105-feet in length and has about 3600 square feet of sail ... More

Free Cancellation
Private Tour
Start From $90.12
 
New York City Sunset Sail to the Statue of Liberty Likely to Sell Out

New York City Sunset Sail to the Statue of Liberty

  • USA
  • Superb69 reviews4.8

Experience a sunset from New York Harbor and enjoy sweeping views of Manhattan's skyline, parts of B....

    Free Cancellation
    Private Tour
    Start From $90.12
 
 

Dolphin Adventure Sail in Cocoa Beach

(4.9 of 194 reviews)

Experience the Magic of Cocoa Beach with Our Dolphin Adventure Sail! Join Cocoa Beach Catamaran for an unforgettable journey through the Banana River Lagoon! Glide across calm waters on our spacious catamaran as you encounter pla... More

Free Cancellation
Private Tour
Start From $50.85
 
Dolphin Adventure Sail in Cocoa Beach Likely to Sell Out

Dolphin Adventure Sail in Cocoa Beach

  • USA
  • Superb194 reviews4.9

Experience the Magic of Cocoa Beach with Our Dolphin Adventure Sail! Join Cocoa Beach Catamaran for....

    Free Cancellation
    Private Tour
    Start From $50.85
 
 

Maui Catamaran Sunset Cocktail Cruise from Ma'alaea Harbor

(4.6 of 19 reviews)

Join us aboard the Malolo for drinks as we cruise gently along the Maui coastline. Sit back, relax, socialize with friends and family and take in the spectacular Maui sunset.... More

Free Cancellation
Private Tour
Start From $59.95
 
Maui Catamaran Sunset Cocktail Cruise from Ma'alaea Harbor Likely to Sell Out

Maui Catamaran Sunset Cocktail Cruise from Ma'alaea Harbor

  • USA
  • Superb19 reviews4.6

Join us aboard the Malolo for drinks as we cruise gently along the Maui coastline. Sit back, relax, ....

    Free Cancellation
    Private Tour
    Start From $59.95
 
 

Private Sailing on Beautiful Lake Michigan - Navy Pier, Chicago

(5 of 70 reviews)

Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront. Kick back, relax, and let the US Coast Guard licensed captain treat you to stunning views of Chicago’s spectacular skyline. ... More

Free Cancellation
Private Tour
Start From $566.82
 
Private Sailing on Beautiful Lake Michigan - Navy Pier, Chicago Likely to Sell Out

Private Sailing on Beautiful Lake Michigan - Navy Pier, Chicago

  • USA
  • Superb70 reviews5

Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefro....

    Free Cancellation
    Private Tour
    Start From $566.82
 
 

Morning Mimosa Sightseeing Sail on Schooner Madeleine in Newport

(4.8 of 43 reviews)

Start your day with a morning sightseeing sail around Newport on a classic sailboat. Sailing aboard Schooner Madeleine is a great experience for friends and family to see all the iconic waterfront sights of Newport and Narraganset... More

Free Cancellation
Private Tour
Start From $57.24
 
Morning Mimosa Sightseeing Sail on Schooner Madeleine in Newport Likely to Sell Out

Morning Mimosa Sightseeing Sail on Schooner Madeleine in Newport

  • USA
  • Superb43 reviews4.8

Start your day with a morning sightseeing sail around Newport on a classic sailboat. Sailing aboard ....

    Free Cancellation
    Private Tour
    Start From $57.24
 
 

Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure

(5 of 711 reviews)

Join us aboard our luxurious 50’ catamaran “Kona Style”, as we sail the Kona coast. Scan the horizon for dolphins and whales (seasonal) from our shaded cabin or sunny splash nets. Snorkel calm waters and lush coral gardens u... More

Free Cancellation
Private Tour
Start From $189.00
 
Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure Likely to Sell Out

Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure

  • USA
  • Superb711 reviews5

Join us aboard our luxurious 50’ catamaran “Kona Style”, as we sail the Kona coast. Scan the h....

    Free Cancellation
    Private Tour
    Start From $189.00
 
 

Skagway Trail and Sail

(4.7 of 7 reviews)

This eco-friendly tour of Skagway is like no other experience around! Your tour starts at Klondike Electric Bicycles where you will join us for a self-guided ride to some of Skagway's best sites! You will visit a waterfall, scenic... More

Free Cancellation
Private Tour
Start From $299.00
 
Skagway Trail and Sail Likely to Sell Out

Skagway Trail and Sail

  • USA
  • Superb7 reviews4.7

This eco-friendly tour of Skagway is like no other experience around! Your tour starts at Klondike E....

    Free Cancellation
    Private Tour
    Start From $299.00
 
 

Private Guided Sunset and Eco Tour up to 6 Passengers

(5 of 76 reviews)

Our cruise is a private tour to see Destin's sunset as you want to see it. We can look for Dolphins, or watch the sunset from classic Destin Locations Crab Island and Norriego Point. Our boat includes a cooler with bottled water a... More

Free Cancellation
Private Tour
Start From $249.99
 
Private Guided Sunset and Eco Tour up to 6 Passengers Likely to Sell Out

Private Guided Sunset and Eco Tour up to 6 Passengers

  • USA
  • Superb76 reviews5

Our cruise is a private tour to see Destin's sunset as you want to see it. We can look for Dolphins,....

