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Top 10 Best North America Sailing Trips

Found 734 Sailing Trips activities in North America. Sort by Popularity. - Page 7
 

Private Sailing Charter with Captain, BYOB

(5 of 65 reviews)

Embark on an exclusive sailing adventure on board "Esprit de Joy," tailor-made for groups of up to 6 guests for a 2.5-hour charter embracing Charleston's scenic Harbor. The golden hour of sunset is our prime booking time, offering... More

Free Cancellation
Private Tour
Start From $500.00
 
Private Sailing Charter with Captain, BYOB Likely to Sell Out

Private Sailing Charter with Captain, BYOB

  • North America
  • Superb65 reviews5

Embark on an exclusive sailing adventure on board "Esprit de Joy," tailor-made for groups of up to 6....

    Free Cancellation
    Private Tour
    Start From $500.00
 
 

Sunset Dolphin Sail Aboard the Footloose Catamaran

(4.8 of 443 reviews)

If you are looking to unwind before dinner or a night out on the town, come take a romantic Sunset Sail on SV Footloose, our 38 passenger catamaran, with Paradise Adventures! This breathtaking sunset sail along the Gulf of Mexico ... More

Free Cancellation
Private Tour
Start From $40.00
 
Sunset Dolphin Sail Aboard the Footloose Catamaran Likely to Sell Out

Sunset Dolphin Sail Aboard the Footloose Catamaran

  • North America
  • Superb443 reviews4.8

If you are looking to unwind before dinner or a night out on the town, come take a romantic Sunset S....

    Free Cancellation
    Private Tour
    Start From $40.00
 
 

Key West Private Charter: Sandbar and Snorkeling

(5 of 9 reviews)

This private charter is designed for a relaxed, flexible day on the water, perfect for groups who want a casual, unstructured experience. Instead of a formal, guided eco-tour, this trip offers a more laid-back vibe, allowing you t... More

Free Cancellation
Private Tour
Start From $950.00
 
Key West Private Charter: Sandbar and Snorkeling Likely to Sell Out

Key West Private Charter: Sandbar and Snorkeling

  • North America
  • Superb9 reviews5

This private charter is designed for a relaxed, flexible day on the water, perfect for groups who wa....

    Free Cancellation
    Private Tour
    Start From $950.00
 
 

Small Group Waikiki Sunset Sailing Tour

(4.9 of 111 reviews)

Hawaii is well known for its majestic sunsets, and there is truly no better way to experience it than on our boat, The Universe. Come and enjoy the Golden hour with your loved ones to make memories of a lifetime ,why go with overc... More

Free Cancellation
Private Tour
Start From $99.00
 
Small Group Waikiki Sunset Sailing Tour Likely to Sell Out

Small Group Waikiki Sunset Sailing Tour

  • North America
  • Superb111 reviews4.9

Hawaii is well known for its majestic sunsets, and there is truly no better way to experience it tha....

    Free Cancellation
    Private Tour
    Start From $99.00
 
 

Whale Tale Adventures in Los cabos

(4.6 of 14 reviews)

Whale watching is a magical experience for all ages. Seeing the gray whale, known for its long migration and friendly nature, or the majestic humpback whale, famous for its powerful breaches and haunting songs, is unforgettable. T... More

Free Cancellation
Private Tour
Start From $34.00
 
Whale Tale Adventures in Los cabos Likely to Sell Out

Whale Tale Adventures in Los cabos

  • North America
  • Superb14 reviews4.6

Whale watching is a magical experience for all ages. Seeing the gray whale, known for its long migra....

