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Top 10 Best North America Sailing Trips

Found 712 Sailing Trips activities in North America. Sort by Popularity. - Page 4
 

Amazing Romantic Dinner on a Spanish Galeon with Saxophone Music

(4.6 of 98 reviews)

Have you run out of ideas to celebrate love with your partner? Imagine reconquering your true love. In Cancun, you have an incredible opportunity to fall in love again at the rhythm of the live sax with a sunset as enchanting as t... More

Free Cancellation
Start From $95.00
 
Amazing Romantic Dinner on a Spanish Galeon with Saxophone Music Likely to Sell Out

Amazing Romantic Dinner on a Spanish Galeon with Saxophone Music

  • North America
  • Superb98 reviews4.6

Have you run out of ideas to celebrate love with your partner? Imagine reconquering your true love. ....

    Free Cancellation
    Start From $95.00
 
 

Panama City Beach Sunset Catamaran Sail on The Privateer

(4.8 of 707 reviews)

If you are looking to unwind before dinner or a night out on the town, come take a romantic Sunset Sail on the SV Privateer, our 78-passenger catamaran, with Paradise Adventures! This breathtaking sunset sail along the Gulf of Mex... More

Free Cancellation
Start From $45.00
 
Panama City Beach Sunset Catamaran Sail on The Privateer Likely to Sell Out

Panama City Beach Sunset Catamaran Sail on The Privateer

  • North America
  • Superb707 reviews4.8

If you are looking to unwind before dinner or a night out on the town, come take a romantic Sunset S....

    Free Cancellation
    Start From $45.00
 
 

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

(4.4 of 365 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
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
  • Exellent365 reviews4.4

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

    Free Cancellation
    Start From $59.95
 
 

Key West Sunset Sail: Dolphin Watching, Wine, and Tapas

(4.6 of 676 reviews)

Our Captain’s Choice Dolphin Watch Sunset Sail is the ultimate VIP sailing experience! Limited to an intimate number of passengers, this 2.5 hour sail is more like a private cruise than a group tour and is one of the top things ... More

Free Cancellation
Start From $89.00
 
Key West Sunset Sail: Dolphin Watching, Wine, and Tapas Likely to Sell Out

Key West Sunset Sail: Dolphin Watching, Wine, and Tapas

  • North America
  • Superb676 reviews4.6

Our Captain’s Choice Dolphin Watch Sunset Sail is the ultimate VIP sailing experience! Limited to ....

    Free Cancellation
    Start From $89.00
 
 

4-Hour Fort Lauderdale Sailing Charter

(4.9 of 307 reviews)

Enjoy some time on the water with this 4-Hour Half Day Sailing Charter located in Fort Lauderdale. Your sail is entirely customizable, and travelers have the option(PRIVATE CRUISES) to use their time docked or sailing out to sea. ... More

Free Cancellation
Start From $148.00
 
4-Hour Fort Lauderdale Sailing Charter Likely to Sell Out

4-Hour Fort Lauderdale Sailing Charter

  • North America
  • Superb307 reviews4.9

Enjoy some time on the water with this 4-Hour Half Day Sailing Charter located in Fort Lauderdale. Y....

    Free Cancellation
    Start From $148.00
 
 

2-Hour Oahu Sunset Catamaran Sail

(4.9 of 117 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
Start From $125.00
 
2-Hour Oahu Sunset Catamaran Sail Likely to Sell Out

2-Hour Oahu Sunset Catamaran Sail

  • North America
  • Superb117 reviews4.9

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

    Free Cancellation
    Start From $125.00
 
 

Private Catamaran Escape for 2–6 Guests – Celebrate Your Way”

(4.9 of 316 reviews)

Set sail on a one-of-a-kind ocean escape designed for small, meaningful moments. Whether you’re celebrating a bachelorette, a birthday, or simply enjoying time with your favorite people, this catamaran getaway for up to six gues... More

Free Cancellation
Private Tour
Start From $595.00
 
Private Catamaran Escape for 2–6 Guests – Celebrate Your Way” Likely to Sell Out

Private Catamaran Escape for 2–6 Guests – Celebrate Your Way....

  • North America
  • Superb316 reviews4.9

Set sail on a one-of-a-kind ocean escape designed for small, meaningful moments. Whether you’re ce....

