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Top 10 Best North America Sailing Trips

Found 674 Sailing Trips activities in North America. Sort by Popularity. - Page 13
 

2-Hour Morning Sail in San Diego

(5 of 18 reviews)

Set sail from America's Cup Harbor on your morning sailing tour, and enjoy the sights of Point Loma, San Diego Bay and the downtown waterfront. This two-hour adventure on a Catalina sailboat is limited to a maximum of six (6) gues... More

Free Cancellation
Start From $95.00
 
2-Hour Morning Sail in San Diego Likely to Sell Out

2-Hour Morning Sail in San Diego

  • North America
  • Superb18 reviews5

Set sail from America's Cup Harbor on your morning sailing tour, and enjoy the sights of Point Loma,....

    Free Cancellation
    Start From $95.00
 
 

Tulum: Snorkeling and Private Sailing Tour

(4.9 of 149 reviews)

We will enjoy a wonderful catamaran tour, powered only by the wind, we will be able to enjoy a spectacular view of the Tulum ruins from the sea... More

Free Cancellation
Private Tour
Start From $56.39
 
Tulum: Snorkeling and Private Sailing Tour Likely to Sell Out

Tulum: Snorkeling and Private Sailing Tour

  • North America
  • Superb149 reviews4.9

We will enjoy a wonderful catamaran tour, powered only by the wind, we will be able to enjoy a spect....

    Free Cancellation
    Private Tour
    Start From $56.39
 
 

Tour to The Arch and Lover's Beach (optional) from Cabo

(5 of 3 reviews)

This is a tour in a boat that will take you to Divorce Beach, Lover's Beach, the Arch, Land's End, and through the Marina. See it all in one tour! During this awesome experience, you will be able to see a great variety of tropical... More

Free Cancellation
Private Tour
Start From $30.00
 
Tour to The Arch and Lover's Beach (optional) from Cabo Likely to Sell Out

Tour to The Arch and Lover's Beach (optional) from Cabo

  • North America
  • Superb3 reviews5

This is a tour in a boat that will take you to Divorce Beach, Lover's Beach, the Arch, Land's End, a....

    Free Cancellation
    Private Tour
    Start From $30.00
 
 

Kona Coastline Escape: Sail with Dolphins & Turtles on Honi Olani

(4.8 of 35 reviews)

Set sail on the Honi Olani, a 53-foot sailing catamaran, and explore the stunning Kona coastline. This 1.5-hour journey from Honokohau Harbor offers a chance to bask in the sun and enjoy the ocean breeze while taking in the breath... More

Free Cancellation
Private Tour
Start From $117.76
 
Kona Coastline Escape: Sail with Dolphins & Turtles on Honi Olani Likely to Sell Out

Kona Coastline Escape: Sail with Dolphins & Turtles on Honi Olani

  • North America
  • Superb35 reviews4.8

Set sail on the Honi Olani, a 53-foot sailing catamaran, and explore the stunning Kona coastline. Th....

    Free Cancellation
    Private Tour
    Start From $117.76
 
 

Luxury Catamaran Sailing Charters in Maine

(4.9 of 85 reviews)

Sail in luxury on a 44-ft catamaran yacht! We are one of the only sailing catamaran charters in Maine, and our luxurious yacht makes for a relaxing and fun experience. Our catamaran is stable and does not bounce in waves, providin... More

Free Cancellation
Private Tour
Start From $135.00
 
Luxury Catamaran Sailing Charters in Maine Likely to Sell Out

Luxury Catamaran Sailing Charters in Maine

  • North America
  • Superb85 reviews4.9

Sail in luxury on a 44-ft catamaran yacht! We are one of the only sailing catamaran charters in Main....

    Free Cancellation
    Private Tour
    Start From $135.00
 
 

Catamaran Sailing Cruise in Monterey

(4.9 of 11 reviews)

Enjoy sailing the Monterey Bay without engine noise. You will be offered a complimentary beverage after your captain hoists the sails and catches the wind to make for a peaceful and exciting cruise on the bay. On the way out of t... More

Free Cancellation
Private Tour
Start From $65.00
 
Catamaran Sailing Cruise in Monterey Likely to Sell Out

Catamaran Sailing Cruise in Monterey

  • North America
  • Superb11 reviews4.9

Enjoy sailing the Monterey Bay without engine noise. You will be offered a complimentary beverage af....

