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Top 10 Best North America Sailing Trips

Found 723 Sailing Trips activities in North America. Sort by Popularity. - Page 26
 

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
Start From $179.00
 
2 hours - Shared Sunset Sail along Historic St Augustine Bayfront

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
    Start From $179.00
 
 

New York Fall Foliage Sail up the Hudson River

(4.5 of 11 reviews)

Enjoy a 3.5-hour scenic sail up the Hudson River to the Palisades aboard Schooner Adirondack or Schooner America 2.0, both 1800s-style sailboats. Bordering the Hudson River north of Fort Lee, New Jersey, the Palisade Cliffs are am... More

Free Cancellation
Start From $143.27
 
New York Fall Foliage Sail up the Hudson River Likely to Sell Out

New York Fall Foliage Sail up the Hudson River

  • North America
  • Exellent11 reviews4.5

Enjoy a 3.5-hour scenic sail up the Hudson River to the Palisades aboard Schooner Adirondack or Scho....

    Free Cancellation
    Start From $143.27
 
 

Private Sail Around New York City and The Statue of Liberty

(5 of 7 reviews)

Discover NYC from a completely different perspective on a private sailboat charter. You and your group will view New York City in ways that are breath taking. See the Statue of Liberty up close like you can almost touch it. Sit ba... More

Free Cancellation
Private Tour
Start From $650.00
 
Private Sail Around New York City and The Statue of Liberty Likely to Sell Out

Private Sail Around New York City and The Statue of Liberty

  • North America
  • Superb7 reviews5

Discover NYC from a completely different perspective on a private sailboat charter. You and your gro....

    Free Cancellation
    Private Tour
    Start From $650.00
 
 

2-Hour Rosé Luxury Day Sail

(5 of 1 review)

This 2-hour daytime sail offers a smooth, spacious ride through the scenic Calibogue Sound with expert captains leading the way. Keep an eye out for dolphins, seabirds, and Lowcountry landmarks as you relax, unwind, and enjoy the ... More

Free Cancellation
Private Tour
Start From $54.32
 
2-Hour Rosé Luxury Day Sail Likely to Sell Out

2-Hour Rosé Luxury Day Sail

  • North America
  • Superb1 review5

This 2-hour daytime sail offers a smooth, spacious ride through the scenic Calibogue Sound with expe....

    Free Cancellation
    Private Tour
    Start From $54.32
 
 

Hawaiian Sail and Snorkel in Kailua-Kona, Hawaii

(4.9 of 9 reviews)

Welcome to the only place in Hawaii where the spirit of ancient Hawaiian seafaring meets modern expectations on the pristine waters of the Kona coast. Immerse yourself in a unique and unforgettable experience as we invite you to j... More

Free Cancellation
Private Tour
Start From $125.00
 
Hawaiian Sail and Snorkel in Kailua-Kona, Hawaii Likely to Sell Out

Hawaiian Sail and Snorkel in Kailua-Kona, Hawaii

  • North America
  • Superb9 reviews4.9

Welcome to the only place in Hawaii where the spirit of ancient Hawaiian seafaring meets modern expe....

    Free Cancellation
    Private Tour
    Start From $125.00
 
 

Top Tour Sail To Isla Mujeres By Catamaran Buffet And Drinks Included

(3 of 1 review)

Stop looking for the perfect tour to Isla mujeres, we are the best option. Why? With us you´ll have: 1.No long lines, direct access 2.Quality food 3.Quality drinks 4.Best Service 5.We will take you to special reefs where on... More

Free Cancellation
Private Tour
Start From $55.00
 
Top Tour Sail To Isla Mujeres By Catamaran Buffet And Drinks Included Likely to Sell Out

Top Tour Sail To Isla Mujeres By Catamaran Buffet And Drinks Incl....

  • North America

Stop looking for the perfect tour to Isla mujeres, we are the best option. Why? With us you´ll hav....