    Free Cancellation
    Private Tour
    Start From $595.00
 
 

Sunset Catamaran Sail in Cocoa Beach

(4.9 of 171 reviews)

Experience a Magical Sunset in Cocoa Beach! 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 beauty of Florida... More

Free Cancellation
Private Tour
Start From $56.49
 
Sunset Catamaran Sail in Cocoa Beach Likely to Sell Out

Sunset Catamaran Sail in Cocoa Beach

  • North America
  • Superb171 reviews4.9

Experience a Magical Sunset in Cocoa Beach! Set sail into the golden hour and enjoy a stunning eveni....

    Free Cancellation
    Private Tour
    Start From $56.49
 
 

Half-Day Luxury Sailing in Puerto Morelos with Open Bar

(4.9 of 171 reviews)

Set sail on the tranquil turquoise waters of Puerto Morelos aboard a luxury catamaran for an unforgettable half-day adventure. This experience offers a guided snorkeling session at a vibrant reef in the Mesoamerican Barrier Reef, ... More

Free Cancellation
Private Tour
Start From $139.00
 
Half-Day Luxury Sailing in Puerto Morelos with Open Bar Likely to Sell Out

Half-Day Luxury Sailing in Puerto Morelos with Open Bar

  • North America
  • Superb171 reviews4.9

Set sail on the tranquil turquoise waters of Puerto Morelos aboard a luxury catamaran for an unforge....

    Free Cancellation
    Private Tour
    Start From $139.00
 
 

Key West Afternoon Reef Snorkeling with Open Bar

(4.5 of 399 reviews)

Dip and Sip Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip will start a sail to the Key West living reef where you will see coral and tropical fish. All snorkeling equipment is provided an... More

Free Cancellation
Private Tour
Start From $59.95
 
Key West Afternoon Reef Snorkeling with Open Bar Likely to Sell Out

Key West Afternoon Reef Snorkeling with Open Bar

  • North America
  • Exellent399 reviews4.5

Dip and Sip Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip w....

    Free Cancellation
    Private Tour
    Start From $59.95
 
 

Sunset & Dolphin Catamaran Cruise with Island Time

(4.9 of 1,868 reviews)

The Dolphin Watching & Sunset Sail is a 2 hour cruise aboard the Island Time Sailing Catamaran which departs from the Lagoon Pontoons Marina in Panama City Beach, FL. Enjoy a rum punch while cruising along the beautiful Gulf Coa... More

Free Cancellation
Private Tour
Start From $57.59
 
Sunset & Dolphin Catamaran Cruise with Island Time Likely to Sell Out

Sunset & Dolphin Catamaran Cruise with Island Time

  • North America
  • Superb1,868 reviews4.9

The Dolphin Watching & Sunset Sail is a 2 hour cruise aboard the Island Time Sailing Catamaran which....

    Free Cancellation
    Private Tour
    Start From $57.59
 
 

Sunset Sail Along the San Diego Skyline

(4.9 of 592 reviews)

Enjoy an evening sailing under the sunset on a relaxing sailing cruise with a unique perspective on San Diego that you can only get from the water.  Our San Diego Bay Sunset Sailing Cruises provide an up-close and personal view o... More

Free Cancellation
Private Tour
Start From $89.00
 
Sunset Sail Along the San Diego Skyline Likely to Sell Out

Sunset Sail Along the San Diego Skyline

  • North America
  • Superb592 reviews4.9

Enjoy an evening sailing under the sunset on a relaxing sailing cruise with a unique perspective on ....

    Free Cancellation
    Private Tour
    Start From $89.00
 
 

2 hour Tiki Pub Sensational Dolphin Sunset Cruise (Adults only)

(5 of 93 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
Private Tour
Start From $69.00
 
2 hour Tiki Pub Sensational Dolphin Sunset Cruise (Adults only) Likely to Sell Out

2 hour Tiki Pub Sensational Dolphin Sunset Cruise (Adults only)

  • North America
  • Superb93 reviews5

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

    Free Cancellation
    Private Tour
    Start From $69.00
 
 

Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure

(4.7 of 930 reviews)

Snorkel Turtle Canyon on the Largest Luxury Catamaran! Top Quality Gear, Certified Crew & Premium On Board Bar. When you trust Moana Sailing Co. for your snorkel adventure, you’re choosing the tour with the most professionalis... More

Special Offer
Free Cancellation
Private Tour
Start From $84.49
(Saving 6% ) $89.99
 
-6% Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure Likely to Sell Out

Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventu....