    Free Cancellation
    Private Tour
    Start From $65.00
 
 

Sailing Charters in Wilmington

(5 of 141 reviews)

After a successful first season I am happy to be here for back to back seasons. Sail in style on the historic Wilmington river walk. Enjoy a personalized Charter experience with up to six guests. Very few sailboats are up for publ... More

Free Cancellation
Private Tour
Start From $89.00
 
Sailing Charters in Wilmington Likely to Sell Out

Sailing Charters in Wilmington

  • North America
  • Superb141 reviews5

After a successful first season I am happy to be here for back to back seasons. Sail in style on the....

    Free Cancellation
    Private Tour
    Start From $89.00
 
 

Majahuitas Island Pirate Ship Adventure

(5 of 1 review)

A Vallarta Pirate Ship tour invites you to sail away to explore the Isla Majahuitas Nature Reserve. Along the way, enjoy stops for swimming, snorkeling, kayaking and treasure hunts and a live pirate show onboard. All-inclusive Val... More

Free Cancellation
Private Tour
Start From $170.00
 
Majahuitas Island Pirate Ship Adventure Likely to Sell Out

Majahuitas Island Pirate Ship Adventure

  • North America
  • Superb1 review5

A Vallarta Pirate Ship tour invites you to sail away to explore the Isla Majahuitas Nature Reserve. ....

    Free Cancellation
    Private Tour
    Start From $170.00
 
 

Friday Night Firework Cruise in Waikiki

(4.8 of 21 reviews)

After the sun goes down, the fun goes up! On Friday nights, you’ll be front and center as the fireworks explode over the city’s skyline, truly making this the ultimate party experience. Enjoy the Premium drinks of your choice ... More

Free Cancellation
Private Tour
Start From $69.99
 
Friday Night Firework Cruise in Waikiki Likely to Sell Out

Friday Night Firework Cruise in Waikiki

  • North America
  • Superb21 reviews4.8

After the sun goes down, the fun goes up! On Friday nights, you’ll be front and center as the fire....

    Free Cancellation
    Private Tour
    Start From $69.99
 
 

Dolphin Adventure Sail in Cocoa Beach

(5 of 129 reviews)

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

  • North America
  • Superb129 reviews5

Experience the Magic of Cocoa Beach with Our Dolphin Tour! Join Cocoa Beach Catamaran for an unforg....

    Free Cancellation
    Private Tour
    Start From $50.85
 
 

Private Whale Watching Sailing Tour

(5 of 6 reviews)

Amaze yourself appreciating our most awaited visitors of the year, the Humpback Whales! Book this half-day tour on a beautiful and comfortable sailboat while you enjoy the breeze , the sun and the tide while you look for whales, d... More

Special Offer
Free Cancellation
Private Tour
Start From $692.07
(Saving 4% ) $717.71
 
-4% Private Whale Watching Sailing Tour Likely to Sell Out

Private Whale Watching Sailing Tour

  • North America
  • Superb6 reviews5

Amaze yourself appreciating our most awaited visitors of the year, the Humpback Whales! Book this ha....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $692.07
    (Saving 4% ) $717.71
 
 

Come Sailing at Navy Pier Marina - Sunset Sail on Lake Michigan

(5 of 24 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 $507.96
 
Come Sailing at Navy Pier Marina - Sunset Sail on Lake Michigan Likely to Sell Out

Come Sailing at Navy Pier Marina - Sunset Sail on Lake Michigan

  • North America
  • Superb24 reviews5

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

    Free Cancellation
    Private Tour
    Start From $507.96
 
 

2-Hour Private Luxury Boat Tour in New York City

(5 of 68 reviews)

Experience the breathtaking beauty of New York City on this private, 2-hour cruise around lower Manhattan aboard a 30' luxurious powerboat. Get an unobstructed view of the Manhattan skyline, Freedom Tower, Brooklyn Bridge, Empire ... More

Free Cancellation
Private Tour
Start From $499.99
 
2-Hour Private Luxury Boat Tour in New York City Likely to Sell Out

2-Hour Private Luxury Boat Tour in New York City

  • North America
  • Superb68 reviews5

Experience the breathtaking beauty of New York City on this private, 2-hour cruise around lower Manh....

    Free Cancellation
    Private Tour
    Start From $499.99
 
 

Private sailing excursions, nice spacious sailboats.

(4.9 of 20 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 $256.32
 
Private sailing excursions, nice spacious sailboats. Likely to Sell Out

Private sailing excursions, nice spacious sailboats.

