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Top 10 Best North America Sailing Trips

Found 735 Sailing Trips activities in North America. Sort by Popularity. - Page 29
 

2hr Luxury Private Sailing Catamaran for 7-12 People

(5 of 3 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 $1,495.00
 
2hr Luxury Private Sailing Catamaran for 7-12 People

2hr Luxury Private Sailing Catamaran for 7-12 People

  • North America
  • Superb3 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 $1,495.00
 
 

Guided Tour of Puerto Morelos Reefs with Snorkeling Experience

(4 of 3 reviews)

Welcome to an incredible adventure, if what you like is getting to know new places and being in contact with nature, then this activity is for you. We will take you to know the second largest coral reef in the world, the first one... More

Free Cancellation
Private Tour
Start From $44.25
 
Guided Tour of Puerto Morelos Reefs with Snorkeling Experience Likely to Sell Out

Guided Tour of Puerto Morelos Reefs with Snorkeling Experience

  • North America
  • Very Good3 reviews4

Welcome to an incredible adventure, if what you like is getting to know new places and being in cont....

    Free Cancellation
    Private Tour
    Start From $44.25
 
 

Whale Shark Snorkel Tour in Cancun (Snack Lunch included)

(4 of 3 reviews)

Experience this must-do activity in the Caribbean Sea and swim with this impressive animal. The whale shark adventure is the most enigmatic activity in Mexico. It is a very docile animal that is just as impressive as any other a... More

Free Cancellation
Private Tour
Start From $189.00
 
Whale Shark Snorkel Tour in Cancun (Snack Lunch included) Likely to Sell Out

Whale Shark Snorkel Tour in Cancun (Snack Lunch included)

  • North America
  • Very Good3 reviews4

Experience this must-do activity in the Caribbean Sea and swim with this impressive animal. The whal....

    Free Cancellation
    Private Tour
    Start From $189.00
 
 

Discover Hobie-Cat Sailing and Fish your own Lunch

(5 of 9 reviews)

Becoming able to sail a sailboat only with the wind is a skill that will give you the sense of Freedom that only the ocean can give. You'll realize that you will be able to get to some of the most beautiful places on the planet wi... More

Free Cancellation
Private Tour
Start From $225.00
 
Discover Hobie-Cat Sailing and Fish your own Lunch Likely to Sell Out

Discover Hobie-Cat Sailing and Fish your own Lunch

  • North America
  • Superb9 reviews5

Becoming able to sail a sailboat only with the wind is a skill that will give you the sense of Freed....

    Free Cancellation
    Private Tour
    Start From $225.00
 
 

Friday Night Waikiki Fireworks Sail

(3 of 1 review)

Sunset, Sailing and Fireworks! Highlights of Hawaii! Top Rated Sailing adventure in Waikiki. Enjoy a spectacular Hawaiian sunset and the Friday Night Fireworks onboard a luxury private yacht.... More

Free Cancellation
Private Tour
Start From $699.00
 
Friday Night Waikiki Fireworks Sail Likely to Sell Out

Friday Night Waikiki Fireworks Sail

  • North America

Sunset, Sailing and Fireworks! Highlights of Hawaii! Top Rated Sailing adventure in Waikiki. Enjoy a....

    Free Cancellation
    Private Tour
    Start From $699.00
 
 

2 hours - Shared Sunset Sail along Historic St Augustine Bayfront

(4.7 of 7 reviews)

We would welcome an opportunity to host you and your guest aboard our luxury sailing yachts. Our staff and captains are friendly and eager to assist in making your experience a wonder memory. This 2-hour sail gives passengers a ... More

Free Cancellation
Private Tour
Start From $179.00
 
2 hours - Shared Sunset Sail along Historic St Augustine Bayfront Likely to Sell Out

2 hours - Shared Sunset Sail along Historic St Augustine Bayfront

  • North America
  • Superb7 reviews4.7

We would welcome an opportunity to host you and your guest aboard our luxury sailing yachts. Our sta....

