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Top 10 Best North America Sailing Trips

Found 727 Sailing Trips activities in North America. Sort by Popularity. - Page 13
 

Deluxe Private Boats - 40 ft Catamaran

(5 of 111 reviews)

We are a company that understands privacy, attention to detail, and quality in everything we get our hands-on. We want you to feel relaxed and at home. We understand you are here to be pampered and have the nicest drinks and lunc... More

Free Cancellation
Private Tour
Start From $1,835.00
 
Deluxe Private Boats - 40 ft Catamaran

Deluxe Private Boats - 40 ft Catamaran

  • North America
  • Superb111 reviews5

We are a company that understands privacy, attention to detail, and quality in everything we get our....

    Free Cancellation
    Private Tour
    Start From $1,835.00
 
 

Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure

(5 of 693 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

Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure

  • North America
  • Superb693 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
 
 

Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)

(4.8 of 42 reviews)

Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui sunset begin to paint the sky. As you step aboard, you're greeted by the friendly crew who welcome you with warm aloha spirit. The c... More

Free Cancellation
Private Tour
Start From $289.00
 
Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)

Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)

  • North America
  • Superb42 reviews4.8

Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui su....

    Free Cancellation
    Private Tour
    Start From $289.00
 
 

Honolulu Sunset Sail from Kewalo Harbor Including Drinks

(4.9 of 166 reviews)

Our Sunset Sail tour is a fun and wild 90-minute sail where all drinks are complimentary! (Must be 21+ with valid ID to consume alcoholic beverages). Sail the south shore from Kaka'ako Waterfront to Waikiki, with beautiful views ... More

Free Cancellation
Private Tour
Start From $61.50
 
Honolulu Sunset Sail from Kewalo Harbor Including Drinks

Honolulu Sunset Sail from Kewalo Harbor Including Drinks

  • North America
  • Superb166 reviews4.9

Our Sunset Sail tour is a fun and wild 90-minute sail where all drinks are complimentary! (Must be 2....

    Free Cancellation
    Private Tour
    Start From $61.50
 
 

Small-Group San Diego Sunset Sailing Excursion

(4.9 of 586 reviews)

Set sail from San Diego on this small-group sailing tour on a sunset sail on the open ocean. This three-hour adventure on a Catalina sailboat is limited to six (6) guests allowing you a comfortable, semi-private experience (or, pu... More

Free Cancellation
Private Tour
Start From $127.00
 
Small-Group San Diego Sunset Sailing Excursion Likely to Sell Out

Small-Group San Diego Sunset Sailing Excursion

  • North America
  • Superb586 reviews4.9

Set sail from San Diego on this small-group sailing tour on a sunset sail on the open ocean. This th....

    Free Cancellation
    Private Tour
    Start From $127.00
 
 

El Cielo Cozumel Snorkeling trip by Catamaran

(4.4 of 275 reviews)

TRAVELER’S FAVORITE TRIP! Get in the mood for fun aboard your Catamaran in a fun sail to magnificent reefs and great snorkeling and after, head back to a secluded Beach to relax and enjoy the beauty of Cozumel turquoise waters.... More

Free Cancellation
Private Tour
Start From $95.00
 
El Cielo Cozumel Snorkeling trip by Catamaran Likely to Sell Out

El Cielo Cozumel Snorkeling trip by Catamaran

  • North America
  • Exellent275 reviews4.4

TRAVELER’S FAVORITE TRIP! Get in the mood for fun aboard your Catamaran in a fun sail to magnific....

    Free Cancellation
    Private Tour
    Start From $95.00
 
 

Maui: Kaanapali Beach 5-hour Snorkel w/ BBQ Lunch & Open Bar

(5 of 4 reviews)

5-hour, two-spot snorkel is unlike any other on Ka'anapali Beach as it's aboard Ka'anapali's newest luxury custom built catamarans and includes breakfast, lunch, dessert and an open bar. This is our award-winning snorkel tour that... More

Free Cancellation
Private Tour
Start From $203.16
 
Maui: Kaanapali Beach 5-hour Snorkel w/ BBQ Lunch & Open Bar Likely to Sell Out

Maui: Kaanapali Beach 5-hour Snorkel w/ BBQ Lunch & Open Bar

  • North America
  • Superb4 reviews5

5-hour, two-spot snorkel is unlike any other on Ka'anapali Beach as it's aboard Ka'anapali's newest ....

