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Top 10 Best North America Sailing Trips

Found 727 Sailing Trips activities in North America. Sort by Popularity. - Page 15
 

Sunset sail Aboard Manakai Catamaran

(5 of 13 reviews)

Step aboard Mana Kai, a handcrafted catamaran built by William Brown, son of legendary waterman Woody Brown—a true piece of Hawaiian sailing history. With a smaller guest capacity and open-deck layout, it offers an intimate, lai... More

Free Cancellation
Start From $49.82
 
Sunset sail Aboard Manakai Catamaran

Sunset sail Aboard Manakai Catamaran

  • North America
  • Superb13 reviews5

Step aboard Mana Kai, a handcrafted catamaran built by William Brown, son of legendary waterman Wood....

    Free Cancellation
    Start From $49.82
 
 

kayaking in Huatulco

(5 of 1 review)

The geographical position favors us to observe whales, dolphins, turtles and much more while sailing in the kayak in calm waters, we have contact with the most 95% of the time on the tour, so it is highly recommended for biologist... More

Free Cancellation
Private Tour
Start From $75.62
 
kayaking in Huatulco

kayaking in Huatulco

  • North America
  • Superb1 review5

The geographical position favors us to observe whales, dolphins, turtles and much more while sailing....

    Free Cancellation
    Private Tour
    Start From $75.62
 
 

Los Cabos Seasonal Whale Watch and Snorkel Tour

(4.7 of 19 reviews)

Available December 15th to April 15th. Enjoy an incredible adventure, departing from the beautiful Marina in Cabo San Lucas the boat as sails towards the Santa Maria or Chileno Bay, will ride along the Sea of Cortes, and you will ... More

Free Cancellation
Private Tour
Start From $239.00
 
Los Cabos Seasonal Whale Watch and Snorkel Tour

Los Cabos Seasonal Whale Watch and Snorkel Tour

  • North America
  • Superb19 reviews4.7

Available December 15th to April 15th. Enjoy an incredible adventure, departing from the beautiful M....

    Free Cancellation
    Private Tour
    Start From $239.00
 
 

Shallow Water Snorkeling and Dolphin Watching in Key West

(4.6 of 464 reviews)

All while avoiding the crowded big boats, spend part of your Florida vacation day out on the tropical waters of Key West on Catamaran Echo - making vacation memories since 1991. Enjoy a premium shallow snorkeling and dolphin-watc... More

Free Cancellation
Private Tour
Start From $108.91
 
Shallow Water Snorkeling and Dolphin Watching in Key West Likely to Sell Out

Shallow Water Snorkeling and Dolphin Watching in Key West

  • North America
  • Superb464 reviews4.6

All while avoiding the crowded big boats, spend part of your Florida vacation day out on the tropica....

    Free Cancellation
    Private Tour
    Start From $108.91
 
 

2.5-Hour Small-Group Catamaran Sailing Adventure with Drinks

(5 of 81 reviews)

With over 38 years of experience sharing our love of sailing with San Diego visitors, we are prepared to offer you a memorable day on the sea. 2.5 hour tour length is perfect for seeing all the beautiful sights. Catamarans reall... More

Free Cancellation
Private Tour
Start From $119.00
 
2.5-Hour Small-Group Catamaran Sailing Adventure with Drinks Likely to Sell Out

2.5-Hour Small-Group Catamaran Sailing Adventure with Drinks

  • North America
  • Superb81 reviews5

With over 38 years of experience sharing our love of sailing with San Diego visitors, we are prepare....

    Free Cancellation
    Private Tour
    Start From $119.00
 
 

Key West Day Sail on Schooner America 2.0 with 2 Drinks

(4.9 of 192 reviews)

Sail aboard the fastest and most elegant schooner in Key West, Schooner America 2.0! This boat is a replica of the 1851 Schooner America that won the first America's Cup Race in 1851. Admire her beauty on the clear, calm Caribbean... More

Free Cancellation
Private Tour
Start From $73.10
 
Key West Day Sail on Schooner America 2.0 with 2 Drinks Likely to Sell Out

Key West Day Sail on Schooner America 2.0 with 2 Drinks

  • North America
  • Superb192 reviews4.9

Sail aboard the fastest and most elegant schooner in Key West, Schooner America 2.0! This boat is a ....