  • North America
  • Superb20 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 $256.32
 
 

Bacalar: 4hr Private Sailing Tour with Guacamole & Drinks

(4.9 of 91 reviews)

Explore the Bacalar Lagoon aboard a classic sailboat and enjoy a trip in privacy and comfort. Feel safe sailing with highly trained and bilingual staff in this beautiful freshwater paradise. Our years of experience back us up. Qua... More

Free Cancellation
Private Tour
Start From $220.44
 
Bacalar: 4hr Private Sailing Tour with Guacamole & Drinks Likely to Sell Out

Bacalar: 4hr Private Sailing Tour with Guacamole & Drinks

  • North America
  • Superb91 reviews4.9

Explore the Bacalar Lagoon aboard a classic sailboat and enjoy a trip in privacy and comfort. Feel s....

    Free Cancellation
    Private Tour
    Start From $220.44
 
 

Private Sunset Sailing with Dolphin and History Tours on Mystique

(5 of 23 reviews)

Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charter company in Charleston's history. #1 activity on Tripadvisor for over 12 years, our sailing yachts are the highest quality and op... More

Free Cancellation
Private Tour
Start From $599.00
 
Private Sunset Sailing with Dolphin and History Tours on Mystique Likely to Sell Out

Private Sunset Sailing with Dolphin and History Tours on Mystique

  • North America
  • Superb23 reviews5

Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charte....

    Free Cancellation
    Private Tour
    Start From $599.00
 
 

Snorkel Sail Adventure off Ka'anapali Beach, Maui

(4.9 of 9 reviews)

While snorkeling along West Maui’s coastline, experience warm waters abundant with sea life. You will see a variety of tropical fish, and if you’re lucky, an endangered Hawaiian Green Sea turtle called a ‘Honu’. A hot buff... More

Free Cancellation
Private Tour
Start From $172.85
 
Snorkel Sail Adventure off Ka'anapali Beach, Maui Likely to Sell Out

Snorkel Sail Adventure off Ka'anapali Beach, Maui

  • North America
  • Superb9 reviews4.9

While snorkeling along West Maui’s coastline, experience warm waters abundant with sea life. You w....

    Free Cancellation
    Private Tour
    Start From $172.85
 
 

2.5 Hour Private Sunset Sailing Tour in San Diego up to 12 guests

(5 of 60 reviews)

Sea Monkey Adventures is San Diego’s first family-friendly sailing tour company, dedicated to helping families create unforgettable memories. Our vessel is thoughtfully designed to be warm and inviting, featuring handcrafted yel... More

Free Cancellation
Private Tour
Start From $260.00
 
2.5 Hour Private Sunset Sailing Tour in San Diego up to 12 guests Likely to Sell Out

2.5 Hour Private Sunset Sailing Tour in San Diego up to 12 guests

  • North America
  • Superb60 reviews5

Sea Monkey Adventures is San Diego’s first family-friendly sailing tour company, dedicated to help....

    Free Cancellation
    Private Tour
    Start From $260.00
 
 

6 Hours Private Yacht in Puerto Vallarta with Snorkeling & Beach

(5 of 60 reviews)

Sail on a 6-hour private trip aboard our 55-foot private yacht, ideal for up to 12 passengers. We are sure that with us you will know the best part of our beautiful bay of Puerto Vallarta. Do not miss the opportunity we offer to ... More

Free Cancellation
Private Tour
Start From $1,384.10
 
6 Hours Private Yacht in Puerto Vallarta with Snorkeling & Beach Likely to Sell Out

6 Hours Private Yacht in Puerto Vallarta with Snorkeling & Beach

  • North America
  • Superb60 reviews5

Sail on a 6-hour private trip aboard our 55-foot private yacht, ideal for up to 12 passengers. We a....

    Free Cancellation
    Private Tour
    Start From $1,384.10
 
 

Romantic Lobster Dinner Cruise at Sunset

(4.3 of 6 reviews)

Cruise across the scenic Nichupte Lagoon on an elegant Spanish Galeon, treating your better half to an amazing romantic experience and an exquisite 3-course dinner. Following you check-in, get aboard the spectacular ship under t... More

Free Cancellation
Private Tour
Start From $101.50
 
Romantic Lobster Dinner Cruise at Sunset Likely to Sell Out

Romantic Lobster Dinner Cruise at Sunset

  • North America
  • Exellent6 reviews4.3

Cruise across the scenic Nichupte Lagoon on an elegant Spanish Galeon, treating your better half to ....

    Free Cancellation
    Private Tour
    Start From $101.50
 
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