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Top 10 Best North America Sailing Trips

Found 692 Sailing Trips activities in North America. Sort by Popularity. - Page 16
 

Tulum: Snorkeling and Private Sailing Tour

(4.9 of 153 reviews)

We will enjoy a wonderful catamaran tour, powered only by the wind, we will be able to enjoy a spectacular view of the Tulum ruins from the sea... More

Free Cancellation
Private Tour
Start From $59.45
 
Tulum: Snorkeling and Private Sailing Tour

Tulum: Snorkeling and Private Sailing Tour

  • North America
  • Superb153 reviews4.9

We will enjoy a wonderful catamaran tour, powered only by the wind, we will be able to enjoy a spect....

    Free Cancellation
    Private Tour
    Start From $59.45
 
 

Honolulu BYOB Fireworks Boat Cruise

(4.5 of 26 reviews)

Experience authentic aloha vibes with us. Our knowledgeable guides and crew are ready to share insights on local culture, marine life, and island tips. Bring your favorite beverages and join us for Waikiki's weekly fireworks displ... More

Free Cancellation
Private Tour
Start From $75.00
 
Honolulu BYOB Fireworks Boat Cruise

Honolulu BYOB Fireworks Boat Cruise

  • North America
  • Exellent26 reviews4.5

Experience authentic aloha vibes with us. Our knowledgeable guides and crew are ready to share insig....

    Free Cancellation
    Private Tour
    Start From $75.00
 
 

2-Hour Oahu Sunset Catamaran Sail

(4.9 of 104 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 $125.00
 
2-Hour Oahu Sunset Catamaran Sail Likely to Sell Out

2-Hour Oahu Sunset Catamaran Sail

  • North America
  • Superb104 reviews4.9

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 $125.00
 
 

Luxury Sailboat Tour at Sunset in Los Cabos + Snacks + Premium Drinks

(5 of 12 reviews)

Sail along the coast, enjoying the refreshing breeze in this exclusive sailing experience. Marvel at the beauty that makes Los Cabos a unique destination and enjoy this adventure aboard our luxurious French-made sailboats and cat... More

Free Cancellation
Private Tour
Start From $180.00
 
Luxury Sailboat Tour at Sunset in Los Cabos + Snacks + Premium Drinks Likely to Sell Out

Luxury Sailboat Tour at Sunset in Los Cabos + Snacks + Premium Dr....

  • North America
  • Superb12 reviews5

Sail along the coast, enjoying the refreshing breeze in this exclusive sailing experience. Marvel a....

    Free Cancellation
    Private Tour
    Start From $180.00
 
 

Sailing Charter

(5 of 2 reviews)

Experiencing the Olympic Peninsula wouldn’t be complete without a little time on the water. Make an adventure out of it, and sail a living legend out of scenic Sequim Bay! Ingrid Princess is an ocean going, full keel ketch avail... More

Free Cancellation
Private Tour
Start From $195.00
 
Sailing Charter Likely to Sell Out

Sailing Charter

  • North America
  • Superb2 reviews5

Experiencing the Olympic Peninsula wouldn’t be complete without a little time on the water. Make a....

    Free Cancellation
    Private Tour
    Start From $195.00
 
 

BYOB Friday Night Fireworks Cruise

(4.2 of 5 reviews)

BYOB Fireworks Cruise! Relax and enjoy the views as you cruise along the beautiful coast of Waikiki. You'll enjoy the view of the city lights and be in awe with this unobstructed view of fireworks from the water! With plenty of... More

Free Cancellation
Private Tour
Start From $138.95
 
BYOB Friday Night Fireworks Cruise Likely to Sell Out

BYOB Friday Night Fireworks Cruise

  • North America
  • Exellent5 reviews4.2

BYOB Fireworks Cruise! Relax and enjoy the views as you cruise along the beautiful coast of Waikiki....

    Free Cancellation
    Private Tour
    Start From $138.95
 
 

Nights of Lights Viewing with Drinks and Live Music Sunset Sail

(4.5 of 45 reviews)

Come celebrate the magic of the Nights of Lights celebration with us from the water! You will see Historic St. Augustine from a whole new vantage point. It is a sight you won't soon forget. After enjoying a breathtaking sunset you... More

Free Cancellation
Private Tour
Start From $74.50
 
Nights of Lights Viewing with Drinks and Live Music Sunset Sail Likely to Sell Out

Nights of Lights Viewing with Drinks and Live Music Sunset Sail

  • North America
  • Exellent45 reviews4.5

Come celebrate the magic of the Nights of Lights celebration with us from the water! You will see Hi....

