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Top 10 Best North America Sailing Trips

Found 696 Sailing Trips activities in North America. Sort by Popularity. - Page 21
 

Nights of Lights Sailboat Tour at St Augustine Sailing

(5 of 9 reviews)

What sets St Augustine Sailing apart from other Nights of Lights boat tours is the elevated experience aboard a luxury sailing yacht. While many tours offer a simple ride, St Augustine Sailing provides an intimate, serene setting ... More

Free Cancellation
Start From $99.00
 
Nights of Lights Sailboat Tour at St Augustine Sailing

Nights of Lights Sailboat Tour at St Augustine Sailing

  • North America
  • Superb9 reviews5

What sets St Augustine Sailing apart from other Nights of Lights boat tours is the elevated experien....

    Free Cancellation
    Start From $99.00
 
 

Sailing Snorkel Adventure

(4.5 of 6 reviews)

Interactive Sailing Adventure, Snorkeling, Surf Up Paddle, Premium Bar and Incredible views. This Sailing Boat Adventure is unbeatable Value. ... More

Free Cancellation
Start From $145.00
 
Sailing Snorkel Adventure Likely to Sell Out

Sailing Snorkel Adventure

  • North America
  • Exellent6 reviews4.5

Interactive Sailing Adventure, Snorkeling, Surf Up Paddle, Premium Bar and Incredible views. This Sa....

    Free Cancellation
    Start From $145.00
 
 

Private Sunset Sail for Two

(5 of 6 reviews)

A Romantic Private Sail for Two on the San Diego Bay offers a Beautiful Sunset and Downtown City Skyline.... More

Free Cancellation
Start From $499.00
 
Private Sunset Sail for Two Likely to Sell Out

Private Sunset Sail for Two

  • North America
  • Superb6 reviews5

A Romantic Private Sail for Two on the San Diego Bay offers a Beautiful Sunset and Downtown City Sky....

    Free Cancellation
    Start From $499.00
 
 

Yo Ho Pirate Show at Sunset, Dinner and Legends on the High Seas

(5 of 1 review)

Go back in time, to the days when Cabo was home to pirates A fantastic sunset cruise with a show which is the joy of children and adults alike. Our pirates dance, sing, climb the ropes, while you enjoy the beautiful sunset and li... More

Free Cancellation
Start From $135.40
 
Yo Ho Pirate Show at Sunset, Dinner and Legends on the High Seas Likely to Sell Out

Yo Ho Pirate Show at Sunset, Dinner and Legends on the High Seas

  • North America
  • Superb1 review5

Go back in time, to the days when Cabo was home to pirates A fantastic sunset cruise with a show whi....

    Free Cancellation
    Start From $135.40
 
 

Romantic Dinner in the Spanish Galeon with Sax in Cancun. Lobster & Beef menu.

(4.4 of 7 reviews)

Don't wait any longer; this ultimate romance tour will enrich your life forever! Have you run out of ideas to celebrate love with your partner? Imagine to reconquer your true love. In Cancun you have an incredible opportunity to ... More

Free Cancellation
Start From $95.00
 
Romantic Dinner in the Spanish Galeon with Sax in Cancun. Lobster & Beef menu. Likely to Sell Out

Romantic Dinner in the Spanish Galeon with Sax in Cancun. Lobster....

  • North America
  • Exellent7 reviews4.4

Don't wait any longer; this ultimate romance tour will enrich your life forever! Have you run out o....

    Free Cancellation
    Start From $95.00
 
 

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
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
    Start From $195.00
 
 

2-Hour Private Hilton Head Afternoon Dolphin Watching Sail

(4.9 of 117 reviews)

This 2 hour Private Afternoon Sailing tour will take us to Port Royal Sound (generally the best wind for sailing on Hilton Head) on the North side of the island. During the day, this is generally filled with exciting winds for gre... More

Free Cancellation
Private Tour
Start From $475.00
 
2-Hour Private Hilton Head Afternoon Dolphin Watching Sail Likely to Sell Out

2-Hour Private Hilton Head Afternoon Dolphin Watching Sail

  • North America
  • Superb117 reviews4.9

This 2 hour Private Afternoon Sailing tour will take us to Port Royal Sound (generally the best wind....

