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Top 10 Best North America Sailing Trips

Found 765 Sailing Trips activities in North America. Sort by Popularity. - Page 9
 

Southwest Florida Sunset Sail

(4.9 of 507 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

Southwest Florida Sunset Sail

  • North America
  • Superb507 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
 
 

America's Cup 12-Meter Yacht Afternoon Sail from Hilton Head

(4.6 of 552 reviews)

Only on Hilton Head and only in Harbour Town can you sail aboard the real America's Cup, 12 meter, Stars & Stripes once skippered by the famous Dennis Connor. All trips take place under full sail. We only use our motor to get in a... More

Free Cancellation
Start From $55.00
 
America's Cup 12-Meter Yacht Afternoon Sail from Hilton Head

America's Cup 12-Meter Yacht Afternoon Sail from Hilton Head

  • North America
  • Superb552 reviews4.6

Only on Hilton Head and only in Harbour Town can you sail aboard the real America's Cup, 12 meter, S....

    Free Cancellation
    Start From $55.00
 
 

Boat Ride to the Arch with Snorkeling in Cabo

(5 of 166 reviews)

Check these must-do Cabo activities off your list and spend a proper day in the sun, relaxing on a smooth ride through the Sea of ​​Cortez Our guide and captain who are biologists will share interesting and professional infor... More

Free Cancellation
Start From $80.67
 
Boat Ride to the Arch with Snorkeling in Cabo

Boat Ride to the Arch with Snorkeling in Cabo

  • North America
  • Superb166 reviews5

Check these must-do Cabo activities off your list and spend a proper day in the sun, relaxing on a s....

    Free Cancellation
    Start From $80.67
 
 

El Cielo Cozumel by Private Boat

(4.8 of 141 reviews)

Awarded Private Tour! Have fun aboard your Private boat and experience Cozumel water treasures in this incredible snorkeling adventure. This 4 hours family-friendly Private tour will take you out to the most renowned reefs and s... More

Free Cancellation
Private Tour
Start From $649.00
 
El Cielo Cozumel by Private Boat

El Cielo Cozumel by Private Boat

  • North America
  • Superb141 reviews4.8

Awarded Private Tour! Have fun aboard your Private boat and experience Cozumel water treasures in t....

    Free Cancellation
    Private Tour
    Start From $649.00
 
 

Escape from the Rock! Cruise around Alcatraz

(4.2 of 160 reviews)

Embark on a 90-minute cruise along the San Francisco waterfront, under the Golden Gate Bridge and past Angel Island State Park before circling Alcatraz Island for an in-depth view of the prison. Take in the sights and sounds of ... More

Free Cancellation
Private Tour
Start From $39.00
 
Escape from the Rock! Cruise around Alcatraz

Escape from the Rock! Cruise around Alcatraz

  • North America
  • Exellent160 reviews4.2

Embark on a 90-minute cruise along the San Francisco waterfront, under the Golden Gate Bridge and ....

    Free Cancellation
    Private Tour
    Start From $39.00
 
 

Sunset Cocktail Cruise on our Sailing Catamaran

(4.8 of 64 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
Private Tour
Start From $165.00
 
Sunset Cocktail Cruise on our Sailing Catamaran

Sunset Cocktail Cruise on our Sailing Catamaran

  • North America
  • Superb64 reviews4.8

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

    Free Cancellation
    Private Tour
    Start From $165.00
 
 

Portland Tall Ship Cruise on Casco Bay

(4.6 of 239 reviews)

What better way to see the delights of Portland than from the sea in one of the famous schooner tall ships. Join us for this mid morning cruise that will make your visit to Portland live long in the memory.... More

Free Cancellation
Private Tour
Start From $101.29
 
Portland Tall Ship Cruise on Casco Bay

Portland Tall Ship Cruise on Casco Bay

  • North America
  • Superb239 reviews4.6

What better way to see the delights of Portland than from the sea in one of the famous schooner tall....

    Free Cancellation
    Private Tour
    Start From $101.29
 
 

Seattle's Best Private Sailing Adventure on the Puget Sound BYOB!

(5 of 134 reviews)

Escape the hustle and bustle of city life and embark on an exclusive 3-hour private sailing tour in the Puget Sound. This personalized voyage is designed for up to six passengers, offering an intimate and unforgettable experience ... More

Free Cancellation
Private Tour
Start From $549.00
 
Seattle's Best Private Sailing Adventure on the Puget Sound BYOB!

Seattle's Best Private Sailing Adventure on the Puget Sound BYOB!

