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Top 10 Best North America Sailing Trips

Found 767 Sailing Trips activities in North America. Sort by Popularity. - Page 19
 

Harbor Sail Aboard the Tall Ship Denis Sullivan

(4.6 of 65 reviews)

Set sail on the magnificent tall ship Denis Sullivan, a Great Lakes schooner offering a unique opportunity to connect with the sea. Whether you choose to help the crew raise the sails or simply soak in the stunning views, this pub... More

Free Cancellation
Start From $55.00
 
Harbor Sail Aboard the Tall Ship Denis Sullivan Likely to Sell Out

Harbor Sail Aboard the Tall Ship Denis Sullivan

  • North America
  • Superb65 reviews4.6

Set sail on the magnificent tall ship Denis Sullivan, a Great Lakes schooner offering a unique oppor....

    Free Cancellation
    Start From $55.00
 
 

Half Day Oahu Combo Adventure: Bike, Sail and Snorkel

(4.7 of 68 reviews)

Join our Honolulu bike tour on the Bike, Sail & Snorkel adventure. This exhilarating Oahu combo tour from rainforest to reef combines views high above Honolulu to snorkeling off a catamaran off Waikiki. Explore lush rainforest and... More

Free Cancellation
Start From $196.63
 
Half Day Oahu Combo Adventure: Bike, Sail and Snorkel Likely to Sell Out

Half Day Oahu Combo Adventure: Bike, Sail and Snorkel

  • North America
  • Superb68 reviews4.7

Join our Honolulu bike tour on the Bike, Sail & Snorkel adventure. This exhilarating Oahu combo tour....

    Free Cancellation
    Start From $196.63
 
 

Day Sailing Adventure in the Florida Marine Sanctuary

(5 of 44 reviews)

Escape the ordinary and embark on an unforgettable journey aboard our 50 foot sailboat, “Chao Lay”. Choose our popular 3-hour Day Sail through the Florida Keys Marine Sanctuary in Marathon, Florida. Our sailboat rides feature ... More

Free Cancellation
Start From $120.00
 
Day Sailing Adventure in the Florida Marine Sanctuary Likely to Sell Out

Day Sailing Adventure in the Florida Marine Sanctuary

  • North America
  • Superb44 reviews5

Escape the ordinary and embark on an unforgettable journey aboard our 50 foot sailboat, “Chao Lay....

    Free Cancellation
    Start From $120.00
 
 

Best Waikiki Whale Watching in Honolulu: Whales Guaranteed

(4.6 of 250 reviews)

Guaranteed whale sightings* Spacious and modern Trimaran with unobstructed open air views as well as ample seating and shade on board. Knowledgeable staff with plenty of interesting whale information Convenient location walking... More

Free Cancellation
Start From $79.00
 
Best Waikiki Whale Watching in Honolulu: Whales Guaranteed Likely to Sell Out

Best Waikiki Whale Watching in Honolulu: Whales Guaranteed

  • North America
  • Superb250 reviews4.6

Guaranteed whale sightings* Spacious and modern Trimaran with unobstructed open air views as well a....

    Free Cancellation
    Start From $79.00
 
 

Speedboat and Snorkeling Adventure in Cancun

(5 of 1 review)

Explore the vibrant Cancun jungle with an exhilarating water adventure that combines speed and serenity. Hop into a 2-passenger speedboat and zip around the stunning Nichupte Lagoon, feeling the thrill of the wind and water. Then,... More

Free Cancellation
Start From $16.00
 
Speedboat and Snorkeling Adventure in Cancun Likely to Sell Out

Speedboat and Snorkeling Adventure in Cancun

  • North America
  • Superb1 review5

Explore the vibrant Cancun jungle with an exhilarating water adventure that combines speed and seren....

    Free Cancellation
    Start From $16.00
 
 

Let's Go Sail the York River in Gloucester Point, Virginia

(4.9 of 156 reviews)

Couples and families enjoy a unique opportunity to sail their own 32-foot sloop with all the modern conveniences. Or sit back and relax in the cockpit or up on the bow of the boat for greater privacy. Great idea for engagement, bi... More

Free Cancellation
Start From $96.42
 
Let's Go Sail the York River in Gloucester Point, Virginia Likely to Sell Out

Let's Go Sail the York River in Gloucester Point, Virginia

  • North America
  • Superb156 reviews4.9

Couples and families enjoy a unique opportunity to sail their own 32-foot sloop with all the modern ....