    Free Cancellation
    Private Tour
    Start From $73.10
 
 

Charleston Iconic Sunset Sail - Lux Catamaran w/Bar & Bathrooms

(4.9 of 45 reviews)

Set sail aboard the Palmetto Breeze for a spectacular sunset experience on Charleston’s harbor. This spacious 50-foot catamaran offers a perfect setting to watch the sky transform into a palette of golden hues as the sun dips be... More

Free Cancellation
Private Tour
Start From $63.00
 
Charleston Iconic Sunset Sail - Lux Catamaran w/Bar & Bathrooms Likely to Sell Out

Charleston Iconic Sunset Sail - Lux Catamaran w/Bar & Bathrooms

  • North America
  • Superb45 reviews4.9

Set sail aboard the Palmetto Breeze for a spectacular sunset experience on Charleston’s harbor. Th....

    Free Cancellation
    Private Tour
    Start From $63.00
 
 

NYC Statue of Liberty Tall Ship Sail aboard Clipper City

(4.3 of 264 reviews)

Step aboard the majestic Clipper City and feel the city fade into the background as the wind fills the sails. Glide through New York Harbor in style, with the Brooklyn Bridge, Statue of Liberty, Ellis Island, and the glittering Ma... More

Free Cancellation
Private Tour
Start From $68.00
 
NYC Statue of Liberty Tall Ship Sail aboard Clipper City Likely to Sell Out

NYC Statue of Liberty Tall Ship Sail aboard Clipper City

  • North America
  • Exellent264 reviews4.3

Step aboard the majestic Clipper City and feel the city fade into the background as the wind fills t....

    Free Cancellation
    Private Tour
    Start From $68.00
 
 

Vancouver Sailing Experience on a 50 foot Sailboat

(5 of 100 reviews)

I have been living aboard full time for the past 12 years, sailing the Vancouver waterways for over 45 years. I have raced competitively for 20 of those, have extensive sailing and local knowledge, 12 years experience volunteering... More

Free Cancellation
Private Tour
Start From $110.24
 
Vancouver Sailing Experience on a 50 foot Sailboat Likely to Sell Out

Vancouver Sailing Experience on a 50 foot Sailboat

  • North America
  • Superb100 reviews5

I have been living aboard full time for the past 12 years, sailing the Vancouver waterways for over ....

    Free Cancellation
    Private Tour
    Start From $110.24
 
 

Miami Beach Luxury Yacht Adventure: Explore Stunning Coastline

(4.8 of 23 reviews)

Embark on a private yacht journey, perfect for families, couples, & adventurers seeking a unique Miami Beach experience. Connect with nature, discover new landscapes, & create lasting memories as you explore the stunning coastline... More

Free Cancellation
Private Tour
Start From $600.00
 
Miami Beach Luxury Yacht Adventure: Explore Stunning Coastline Likely to Sell Out

Miami Beach Luxury Yacht Adventure: Explore Stunning Coastline

  • North America
  • Superb23 reviews4.8

Embark on a private yacht journey, perfect for families, couples, & adventurers seeking a unique Mia....

    Free Cancellation
    Private Tour
    Start From $600.00
 
 

Suncoast Sailing's Day Sailing Experience!

(4.9 of 104 reviews)

Join us aboard the iconic schooner, Suncoast Horizon and step aboard our 2 hour sailing excursion. Feel the wind as it glides us through the picturesque waters of Treasure Island and Gulf of Mexico. Come face to face with nature a... More

Free Cancellation
Private Tour
Start From $64.99
 
Suncoast Sailing's Day Sailing Experience! Likely to Sell Out

Suncoast Sailing's Day Sailing Experience!

  • North America
  • Superb104 reviews4.9

Join us aboard the iconic schooner, Suncoast Horizon and step aboard our 2 hour sailing excursion. F....

    Free Cancellation
    Private Tour
    Start From $64.99
 
 

Kona Tradewind Catamaran Day Sail

(4.8 of 42 reviews)

Experience the beauty of the Kona Coast from a new perspective aboard the Spirit of Aloha sailing catamaran. Feel the trade winds fill the sails as you glide across the water, taking in panoramic views of volcanic cliffs, sparklin... More

Free Cancellation
Private Tour
Start From $89.95
 
Kona Tradewind Catamaran Day Sail Likely to Sell Out

Kona Tradewind Catamaran Day Sail

  • North America
  • Superb42 reviews4.8

Experience the beauty of the Kona Coast from a new perspective aboard the Spirit of Aloha sailing ca....

