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Top 10 Best North America Sailing Trips

Found 734 Sailing Trips activities in North America. Sort by Popularity. - Page 18
 

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

(4.8 of 12 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
Start From $30.00
 
Tour to The Arch and Lover's Beach (optional) from Cabo

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

  • North America
  • Superb12 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
    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
Start From $156.79
 
Hilton Hawaiian Village Turtle Snorkel with Optional Lunch

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
    Start From $156.79
 
 

Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon

(4.8 of 300 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

Free Cancellation
Start From $99.00
 
Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon

Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon

  • North America
  • Superb300 reviews4.8

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

    Free Cancellation
    Start From $99.00
 
 

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

(4.6 of 10 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
Start From $203.16
 
Maui: Kaanapali Beach 5-hour Snorkel w/ BBQ Lunch & Open Bar

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

  • North America
  • Superb10 reviews4.6

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

    Free Cancellation
    Start From $203.16
 
 

Key West Historic Schooner When And If Sunset Cruise

(4.9 of 123 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
Start From $109.00
 
Key West Historic Schooner When And If Sunset Cruise

Key West Historic Schooner When And If Sunset Cruise

  • North America
  • Superb123 reviews4.9

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

    Free Cancellation
    Start From $109.00
 
 

Isla Contoy Experience incl. Breakfast and Lunch

(2 of 1 review)

Your adventure kicks off at Marina Punta Norte, from where you'll sail towards Isla Mujeres while enjoying breakfast on board. You'll have an hour or so to explore the island or lounge on one of its powdery beaches. Hop back on th... More

Free Cancellation
Start From $142.00
 
Isla Contoy Experience incl. Breakfast and Lunch Likely to Sell Out

Isla Contoy Experience incl. Breakfast and Lunch

  • North America

Your adventure kicks off at Marina Punta Norte, from where you'll sail towards Isla Mujeres while en....

    Free Cancellation
    Start From $142.00
 
 

kayaking in Huatulco

(5 of 2 reviews)

The geographical position favors us to observe whales, dolphins, turtles and much more while sailing in the kayak in calm waters, we have contact with the most 95% of the time on the tour, so it is highly recommended for biologist... More

Free Cancellation
Private Tour
Start From $75.59
 
kayaking in Huatulco Likely to Sell Out

kayaking in Huatulco

  • North America
  • Superb2 reviews5

The geographical position favors us to observe whales, dolphins, turtles and much more while sailing....

    Free Cancellation
    Private Tour
    Start From $75.59
 
 

2.5-Hour Small-Group Catamaran Sailing Adventure with Drinks

(5 of 89 reviews)

With over 38 years of experience sharing our love of sailing with San Diego visitors, we are prepared to offer you a memorable day on the sea. 2.5 hour tour length is perfect for seeing all the beautiful sights. Catamarans reall... More

Free Cancellation
Private Tour
Start From $119.00
 
2.5-Hour Small-Group Catamaran Sailing Adventure with Drinks Likely to Sell Out

2.5-Hour Small-Group Catamaran Sailing Adventure with Drinks

  • North America
  • Superb89 reviews5

With over 38 years of experience sharing our love of sailing with San Diego visitors, we are prepare....

    Free Cancellation
    Private Tour
    Start From $119.00
 
 

Afternoon Sail & Snorkel to the Captain Cook Monument

(4.9 of 724 reviews)

A three hour tour you won't want to miss! 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 a... More

Free Cancellation
Private Tour
Start From $136.19
 
Afternoon Sail & Snorkel to the Captain Cook Monument Likely to Sell Out

Afternoon Sail & Snorkel to the Captain Cook Monument

  • North America
  • Superb724 reviews4.9

A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathta....