    Free Cancellation
    Start From $96.42
 
 

Snorkeling Adventure in Puerto Morelos with snack and round trip

(3.9 of 95 reviews)

You must live this experience once in your life, This activity is only for travelers that love to be in a unique place in the world. You will discover the 2nd biggest reef wall in the world, you will see a huge variety of fish of... More

Free Cancellation
Start From $44.25
 
Snorkeling Adventure in Puerto Morelos with snack and round trip Likely to Sell Out

Snorkeling Adventure in Puerto Morelos with snack and round trip

  • North America
  • Very Good95 reviews3.9

You must live this experience once in your life, This activity is only for travelers that love to be....

    Free Cancellation
    Start From $44.25
 
 

Private Hilton Head Sunset Sailing Tour with Dolphin Watching

(5 of 125 reviews)

This 2 hour Private Sunset Sail, the Captain will take you (and up to 6 people) to Port Royal Sound (North side of island - generally best conditions for sailing). During Sunset, This is generally still pretty breezy with some goo... More

Free Cancellation
Private Tour
Start From $525.00
 
Private Hilton Head Sunset Sailing Tour with Dolphin Watching Likely to Sell Out

Private Hilton Head Sunset Sailing Tour with Dolphin Watching

  • North America
  • Superb125 reviews5

This 2 hour Private Sunset Sail, the Captain will take you (and up to 6 people) to Port Royal Sound ....

    Free Cancellation
    Private Tour
    Start From $525.00
 
 

2-Hour Private Hilton Head Afternoon Dolphin Watching Sail

(5 of 124 reviews)

This 2 hour Private Afternoon Sailing tour will take us to Port Royal Sound (generally the best wind for sailing on Hilton Head) on the North side of the island. During the day, this is generally filled with exciting winds for gre... More

Free Cancellation
Private Tour
Start From $485.00
 
2-Hour Private Hilton Head Afternoon Dolphin Watching Sail Likely to Sell Out

2-Hour Private Hilton Head Afternoon Dolphin Watching Sail

  • North America
  • Superb124 reviews5

This 2 hour Private Afternoon Sailing tour will take us to Port Royal Sound (generally the best wind....

    Free Cancellation
    Private Tour
    Start From $485.00
 
 

Catamaran in Cozumel with snorkeling at El Cielo and open Bar

(3.9 of 19 reviews)

Snorkel, Sip & Celebrate in Cozumel’s Caribbean Paradise Your captain and crew welcome you aboard with open arms—and an open bar. Margaritas, beer, soft drinks, and bottled water flow as music fills the air and the sea sets t... More

Free Cancellation
Private Tour
Start From $38.50
 
Catamaran in Cozumel with snorkeling at El Cielo and open Bar Likely to Sell Out

Catamaran in Cozumel with snorkeling at El Cielo and open Bar

  • North America
  • Very Good19 reviews3.9

Snorkel, Sip & Celebrate in Cozumel’s Caribbean Paradise Your captain and crew welcome you aboard....

    Free Cancellation
    Private Tour
    Start From $38.50
 
 

Exciting Public Afternoon Sail in Hilton Head

(3.9 of 19 reviews)

Looking for a more personal sailing experience without booking an entire private charter? The Afternoon Public Sail is the perfect balance. With a maximum of just six guests onboard, you’ll enjoy an intimate, relaxed atmosphere.... More

Free Cancellation
Private Tour
Start From $119.00
 
Exciting Public Afternoon Sail in Hilton Head Likely to Sell Out

Exciting Public Afternoon Sail in Hilton Head

  • North America
  • Very Good19 reviews3.9

Looking for a more personal sailing experience without booking an entire private charter? The Aftern....

    Free Cancellation
    Private Tour
    Start From $119.00
 
 

Private Long Island Sound Sailing Experience

(3.9 of 19 reviews)

Sail the Long Island Sound with Captain Steve. Sit back and relax as we tour Manhasset Bay, nestled between Great Neck's Kings Point and Port Washington's Sands Point. Oogle at the multi million dollar Mansions lining the coast un... More

Free Cancellation
Private Tour
Start From $650.00
 
Private Long Island Sound Sailing Experience Likely to Sell Out

Private Long Island Sound Sailing Experience

  • North America
  • Very Good19 reviews3.9

Sail the Long Island Sound with Captain Steve. Sit back and relax as we tour Manhasset Bay, nestled ....

