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Top 10 Best North America Sailing Trips

Found 720 Sailing Trips activities in North America. Sort by Popularity. - Page 27
 

Private Key West Sunset Sail

(4.7 of 48 reviews)

2 Hr. Private charter sailing from downtown Key West onboard Key West's First sailing charter boat, the pretty green sloop "High Tide" USCG Certified for up to 12 passengers, the Sloop High Tide and Sunset Sail Key West make for t... More

Private Tour
Start From $695.00
 
Private Key West Sunset Sail Likely to Sell Out

Private Key West Sunset Sail

  • North America
  • Superb48 reviews4.7

2 Hr. Private charter sailing from downtown Key West onboard Key West's First sailing charter boat, ....

    Private Tour
    Start From $695.00
 
 

Cozumel Catamaran Experience with Snorkeling & Beach Club

(4.2 of 6 reviews)

Spend a fun-packed half day in paradise, snorkeling and swimming on one of Mexico's top beaches. Cruise in a luxurious catamaran along the Cozumel coastline, and snorkel above the fascinating El Palancar Reef. The adventure conti... More

Free Cancellation
Private Tour
Start From $129.00
 
Cozumel Catamaran Experience with Snorkeling & Beach Club Likely to Sell Out

Cozumel Catamaran Experience with Snorkeling & Beach Club

  • North America
  • Exellent6 reviews4.2

Spend a fun-packed half day in paradise, snorkeling and swimming on one of Mexico's top beaches. Cru....

    Free Cancellation
    Private Tour
    Start From $129.00
 
 

San Diego Small Group Classic Sailboat Snacks And Drinks Included

(5 of 4 reviews)

Escape the congestion of large tour groups; we only take six passengers per trip. Book an unforgettable tour with Captain Phil and sail in style aboard Liberty, a stunning replica of a 1904 gaff-rigged Friendship sloop. Our boat... More

Free Cancellation
Private Tour
Start From $125.00
 
San Diego Small Group Classic Sailboat Snacks And Drinks Included Likely to Sell Out

San Diego Small Group Classic Sailboat Snacks And Drinks Included

  • North America
  • Superb4 reviews5

Escape the congestion of large tour groups; we only take six passengers per trip. Book an unforget....

    Free Cancellation
    Private Tour
    Start From $125.00
 
 

Golden Hour Escape: Private Sunset Sail in Coastal Maine

(5 of 20 reviews)

Experience the Magic of our Private Sunset Sail. Witness the enchanting transformation as the setting sun bathes the world in mesmerizing hues, crafting memories destined to endure. Set sail along Maine's exquisite coastline aboar... More

Free Cancellation
Private Tour
Start From $849.00
 
Golden Hour Escape: Private Sunset Sail in Coastal Maine Likely to Sell Out

Golden Hour Escape: Private Sunset Sail in Coastal Maine

  • North America
  • Superb20 reviews5

Experience the Magic of our Private Sunset Sail. Witness the enchanting transformation as the settin....

    Free Cancellation
    Private Tour
    Start From $849.00
 
 

Vancouver Sailing Tour - Learn the Ropes

(5 of 2 reviews)

Escape to the open waters of Vancouver on a sailing adventure that offers the best of the city’s scenic vistas. This 2.5-3 hour sailing experience takes you through the picturesque False Creek and English Bay, where you’ll be ... More

Free Cancellation
Private Tour
Start From $140.35
 
Vancouver Sailing Tour - Learn the Ropes Likely to Sell Out

Vancouver Sailing Tour - Learn the Ropes

  • North America
  • Superb2 reviews5

Escape to the open waters of Vancouver on a sailing adventure that offers the best of the city’s s....

    Free Cancellation
    Private Tour
    Start From $140.35
 
 

6 Hours Private Yacht in Puerto Vallarta with Snorkeling & Beach

(5 of 2 reviews)

Sail on a 6-hour private trip aboard our 55-foot private yacht, ideal for up to 12 passengers. We are sure that with us you will know the best part of our beautiful bay of Puerto Vallarta. Do not miss the opportunity we offer to ... More

Free Cancellation
Private Tour
Start From $1,536.89
 
6 Hours Private Yacht in Puerto Vallarta with Snorkeling & Beach Likely to Sell Out

6 Hours Private Yacht in Puerto Vallarta with Snorkeling & Beach

  • North America
  • Superb2 reviews5

Sail on a 6-hour private trip aboard our 55-foot private yacht, ideal for up to 12 passengers. We a....

