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Top 10 Best North America Sailing Trips

Found 727 Sailing Trips activities in North America. Sort by Popularity. - Page 12
 

Bacalar: 4hr Private Sailing Tour with Guacamole & Drinks

(4.9 of 103 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 $250.12
 
Bacalar: 4hr Private Sailing Tour with Guacamole & Drinks

Bacalar: 4hr Private Sailing Tour with Guacamole & Drinks

  • North America
  • Superb103 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 $250.12
 
 

Private Sunset Catamaran Sail in Cocoa Beach

(4.9 of 103 reviews)

Experience a magical sunset in with Cocoa Beach Catamaran Set sail into the golden hour and enjoy a stunning evening on the serene waters of the Banana River Lagoon. Our Sunset Sail is the perfect way to relax and take in the bea... More

Free Cancellation
Private Tour
Start From $337.87
 
Private Sunset Catamaran Sail in Cocoa Beach Likely to Sell Out

Private Sunset Catamaran Sail in Cocoa Beach

  • North America
  • Superb103 reviews4.9

Experience a magical sunset in with Cocoa Beach Catamaran Set sail into the golden hour and enjoy a....

    Free Cancellation
    Private Tour
    Start From $337.87
 
 

Luxury Catamaran tour to isla mujeres with transportation from Tulum

(3.5 of 63 reviews)

Excellent service on board Professional crew members Safety measures in all our activities Sanitary prevention protocols for all our guests and staff Once in a lifetime experience Delicious buffet lunch and drinks Beach club (beac... More

Free Cancellation
Private Tour
Start From $110.77
 
Luxury Catamaran tour to isla mujeres with transportation from Tulum Likely to Sell Out

Luxury Catamaran tour to isla mujeres with transportation from Tu....

  • North America
  • Good63 reviews3.5

Excellent service on board Professional crew members Safety measures in all our activities Sanitary ....

    Free Cancellation
    Private Tour
    Start From $110.77
 
 

Private sailing excursions, nice spacious sailboats.

(4.9 of 27 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 $290.84
 
Private sailing excursions, nice spacious sailboats. Likely to Sell Out

Private sailing excursions, nice spacious sailboats.

  • North America
  • Superb27 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 $290.84
 
 

All Inclusive Caribbean adventure, reef snorkeling, Food & Drinks

(3.7 of 33 reviews)

Admire the peaceful waters of the Caribbean Sea, aboard a catamaran and enjoy a spectacular day sailing to Isla Mujeres on a fun-filled experience. Explore Isla Mujeres impressive sites are waiting for you. You will visit one of ... More

Free Cancellation
Skip The Line
Private Tour
Start From $65.00
 
All Inclusive Caribbean adventure, reef snorkeling, Food & Drinks Likely to Sell Out

All Inclusive Caribbean adventure, reef snorkeling, Food & Drinks

  • North America
  • Very Good33 reviews3.7

Admire the peaceful waters of the Caribbean Sea, aboard a catamaran and enjoy a spectacular day sail....

    Free Cancellation
    Skip The Line
    Private Tour
    Start From $65.00
 
 

Sunset Cocktail Cruise on our Sailing Catamaran

(4.8 of 62 reviews)

Enjoy the warm tropical breezes and unparalleled views of the Big Island as you sail along the Kohala Coast aboard our legendary sailing catamaran Seasmoke. This cruise includes unlimited soft drinks, tropical juices, beers, wines... More

Free Cancellation
Skip The Line
Private Tour
Start From $165.00
 
Sunset Cocktail Cruise on our Sailing Catamaran Likely to Sell Out

Sunset Cocktail Cruise on our Sailing Catamaran

  • North America
  • Superb62 reviews4.8

Enjoy the warm tropical breezes and unparalleled views of the Big Island as you sail along the Kohal....

    Free Cancellation
    Skip The Line
    Private Tour
    Start From $165.00
 
 

Sunset Sail in the Gulf of Mexico for up to 6 Guests

(5 of 6 reviews)

Sailing aboard a modern 38' sailboat, this sunset cruise offers a unique chance to witness the romantic beauty of the Gulf of Mexico as the sun dips below the horizon. For two and a half hours, enjoy the stunning views along Fort ... More

Free Cancellation
Skip The Line
Private Tour
Start From $149.00
 
Sunset Sail in the Gulf of Mexico for up to 6 Guests Likely to Sell Out

Sunset Sail in the Gulf of Mexico for up to 6 Guests

  • North America
  • Superb6 reviews5

Sailing aboard a modern 38' sailboat, this sunset cruise offers a unique chance to witness the roman....