    Free Cancellation
    Private Tour
    Start From $203.16
 
 

2-Hour Oahu Sunset Catamaran Sail

(4.8 of 121 reviews)

Relax, sit back and delight in our 2-hour sunset sailing cruise on a gorgeous, 53' foot catamaran from the beautiful Ko Olina Marina on Oahu. Sip a cocktail and enjoy warm wind in your hair as you scan for dolphins and listen for... More

Free Cancellation
Private Tour
Start From $130.00
 
2-Hour Oahu Sunset Catamaran Sail Likely to Sell Out

2-Hour Oahu Sunset Catamaran Sail

  • North America
  • Superb121 reviews4.8

Relax, sit back and delight in our 2-hour sunset sailing cruise on a gorgeous, 53' foot catamaran f....

    Free Cancellation
    Private Tour
    Start From $130.00
 
 

Key West Rum and Reggae: Reef Snorkel Adventure and Sunset Sail

(4.4 of 370 reviews)

Fury’s Snorkel Adventure is unique for its combination of thrilling snorkeling and a vibrant sailing experience. Guests board a spacious Fury Catamaran, part of the largest luxury fleet in the Florida Keys, and sail to North Ame... More

Free Cancellation
Private Tour
Start From $59.95
 
Key West Rum and Reggae: Reef Snorkel Adventure and Sunset Sail Likely to Sell Out

Key West Rum and Reggae: Reef Snorkel Adventure and Sunset Sail

  • North America
  • Exellent370 reviews4.4

Fury’s Snorkel Adventure is unique for its combination of thrilling snorkeling and a vibrant saili....

    Free Cancellation
    Private Tour
    Start From $59.95
 
 

Maui: Ka'anapali Luxury Sunset Cocktail Sail with Open Bar

(3.3 of 4 reviews)

Set sail on a luxurious journey along West Maui's stunning coastline with the Holo Holo Sunset Cocktail Sail. Departing from Ka’anapali Beach, this 2-hour experience offers breathtaking views of the sunset complemented by deligh... More

Free Cancellation
Private Tour
Start From $141.98
 
Maui: Ka'anapali Luxury Sunset Cocktail Sail with Open Bar Likely to Sell Out

Maui: Ka'anapali Luxury Sunset Cocktail Sail with Open Bar

  • North America
  • Good4 reviews3.3

Set sail on a luxurious journey along West Maui's stunning coastline with the Holo Holo Sunset Cockt....

    Free Cancellation
    Private Tour
    Start From $141.98
 
 

Puerto Vallarta Luxury Sailing with Premium Open bar & lunch

(4.8 of 297 reviews)

Sail across Banderas Bay in luxury aboard our exclusive Leopard and Beneteau yachts, taking in breathtaking views of Puerto Vallarta’s coastline and the majestic Sierra Madre mountains. This small-group experience offers a perfe... More

Free Cancellation
Private Tour
Start From $129.00
 
Puerto Vallarta Luxury Sailing with Premium Open bar & lunch Likely to Sell Out

Puerto Vallarta Luxury Sailing with Premium Open bar & lunch

  • North America
  • Superb297 reviews4.8

Sail across Banderas Bay in luxury aboard our exclusive Leopard and Beneteau yachts, taking in breat....

    Free Cancellation
    Private Tour
    Start From $129.00
 
 

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

(4.8 of 276 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
  • Superb276 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
 
 

Key West Sailing & Snorkeling: A Reef Adventure

(4.7 of 177 reviews)

Join us for a snorkel adventure to the only living coral reef in North America. We have several fantastic reefs to choose from on both the north and south sides of Key West, each offering a unique experience. It’s about an hour ... More

Free Cancellation
Private Tour
Start From $79.00
 
Key West Sailing & Snorkeling: A Reef Adventure Likely to Sell Out

Key West Sailing & Snorkeling: A Reef Adventure

  • North America
  • Superb177 reviews4.7

Join us for a snorkel adventure to the only living coral reef in North America. We have several fant....

    Free Cancellation
    Private Tour
    Start From $79.00
 
 

Key West Morning Snorkel Sail with Mimosas and Gourmet Breakfast

(4.5 of 79 reviews)

Embark on an adventure off the shores of Key West, where the turquiose waters of the Gulf of Mexico and the Atlantic Ocean meet in a symphony of beauty and tranquility. Your day begins as you board a luxurious catamaran, your vess... More

Free Cancellation
Private Tour
Start From $49.00
 
Key West Morning Snorkel Sail with Mimosas and Gourmet Breakfast Likely to Sell Out

Key West Morning Snorkel Sail with Mimosas and Gourmet Breakfast

  • North America
  • Exellent79 reviews4.5

Embark on an adventure off the shores of Key West, where the turquiose waters of the Gulf of Mexico ....