    Free Cancellation
    Private Tour
    Start From $475.00
 
 

Rosé Brunch Under Sail

(4 of 1 review)

Wake up with our daily Brunch Under Sail aboard a luxury catamaran. Cruise through the calm morning waters of Hilton Head while enjoying complimentary mimosas and light brunch bites. This relaxing 2-hour sail is the perfect blend ... More

Free Cancellation
Private Tour
Start From $95.23
 
Rosé Brunch Under Sail Likely to Sell Out

Rosé Brunch Under Sail

  • North America
  • Very Good1 review4

Wake up with our daily Brunch Under Sail aboard a luxury catamaran. Cruise through the calm morning ....

    Free Cancellation
    Private Tour
    Start From $95.23
 
 

Whale Watching Amazing Adventure

(4 of 1 review)

Get ready for the adventure of a lifetime as we make our way out onto the waters surrounding Los Cabos in search of the Cabo’s Whales.” Enjoy listening to the beautiful song of the whales, with the help of our new hydrophones... More

Free Cancellation
Private Tour
Start From $97.00
 
Whale Watching Amazing Adventure Likely to Sell Out

Whale Watching Amazing Adventure

  • North America
  • Very Good1 review4

Get ready for the adventure of a lifetime as we make our way out onto the waters surrounding Los Cab....

    Free Cancellation
    Private Tour
    Start From $97.00
 
 

Sunset Sail on the Black Pearl

(4.3 of 6 reviews)

Come experience the tranquility of gliding through the water under sail on the Black Pearl while appreciating our beautiful Lake Erie sunsets. See Cedar Point Amusement Park from the water, sail past the Marblehead Lighthouse, and... More

Free Cancellation
Private Tour
Start From $595.00
 
Sunset Sail on the Black Pearl Likely to Sell Out

Sunset Sail on the Black Pearl

  • North America
  • Exellent6 reviews4.3

Come experience the tranquility of gliding through the water under sail on the Black Pearl while app....

    Free Cancellation
    Private Tour
    Start From $595.00
 
 

Private Sailboat + Captain for a Day Experience

(5 of 558 reviews)

RECENTLY AWARDED #7 WORLDWIDE AS BEST SAILING AND DAY CRUISES OPTIONS BY TRIPADVISOR TRAVELER'S CHOICE AWARDS 2022!!! Everyone´s favorite! Enjoy an easy ride around the most relevant landmarks in the lagoon on board of a beautif... More

Free Cancellation
Private Tour
Start From $222.44
 
Private Sailboat + Captain for a Day Experience Likely to Sell Out

Private Sailboat + Captain for a Day Experience

  • North America
  • Superb558 reviews5

RECENTLY AWARDED #7 WORLDWIDE AS BEST SAILING AND DAY CRUISES OPTIONS BY TRIPADVISOR TRAVELER'S CHOI....

    Free Cancellation
    Private Tour
    Start From $222.44
 
 

Private Luxury Sailing Cruise in Los Cabos with Lunch and Open Bar

(4.9 of 292 reviews)

Cruise aboard a private sailboat for just you and your group into the Sea of Cortes. Enjoy great photo opportunities as you pass by the famous Arch, Land's end, and Sea Lion Colony before you head out of the bay.  Visit a secl... More

Free Cancellation
Private Tour
Start From $2,299.00
 
Private Luxury Sailing Cruise in Los Cabos with Lunch and Open Bar Likely to Sell Out

Private Luxury Sailing Cruise in Los Cabos with Lunch and Open Ba....

  • North America
  • Superb292 reviews4.9

Cruise aboard a private sailboat for just you and your group into the Sea of Cortes. Enjoy great ph....

    Free Cancellation
    Private Tour
    Start From $2,299.00
 
 

San Diego Bay Sailing Tour

(5 of 16 reviews)

San Diego Bay is one of the most beautiful bodies of water on the West Coast of the United States. Why not enjoy this natural wonder aboard a beautiful sailing yacht with a knowledgeable and friendly Captain? This group sail is li... More

Free Cancellation
Private Tour
Start From $95.00
 
San Diego Bay Sailing Tour Likely to Sell Out

San Diego Bay Sailing Tour

  • North America
  • Superb16 reviews5

San Diego Bay is one of the most beautiful bodies of water on the West Coast of the United States. W....