    Free Cancellation
    Private Tour
    Start From $136.19
 
 

Afternoon Sail & Snorkel to the Captain Cook Monument

(4.9 of 246 reviews)

A three hour tour you won't want to miss! 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 adve... More

Free Cancellation
Private Tour
Start From $136.19
 
Afternoon Sail & Snorkel to the Captain Cook Monument Likely to Sell Out

Afternoon Sail & Snorkel to the Captain Cook Monument

  • North America
  • Superb246 reviews4.9

A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathtakin....

    Free Cancellation
    Private Tour
    Start From $136.19
 
 

Visit Private Beaches around Puerto Vallarta in a Private Yacht

(5 of 126 reviews)

Enjoy the most exclusive beaches just accessible by sea and reach places that other regular tours don’t go. Also enjoy the explanation from our captain on the art of sailing. This is not a boat trip, this is an experience to enj... More

Free Cancellation
Private Tour
Start From $1,500.00
 
Visit Private Beaches around Puerto Vallarta in a Private Yacht Likely to Sell Out

Visit Private Beaches around Puerto Vallarta in a Private Yacht

  • North America
  • Superb126 reviews5

Enjoy the most exclusive beaches just accessible by sea and reach places that other regular tours do....

    Free Cancellation
    Private Tour
    Start From $1,500.00
 
 

Serene Private Sunset Sail on Lake Michigan - Navy Pier, Chicago

(5 of 27 reviews)

Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront. Kick back, relax, and let the US Coast Guard licensed captain treat you to stunning views of Chicago’s spectacular skyline. ... More

Free Cancellation
Private Tour
Start From $507.96
 
Serene Private Sunset Sail on Lake Michigan - Navy Pier, Chicago Likely to Sell Out

Serene Private Sunset Sail on Lake Michigan - Navy Pier, Chicago

  • North America
  • Superb27 reviews5

Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefro....

    Free Cancellation
    Private Tour
    Start From $507.96
 
 

Private Family Catamaran From Isla Mujeres

(5 of 1 review)

Enjoy our “Lite Sailing Charters” Sail through the wonderful Bay of Isla Mujeres! Why invest all day when you can do it in less time? Affordable Private Catamaran, avoid crowded vessels Half-day fun catamaran, with a guided sn... More

Free Cancellation
Private Tour
Start From $950.00
 
Private Family Catamaran From Isla Mujeres Likely to Sell Out

Private Family Catamaran From Isla Mujeres

  • North America
  • Superb1 review5

Enjoy our “Lite Sailing Charters” Sail through the wonderful Bay of Isla Mujeres! Why invest all....

    Free Cancellation
    Private Tour
    Start From $950.00
 
 

Diamond Head Sunset Sail

(4.7 of 15 reviews)

Hawaii’s Best Sunset Cruise is the experience you don’t want to miss. Our Diamond Head Sunset Sail features a two hour cruise aboard a private luxury yacht. Immerse yourself in a gorgeous Hawaiian sunset the only way, from the... More

Free Cancellation
Private Tour
Start From $695.00
 
Diamond Head Sunset Sail Likely to Sell Out

Diamond Head Sunset Sail

  • North America
  • Superb15 reviews4.7

Hawaii’s Best Sunset Cruise is the experience you don’t want to miss. Our Diamond Head Sunset Sa....

    Free Cancellation
    Private Tour
    Start From $695.00
 
 

Catamaran Adventure: Sailing and Swimming in the Bacalar Lagoon

(4.9 of 96 reviews)

Bacalar is the perfect place to live this experience. This wonderful region has the calmest waters in the Caribbean and has the most fascinating tropical landscapes. You will visit the most beautiful places in the lagoon where yo... More

Free Cancellation
Private Tour
Start From $55.00
 
Catamaran Adventure: Sailing and Swimming in the Bacalar Lagoon Likely to Sell Out

Catamaran Adventure: Sailing and Swimming in the Bacalar Lagoon

  • North America
  • Superb96 reviews4.9

Bacalar is the perfect place to live this experience. This wonderful region has the calmest waters i....

