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Top 10 Best North America Sailing Trips

Found 727 Sailing Trips activities in North America. Sort by Popularity. - Page 4
 

Sunset Sailing on a Floating Tiki Bar Charming Hawaiian Catamaran

(4.7 of 83 reviews)

Experience the resilience and spirit of Maui aboard the Winona, a vessel that bravely survived the Lahaina harbor wildfires, moored outside of the harbor breakwall. Now operating from Ma'alaea Harbor, we invite you to join our cap... More

Free Cancellation
Start From $119.00
 
Sunset Sailing on a Floating Tiki Bar Charming Hawaiian Catamaran

Sunset Sailing on a Floating Tiki Bar Charming Hawaiian Catamaran

  • North America
  • Superb83 reviews4.7

Experience the resilience and spirit of Maui aboard the Winona, a vessel that bravely survived the L....

    Free Cancellation
    Start From $119.00
 
 

Sunset Sail Along the San Diego Skyline

(4.9 of 600 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
Start From $89.00
 
Sunset Sail Along the San Diego Skyline

Sunset Sail Along the San Diego Skyline

  • North America
  • Superb600 reviews4.9

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

    Free Cancellation
    Start From $89.00
 
 

Shell Island Snorkel and Dolphin Catamaran Cruise with Island Time

(4.9 of 4,361 reviews)

The 3-Hr Shell Island Snorkel & Dolphin Cruise aboard the Island Time Sailing Catamaran is a great way to have fun in the sun and enjoy the best of what Panama City Beach has to offer! Cruise over to Shell Island where you and the... More

Free Cancellation
Start From $57.59
 
Shell Island Snorkel and Dolphin Catamaran Cruise with Island Time Likely to Sell Out

Shell Island Snorkel and Dolphin Catamaran Cruise with Island Tim....

  • North America
  • Superb4,361 reviews4.9

The 3-Hr Shell Island Snorkel & Dolphin Cruise aboard the Island Time Sailing Catamaran is a great w....

    Free Cancellation
    Start From $57.59
 
 

Sail Biscayne Bay: An Intimate Eco-Adventure with Snorkeling

(4.9 of 438 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
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
  • Superb438 reviews4.9

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

    Free Cancellation
    Start From $129.00
 
 

2-Hour Sunset Sail on the San Francisco Bay

(4.7 of 391 reviews)

Whether you want to kick off a fabulous date night or wrap up an enjoyable afternoon, this two-hour sunset sail is just the ticket. Step aboard the gorgeous traditional vessel to take in the sights at the most bewitching time of d... More

Free Cancellation
Start From $129.00
 
2-Hour Sunset Sail on the San Francisco Bay Likely to Sell Out

2-Hour Sunset Sail on the San Francisco Bay

  • North America
  • Superb391 reviews4.7

Whether you want to kick off a fabulous date night or wrap up an enjoyable afternoon, this two-hour ....

    Free Cancellation
    Start From $129.00
 
 

Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbor

(4.5 of 620 reviews)

Meet us at Aquarium Wharf near Concord St. and Calhoun St. in Charleston SC as you experience historic Charleston Harbor aboard our classic 84-foot Tall Ship for a unique sailing experience. There is no better way to witness all o... More

Free Cancellation
Start From $45.00
 
Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbor Likely to Sell Out

Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbo....

  • North America
  • Exellent620 reviews4.5

Meet us at Aquarium Wharf near Concord St. and Calhoun St. in Charleston SC as you experience histor....

    Free Cancellation
    Start From $45.00
 
 

Mexico City: Xochimilco at sunrise + Breakfast and transportation

(5 of 97 reviews)

Discover a totally different face of Xochimilco, away from the tourist bustle and focused on natural beauty, the tranquility of the sunrise and respect for the environment. This is not the traditional Xochimilco of the trajineras;... More

Free Cancellation
Start From $168.69
 
Mexico City: Xochimilco at sunrise + Breakfast and transportation Likely to Sell Out

Mexico City: Xochimilco at sunrise + Breakfast and transportation

  • North America
  • Superb97 reviews5

Discover a totally different face of Xochimilco, away from the tourist bustle and focused on natural....