    Free Cancellation
    Private Tour
    Start From $95.00
 
 

Sailing Adventures 3-Hour Activity in Destin

(5 of 4 reviews)

There’s nothing like seeing the clear emerald waters pass under the hull while sailing on the Stiletto Catamaran. Harnessing the power of the wind as we sail along these beautiful waters is magical. You might even get to experie... More

Free Cancellation
Private Tour
Start From $525.00
 
Sailing Adventures 3-Hour Activity in Destin Likely to Sell Out

Sailing Adventures 3-Hour Activity in Destin

  • North America
  • Superb4 reviews5

There’s nothing like seeing the clear emerald waters pass under the hull while sailing on the Stil....

    Free Cancellation
    Private Tour
    Start From $525.00
 
 

3 Hour Luxury Private Sailing Catamaran for 7-12 People

(5 of 4 reviews)

Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allow more flexibility with the day’s schedule and activities. Book a sail, swim, and snorkel time that works with your schedule. Yo... More

Free Cancellation
Private Tour
Start From $1,995.00
 
3 Hour Luxury Private Sailing Catamaran for 7-12 People Likely to Sell Out

3 Hour Luxury Private Sailing Catamaran for 7-12 People

  • North America
  • Superb4 reviews5

Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allo....

    Free Cancellation
    Private Tour
    Start From $1,995.00
 
 

Afternoon Sail

(5 of 28 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
 
Afternoon Sail Likely to Sell Out

Afternoon Sail

  • North America
  • Superb28 reviews5

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
 
 

Hilton Hawaiian Village Turtle Snorkel with Optional Lunch

(4.6 of 13 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
  • Superb13 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
 
 

2 Hour Sailing Adventure in Lake Michigan (up to 6 people)

(5 of 6 reviews)

Our trips are perfect for starters or advanced sailors. We offer a 2 -hour sailing trip overlooking views of the city of Racine and on clear day views of Milwaukee and Kenosha You can lay back and relax to the sounds of the wave... More

Free Cancellation
Private Tour
Start From $99.00
 
2 Hour Sailing Adventure in Lake Michigan (up to 6 people) Likely to Sell Out

2 Hour Sailing Adventure in Lake Michigan (up to 6 people)

  • North America
  • Superb6 reviews5

Our trips are perfect for starters or advanced sailors. We offer a 2 -hour sailing trip overlooking ....

    Free Cancellation
    Private Tour
    Start From $99.00
 
 

Sunset Sail from Ma'alaea Harbor

(4.6 of 211 reviews)

Enjoy tantalizing pupus (appetizers) and island-style music against the backdrop of a stunning sunset over the Pacific Ocean.This relaxing cruise is aboard our  luxury sailing catamaran, Ocean Spirit. It’s the perfect way to ex... More

Free Cancellation
Private Tour
Start From $151.00
 
Sunset Sail from Ma'alaea Harbor Likely to Sell Out

Sunset Sail from Ma'alaea Harbor

  • North America
  • Superb211 reviews4.6

Enjoy tantalizing pupus (appetizers) and island-style music against the backdrop of a stunning sunse....

    Free Cancellation
    Private Tour
    Start From $151.00
 
 

Sunset Boat Tour Includes Open Bar and Dinner

(4.6 of 211 reviews)

No trip to Cabo is complete with a sunset boat tour of the world famous arch. This is the sunset boat tour that covers all of your bucket list checks! Open bar, light food, a sunset boat tour and memories to last a lifetime!... More

Free Cancellation
Private Tour
Start From $99.00
 
Sunset Boat Tour Includes Open Bar and Dinner Likely to Sell Out

Sunset Boat Tour Includes Open Bar and Dinner

  • North America
  • Superb211 reviews4.6

No trip to Cabo is complete with a sunset boat tour of the world famous arch. This is the sunset boa....

    Free Cancellation
    Private Tour
    Start From $99.00