    Free Cancellation
    Skip The Line
    Private Tour
    Start From $149.00
 
 

Paddle at Dawn with visit to Cenotes and Islands

(4.9 of 65 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
Skip The Line
Private Tour
Start From $24.43
 
Paddle at Dawn with visit to Cenotes and Islands Likely to Sell Out

Paddle at Dawn with visit to Cenotes and Islands

  • North America
  • Superb65 reviews4.9

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

    Free Cancellation
    Skip The Line
    Private Tour
    Start From $24.43
 
 

Sail on Tall Ship Windy, join us for our "Chicago Skyline Sail"

(4.8 of 20 reviews)

Join us for an unforgettable sail on Tall Ship Windy, Chicago's Official Tall Ship Ambassador! This is a relaxing sailing Adventure, that you will enjoy, on Lake Michigan, while enjoying the views, and the fresh air! Fun for all ... More

Free Cancellation
Skip The Line
Private Tour
Start From $91.23
 
Sail on Tall Ship Windy, join us for our Likely to Sell Out

Sail on Tall Ship Windy, join us for our "Chicago Skyline Sail"

  • North America
  • Superb20 reviews4.8

Join us for an unforgettable sail on Tall Ship Windy, Chicago's Official Tall Ship Ambassador! This ....

    Free Cancellation
    Skip The Line
    Private Tour
    Start From $91.23
 
 

South Shore Open Sail from Kewalo Harbor Including Drinks

(5 of 21 reviews)

Join us for a 90-minute daytime sailing experience from Kewalo Basin Harbor on one of the most iconic catamarans in Honolulu! Our sails always have complimentary drinks (alcoholic beverages available for adults 21+ with valid ID o... More

Free Cancellation
Skip The Line
Private Tour
Start From $47.50
 
South Shore Open Sail from Kewalo Harbor Including Drinks Likely to Sell Out

South Shore Open Sail from Kewalo Harbor Including Drinks

  • North America
  • Superb21 reviews5

Join us for a 90-minute daytime sailing experience from Kewalo Basin Harbor on one of the most iconi....

    Free Cancellation
    Skip The Line
    Private Tour
    Start From $47.50
 
 

Waikiki Sunset Cruise Catamaran Boat Tour on Oahu

(4.7 of 17 reviews)

Our tour offers a plethora of beautiful views such as Waikiki bay itself, Diamond head crater (Lē‘ahi), crystal blue waters, a gorgeous sunset, and from December-March, of course, the annual humpback whales!... More

Free Cancellation
Skip The Line
Private Tour
Start From $80.00
 
Waikiki Sunset Cruise Catamaran Boat Tour on Oahu Likely to Sell Out

Waikiki Sunset Cruise Catamaran Boat Tour on Oahu

  • North America
  • Superb17 reviews4.7

Our tour offers a plethora of beautiful views such as Waikiki bay itself, Diamond head crater (LÄ“â€....

    Free Cancellation
    Skip The Line
    Private Tour
    Start From $80.00
 
 

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

(4.8 of 11 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
Skip The Line
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
  • Superb11 reviews4.8

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
    Skip The Line
    Private Tour
    Start From $30.00
 
 

Hilton Hawaiian Village Turtle Snorkel with Optional Lunch

(4.7 of 31 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
Skip The Line
Private Tour
Start From $156.79
 
Hilton Hawaiian Village Turtle Snorkel with Optional Lunch Likely to Sell Out

Hilton Hawaiian Village Turtle Snorkel with Optional Lunch

  • North America
  • Superb31 reviews4.7

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

    Free Cancellation
    Skip The Line
    Private Tour
    Start From $156.79
 
 

Honolulu Sailing and Snorkeling Activity

(4.7 of 31 reviews)

You’re guaranteed to see an array of endemic reef fish, colorful corals, and other unique marine creatures that call the Hawaiian islands home. ... More

Free Cancellation
Skip The Line
Private Tour
Start From $105.00
 
Honolulu Sailing and Snorkeling Activity Likely to Sell Out

Honolulu Sailing and Snorkeling Activity

  • North America
  • Superb31 reviews4.7

You’re guaranteed to see an array of endemic reef fish, colorful corals, and other unique marine c....