    Free Cancellation
    Start From $168.69
 
 

Sunset and Manta Ray Snorkel Adventure

(4.9 of 838 reviews)

Our most popular tour!  Watch a legendary Kona sunset from our spacious 50’ catamaran as you sail the Kona coast, followed by the adventure of a lifetime - snorkeling with the majestic manta rays!  Upon arriving, receive an in... More

Free Cancellation
Start From $154.51
 
Sunset and Manta Ray Snorkel Adventure Likely to Sell Out

Sunset and Manta Ray Snorkel Adventure

  • North America
  • Superb838 reviews4.9

Our most popular tour!  Watch a legendary Kona sunset from our spacious 50’ catamaran as you sail....

    Free Cancellation
    Start From $154.51
 
 

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

(4.9 of 1,478 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
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
  • Superb1,478 reviews4.9

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

    Free Cancellation
    Start From $35.00
 
 

Private Fishing Trip "All Inclusive" in Cabo San Lucas, Mexico

(4.7 of 397 reviews)

Embark on the most exciting fishing adventure in the crystal-clear waters of Cabo San Lucas. Our all-inclusive fishing tour offers you a unique opportunity to immerse yourself in an authentic, action-packed fishing experience, wit... More

Free Cancellation
Private Tour
Start From $625.00
 
Private Fishing Trip Likely to Sell Out

Private Fishing Trip "All Inclusive" in Cabo San Lucas, Mexico

  • North America
  • Superb397 reviews4.7

Embark on the most exciting fishing adventure in the crystal-clear waters of Cabo San Lucas. Our all....

    Free Cancellation
    Private Tour
    Start From $625.00
 
 

Sunset Sail in Miami: Complimentary Champagne Toast

(4.8 of 230 reviews)

Sunset Cruise, Cast away the day with the perfect way to end the day. This evening cruise calls for sun dresses, sandals and chilled wine. Take advantage of one of Florida's finest highlights upon our comfortable 80 ft catamaran a... More

Free Cancellation
Private Tour
Start From $99.00
 
Sunset Sail in Miami: Complimentary Champagne Toast Likely to Sell Out

Sunset Sail in Miami: Complimentary Champagne Toast

  • North America
  • Superb230 reviews4.8

Sunset Cruise, Cast away the day with the perfect way to end the day. This evening cruise calls for ....

    Free Cancellation
    Private Tour
    Start From $99.00
 
 

Waikiki small group turtle snorkeling & sailing

(5 of 86 reviews)

Witness the brilliant colors of a sunrise over Diamond Head crater. Ideal for early birds, couples or families who are up at the crack of dawn during their Hawaiian vacation due to time zone changes. As we start out our tour from ... More

Free Cancellation
Private Tour
Start From $99.00
 
Waikiki small group turtle snorkeling & sailing Likely to Sell Out

Waikiki small group turtle snorkeling & sailing

  • North America
  • Superb86 reviews5

Witness the brilliant colors of a sunrise over Diamond Head crater. Ideal for early birds, couples o....

    Free Cancellation
    Private Tour
    Start From $99.00
 
 

Cancun Adults Only Party Cruise to Isla Mujeres with Open Bar

(3.7 of 205 reviews)

Take a Party Cruise Adult Only from Cancun to Isla Mujeres. Make a stop to snorkel at one of the best reefs and see beautiful tropical fish. Enjoy a delicious buffet lunch on our private beach club, and then tour Isla Mujeres to s... More

Free Cancellation
Private Tour
Start From $69.99
 
Cancun Adults Only Party Cruise to Isla Mujeres with Open Bar Likely to Sell Out

Cancun Adults Only Party Cruise to Isla Mujeres with Open Bar

  • North America
  • Very Good205 reviews3.7

Take a Party Cruise Adult Only from Cancun to Isla Mujeres. Make a stop to snorkel at one of the bes....

