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Top 10 Best North America Sailing Trips

Found 714 Sailing Trips activities in North America. Sort by Popularity. - Page 8
 

Ft Myers Beach 2 Hour Tiki Pub Fun in the Sun Dolphin Cruise

(4.9 of 116 reviews)

Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages (BYOB), take pics, get some sun, make friends, play party games and have a blast! With a cozy capacity for 25, choose between mingling with new pal... More

Free Cancellation
Start From $59.95
 
Ft Myers Beach 2 Hour Tiki Pub Fun in the Sun Dolphin Cruise Likely to Sell Out

Ft Myers Beach 2 Hour Tiki Pub Fun in the Sun Dolphin Cruise

  • North America
  • Superb116 reviews4.9

Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages (BYOB), take pics,....

    Free Cancellation
    Start From $59.95
 
 

Southwest Florida Sunset Sail

(4.9 of 515 reviews)

SWFL sunsets are the best, and there is no better place to watch them than from the deck of our 36ft. Sailing Catamaran, "Copacetic". The sunset hours are a magical time to be out on the water. With the winds calm, the sun turns g... More

Free Cancellation
Start From $70.00
 
Southwest Florida Sunset Sail Likely to Sell Out

Southwest Florida Sunset Sail

  • North America
  • Superb515 reviews4.9

SWFL sunsets are the best, and there is no better place to watch them than from the deck of our 36ft....

    Free Cancellation
    Start From $70.00
 
 

Waikiki Sunset Cocktail Cruise - Hilton Hawaiian Village

(4.5 of 66 reviews)

Explore the Waikiki coastline aboard the new Spirit of Aloha, a 65-foot sailing catamaran custom-built for the Hilton Hawaiian Village Waikiki Beach Resort. See the island like never before as you set sail from the only pier in W... More

Free Cancellation
Start From $119.95
 
Waikiki Sunset Cocktail Cruise - Hilton Hawaiian Village Likely to Sell Out

Waikiki Sunset Cocktail Cruise - Hilton Hawaiian Village

  • North America
  • Exellent66 reviews4.5

Explore the Waikiki coastline aboard the new Spirit of Aloha, a 65-foot sailing catamaran custom-bui....

    Free Cancellation
    Start From $119.95
 
 

Key West Sunset Sail Aboard Legendary Schooner Appledore

(5 of 368 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
Start From $99.00
 
Key West Sunset Sail Aboard Legendary Schooner Appledore Likely to Sell Out

Key West Sunset Sail Aboard Legendary Schooner Appledore

  • North America
  • Superb368 reviews5

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

    Free Cancellation
    Start From $99.00
 
 

Private Catamaran Sunset Sail in Waikiki

(5 of 11 reviews)

Established in 2017. As a private charter company, we always cater to your preferences. Our 48-foot catamaran, Hawaiian Style, has a sleek low-profile design which makes it optimal for stability out on the ocean. It has 2 large ... More

Free Cancellation
Private Tour
Start From $900.00
 
Private Catamaran Sunset Sail in Waikiki Likely to Sell Out

Private Catamaran Sunset Sail in Waikiki

  • North America
  • Superb11 reviews5

Established in 2017. As a private charter company, we always cater to your preferences. Our 48-foo....

    Free Cancellation
    Private Tour
    Start From $900.00
 
 

Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea

(4.8 of 326 reviews)

Our rainbow sails can be spotted from miles away. While on board you may capture such nice photos with the rainbow sails and also the beautiful scenery with Diamond head in the background. The net is also a fun ride and you’ll g... More

Free Cancellation
Private Tour
Start From $72.96
 
Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea Likely to Sell Out

Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea

  • North America
  • Superb326 reviews4.8

Our rainbow sails can be spotted from miles away. While on board you may capture such nice photos wi....