    Free Cancellation
    Private Tour
    Start From $1,536.89
 
 

Isla Mujeres by Private Catamaran

(5 of 2 reviews)

Discover Isla Mujeres on an unforgettable journey that combines adventure, relaxation, and Caribbean beauty. Sail aboard an exclusive private catamaran, feeling the sea breeze and admiring panoramic views of the turquoise Caribbe... More

Free Cancellation
Private Tour
Start From $1,100.00
 
Isla Mujeres by Private Catamaran Likely to Sell Out

Isla Mujeres by Private Catamaran

  • North America
  • Superb2 reviews5

Discover Isla Mujeres on an unforgettable journey that combines adventure, relaxation, and Caribbean....

    Free Cancellation
    Private Tour
    Start From $1,100.00
 
 

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
 
 

Luxury Catamaran tour to Isla Mujeres with transportation from Playa del Carmen

(4.3 of 62 reviews)

Because it's an amazing place where you can relax in the beautiful Caribbean Sea, we offer you a personal assistance from our incredible crew that will make you have a great time, you will snorkel in an amazing part of the second ... More

Free Cancellation
Private Tour
Start From $93.87
 
Luxury Catamaran tour to Isla Mujeres with transportation from Playa del Carmen Likely to Sell Out

Luxury Catamaran tour to Isla Mujeres with transportation from Pl....

  • North America
  • Exellent62 reviews4.3

Because it's an amazing place where you can relax in the beautiful Caribbean Sea, we offer you a per....

    Free Cancellation
    Private Tour
    Start From $93.87
 
 

4 Hour Private Sail for up to 6 people

(4.8 of 12 reviews)

This private excursion allows a party of six passengers to cruise the San Diego Bay and Coast on a customizable charter. Create your own adventure on a vintage sailing yacht for 4 hours with an experienced captain.... More

Free Cancellation
Private Tour
Start From $1,100.00
 
4 Hour Private Sail for up to 6 people Likely to Sell Out

4 Hour Private Sail for up to 6 people

  • North America
  • Superb12 reviews4.8

This private excursion allows a party of six passengers to cruise the San Diego Bay and Coast on a c....

    Free Cancellation
    Private Tour
    Start From $1,100.00
 
 

South Beach Miami BACHELORETTE Boat Day!

(5 of 1 review)

Enjoy a yacht-day bachelorette trip where everything is already set to go right from the biggest and best marina in SOUTH BEACH... We've found the boats, brought on the food and drinks, and made sure that everything that a good y... More

Free Cancellation
Private Tour
Start From $1,795.00
 
South Beach Miami BACHELORETTE Boat Day! Likely to Sell Out

South Beach Miami BACHELORETTE Boat Day!

  • North America
  • Superb1 review5

Enjoy a yacht-day bachelorette trip where everything is already set to go right from the biggest and....

    Free Cancellation
    Private Tour
    Start From $1,795.00
 
 

Exclusive Private Sailing Luxury Tour in Los Cabos

(5 of 1 review)

Experience snorkeling in crystal waters, the beach Palmilla has a blue flag recognition and is one of the best beach areas to discover the underwater world of the Los Cabos area. During the months of December thru March, you can w... More

Free Cancellation
Private Tour
Start From $1,600.00
 
Exclusive Private Sailing Luxury Tour in Los Cabos Likely to Sell Out

Exclusive Private Sailing Luxury Tour in Los Cabos

  • North America
  • Superb1 review5

Experience snorkeling in crystal waters, the beach Palmilla has a blue flag recognition and is one o....

    Free Cancellation
    Private Tour
    Start From $1,600.00
 
 

Fishing and snorkel tour in Puerto Vallarta and Nuevo Vallarta

(4.3 of 17 reviews)

Our crew will support you on board the boat, in the water and during your visit. They will teach you all the basics for fishing and they will take you to unique places in the bay so you can enjoy a good dip in the salty sea water... More

Free Cancellation
Private Tour
Start From $1,075.00
 
Fishing and snorkel tour in Puerto Vallarta and Nuevo Vallarta Likely to Sell Out

Fishing and snorkel tour in Puerto Vallarta and Nuevo Vallarta

  • North America
  • Exellent17 reviews4.3

Our crew will support you on board the boat, in the water and during your visit. They will teach yo....