    Free Cancellation
    Private Tour
    Start From $179.00
 
 

Private Paddle Tour at Sunrise

(5 of 220 reviews)

With this amazing experience through the Bacalar Lagoon you will live unbeatable moments for 3.5 hours, we have all the necessary equipment for this activity to be complete. We are an ecologically responsible company that promotes... More

Free Cancellation
Private Tour
Start From $72.68
 
Private Paddle Tour at Sunrise Likely to Sell Out

Private Paddle Tour at Sunrise

  • North America
  • Superb220 reviews5

With this amazing experience through the Bacalar Lagoon you will live unbeatable moments for 3.5 hou....

    Free Cancellation
    Private Tour
    Start From $72.68
 
 

Cabo Yacht Tour to Lovers or Pelícano Beach + Beach Time

(3.7 of 3 reviews)

Set sail for a day of relaxation on our yacht tour to Lovers Beach. This 45-minute journey offers you the chance to unwind on the beautiful sands of Pelícano Beach, where you can enjoy a minimum of 2 hours of free time to soak up... More

Free Cancellation
Private Tour
Start From $35.00
 
Cabo Yacht Tour to Lovers or Pelícano Beach + Beach Time Likely to Sell Out

Cabo Yacht Tour to Lovers or Pelícano Beach + Beach Time

  • North America
  • Very Good3 reviews3.7

Set sail for a day of relaxation on our yacht tour to Lovers Beach. This 45-minute journey offers yo....

    Free Cancellation
    Private Tour
    Start From $35.00
 
 

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

(4.3 of 63 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
  • Exellent63 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
 
 

Snorkel in the beautiful reef of Puerto Morelos with transport

(3 of 1 review)

The most amazing and exciting tour in the Mexican Caribbean is here. Visit the national park of reefs in Puerto Morelos. Sail through the turquoise clear water of the Caribbean Sea and arrive to the Mesoamerican reef. Our captain... More

Free Cancellation
Private Tour
Start From $44.25
 
Snorkel in the beautiful reef of Puerto Morelos with transport Likely to Sell Out

Snorkel in the beautiful reef of Puerto Morelos with transport

  • North America

The most amazing and exciting tour in the Mexican Caribbean is here. Visit the national park of reef....

    Free Cancellation
    Private Tour
    Start From $44.25
 
 

Private Sunset Sail of NYC Skyline and Statue of Liberty

(5 of 2 reviews)

Discover NYC from a completely different perspective on a private sailboat charter during sunset hours when the views are even more spectacular. You and your group will view New York City in ways that are breath taking. See the St... More

Free Cancellation
Private Tour
Start From $725.00
 
Private Sunset Sail of NYC Skyline and Statue of Liberty Likely to Sell Out

Private Sunset Sail of NYC Skyline and Statue of Liberty

  • North America
  • Superb2 reviews5

Discover NYC from a completely different perspective on a private sailboat charter during sunset hou....

    Free Cancellation
    Private Tour
    Start From $725.00
 
 

Private Sailing Experience on Galveston Bay

(5 of 1 review)

See the Texas Gulf Coast in a whole new way. Feel the sea breeze, explore the Texas Gulf Coast, and discover a new way to travel aboard our luxury charter yacht. We offer the perfect blend of comfort and adventure, making it the ... More

Free Cancellation
Private Tour
Start From $800.00
 
Private Sailing Experience on Galveston Bay Likely to Sell Out

Private Sailing Experience on Galveston Bay

  • North America
  • Superb1 review5

See the Texas Gulf Coast in a whole new way. Feel the sea breeze, explore the Texas Gulf Coast, and....

    Free Cancellation
    Private Tour
    Start From $800.00
 
 

Private Sunset Sail in Key West Florida

(5 of 1 review)

Enjoy a private Sunset Sail on a Classic 60 ft Schooner Serenity and get a front-row seat with just your family and friends to watch Key West's Famous sunsets. View Dolphins, Turtles, and all kinds of Marine Life. Take the helm, l... More

Free Cancellation
Private Tour
Start From $750.00
 
Private Sunset Sail in Key West Florida Likely to Sell Out

Private Sunset Sail in Key West Florida

  • North America
  • Superb1 review5

Enjoy a private Sunset Sail on a Classic 60 ft Schooner Serenity and get a front-row seat with just ....