    Free Cancellation
    Private Tour
    Start From $72.96
 
 

Waikiki Best Whale Watching in Honolulu: Whales Guaranteed

(4.6 of 251 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
Private Tour
Start From $79.00
 
Waikiki Best Whale Watching in Honolulu: Whales Guaranteed Likely to Sell Out

Waikiki Best Whale Watching in Honolulu: Whales Guaranteed

  • North America
  • Superb251 reviews4.6

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

    Free Cancellation
    Private Tour
    Start From $79.00
 
 

Puerto Vallarta Adults-Only Luxury Sunset Sail

(4.6 of 457 reviews)

Sail into one of Puerto Vallarta's stunning sunsets aboard our luxurious French sailboats or catamarans. Relax and unwind as you enjoy delicious appetizers, a premium open bar, and top-tier service from our attentive crew. This i... More

Free Cancellation
Private Tour
Start From $99.00
 
Puerto Vallarta Adults-Only Luxury Sunset Sail Likely to Sell Out

Puerto Vallarta Adults-Only Luxury Sunset Sail

  • North America
  • Superb457 reviews4.6

Sail into one of Puerto Vallarta's stunning sunsets aboard our luxurious French sailboats or catamar....

    Free Cancellation
    Private Tour
    Start From $99.00
 
 

Tour Sailing boat 4 Hours

(4.8 of 29 reviews)

We will sail in a beautiful, clean sailboat, with full safety equipment and in good condition, boat equipped with bathroom for emergencies. Surrounded by lush nature and crystal clear waters of the most beautiful lagoon in the wor... More

Free Cancellation
Private Tour
Start From $35.71
 
Tour Sailing boat 4 Hours Likely to Sell Out

Tour Sailing boat 4 Hours

  • North America
  • Superb29 reviews4.8

We will sail in a beautiful, clean sailboat, with full safety equipment and in good condition, boat ....

    Free Cancellation
    Private Tour
    Start From $35.71
 
 

Riviera Maya Luxury Sunset Sailing plus Light Dinner and Open Bar

(4.5 of 456 reviews)

Experience the sunset like never before on this fabulous Sunset Sailing excursion. You’ll sail along the stunning coastline of the Riviera Maya aboard a luxurious catamaran, while Mother Nature prepares for her nightly performan... More

Free Cancellation
Private Tour
Start From $89.00
 
Riviera Maya Luxury Sunset Sailing plus Light Dinner and Open Bar Likely to Sell Out

Riviera Maya Luxury Sunset Sailing plus Light Dinner and Open Bar

  • North America
  • Exellent456 reviews4.5

Experience the sunset like never before on this fabulous Sunset Sailing excursion. You’ll sail alo....

    Free Cancellation
    Private Tour
    Start From $89.00
 
 

Sailing Charters in Wilmington

(5 of 214 reviews)

After a successful first three seasons I am happy to be here for a fourth season!!! 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 ... More

Free Cancellation
Private Tour
Start From $89.48
 
Sailing Charters in Wilmington Likely to Sell Out

Sailing Charters in Wilmington

  • North America
  • Superb214 reviews5

After a successful first three seasons I am happy to be here for a fourth season!!! Sail in style on....

    Free Cancellation
    Private Tour
    Start From $89.48
 
 

Private BYOB Afternoon Harbor Sail On 50ft Sailing Yacht Fate

(5 of 59 reviews)

Sail the Charleston Harbor, see dolphins, historic forts, or even participate in real sailing yacht regattas. Fate is not only the most demanded but also the largest and nicest sailing yacht available for Charter in Charleston, kn... More

Free Cancellation
Private Tour
Start From $599.00
 
Private BYOB Afternoon Harbor Sail On 50ft Sailing Yacht Fate Likely to Sell Out

Private BYOB Afternoon Harbor Sail On 50ft Sailing Yacht Fate

  • North America
  • Superb59 reviews5

Sail the Charleston Harbor, see dolphins, historic forts, or even participate in real sailing yacht ....

    Free Cancellation
    Private Tour
    Start From $599.00
 
 

Private Sailing Charter on San Diego Bay

(4.9 of 50 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 charterÂ... More

Free Cancellation
Private Tour
Start From $499.00
 
Private Sailing Charter on San Diego Bay Likely to Sell Out

Private Sailing Charter on San Diego Bay

  • North America
  • Superb50 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 $499.00
 
 

Whale-Watching Pirate Ship Cruise in Los Cabos

(4.7 of 119 reviews)

Go whale-watching in Cabo San Lucas aboard a real pirate ship called the Bucaneer Queen. Sail the Pacific Ocean and the Sea of Cortez in search of these amazing creatures. You will be accompanied by an experienced bilingual guide ... More

Free Cancellation
Private Tour
Start From $99.00
 
Whale-Watching Pirate Ship Cruise in Los Cabos Likely to Sell Out

Whale-Watching Pirate Ship Cruise in Los Cabos

  • North America
  • Superb119 reviews4.7

Go whale-watching in Cabo San Lucas aboard a real pirate ship called the Bucaneer Queen. Sail the Pa....