    Free Cancellation
    Private Tour
    Start From $34.00
 
 

4-Hour Fort Lauderdale Sailing Charter

(4.9 of 314 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
Private Tour
Start From $148.00
 
4-Hour Fort Lauderdale Sailing Charter Likely to Sell Out

4-Hour Fort Lauderdale Sailing Charter

  • North America
  • Superb314 reviews4.9

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

    Free Cancellation
    Private Tour
    Start From $148.00
 
 

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

(4.9 of 238 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

Special Offer
Free Cancellation
Private Tour
Start From $34.99
(Saving 30% ) $49.99
 
-30% 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

  • North America
  • Superb238 reviews4.9

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

    Special Offer
    Free Cancellation
    Private Tour
    Start From $34.99
    (Saving 30% ) $49.99
 
 

2hr. INTERACTIVE Sailing Experience on San Francisco Bay

(5 of 87 reviews)

This is an Interactive Sailing Experience on San Francisco Bay with a maximum 6 passengers on a private yacht with a USCG licensed captain and crew where you'll sail beneath the Golden Gate Bridge, across the San Francisco waterfr... More

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

2hr. INTERACTIVE Sailing Experience on San Francisco Bay

  • North America
  • Superb87 reviews5

This is an Interactive Sailing Experience on San Francisco Bay with a maximum 6 passengers on a priv....

    Free Cancellation
    Private Tour
    Start From $149.00
 
 

Sunset Dolphin Sail Aboard the Privateer Catamaran

(4.8 of 711 reviews)

If you are looking to unwind before dinner or a night out on the town, come take a romantic Sunset Sail on the SV Privateer, our 78-passenger catamaran, with Paradise Adventures! This breathtaking sunset sail along the Gulf of Mex... More

Free Cancellation
Private Tour
Start From $45.00
 
Sunset Dolphin Sail Aboard the Privateer Catamaran Likely to Sell Out

Sunset Dolphin Sail Aboard the Privateer Catamaran

  • North America
  • Superb711 reviews4.8

If you are looking to unwind before dinner or a night out on the town, come take a romantic Sunset S....

    Free Cancellation
    Private Tour
    Start From $45.00
 
 

Sunset Sailing Tour in Bacalar with Outdoor Bar and Lunch

(4.9 of 78 reviews)

This sailing tour is born of our love of the 7 Colors Lagoon and the desire to share it in an authentic and relaxed way. It’s not just a walk – it’s a space to live together, laugh, toast and connect, whether you come with f... More

Free Cancellation
Private Tour
Start From $76.04
 
Sunset Sailing Tour in Bacalar with Outdoor Bar and Lunch Likely to Sell Out

Sunset Sailing Tour in Bacalar with Outdoor Bar and Lunch

  • North America
  • Superb78 reviews4.9

This sailing tour is born of our love of the 7 Colors Lagoon and the desire to share it in an authen....

    Free Cancellation
    Private Tour
    Start From $76.04
 
 

Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure

(5 of 700 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

  • North America
  • Superb700 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
 
 

Full-Day Luxurious Catamaran Adventure - Cancún to Isla Mujeres

(4.4 of 301 reviews)

Discover Isla Mujeres in our luxury 45-foot catamaran over the beautiful Caribbean Sea, enjoying a delicious drink and the entertainment from the crew. Unique and quality service is our priority. We are sure that you will love all... More

Free Cancellation
Private Tour
Start From $62.00
 
Full-Day Luxurious Catamaran Adventure - Cancún to Isla Mujeres Likely to Sell Out

Full-Day Luxurious Catamaran Adventure - Cancún to Isla Mujeres

  • North America
  • Exellent301 reviews4.4

Discover Isla Mujeres in our luxury 45-foot catamaran over the beautiful Caribbean Sea, enjoying a d....

    Free Cancellation
    Private Tour
    Start From $62.00
 
 

Private Sailboat + Captain for a Day Experience

(5 of 589 reviews)

RECENTLY AWARDED #7 WORLDWIDE AS BEST SAILING AND DAY CRUISES OPTIONS BY TRIPADVISOR TRAVELER'S CHOICE AWARDS 2022!!! Everyone´s favorite! Enjoy an easy ride around the most relevant landmarks in the lagoon on board of a beautif... More

Free Cancellation
Private Tour
Start From $235.61
 
Private Sailboat + Captain for a Day Experience Likely to Sell Out

Private Sailboat + Captain for a Day Experience

  • North America
  • Superb589 reviews5

RECENTLY AWARDED #7 WORLDWIDE AS BEST SAILING AND DAY CRUISES OPTIONS BY TRIPADVISOR TRAVELER'S CHOI....