    Free Cancellation
    Private Tour
    Start From $750.00
 
 

Super Combo ATV in Cancun with Zipline, Snorkel, Cenote, transfer

(3.7 of 3 reviews)

Welcome to the super combo tour, the best activity in Mexico and the Caribbean. You will start the trip in the town of Puerto Morelos. There you will be able to visit the 2nd biggest barrier reef in the world. Swim and explore the... More

Free Cancellation
Private Tour
Start From $109.65
 
Super Combo ATV in Cancun with Zipline, Snorkel, Cenote, transfer Likely to Sell Out

Super Combo ATV in Cancun with Zipline, Snorkel, Cenote, transfer

  • North America
  • Very Good3 reviews3.7

Welcome to the super combo tour, the best activity in Mexico and the Caribbean. You will start the t....

    Free Cancellation
    Private Tour
    Start From $109.65
 
 

The Best Catamaran tour to Isla Mujeres with Open Bar and Lunch

(4 of 4 reviews)

Enjoy the most complete Isla Mujeres experience! Start with round-trip transportation from your hotel, then sail across the Caribbean on a catamaran with open bar and music on board. Snorkel in crystal-clear waters, savor a delici... More

Free Cancellation
Private Tour
Start From $39.90
 
The Best Catamaran tour to Isla Mujeres with Open Bar and Lunch Likely to Sell Out

The Best Catamaran tour to Isla Mujeres with Open Bar and Lunch

  • North America
  • Very Good4 reviews4

Enjoy the most complete Isla Mujeres experience! Start with round-trip transportation from your hote....

    Free Cancellation
    Private Tour
    Start From $39.90
 
 

Cancun ATV Jungle Adventure & Isla Mujeres Catamaran Combo

(4 of 4 reviews)

Embark on two unforgettable Cancun adventures with this incredible combo package! Day 1: Unleash your inner thrill-seeker on a wild ATV Jungle Tour. Race through the Mayan jungle, soar through the treetops on ziplines, and refres... More

Free Cancellation
Private Tour
Start From $135.00
 
Cancun ATV Jungle Adventure & Isla Mujeres Catamaran Combo Likely to Sell Out

Cancun ATV Jungle Adventure & Isla Mujeres Catamaran Combo

  • North America
  • Very Good4 reviews4

Embark on two unforgettable Cancun adventures with this incredible combo package! Day 1: Unleash yo....

    Free Cancellation
    Private Tour
    Start From $135.00
 
 

Waikiki Sunset Cruise and Iconic Views with Swimming

(5 of 1 review)

Set sail on a spacious catamaran for a memorable sunset cruise that begins with a refreshing swim in the crystal-clear waters off Waikīkī Beach. Glide along the iconic Gold Coast as the sun sets, painting the sky with vibrant co... More

Free Cancellation
Private Tour
Start From $47.00
 
Waikiki Sunset Cruise and Iconic Views with Swimming Likely to Sell Out

Waikiki Sunset Cruise and Iconic Views with Swimming

  • North America
  • Superb1 review5

Set sail on a spacious catamaran for a memorable sunset cruise that begins with a refreshing swim in....

    Free Cancellation
    Private Tour
    Start From $47.00
 
 

Oyster Bay Two Hour Sailing Experience

(5 of 2 reviews)

Oyster Bay Harbor's natural beauty affords visitors a temporary respite from bustling city life. Oyster Bay is known for its spectacular sunsets, diverse wildlife, and the impressive estates that line the bay. WINDSWEPT is metic... More

Free Cancellation
Private Tour
Start From $595.00
 
Oyster Bay Two Hour Sailing Experience Likely to Sell Out

Oyster Bay Two Hour Sailing Experience

  • North America
  • Superb2 reviews5

Oyster Bay Harbor's natural beauty affords visitors a temporary respite from bustling city life. Oys....

    Free Cancellation
    Private Tour
    Start From $595.00
 
 

Catamaran Sail with Snorkeling and Beach Club of Isla Mujeres

(5 of 2 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 $65.00
 
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
  • Superb2 reviews5

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

    Free Cancellation
    Private Tour
    Start From $65.00
 
 

Sunset Sail on the Black Pearl

(4.4 of 7 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
  • Exellent7 reviews4.4

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
 
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