  • North America
  • Superb930 reviews4.7

Snorkel Turtle Canyon on the Largest Luxury Catamaran! Top Quality Gear, Certified Crew & Premium On....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $84.49
    (Saving 6% ) $89.99
 
 

1-Hour Interactive Pirate Cruise (arrive 30 minutes early)

(4.9 of 1,469 reviews)

Prepare for high seas adventure on this fully interactive, family-friendly, 1-Hour Pirate Adventure Cruise (check in is a half hour before the sail time) along Florida’s Intracoastal Waterway that’s fun for the whole family! T... More

Free Cancellation
Private Tour
Start From $35.00
 
1-Hour Interactive Pirate Cruise (arrive 30 minutes early) Likely to Sell Out

1-Hour Interactive Pirate Cruise (arrive 30 minutes early)

  • North America
  • Superb1,469 reviews4.9

Prepare for high seas adventure on this fully interactive, family-friendly, 1-Hour Pirate Adventure ....

    Free Cancellation
    Private Tour
    Start From $35.00
 
 

Deluxe Sail & Snorkel to the Captain Cook Monument

(4.9 of 467 reviews)

Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient lava flows. As you arrive at the "World Famous Captain Cook Monument" your snorkeling adventure will begin in the turquoise waters... More

Free Cancellation
Private Tour
Start From $179.27
 
Deluxe Sail & Snorkel to the Captain Cook Monument Likely to Sell Out

Deluxe Sail & Snorkel to the Captain Cook Monument

  • North America
  • Superb467 reviews4.9

Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient ....

    Free Cancellation
    Private Tour
    Start From $179.27
 
 

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

(3.5 of 2 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
  • Good2 reviews3.5

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
 
 

Sail Biscayne Bay: An Intimate Eco-Adventure with Snorkeling

(4.9 of 437 reviews)

This tour is an intimate experience, our groups are 3-5 people per boat maximum. We have two boats. We have been sailing the Biscayne Bay for over 15 years, just for the fun of it. We started this eco-tour in 2018 to share the ama... More

Free Cancellation
Private Tour
Start From $129.00
 
Sail Biscayne Bay: An Intimate Eco-Adventure with Snorkeling Likely to Sell Out

Sail Biscayne Bay: An Intimate Eco-Adventure with Snorkeling

  • North America
  • Superb437 reviews4.9

This tour is an intimate experience, our groups are 3-5 people per boat maximum. We have two boats. ....

    Free Cancellation
    Private Tour
    Start From $129.00
 
 

Panama City Beach Sunset Sail on The Footloose Catamaran

(4.8 of 438 reviews)

If you are looking to unwind before dinner or a night out on the town, come take a romantic Sunset Sail on SV Footloose, our 38 passenger catamaran, with Paradise Adventures! This breathtaking sunset sail along the Gulf of Mexico ... More

Free Cancellation
Private Tour
Start From $40.00
 
Panama City Beach Sunset Sail on The Footloose Catamaran Likely to Sell Out

Panama City Beach Sunset Sail on The Footloose Catamaran

  • North America
  • Superb438 reviews4.8

If you are looking to unwind before dinner or a night out on the town, come take a romantic Sunset S....

    Free Cancellation
    Private Tour
    Start From $40.00
 
 

San Francisco Bay Sailing Cruise

(4.9 of 629 reviews)

Experience the beauty of San Francisco during a 1.5-hour catamaran cruise over San Francisco Bay. Sail away from bustling city and enjoy photo ops from the vantage point of the water. You’ll coast past the city skyline, the Gold... More

Free Cancellation
Private Tour
Start From $72.00
 
San Francisco Bay Sailing Cruise Likely to Sell Out

San Francisco Bay Sailing Cruise

  • North America
  • Superb629 reviews4.9

Experience the beauty of San Francisco during a 1.5-hour catamaran cruise over San Francisco Bay. Sa....

    Free Cancellation
    Private Tour
    Start From $72.00
 
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