    Free Cancellation
    Private Tour
    Start From $89.95
 
 

Ft Myers Beach 3 Hour Tiki Pub Tropical Sandbar Getaway Cruise

(5 of 26 reviews)

Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages, 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 pals on ou... More

Free Cancellation
Private Tour
Start From $89.00
 
Ft Myers Beach 3 Hour Tiki Pub Tropical Sandbar Getaway Cruise Likely to Sell Out

Ft Myers Beach 3 Hour Tiki Pub Tropical Sandbar Getaway Cruise

  • North America
  • Superb26 reviews5

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

    Free Cancellation
    Private Tour
    Start From $89.00
 
 

Whale Watching Sail in Honolulu with Open Bar

(5 of 6 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 $49.00
 
Whale Watching Sail in Honolulu with Open Bar Likely to Sell Out

Whale Watching Sail in Honolulu with Open Bar

  • North America
  • Superb6 reviews5

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

    Free Cancellation
    Private Tour
    Start From $49.00
 
 

Sunrise by Paddle or Kayak with Floating Picnic

(5 of 339 reviews)

Dare to live a new experience! During this activity you will connect with your ecological SELF as you paddle towards sunrise. Enjoy a delicious picnic in a natural environment while you immerse yourself in warm and crystal clear w... More

Free Cancellation
Private Tour
Start From $29.08
 
Sunrise by Paddle or Kayak with Floating Picnic Likely to Sell Out

Sunrise by Paddle or Kayak with Floating Picnic

  • North America
  • Superb339 reviews5

Dare to live a new experience! During this activity you will connect with your ecological SELF as yo....

    Free Cancellation
    Private Tour
    Start From $29.08
 
 

Sunset Sail Aboard the 47 ft Daydreams Sailboat

(4.9 of 32 reviews)

Your 2 hour sunset charter on our 47-foot sailboat Daydreams will include a scenic trip through Grand Lagoon and along the coast of Shell Island. Enjoy a relaxing sail in the Gulf of Mexico and look for dolphins along the way. Wit... More

Free Cancellation
Private Tour
Start From $99.00
 
Sunset Sail Aboard the 47 ft Daydreams Sailboat Likely to Sell Out

Sunset Sail Aboard the 47 ft Daydreams Sailboat

  • North America
  • Superb32 reviews4.9

Your 2 hour sunset charter on our 47-foot sailboat Daydreams will include a scenic trip through Gran....

    Free Cancellation
    Private Tour
    Start From $99.00
 
 

Cancun to Isla Mujeres Full Day Tour with Snorkeling

(1 of 1 review)

Live a fun and relaxed day aboard a catamaran with open bar on board meeting the pearl of the Caribbean – Isla Mujeres, with its paradise beaches. We start the catamaran tour with national open bar included on board throughout ... More

Free Cancellation
Private Tour
Start From $70.00
 
Cancun to Isla Mujeres Full Day Tour with Snorkeling Likely to Sell Out

Cancun to Isla Mujeres Full Day Tour with Snorkeling

  • North America

Live a fun and relaxed day aboard a catamaran with open bar on board meeting the pearl of the Carib....

    Free Cancellation
    Private Tour
    Start From $70.00
 
 

Jungle Tour

(5 of 1 review)

This boat and snorkeling tour from Cancun gives you a 2-for-1 value—take a speedboat ride through Nichupte Lagoon and snorkel in the El Angel coral reef. Choose to take the driver’s seat or ride shotgun in a 2-seat speedboat a... More

Free Cancellation
Private Tour
Start From $70.00
 
Jungle Tour Likely to Sell Out

Jungle Tour

  • North America
  • Superb1 review5

This boat and snorkeling tour from Cancun gives you a 2-for-1 value—take a speedboat ride through ....

    Free Cancellation
    Private Tour
    Start From $70.00
 
 

Waikiki 3pm Tradewind Sail - Open Bar Included

(4.8 of 245 reviews)

Open Bar: Included with the price of General Admission until 8/31/2025 This is an excellent cruise for families and sailors wanting to relax and enjoy a beautiful afternoon in the sun. We'll be keeping a sharp eye out for dolphin... More

Free Cancellation
Private Tour
Start From $53.36
 
Waikiki 3pm Tradewind Sail - Open Bar Included Likely to Sell Out

Waikiki 3pm Tradewind Sail - Open Bar Included

  • North America
  • Superb245 reviews4.8

Open Bar: Included with the price of General Admission until 8/31/2025 This is an excellent cruise ....

    Free Cancellation
    Private Tour
    Start From $53.36
 
 

Snorkeling Adventure in Isla Mujeres

(3.8 of 12 reviews)

Dare to be part of one of the most enigmatic activities in Cancun and Mexico. The underwater museum is a unique activity in the world since there is no such thing anywhere. This activity is cataloged as mandatory for all traveler... More

Free Cancellation
Private Tour
Start From $55.00
 
Snorkeling Adventure in Isla Mujeres Likely to Sell Out

Snorkeling Adventure in Isla Mujeres

  • North America
  • Very Good12 reviews3.8

Dare to be part of one of the most enigmatic activities in Cancun and Mexico. The underwater museum....

    Free Cancellation
    Private Tour
    Start From $55.00
 
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