    Free Cancellation
    Private Tour
    Start From $69.99
 
 

Classic Key West Schooner Sunset Sail with Full Open Bar

(4.9 of 207 reviews)

There's no better way to savor the magic of a Key West sunset than aboard a majestic schooner, complete with a full open bar. This enchanting journey blends the timeless elegance of traditional sailing with the lively spirit of Ke... More

Free Cancellation
Private Tour
Start From $109.00
 
Classic Key West Schooner Sunset Sail with Full Open Bar Likely to Sell Out

Classic Key West Schooner Sunset Sail with Full Open Bar

  • North America
  • Superb207 reviews4.9

There's no better way to savor the magic of a Key West sunset than aboard a majestic schooner, compl....

    Free Cancellation
    Private Tour
    Start From $109.00
 
 

Panama City Beach Sunset Catamaran Sail on The Privateer

(4.8 of 709 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
Private Tour
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
  • Superb709 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 $45.00
 
 

Private 40' Bali Catamaran – Drinks & Food Included

(5 of 348 reviews)

It is an incredible and unique experiences because for 4 hours you will be the owner of this incredible sailing catamaran, with a host and a chef at your disposal, the captain will take you to sail in the most beautiful waters of ... More

Free Cancellation
Private Tour
Start From $2,100.00
 
Private 40' Bali Catamaran – Drinks & Food Included Likely to Sell Out

Private 40' Bali Catamaran – Drinks & Food Included

  • North America
  • Superb348 reviews5

It is an incredible and unique experiences because for 4 hours you will be the owner of this incredi....

    Free Cancellation
    Private Tour
    Start From $2,100.00
 
 

Golden Hour Whale Watch from Lahaina

(5 of 9 reviews)

Set sail aboard ‘Alihilani, our 64-foot Gold Coast sailing catamaran, for a stunning Late Afternoon Whale Watch from 3:30 to 5:30 PM, departing daily from Lahaina Harbor. Enjoy Maui’s golden light as humpback whales breach, gl... More

Free Cancellation
Private Tour
Start From $100.22
 
Golden Hour Whale Watch from Lahaina Likely to Sell Out

Golden Hour Whale Watch from Lahaina

  • North America
  • Superb9 reviews5

Set sail aboard ‘Alihilani, our 64-foot Gold Coast sailing catamaran, for a stunning Late Afternoo....

    Free Cancellation
    Private Tour
    Start From $100.22
 
 

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

(5 of 97 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
  • Superb97 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
 
 

Sunset Catamaran Cruise in Ft. Lauderdale

(4.8 of 692 reviews)

A perfect way to end the day, with a relaxing sail upon the Atlantic Ocean. Imagine taking in the breathtaking views of FT. Lauderdale beach as the sun slips slowly behind the lights of the city. This evening cruise calls for sun ... More

Free Cancellation
Private Tour
Start From $99.00
 
Sunset Catamaran Cruise in Ft. Lauderdale Likely to Sell Out

Sunset Catamaran Cruise in Ft. Lauderdale

  • North America
  • Superb692 reviews4.8

A perfect way to end the day, with a relaxing sail upon the Atlantic Ocean. Imagine taking in the br....

    Free Cancellation
    Private Tour
    Start From $99.00
 
 

Ft Myers Beach 2 Hour Tiki Pub Fun in the Sun Dolphin Cruise

(4.9 of 79 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 $59.95
 
Ft Myers Beach 2 Hour Tiki Pub Fun in the Sun Dolphin Cruise Likely to Sell Out

Ft Myers Beach 2 Hour Tiki Pub Fun in the Sun Dolphin Cruise

  • North America
  • Superb79 reviews4.9

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 $59.95
 
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