    Free Cancellation
    Private Tour
    Start From $249.99
 
 

South Shore Open Sail from Kewalo Harbor Including Drinks

(4.7 of 25 reviews)

Join us for a 90-minute daytime sailing experience from Kewalo Basin Harbor on one of the most iconic catamarans in Honolulu! Our sails always have complimentary drinks (alcoholic beverages available for adults 21+ with valid ID o... More

Free Cancellation
Private Tour
Start From $47.50
 
South Shore Open Sail from Kewalo Harbor Including Drinks Likely to Sell Out

South Shore Open Sail from Kewalo Harbor Including Drinks

  • USA
  • Superb25 reviews4.7

Join us for a 90-minute daytime sailing experience from Kewalo Basin Harbor on one of the most iconi....

    Free Cancellation
    Private Tour
    Start From $47.50
 
 

Miami Private Yacht Celebration Cruise with Captain

(4.6 of 65 reviews)

Ready for the party of a lifetime? Step aboard our luxurious Yacht Tour in Miami Beach and celebrate like never before. This VIP experience is designed for fun, style, and unforgettable memories with your group. Adventure Highlig... More

Free Cancellation
Private Tour
Start From $799.00
 
Miami Private Yacht Celebration Cruise with Captain Likely to Sell Out

Miami Private Yacht Celebration Cruise with Captain

  • USA
  • Superb65 reviews4.6

Ready for the party of a lifetime? Step aboard our luxurious Yacht Tour in Miami Beach and celebrate....

    Free Cancellation
    Private Tour
    Start From $799.00
 
 

Mid-Day & Sunset Sailing on Seattle's Majestic Puget Sound

(5 of 28 reviews)

Experience the magic of being carried by the wind, just as Peter Puget was when he mapped these waters back in 1792. From Seattle’s Shilshole Bay Marina we sail west across Puget Sound toward the magnificent Olympic Mountains. A... More

Free Cancellation
Private Tour
Start From $125.00
 
Mid-Day & Sunset Sailing on Seattle's Majestic Puget Sound Likely to Sell Out

Mid-Day & Sunset Sailing on Seattle's Majestic Puget Sound

  • USA
  • Superb28 reviews5

Experience the magic of being carried by the wind, just as Peter Puget was when he mapped these wate....

    Free Cancellation
    Private Tour
    Start From $125.00
 
 

Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast

(4.9 of 255 reviews)

As you swim off of the coast of the world famous Waikiki beach, you’ll realize you’ve found your very own piece of paradise. Just far away enough from the bustling travelers and crowded beaches, the crystal-clear water will br... More

Free Cancellation
Private Tour
Start From $49.99
 
Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast Likely to Sell Out

Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast

  • USA
  • Superb255 reviews4.9

As you swim off of the coast of the world famous Waikiki beach, you’ll realize you’ve found your....

    Free Cancellation
    Private Tour
    Start From $49.99
 
 

2.5-hour Guided Sailboat Tour

(5 of 182 reviews)

2.5 hour sails for up to six passengers from Pier 5 in Brooklyn Bridge Park, One15 Brooklyn Marina, 159 Bridge Park Drive. Views of the Brooklyn Bridge, Statue of Liberty, World Trade Center, Ellis Island, Governor's Island and M... More

Free Cancellation
Private Tour
Start From $95.00
 
2.5-hour Guided Sailboat Tour Likely to Sell Out

2.5-hour Guided Sailboat Tour

  • USA
  • Superb182 reviews5

2.5 hour sails for up to six passengers from Pier 5 in Brooklyn Bridge Park, One15 Brooklyn Marina, ....

    Free Cancellation
    Private Tour
    Start From $95.00
 
 

Key West Historic Schooner When And If Sunset Cruise

(4.8 of 135 reviews)

Historic Schooner. Champagne Sunset Toast. Elegant and Exclusive. Step aboard the historic schooner When And If, commissioned by General George Patton in the late 1930s, and sail into a breathtaking Key West sunset. Raise a champ... More

Free Cancellation
Private Tour
Start From $109.00
 
Key West Historic Schooner When And If Sunset Cruise Likely to Sell Out

Key West Historic Schooner When And If Sunset Cruise

  • USA
  • Superb135 reviews4.8

Historic Schooner. Champagne Sunset Toast. Elegant and Exclusive. Step aboard the historic schooner....

    Free Cancellation
    Private Tour
    Start From $109.00
 
 

Key West Sunset Sail Aboard Legendary Schooner Appledore

(5 of 360 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
Private Tour
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
  • Superb360 reviews5

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

    Free Cancellation
    Private Tour
    Start From $89.00
 
 

Best Waikiki Sunset Cruise:BYOB Sunset Sail with Swimming

(4.9 of 204 reviews)

Our vessel "Hokulani" is a beautiful and spacious custom built sailing trimaran specifically designed for a comfortable ride in Hawaiian waters. What makes Hokulani unique from every other tour boat operating in Waikiki, is that s... More

Free Cancellation
Private Tour
Start From $79.00
 
Best Waikiki Sunset Cruise:BYOB Sunset Sail with Swimming Likely to Sell Out

Best Waikiki Sunset Cruise:BYOB Sunset Sail with Swimming

  • USA
  • Superb204 reviews4.9

Our vessel "Hokulani" is a beautiful and spacious custom built sailing trimaran specifically designe....

    Free Cancellation
    Private Tour
    Start From $79.00
 
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