    Free Cancellation
    Private Tour
    Start From $1,075.00
 
 

Cabo San Lucas Sailing Snorkeling Adventure

(4.3 of 17 reviews)

ELEGANCE MEETS ADVENTURE – A FAMILY EXPERIENCE LIKE NO OTHER Treat yourself and your loved ones to an unforgettable day at sea aboard our luxurious double-deck Whether you're snorkeling alongside tropical fish, paddleboarding ... More

Free Cancellation
Private Tour
Start From $159.00
 
Cabo San Lucas Sailing Snorkeling Adventure Likely to Sell Out

Cabo San Lucas Sailing Snorkeling Adventure

  • North America
  • Exellent17 reviews4.3

ELEGANCE MEETS ADVENTURE – A FAMILY EXPERIENCE LIKE NO OTHER Treat yourself and your loved ones to....

    Free Cancellation
    Private Tour
    Start From $159.00
 
 

Sunset Sailing Tour of San Diego Bay up to 6 Guests

(5 of 1 review)

A Sunset Sailing Charter on San Diego Bay is an awesome way to spend the day sightseeing in beautiful San Diego. Pacifica Sailing Charters offers several different types of sunset sailing charters and boat tours. Our sunset sailin... More

Free Cancellation
Private Tour
Start From $119.00
 
Sunset Sailing Tour of San Diego Bay up to 6 Guests Likely to Sell Out

Sunset Sailing Tour of San Diego Bay up to 6 Guests

  • North America
  • Superb1 review5

A Sunset Sailing Charter on San Diego Bay is an awesome way to spend the day sightseeing in beautifu....

    Free Cancellation
    Private Tour
    Start From $119.00
 
 

Luxury Private Sunset Experience in San Jose

(5 of 1 review)

Enjoy an amazing experience offering a luxury, unique, complete and breathtaking private sunset tour. The Luxury Private Sailing boat have capacity from 1 to 16 people, the rate offered here is for 8 people, if like to add more pl... More

Free Cancellation
Private Tour
Start From $1,600.00
 
Luxury Private Sunset Experience in San Jose Likely to Sell Out

Luxury Private Sunset Experience in San Jose

  • North America
  • Superb1 review5

Enjoy an amazing experience offering a luxury, unique, complete and breathtaking private sunset tour....

    Free Cancellation
    Private Tour
    Start From $1,600.00
 
 

Luxury Diamond Head Sunset Sail

(5 of 3 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 50' luxury yacht. Immerse yourself in a gorgeous Hawaiian sunset the only way, from... More

Free Cancellation
Private Tour
Start From $1,398.00
 
Luxury Diamond Head Sunset Sail Likely to Sell Out

Luxury Diamond Head Sunset Sail

  • North America
  • Superb3 reviews5

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 $1,398.00
 
 

Cabo's Premier Catamaran Snorkeling: Explore the Waters!

(5 of 3 reviews)

Embark aboard our CaboMar catamaran for an unforgettable snorkeling adventure. First, we’ll cruise by some of Cabo's most iconic spots: Playa del Amor, El Arco, and the Sea Lion Reserve. At each location, we’ll stop for about ... More

Free Cancellation
Private Tour
Start From $129.00
 
Cabo's Premier Catamaran Snorkeling: Explore the Waters! Likely to Sell Out

Cabo's Premier Catamaran Snorkeling: Explore the Waters!

  • North America
  • Superb3 reviews5

Embark aboard our CaboMar catamaran for an unforgettable snorkeling adventure. First, we’ll cruise....

    Free Cancellation
    Private Tour
    Start From $129.00
 
 

3hr Luxury Private Sailing Catamaran in Waikiki for 1 to 6 People

(5 of 1 review)

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 $1,595.00
 
3hr Luxury Private Sailing Catamaran in Waikiki for 1 to 6 People Likely to Sell Out

3hr Luxury Private Sailing Catamaran in Waikiki for 1 to 6 People

  • North America
  • Superb1 review5

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

    Free Cancellation
    Private Tour
    Start From $1,595.00
 
 

Bachelorette Sailing Party on San Diego Bay up to 6 Guests

(5 of 1 review)

Nothing beats a Catamaran Bachelorette Party on San Diego bay for up to 6 guests. Enjoy breathtaking views of downtown, the naval base, aircraft carriers, destroyers, and submarines, not to mention an incredible abundance of sea l... More

Free Cancellation
Private Tour
Start From $750.00
 
Bachelorette Sailing Party on San Diego Bay up to 6 Guests Likely to Sell Out

Bachelorette Sailing Party on San Diego Bay up to 6 Guests

  • North America
  • Superb1 review5

Nothing beats a Catamaran Bachelorette Party on San Diego bay for up to 6 guests. Enjoy breathtaking....

    Free Cancellation
    Private Tour
    Start From $750.00
 
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