  • North America
  • Superb134 reviews5

Escape the hustle and bustle of city life and embark on an exclusive 3-hour private sailing tour in ....

    Free Cancellation
    Private Tour
    Start From $549.00
 
 

Reef Snorkeling with ATV, Zipline, Cenote, lunch & transportation

(4.3 of 3 reviews)

Welcome to the best experience in the entire Riviera Maya and Cancun, here you will enjoy swimming in a unique underwater world, you will discover the second largest coral reef in the world. Imagine swimming with impressive corals... More

Free Cancellation
Private Tour
Start From $109.65
 
Reef Snorkeling with ATV, Zipline, Cenote, lunch & transportation Likely to Sell Out

Reef Snorkeling with ATV, Zipline, Cenote, lunch & transportation

  • North America
  • Exellent3 reviews4.3

Welcome to the best experience in the entire Riviera Maya and Cancun, here you will enjoy swimming i....

    Free Cancellation
    Private Tour
    Start From $109.65
 
 

Wrightsville Beach Sunset Cocktail Sail

(4.9 of 18 reviews)

Relax aboard our 44' catamaran Bella on this evening sail. Enjoy a Caribbean-inspired cocktail while you cruise our local waterways and watch the sunset. Wind permitting, we'll turn off the engines and enjoy the beauty of sailing!... More

Free Cancellation
Private Tour
Start From $150.00
 
Wrightsville Beach Sunset Cocktail Sail Likely to Sell Out

Wrightsville Beach Sunset Cocktail Sail

  • North America
  • Superb18 reviews4.9

Relax aboard our 44' catamaran Bella on this evening sail. Enjoy a Caribbean-inspired cocktail while....

    Free Cancellation
    Private Tour
    Start From $150.00
 
 

Cabo San Lucas Sunset Sailing Shared Cruise

(4.9 of 814 reviews)

Enjoy a 2-hour sunset cruise aboard a beautiful luxury sailing boat. Admire the sights illuminated at night, and see the wonderful sunset contrasting with Cabo San Lucas amazing waters. This is a family-friendly tour and includes... More

Free Cancellation
Private Tour
Start From $120.00
 
Cabo San Lucas Sunset Sailing Shared Cruise Likely to Sell Out

Cabo San Lucas Sunset Sailing Shared Cruise

  • North America
  • Superb814 reviews4.9

Enjoy a 2-hour sunset cruise aboard a beautiful luxury sailing boat. Admire the sights illuminated ....

    Free Cancellation
    Private Tour
    Start From $120.00
 
 

Exclusive Isla Mujeres and Cancun Private Yacht Tour

(5 of 40 reviews)

Embark on an unforgettable yacht adventure in Cancun and Isla Mujeres, where turquoise waters set the stage for a day of exhilaration and relaxation. Cruise along the mesmerizing Cancun coastlines, dive into vibrant coral reefs du... More

Free Cancellation
Private Tour
Start From $720.00
 
Exclusive Isla Mujeres and Cancun Private Yacht Tour Likely to Sell Out

Exclusive Isla Mujeres and Cancun Private Yacht Tour

  • North America
  • Superb40 reviews5

Embark on an unforgettable yacht adventure in Cancun and Isla Mujeres, where turquoise waters set th....

    Free Cancellation
    Private Tour
    Start From $720.00
 
 

Isla Mujeres Day Tour with Catamaran, Snorkeling & Beach Club

(4.5 of 168 reviews)

Embark on a full-day adventure to Isla Mujeres, Cancun's most popular island getaway. Snorkel among vibrant tropical fish, then relax on Playa Norte, one of Mexico's finest beaches. Departing from the pier, begin with a 30-minut... More

Special Offer
Free Cancellation
Private Tour
Start From $79.21
(Saving 11% ) $89.00
 
-11% Isla Mujeres Day Tour with Catamaran, Snorkeling & Beach Club Likely to Sell Out

Isla Mujeres Day Tour with Catamaran, Snorkeling & Beach Club

  • North America
  • Exellent168 reviews4.5

Embark on a full-day adventure to Isla Mujeres, Cancun's most popular island getaway. Snorkel among ....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $79.21
    (Saving 11% ) $89.00
 
 

Dolphin Adventure Sail in Cocoa Beach

(4.9 of 211 reviews)

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

Special Offer
Free Cancellation
Private Tour
Start From $50.85
(Saving inf% ) $0.00
 
-inf% Dolphin Adventure Sail in Cocoa Beach Likely to Sell Out

Dolphin Adventure Sail in Cocoa Beach

  • North America
  • Superb211 reviews4.9

Experience the Magic of Cocoa Beach with Our Dolphin Adventure Sail! Join Cocoa Beach Catamaran for....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $50.85
    (Saving inf% ) $0.00
 