    Free Cancellation
    Private Tour
    Start From $650.00
 
 

2hr. PRIVATE Sailing Experience on San Francisco Bay (6 Guests)

(3.9 of 19 reviews)

This is a "Private Charter" Sailing Experience on San Francisco Bay for up to 6 guests, with a USCG licensed captain and crew where you'll sail past the Golden Gate Bridge, Alcatraz and Angel Islands and across the San Francisco w... More

Free Cancellation
Private Tour
Start From $795.00
 
2hr. PRIVATE Sailing Experience on San Francisco Bay (6 Guests) Likely to Sell Out

2hr. PRIVATE Sailing Experience on San Francisco Bay (6 Guests)

  • North America
  • Very Good19 reviews3.9

This is a "Private Charter" Sailing Experience on San Francisco Bay for up to 6 guests, with a USCG ....

    Free Cancellation
    Private Tour
    Start From $795.00
 
 

2 Hour Sailing Lesson in Wrightsville Beach

(5 of 8 reviews)

Experience the thrill of sailing a 26' performance keelboat! Our knowledgeable captains will take you around the waterways of Wrightsville Beach and out into the Atlantic Ocean. You have the freedom to make this a learning experie... More

Free Cancellation
Private Tour
Start From $360.00
 
2 Hour Sailing Lesson in Wrightsville Beach Likely to Sell Out

2 Hour Sailing Lesson in Wrightsville Beach

  • North America
  • Superb8 reviews5

Experience the thrill of sailing a 26' performance keelboat! Our knowledgeable captains will take yo....

    Free Cancellation
    Private Tour
    Start From $360.00
 
 

Afternoon Ali'i Adventure

(5 of 6 reviews)

Experience the ultimate in luxury and exclusivity with our Afternoon Ali’i Adventure. Unlike crowded tours, we limit our trips to a maximum of 22 guests, allowing for a semi-private experience aboard our spacious 50' catamaran. ... More

Free Cancellation
Private Tour
Start From $276.00
 
Afternoon Ali'i Adventure Likely to Sell Out

Afternoon Ali'i Adventure

  • North America
  • Superb6 reviews5

Experience the ultimate in luxury and exclusivity with our Afternoon Ali’i Adventure. Unlike crowd....

    Free Cancellation
    Private Tour
    Start From $276.00
 
 

Whale Watching Sailboat Tour in San Jose del Cabo

(5 of 3 reviews)

Join us at the marina for a brief orientation before boarding the vessel. As we set sail, you'll cruise past the iconic landmarks of San José del Cabo. Like the Estuary a bird sanctuary and the amazing coastline of the Sea of Cor... More

Free Cancellation
Private Tour
Start From $149.00
 
Whale Watching Sailboat Tour in San Jose del Cabo Likely to Sell Out

Whale Watching Sailboat Tour in San Jose del Cabo

  • North America
  • Superb3 reviews5

Join us at the marina for a brief orientation before boarding the vessel. As we set sail, you'll cru....

    Free Cancellation
    Private Tour
    Start From $149.00
 
 

Afternoon Sail With the Whales from Lahaina Harbor

(5 of 1 review)

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 $100.22
 
Afternoon Sail With the Whales from Lahaina Harbor Likely to Sell Out

Afternoon Sail With the Whales from Lahaina Harbor

  • North America
  • Superb1 review5

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

    Free Cancellation
    Private Tour
    Start From $100.22
 
 

1 Hour Private Charter in New York Harbor for up to 6 people

(4.9 of 52 reviews)

This is a private tour which means it is just you and your party on board. You will be sailing on our beautiful classic sailboat named Tara. Tara is a classic sailboat and one of a kind in NYC. You will sail past Elis Island and t... More

Free Cancellation
Private Tour
Start From $375.00
 
1 Hour Private Charter in New York Harbor for up to 6 people Likely to Sell Out

1 Hour Private Charter in New York Harbor for up to 6 people

  • North America
  • Superb52 reviews4.9

This is a private tour which means it is just you and your party on board. You will be sailing on ou....

    Free Cancellation
    Private Tour
    Start From $375.00
 
 

Private sailing excursions, nice spacious sailboats.

(4.9 of 30 reviews)

We are a new sailboat tour agency in bacalar ~ are sailboats stand out with ease access, very comfortable, 2 canopy’s to keep you protected from the elements and a 5 star crew. We provide an atmosphere for you to take over and T... More

Free Cancellation
Private Tour
Start From $294.57
 
Private sailing excursions, nice spacious sailboats. Likely to Sell Out

Private sailing excursions, nice spacious sailboats.

  • North America
  • Superb30 reviews4.9

We are a new sailboat tour agency in bacalar ~ are sailboats stand out with ease access, very comfor....

    Free Cancellation
    Private Tour
    Start From $294.57
 
 

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

  • North America
  • 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
 
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