    Free Cancellation
    Private Tour
    Start From $55.00
 
 

Party On Sailing Cruise to Isla Mujeres from Cancun

(3.9 of 19 reviews)

Come join the party in our adults-only catamaran from Cancun to Isla Mujeres. Start the day with our national drinks onboard the catamaran. You will snorkel at one of the best reefs and see beautiful tropical fish, then eat lunch ... More

Free Cancellation
Private Tour
Start From $59.99
 
Party On Sailing Cruise to Isla Mujeres from Cancun Likely to Sell Out

Party On Sailing Cruise to Isla Mujeres from Cancun

  • North America
  • Very Good19 reviews3.9

Come join the party in our adults-only catamaran from Cancun to Isla Mujeres. Start the day with our....

    Free Cancellation
    Private Tour
    Start From $59.99
 
 

Squamish Afternoon Sailing Experience

(3.9 of 19 reviews)

Set sail for a tranquil evening on Howe Sound with our enchanting afternoon sailing experience! Our certified instructors are dedicated to providing a safe, comfortable, and unforgettable outing. Guests are welcome to be as hands... More

Free Cancellation
Private Tour
Start From $112.22
 
Squamish Afternoon Sailing Experience Likely to Sell Out

Squamish Afternoon Sailing Experience

  • North America
  • Very Good19 reviews3.9

Set sail for a tranquil evening on Howe Sound with our enchanting afternoon sailing experience! Our....

    Free Cancellation
    Private Tour
    Start From $112.22
 
 

Sunset Sail Experience by Catamaran in Waikiki

(4.8 of 6 reviews)

Enjoy the end of your day on a relaxing 2-hour Waikiki Sunset Sail aboard a 38.6 foot twin-hulled catamaran. Take in the views of Honolulu skyline from offshore Waikiki and feel the warmth of the setting Hawaiian sun and tropical ... More

Free Cancellation
Private Tour
Start From $92.31
 
Sunset Sail Experience by Catamaran in Waikiki Likely to Sell Out

Sunset Sail Experience by Catamaran in Waikiki

  • North America
  • Superb6 reviews4.8

Enjoy the end of your day on a relaxing 2-hour Waikiki Sunset Sail aboard a 38.6 foot twin-hulled ca....

    Free Cancellation
    Private Tour
    Start From $92.31
 
 

Trimaran La Lupita,Sail Away to Isla Mujeres from Cancun

(4 of 54 reviews)

Sail away through Caribbean waters with the best crew in Cancun aboard "La Lupita.¨ Enjoy a spectacular day in the crystal-clear waters of the Mexican Caribbean, sailing from Cancun to Isla Mujeres on a boat full of fun, explorin... More

Free Cancellation
Private Tour
Start From $59.99
 
Trimaran La Lupita,Sail Away to Isla Mujeres from Cancun Likely to Sell Out

Trimaran La Lupita,Sail Away to Isla Mujeres from Cancun

  • North America
  • Very Good54 reviews4

Sail away through Caribbean waters with the best crew in Cancun aboard "La Lupita.¨ Enjoy a spectac....

    Free Cancellation
    Private Tour
    Start From $59.99
 
 

Private 5Hrs Island Tour with 2Hrs Sail and Snorkel with Turtles

(5 of 3 reviews)

This 8 hour private tour includes a 5 hour custom tour of the island, and a 2.5 hour sail on a sailboat including swimming or snorkeling with turtles. You can pick and choose the stops on the island tour and go at your own pace. ... More

Free Cancellation
Private Tour
Start From $1,100.00
 
Private 5Hrs Island Tour with 2Hrs Sail and Snorkel with Turtles Likely to Sell Out

Private 5Hrs Island Tour with 2Hrs Sail and Snorkel with Turtles

  • North America
  • Superb3 reviews5

This 8 hour private tour includes a 5 hour custom tour of the island, and a 2.5 hour sail on a sailb....

    Free Cancellation
    Private Tour
    Start From $1,100.00
 
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