    Free Cancellation
    Private Tour
    Start From $235.61
 
 

Lāna'i Coast Snorkel and Sail

(5 of 23 reviews)

Nobody knows the waters of Maui better than our crew. Let us host you on our Gold Coast catamaran as we explore and snorkel the incredible coastline of Maui. Departing daily from 9:30 am - 2:30 pm. We'll check the conditions for t... More

Free Cancellation
Private Tour
Start From $216.22
 
Lāna'i Coast Snorkel and Sail Likely to Sell Out

Lāna'i Coast Snorkel and Sail

  • North America
  • Superb23 reviews5

Nobody knows the waters of Maui better than our crew. Let us host you on our Gold Coast catamaran as....

    Free Cancellation
    Private Tour
    Start From $216.22
 
 

2 Hour Sailing Cruise on Lake Tahoe

(4.9 of 886 reviews)

Sail Tahoe Blue is the premier sailing charter in South Lake Tahoe. We offer a unique sailing adventure and include complementary local beer and wine, as well as non-alcoholic beverages on all of our daily cruises. Unlike other t... More

Free Cancellation
Private Tour
Start From $140.00
 
2 Hour Sailing Cruise on Lake Tahoe Likely to Sell Out

2 Hour Sailing Cruise on Lake Tahoe

  • North America
  • Superb886 reviews4.9

Sail Tahoe Blue is the premier sailing charter in South Lake Tahoe. We offer a unique sailing advent....

    Free Cancellation
    Private Tour
    Start From $140.00
 
 

Best Private Luxury Daytime Boat Tour in New York City - 2 Hour

(5 of 88 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
 
Best Private Luxury Daytime Boat Tour in New York City - 2 Hour Likely to Sell Out

Best Private Luxury Daytime Boat Tour in New York City - 2 Hour

  • North America
  • Superb88 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
 
 

Cabo San Lucas Private 38 ft Sailing Tour with Snorkeling

(5 of 185 reviews)

Sail from Cabo San Lucas on a beautiful private 38 feet sailing boat and snorkel in tropical waters alongside colorful sea life. The bilingual crew is happy to accommodate any special occasion or request. This unforgettable ex... More

Free Cancellation
Private Tour
Start From $850.00
 
Cabo San Lucas Private 38 ft Sailing Tour with Snorkeling Likely to Sell Out

Cabo San Lucas Private 38 ft Sailing Tour with Snorkeling

  • North America
  • Superb185 reviews5

Sail from Cabo San Lucas on a beautiful private 38 feet sailing boat and snorkel in tropical water....

    Free Cancellation
    Private Tour
    Start From $850.00
 
 

Boston Harbor Sunset Sail Tour

(4.8 of 132 reviews)

Experience a beautiful Boston Harbor sunset sail on the water and see some of the city's waterfront landmarks as the sun dips below the horizon. This elegant sailing experience will be aboard either Schooner Adirondack III or Adir... More

Free Cancellation
Private Tour
Start From $82.27
 
Boston Harbor Sunset Sail Tour Likely to Sell Out

Boston Harbor Sunset Sail Tour

  • North America
  • Superb132 reviews4.8

Experience a beautiful Boston Harbor sunset sail on the water and see some of the city's waterfront ....

    Free Cancellation
    Private Tour
    Start From $82.27
 
 

Skagway Trail and Sail

(4.8 of 5 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

  • North America
  • Superb5 reviews4.8

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
 
 

Whale Watching Sail in Honolulu with Open Bar

(5 of 11 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
Private Tour
Start From $53.36
 
Whale Watching Sail in Honolulu with Open Bar Likely to Sell Out

Whale Watching Sail in Honolulu with Open Bar

  • North America
  • Superb11 reviews5

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

    Free Cancellation
    Private Tour
    Start From $53.36
 
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