    Free Cancellation
    Skip The Line
    Private Tour
    Start From $105.00
 
 

Catamaran Cruise from Costa Mujeres with Snorkeling and Lunch

(2.5 of 4 reviews)

Enjoy the cool ocean breeze and the sparkling turquoise sea as you cruise along the Mexican Caribbean on our spacious catamaran. With music, drinks, and a lively host to keep the good vibes going, this isn’t just a tour — itâ€... More

Free Cancellation
Skip The Line
Private Tour
Start From $139.00
 
Catamaran Cruise from Costa Mujeres with Snorkeling and Lunch Likely to Sell Out

Catamaran Cruise from Costa Mujeres with Snorkeling and Lunch

  • North America

Enjoy the cool ocean breeze and the sparkling turquoise sea as you cruise along the Mexican Caribbea....

    Free Cancellation
    Skip The Line
    Private Tour
    Start From $139.00
 
 

Polynesian Canoe Sunset Sail

(4.9 of 126 reviews)

Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) offering a one-of-a-kind native Hawaiian cultural and educational experience. Come sail along the beautiful Waikiki coastline and b... More

Free Cancellation
Skip The Line
Private Tour
Start From $250.00
 
Polynesian Canoe Sunset Sail Likely to Sell Out

Polynesian Canoe Sunset Sail

  • North America
  • Superb126 reviews4.9

Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) o....

    Free Cancellation
    Skip The Line
    Private Tour
    Start From $250.00
 
 

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
Skip The Line
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
    Skip The Line
    Private Tour
    Start From $38.50
 
 

Key West Signature Sunset Sail with Live Music, Open Bar & Food

(4.5 of 311 reviews)

Sunset Sip & Sail: Come see the legendary Key West Sunset on a Brand New Catamaran Sail Boat. • Open bar • Live Music • Great Appetizers Welcome aboard Key West's newest catamaran, the "Sandie Cat" as we literally... More

Free Cancellation
Skip The Line
Private Tour
Start From $72.00
 
Key West Signature Sunset Sail with Live Music, Open Bar & Food Likely to Sell Out

Key West Signature Sunset Sail with Live Music, Open Bar & Food

  • North America
  • Exellent311 reviews4.5

Sunset Sip & Sail: Come see the legendary Key West Sunset on a Brand New Catamaran Sail Boat. â€....

    Free Cancellation
    Skip The Line
    Private Tour
    Start From $72.00
 
 

Kauai’s Na Pali Coast Snorkel and Sail Tour

(4.8 of 541 reviews)

Set sail for a once-in-a-lifetime adventure along Kauai’s iconic Na Pali Coast. This five-hour catamaran journey combines spectacular sightseeing, exciting snorkeling, and all-inclusive comfort, making it the top choice for fami... More

Free Cancellation
Skip The Line
Private Tour
Start From $292.48
 
Kauai’s Na Pali Coast Snorkel and Sail Tour Likely to Sell Out

Kauai’s Na Pali Coast Snorkel and Sail Tour

  • North America
  • Superb541 reviews4.8

Set sail for a once-in-a-lifetime adventure along Kauai’s iconic Na Pali Coast. This five-hour cat....

    Free Cancellation
    Skip The Line
    Private Tour
    Start From $292.48
 
 

Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon

(4.8 of 293 reviews)

-Guaranteed Hawaiian sea turtles at Turtle Canyon -Ample shade and seating on board -Premium snorkel equipment -Fun, friendly, lifeguard certified crew -BYOB (Bring your own Beverage. No glass bottles)... More

Special Offer
Free Cancellation
Skip The Line
Private Tour
Start From $89.10
(Saving 10% ) $99.00
 
-10% Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon Likely to Sell Out

Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon

  • North America
  • Superb293 reviews4.8

-Guaranteed Hawaiian sea turtles at Turtle Canyon -Ample shade and seating on board -Premium snorkel....

    Special Offer
    Free Cancellation
    Skip The Line
    Private Tour
    Start From $89.10
    (Saving 10% ) $99.00
 
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