    Free Cancellation
    Private Tour
    Start From $99.00
 
 

Maui Molokini Snorkeling Sailing Adventure with Breakfast & Lunch

(4.8 of 223 reviews)

Sail Maui is proud to offer a destination snorkel sail to Molokini, one of Maui’s most incredible snorkeling destinations. The unique, crescent shaped crater is a natural marine preserve, and is home to over 250 species of t... More

Free Cancellation
Private Tour
Start From $220.54
 
Maui Molokini Snorkeling Sailing Adventure with Breakfast & Lunch Likely to Sell Out

Maui Molokini Snorkeling Sailing Adventure with Breakfast & Lunch

  • North America
  • Superb223 reviews4.8

Sail Maui is proud to offer a destination snorkel sail to Molokini, one of Maui’s most incredib....

    Free Cancellation
    Private Tour
    Start From $220.54
 
 

Sunset Catamaran Cruise in Ft. Lauderdale

(4.8 of 716 reviews)

A perfect way to end the day, with a relaxing sail upon the Atlantic Ocean. Imagine taking in the breathtaking views of FT. Lauderdale beach as the sun slips slowly behind the lights of the city. This evening cruise calls for sun ... More

Free Cancellation
Private Tour
Start From $129.00
 
Sunset Catamaran Cruise in Ft. Lauderdale Likely to Sell Out

Sunset Catamaran Cruise in Ft. Lauderdale

  • North America
  • Superb716 reviews4.8

A perfect way to end the day, with a relaxing sail upon the Atlantic Ocean. Imagine taking in the br....

    Free Cancellation
    Private Tour
    Start From $129.00
 
 

Best of Halifax Harbour Boat Tour

(4.9 of 117 reviews)

This 45' luxury boat is the perfect venue to learn about the history of Halifax. You are alongside our Captain and Deckhand throughout the relaxed harbour tour as they share Halifax's history and present day facts!... More

Free Cancellation
Private Tour
Start From $42.97
 
Best of Halifax Harbour Boat Tour Likely to Sell Out

Best of Halifax Harbour Boat Tour

  • North America
  • Superb117 reviews4.9

This 45' luxury boat is the perfect venue to learn about the history of Halifax. You are alongside ....

    Free Cancellation
    Private Tour
    Start From $42.97
 
 

Hilton Hawaiian Village Turtle Snorkel with Optional Lunch

(4.5 of 73 reviews)

Swim with turtles and fish, while enjoying the crystal blue topical waters. Sail the scenic Waikiki coastline and snorkel at Turtle Canyon. Our eco-conscious cruise lets you see whales (December through March), fish, even green s... More

Free Cancellation
Private Tour
Start From $109.95
 
Hilton Hawaiian Village Turtle Snorkel with Optional Lunch Likely to Sell Out

Hilton Hawaiian Village Turtle Snorkel with Optional Lunch

  • North America
  • Exellent73 reviews4.5

Swim with turtles and fish, while enjoying the crystal blue topical waters. Sail the scenic Waikiki....

    Free Cancellation
    Private Tour
    Start From $109.95
 
 

Toronto Tall Ship Boat Cruise

(4.3 of 743 reviews)

This is your chance to experience Toronto's only tall ship boat cruise! Sail aboard the historic 'Tall Ship Kajama,' a traditional 165-foot, 3-masted schooner boat, and sit back and relax with a cold drink from the bar or order fr... More

Free Cancellation
Private Tour
Start From $37.12
 
Toronto Tall Ship Boat Cruise Likely to Sell Out

Toronto Tall Ship Boat Cruise

  • North America
  • Exellent743 reviews4.3

This is your chance to experience Toronto's only tall ship boat cruise! Sail aboard the historic 'Ta....

    Free Cancellation
    Private Tour
    Start From $37.12
 
 

Catamaran Sailing Cruise in Monterey

(4.8 of 44 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
  • Superb44 reviews4.8

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

    Free Cancellation
    Private Tour
    Start From $65.00
 
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