    Free Cancellation
    Private Tour
    Start From $74.50
 
 

Snorkeling Adventure in Puerto Morelos Includes snack, Water and Round Trip.

(4 of 90 reviews)

You must live this experience once in your life, This activity is only for travelers that love to be in a unique place in the world. You will discover the 2nd biggest reef wall in the world, you will see a huge variety of fish of... More

Free Cancellation
Private Tour
Start From $45.00
 
Snorkeling Adventure in Puerto Morelos Includes snack, Water and Round Trip. Likely to Sell Out

Snorkeling Adventure in Puerto Morelos Includes snack, Water and ....

  • North America
  • Very Good90 reviews4

You must live this experience once in your life, This activity is only for travelers that love to be....

    Free Cancellation
    Private Tour
    Start From $45.00
 
 

New York Harbor Wine and Jazz Sail aboard Clipper City

(4.4 of 21 reviews)

Step aboard a historic sailing ship and cruise around New York Harbor, taking in magnificent views of New York City on this entertaining evening jazz sail. From the decks of the boat, you will enjoy breathtaking views of the Manha... More

Free Cancellation
Private Tour
Start From $140.08
 
New York Harbor Wine and Jazz Sail aboard Clipper City Likely to Sell Out

New York Harbor Wine and Jazz Sail aboard Clipper City

  • North America
  • Exellent21 reviews4.4

Step aboard a historic sailing ship and cruise around New York Harbor, taking in magnificent views o....

    Free Cancellation
    Private Tour
    Start From $140.08
 
 

Sunset Sail Tour

(4.9 of 84 reviews)

Take a 2.0 hour sailing cruise on a Sparkman and Stephens Sailing Yacht. With your small-group, engage on this classic 42 ft yacht, that accommodates a 6 passenger maximum for an intimate cruise through the waters of Wrightsvill... More

Free Cancellation
Private Tour
Start From $125.00
 
Sunset Sail Tour Likely to Sell Out

Sunset Sail Tour

  • North America
  • Superb84 reviews4.9

Take a 2.0 hour sailing cruise on a Sparkman and Stephens Sailing Yacht. With your small-group, enga....

    Free Cancellation
    Private Tour
    Start From $125.00
 
 

Schooner Eastwind 2 Hour Day Sail in Boothbay Harbor

(4.6 of 74 reviews)

Sail away from it all on your two-hour voyage aboard Boothbay Harbor's schooner to relax and see the Maine coastline. Lighthouses, fishing lobstermen, wildlife, and remote islands accessible only by boat dot the seascape. Our goa... More

Free Cancellation
Private Tour
Start From $54.95
 
Schooner Eastwind 2 Hour Day Sail in Boothbay Harbor Likely to Sell Out

Schooner Eastwind 2 Hour Day Sail in Boothbay Harbor

  • North America
  • Superb74 reviews4.6

Sail away from it all on your two-hour voyage aboard Boothbay Harbor's schooner to relax and see the....

    Free Cancellation
    Private Tour
    Start From $54.95
 
 

Afternoon Catamaran Sail with Local Culture, Cocktails and Snacks

(4.6 of 74 reviews)

As you step aboard the spacious catamaran, you're immediately greeted by the friendly crew, who are eager to guide you on an unforgettable journey. The vessel is equipped with all the amenities you need for a comfortable and enjoy... More

Free Cancellation
Private Tour
Start From $169.00
 
Afternoon Catamaran Sail with Local Culture, Cocktails and Snacks Likely to Sell Out

Afternoon Catamaran Sail with Local Culture, Cocktails and Snacks

  • North America
  • Superb74 reviews4.6

As you step aboard the spacious catamaran, you're immediately greeted by the friendly crew, who are ....

    Free Cancellation
    Private Tour
    Start From $169.00
 
 

Hilton Hawaiian Village Turtle Snorkel with Optional Lunch

(4.6 of 12 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
Private Tour
Start From $156.79
 
Hilton Hawaiian Village Turtle Snorkel with Optional Lunch Likely to Sell Out

Hilton Hawaiian Village Turtle Snorkel with Optional Lunch

  • North America
  • Superb12 reviews4.6

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

    Free Cancellation
    Private Tour
    Start From $156.79
 
 

Private Therapy Sailing Adventure

(4.8 of 34 reviews)

WHO WE ARE? Old Plank is a boutique luxury sailing charter & aquatic expedition company with gourmet 5 star cuisine. Founded by Captain Matthew Mancini, we live by the currents, plan by the tides, and follow the sun. WHAT DO WE D... More

Free Cancellation
Private Tour
Start From $400.00
 
Private Therapy Sailing Adventure Likely to Sell Out

Private Therapy Sailing Adventure

  • North America
  • Superb34 reviews4.8

WHO WE ARE? Old Plank is a boutique luxury sailing charter & aquatic expedition company with gourmet....