    Free Cancellation
    Private Tour
    Start From $55.00
 
 

Cabo Catamaran Tour: Snorkeling & Unlimited Drinks Included

(3 of 1 review)

Discover the magic of Cabo San Lucas on this exhilarating catamaran cruise! Glide across the sparkling waters of the Pacific Ocean and the Sea of Cortez, where you’ll have the chance to snorkel and explore vibrant underwater lif... More

Free Cancellation
Private Tour
Start From $99.00
 
Cabo Catamaran Tour: Snorkeling & Unlimited Drinks Included Likely to Sell Out

Cabo Catamaran Tour: Snorkeling & Unlimited Drinks Included

  • North America

Discover the magic of Cabo San Lucas on this exhilarating catamaran cruise! Glide across the sparkli....

    Free Cancellation
    Private Tour
    Start From $99.00
 
 

Cancun Half Day Sailing Cataman Cruise to Isla Mujeres

(5 of 1 review)

Original Half Day Sailing since 2012, No need to invest your whole day to visit Isla Mujeres! Lite Tour to Isla Mujeres provides full sailing, snorkeling & enough time to visit Isla Mujeres for shopping or just enjoy this wonderf... More

Free Cancellation
Private Tour
Start From $79.00
 
Cancun Half Day Sailing Cataman Cruise to Isla Mujeres Likely to Sell Out

Cancun Half Day Sailing Cataman Cruise to Isla Mujeres

  • North America
  • Superb1 review5

Original Half Day Sailing since 2012, No need to invest your whole day to visit Isla Mujeres! Lite ....

    Free Cancellation
    Private Tour
    Start From $79.00
 
 

Private Catamaran: Snorkel, Swim and Dolphin Watching

(5 of 1 review)

Sail around in style aboard a catamaran with a fun local avid sailor that wants to share his passion with you. Let Captain Kip take you to some of the best spots the area has to offer while you are visiting the Emerald Coast. ... More

Free Cancellation
Private Tour
Start From $465.00
 
Private Catamaran: Snorkel, Swim and Dolphin Watching Likely to Sell Out

Private Catamaran: Snorkel, Swim and Dolphin Watching

  • North America
  • Superb1 review5

Sail around in style aboard a catamaran with a fun local avid sailor that wants to share his passion....

    Free Cancellation
    Private Tour
    Start From $465.00
 
 

2 - Hour Private Hilton Head Morning Dolphin Watching / Sail

(5 of 33 reviews)

This 2 hour Private Morning Sailing tour, the Captain will take you to Port Royal Sound (North side of the island - generally best conditions for sailing). During the MORNING, this is generally a calm - light wind relaxing sail, a... More

Free Cancellation
Private Tour
Start From $465.00
 
2 - Hour Private Hilton Head Morning Dolphin Watching / Sail Likely to Sell Out

2 - Hour Private Hilton Head Morning Dolphin Watching / Sail

  • North America
  • Superb33 reviews5

This 2 hour Private Morning Sailing tour, the Captain will take you to Port Royal Sound (North side ....

    Free Cancellation
    Private Tour
    Start From $465.00
 
 

Shared Day Sail along Historic St Augustine Bayfront

(5 of 6 reviews)

Not your average tour, this 2-hour small group sail gives passengers a chance to make new memories on the sea. Our cruise is perfect for all water-lovers: families, couples, and friends. Some guests interact with the USCG licensed... More

Free Cancellation
Private Tour
Start From $129.00
 
Shared Day Sail along Historic St Augustine Bayfront Likely to Sell Out

Shared Day Sail along Historic St Augustine Bayfront

  • North America
  • Superb6 reviews5

Not your average tour, this 2-hour small group sail gives passengers a chance to make new memories o....

    Free Cancellation
    Private Tour
    Start From $129.00
 
 

Private Whale Watching Sailing Adventure

(3.5 of 2 reviews)

From the comfort of your private luxury yacht, enjoy an amazing experience with Hawaii’s humpback whales. Departing near Waikiki, enjoy a leisurely sail against the majestic backdrop of Diamond Head as you scan the water for maj... More

Free Cancellation
Private Tour
Start From $695.00
 
Private Whale Watching Sailing Adventure Likely to Sell Out

Private Whale Watching Sailing Adventure

  • North America
  • Good2 reviews3.5

From the comfort of your private luxury yacht, enjoy an amazing experience with Hawaii’s humpback ....