 

Waikiki: Fireworks Cruise from Beach & Cocktail Open Bar | Oahu

(4.8 of 59 reviews)

Set sail with Waikiki’s top-rated fireworks cruise and enjoy the famous Hilton Hawaiian Village display from the best seat on Oahu—the water. Every Friday night, you’ll glide along the coastline and experience an exclusive o... More

Special Offer
Free Cancellation
Private Tour
Start From $90.01
(Saving inf% ) $0.00
 
-inf% Waikiki: Fireworks Cruise from Beach & Cocktail Open Bar | Oahu Likely to Sell Out

Waikiki: Fireworks Cruise from Beach & Cocktail Open Bar | Oahu

  • North America
  • Superb59 reviews4.8

Set sail with Waikiki’s top-rated fireworks cruise and enjoy the famous Hilton Hawaiian Village di....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $90.01
    (Saving inf% ) $0.00
 
 

Puerto Vallarta Adults-Only Luxury Sunset Sail

(4.6 of 442 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

Special Offer
Free Cancellation
Private Tour
Start From $99.00
(Saving inf% ) $0.00
 
-inf% Puerto Vallarta Adults-Only Luxury Sunset Sail Likely to Sell Out

Puerto Vallarta Adults-Only Luxury Sunset Sail

  • North America
  • Superb442 reviews4.6

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

    Special Offer
    Free Cancellation
    Private Tour
    Start From $99.00
    (Saving inf% ) $0.00
 
 

Private Catamaran Charter in Waikiki (1-6 Guests)

(5 of 25 reviews)

Our 48-foot catamaran has a sleek low-profile design which makes it optimal for stability out on the ocean. It has 2 large lounging nets on the front of the boat, as well as 2 small nets on the back of the boat. Not only does Hawa... More

Special Offer
Free Cancellation
Private Tour
Start From $900.00
(Saving inf% ) $0.00
 
-inf% Private Catamaran Charter in Waikiki (1-6 Guests) Likely to Sell Out

Private Catamaran Charter in Waikiki (1-6 Guests)

  • North America
  • Superb25 reviews5

Our 48-foot catamaran has a sleek low-profile design which makes it optimal for stability out on the....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $900.00
    (Saving inf% ) $0.00
 
 

Waikoloa Catamaran Snorkel Sail Including Lunch

(4.6 of 109 reviews)

Set sail from Anaeho‘omalu Bay on a 3-hour snorkel and cruise adventure along Waikoloa’s beautiful Kohala Coast. Aboard the spacious Spirit of Aloha catamaran, enjoy a smooth, comfortable ride to one of the region’s best sno... More

Special Offer
Free Cancellation
Private Tour
Start From $189.00
(Saving inf% ) $0.00
 
-inf% Waikoloa Catamaran Snorkel Sail Including Lunch Likely to Sell Out

Waikoloa Catamaran Snorkel Sail Including Lunch

  • North America
  • Superb109 reviews4.6

Set sail from Anaeho‘omalu Bay on a 3-hour snorkel and cruise adventure along Waikoloa’s beautif....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $189.00
    (Saving inf% ) $0.00
 
 

Hilton Hawaiian Village Turtle Snorkel with Optional Lunch

(4.4 of 45 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

Special Offer
Free Cancellation
Private Tour
Start From $109.95
(Saving inf% ) $0.00
 
-inf% Hilton Hawaiian Village Turtle Snorkel with Optional Lunch Likely to Sell Out

Hilton Hawaiian Village Turtle Snorkel with Optional Lunch

  • North America
  • Exellent45 reviews4.4

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

    Special Offer
    Free Cancellation
    Private Tour
    Start From $109.95
    (Saving inf% ) $0.00
 
 

Private Charleston Harbor Catamaran Sail

(5 of 28 reviews)

Sit back and let us take the helm while you enjoy the harbor breeze aboard a Leopard 40 sailing catamaran. Our modern layout provides a panoramic view with large sliding glass doors between the saloon and the rear deck space, with... More

Special Offer
Free Cancellation
Private Tour
Start From $950.00
(Saving inf% ) $0.00
 
-inf% Private Charleston Harbor Catamaran Sail Likely to Sell Out

Private Charleston Harbor Catamaran Sail

  • North America
  • Superb28 reviews5

Sit back and let us take the helm while you enjoy the harbor breeze aboard a Leopard 40 sailing cata....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $950.00
    (Saving inf% ) $0.00
 
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