    Free Cancellation
    Private Tour
    Start From $400.00
 
 

Suncoast Sailing's Day Sailing Experience!

(4.9 of 103 reviews)

Join us aboard the iconic schooner, Suncoast Horizon and step aboard our 2 hour sailing excursion. Feel the wind as it glides us through the picturesque waters of Treasure Island and Gulf of Mexico. Come face to face with nature a... More

Free Cancellation
Private Tour
Start From $59.99
 
Suncoast Sailing's Day Sailing Experience! Likely to Sell Out

Suncoast Sailing's Day Sailing Experience!

  • North America
  • Superb103 reviews4.9

Join us aboard the iconic schooner, Suncoast Horizon and step aboard our 2 hour sailing excursion. F....

    Free Cancellation
    Private Tour
    Start From $59.99
 
 

1 Hour Private Charter in New York Harbor for up to 6 people

(4.9 of 49 reviews)

This is a private tour which means it is just you and your party on board. You will be sailing on our beautiful classic sailboat named Tara. Tara is a classic sailboat and one of a kind in NYC. You will sail past Elis Island and t... More

Free Cancellation
Private Tour
Start From $375.00
 
1 Hour Private Charter in New York Harbor for up to 6 people Likely to Sell Out

1 Hour Private Charter in New York Harbor for up to 6 people

  • North America
  • Superb49 reviews4.9

This is a private tour which means it is just you and your party on board. You will be sailing on ou....

    Free Cancellation
    Private Tour
    Start From $375.00
 
 

Laguna Grill - Private Boat with on-board BBQ and Drinks Included

(5 of 122 reviews)

One of a kind in Bacalar! Cruise, swim, eat and drink in Bacalars most complete activity. Enjoy nature away from crowds while enjoying an on board BBQ. ... More

Free Cancellation
Private Tour
Start From $180.00
 
Laguna Grill - Private Boat with on-board BBQ and Drinks Included Likely to Sell Out

Laguna Grill - Private Boat with on-board BBQ and Drinks Included

  • North America
  • Superb122 reviews5

One of a kind in Bacalar! Cruise, swim, eat and drink in Bacalars most complete activity. Enjoy natu....

    Free Cancellation
    Private Tour
    Start From $180.00
 
 

Catamaran Sail with Snorkeling and Beach Club of Isla Mujeres

(5 of 122 reviews)

A Caribbean Escape Like No Other! Experience the beauty of the Caribbean on this all-inclusive catamaran tour from Cancun to Isla Mujeres. The day begins with a leisurely sail across the turquoise waters, where you'll enjoy drinks... More

Free Cancellation
Private Tour
Start From $79.00
 
Catamaran Sail with Snorkeling and Beach Club of Isla Mujeres Likely to Sell Out

Catamaran Sail with Snorkeling and Beach Club of Isla Mujeres

  • North America
  • Superb122 reviews5

A Caribbean Escape Like No Other! Experience the beauty of the Caribbean on this all-inclusive catam....

    Free Cancellation
    Private Tour
    Start From $79.00
 
 

Key West Ultimate Beach Pass with Parasailing

(4.2 of 21 reviews)

Join Sunset Watersports, Key West's Original Watersports Company for a day at Smathers Beach. We are the only company offering the Key West Beach Pass. ... More

Free Cancellation
Private Tour
Start From $109.95
 
Key West Ultimate Beach Pass with Parasailing Likely to Sell Out

Key West Ultimate Beach Pass with Parasailing

  • North America
  • Exellent21 reviews4.2

Join Sunset Watersports, Key West's Original Watersports Company for a day at Smathers Beach. We are....

    Free Cancellation
    Private Tour
    Start From $109.95
 
 

Private 90-Minute Harbor Sailing Charter in Key West

(4.9 of 17 reviews)

Live the high life on this private chartered day sail in Key West. Set sail on your boat for a 90-minute adventure around the Florida Keys and view the city from the water in peace and tranquility. You may even get to see some fri... More

Free Cancellation
Private Tour
Start From $395.00
 
Private 90-Minute Harbor Sailing Charter in Key West Likely to Sell Out

Private 90-Minute Harbor Sailing Charter in Key West

  • North America
  • Superb17 reviews4.9

Live the high life on this private chartered day sail in Key West. Set sail on your boat for a 90-mi....

    Free Cancellation
    Private Tour
    Start From $395.00
 
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