    Free Cancellation
    Private Tour
    Start From $49.00
 
 

All Inclusive Beach Club, Water Sports, Horse Ride, Food & Drinks

(3.6 of 7 reviews)

Introducing the ultimate beach getaway - Stone Island! This all-inclusive package offers an unbeatable experience with unlimited drinks, mouth-watering lunch, and your choice of two exciting activities. Whether you want to ride ho... More

Free Cancellation
Private Tour
Start From $59.00
 
All Inclusive Beach Club, Water Sports, Horse Ride, Food & Drinks Likely to Sell Out

All Inclusive Beach Club, Water Sports, Horse Ride, Food & Drinks

  • North America
  • Very Good7 reviews3.6

Introducing the ultimate beach getaway - Stone Island! This all-inclusive package offers an unbeatab....

    Free Cancellation
    Private Tour
    Start From $59.00
 
 

Key West Historic Schooner When And If Sunset Cruise

(4.8 of 108 reviews)

Historic Schooner. Champagne Sunset Toast. Elegant and Exclusive. Step aboard the historic schooner When And If, commissioned by General George Patton in the late 1930s, and sail into a breathtaking Key West sunset. Raise a champ... More

Free Cancellation
Private Tour
Start From $109.00
 
Key West Historic Schooner When And If Sunset Cruise Likely to Sell Out

Key West Historic Schooner When And If Sunset Cruise

  • North America
  • Superb108 reviews4.8

Historic Schooner. Champagne Sunset Toast. Elegant and Exclusive. Step aboard the historic schooner....

    Free Cancellation
    Private Tour
    Start From $109.00
 
 

Waikiki Sunset Boat Cruise

(5 of 89 reviews)

No vacation is complete without experiencing a vibrant Hawaiian sunset from the water. Unobstructed views create the best photo opportunities! Listen to great music as we cruise the Waikiki coastline with views of Diamond head cra... More

Free Cancellation
Private Tour
Start From $50.00
 
Waikiki Sunset Boat Cruise Likely to Sell Out

Waikiki Sunset Boat Cruise

  • North America
  • Superb89 reviews5

No vacation is complete without experiencing a vibrant Hawaiian sunset from the water. Unobstructed ....

    Free Cancellation
    Private Tour
    Start From $50.00
 
 

9am Turtle Canyon Snorkel Adventure

(4.9 of 273 reviews)

What better way to start your day than to slip into the refreshing waters of Turtle Canyon and swim with amazing green sea turtles, beautiful tropical fish, and other incredible marine life? Our snorkel guides help you feel confid... More

Free Cancellation
Private Tour
Start From $84.77
 
9am Turtle Canyon Snorkel Adventure Likely to Sell Out

9am Turtle Canyon Snorkel Adventure

  • North America
  • Superb273 reviews4.9

What better way to start your day than to slip into the refreshing waters of Turtle Canyon and swim ....

    Free Cancellation
    Private Tour
    Start From $84.77
 
 

Luxury Sunset Sailing Cruise in Cancun with Light Dinner and Open Bar

(4.5 of 82 reviews)

*Step into luxury when you board one of our fully-equipped sailboats. *Receive a friendly greeting from our crew who will provide you with unmatched service throughout the excursion. *Take a moment for a photo opportunity with y... More

Free Cancellation
Private Tour
Start From $109.00
 
Luxury Sunset Sailing Cruise in Cancun with Light Dinner and Open Bar Likely to Sell Out

Luxury Sunset Sailing Cruise in Cancun with Light Dinner and Open....

  • North America
  • Exellent82 reviews4.5

*Step into luxury when you board one of our fully-equipped sailboats. *Receive a friendly greeting ....

    Free Cancellation
    Private Tour
    Start From $109.00
 
 

Key West 2 Reef Snorkel Tour & Sunset Cruise with Beer & Wine

(4.7 of 146 reviews)

Enjoy this 3 hour sunset combo trip. We will cruise out to Key West’s best reef location, where you are welcome to jump in and enjoy an evening snorkel. If you do not feel like getting in the water, no worries, the bar is open! ... More

Free Cancellation
Private Tour
Start From $69.95
 
Key West 2 Reef Snorkel Tour & Sunset Cruise with Beer & Wine Likely to Sell Out

Key West 2 Reef Snorkel Tour & Sunset Cruise with Beer & Wine

  • North America
  • Superb146 reviews4.7

Enjoy this 3 hour sunset combo trip. We will cruise out to Key West’s best reef location, where yo....

    Free Cancellation
    Private Tour
    Start From $69.95
 
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Booking.com
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