    Free Cancellation
    Private Tour
    Start From $695.00
 
 

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
Private Tour
Start From $139.46
 
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
    Private Tour
    Start From $139.46
 
 

Explore Turtle Canyons Waikiki Snorkel and Sail Adventure

(4.5 of 4 reviews)

Enjoy your best day in Hawaii and discover a new Adventure! This sailing with snorkeling experience is amazing for you to relax and have fun. ... More

Free Cancellation
Private Tour
Start From $1,199.00
 
Explore Turtle Canyons Waikiki Snorkel and Sail Adventure Likely to Sell Out

Explore Turtle Canyons Waikiki Snorkel and Sail Adventure

  • North America
  • Exellent4 reviews4.5

Enjoy your best day in Hawaii and discover a new Adventure! This sailing with snorkeling experience ....

    Free Cancellation
    Private Tour
    Start From $1,199.00
 
 

Private Cabo San Lucas Sunset Cruise on 33´ sailboat

(4.9 of 61 reviews)

You will enjoy watching the sun set on the horizon from your very own private boat with our accommodating and knowledgeable crew. Every tour includes sightseeing along the spectacular Finisterra Rocky point where you will see the ... More

Free Cancellation
Private Tour
Start From $600.00
 
Private Cabo San Lucas Sunset Cruise on 33´ sailboat Likely to Sell Out

Private Cabo San Lucas Sunset Cruise on 33´ sailboat

  • North America
  • Superb61 reviews4.9

You will enjoy watching the sun set on the horizon from your very own private boat with our accommod....

    Free Cancellation
    Private Tour
    Start From $600.00
 
 

Sunset Cruise Tequila Tasting

(5 of 4 reviews)

Join us for a one-of-a-kind Sunset Sailboat & Tequila tasting in Cabo San Lucas! Discover the history of one of Mexico's most iconic drinks, brought to you by Tequila Cabo Único and Sunrider. You'll get to know the iconic Cabo S... More

Free Cancellation
Private Tour
Start From $115.00
 
Sunset Cruise Tequila Tasting Likely to Sell Out

Sunset Cruise Tequila Tasting

  • North America
  • Superb4 reviews5

Join us for a one-of-a-kind Sunset Sailboat & Tequila tasting in Cabo San Lucas! Discover the histo....

    Free Cancellation
    Private Tour
    Start From $115.00
 
 

Sailing Charter

(5 of 5 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
  • Superb5 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
 
 

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 $59.00
 
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 $59.00
 
 

Private Cancun Sailboat Cruise with Beers and Sodas Included

(5 of 1 review)

Escape to paradise with our exclusive private sailing boat cruise to Isla Mujeres, a pristine island gem just off the coast of Cancun. Step aboard our fine vessel and embark on a journey of discovery and relaxation in the breathta... More

Free Cancellation
Private Tour
Start From $579.00
 
Private Cancun Sailboat Cruise with Beers and Sodas Included Likely to Sell Out

Private Cancun Sailboat Cruise with Beers and Sodas Included

  • North America
  • Superb1 review5

Escape to paradise with our exclusive private sailing boat cruise to Isla Mujeres, a pristine island....

    Free Cancellation
    Private Tour
    Start From $579.00
 
 

SUNSET CRUISE in Key Largo,FL.

(5 of 3 reviews)

KEY LARGO BOAT CHARTERS offers a VIP private sunset excursion for you and your loved ones. No need to worry about large crowds or waiting in long lines. Personalize the trip to your liking. A private charter makes it more personab... More

Free Cancellation
Private Tour
Start From $389.00
 
SUNSET CRUISE in Key Largo,FL. Likely to Sell Out

SUNSET CRUISE in Key Largo,FL.

  • North America
  • Superb3 reviews5

KEY LARGO BOAT CHARTERS offers a VIP private sunset excursion for you and your loved ones. No need t....

    Free Cancellation
    Private Tour
    Start From $389.00
 
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