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Top 10 Best North America Sailing Trips

Found 719 Sailing Trips activities in North America. Sort by Popularity. - Page 6
 

Sunset Sailing Cruise in Monterey Bay

(4.8 of 34 reviews)

Looking to impress your date or just treat yourself to something unforgettable? Our Sunset Cruise is the most popular (and most romantic!) way to experience Monterey Bay. Departing daily, 90 minutes before sunset, this dreamy 1.5-... More

Free Cancellation
Start From $95.00
 
Sunset Sailing Cruise in Monterey Bay

Sunset Sailing Cruise in Monterey Bay

  • North America
  • Superb34 reviews4.8

Looking to impress your date or just treat yourself to something unforgettable? Our Sunset Cruise is....

    Free Cancellation
    Start From $95.00
 
 

Daytime Sailing Along San Diego's Skyline

(4.9 of 145 reviews)

Set sail with your Captain aboard our sail yacht and see some of San Diego's finest highlights on thisfamily-friendly sailing experience. We'll set sail from Safeharbor Sunroad Marina on Harbor Island on San Diego Bay, we often s... More

Free Cancellation
Start From $89.00
 
Daytime Sailing Along San Diego's Skyline Likely to Sell Out

Daytime Sailing Along San Diego's Skyline

  • North America
  • Superb145 reviews4.9

Set sail with your Captain aboard our sail yacht and see some of San Diego's finest highlights on th....

    Free Cancellation
    Start From $89.00
 
 

Private 6 Hrs 47 ft. Catamaran Snorkel & Cielo Charter (30p. max)

(4.7 of 15 reviews)

Sail in style aboard Cozumel’s largest and most spacious catamaran—a 47ft Nautitech—on an unforgettable journey to the famous El Cielo sandbar! Just 5–10 minutes by taxi from any cruise terminal or downtown, enjoy award-wi... More

Free Cancellation
Private Tour
Start From $1,998.65
 
Private 6 Hrs 47 ft. Catamaran Snorkel & Cielo Charter (30p. max) Likely to Sell Out

Private 6 Hrs 47 ft. Catamaran Snorkel & Cielo Charter (30p. max)

  • North America
  • Superb15 reviews4.7

Sail in style aboard Cozumel’s largest and most spacious catamaran—a 47ft Nautitech—on an unfo....

    Free Cancellation
    Private Tour
    Start From $1,998.65
 
 

Waikiki Catamaran Escape: Snorkel with Turtles & Water Sports Fun

(4.8 of 154 reviews)

Embark on a delightful journey through Oahu's pristine waters on a luxurious and comfortable catamaran. Our Turtle Snorkeling Package offers a unique opportunity to snorkel with friendly turtles in the heart of Waikiki's picturesq... More

Free Cancellation
Private Tour
Start From $120.69
 
Waikiki Catamaran Escape: Snorkel with Turtles & Water Sports Fun Likely to Sell Out

Waikiki Catamaran Escape: Snorkel with Turtles & Water Sports Fun

  • North America
  • Superb154 reviews4.8

Embark on a delightful journey through Oahu's pristine waters on a luxurious and comfortable catamar....

    Free Cancellation
    Private Tour
    Start From $120.69
 
 

Key West Rum and Reggae: Reef Snorkel Adventure and Sunset Sail

(4.4 of 363 reviews)

Fury’s Snorkel Adventure is unique for its combination of thrilling snorkeling and a vibrant sailing experience. Guests board a spacious Fury Catamaran, part of the largest luxury fleet in the Florida Keys, and sail to North Ame... More

Free Cancellation
Private Tour
Start From $59.95
 
Key West Rum and Reggae: Reef Snorkel Adventure and Sunset Sail Likely to Sell Out

Key West Rum and Reggae: Reef Snorkel Adventure and Sunset Sail

  • North America
  • Exellent363 reviews4.4

Fury’s Snorkel Adventure is unique for its combination of thrilling snorkeling and a vibrant saili....

    Free Cancellation
    Private Tour
    Start From $59.95
 
 

Kona Tradewind Catamaran Day Sail

(4.8 of 40 reviews)

Set sail aboard the spacious Honi Olani catamaran for a scenic 90-minute adventure along the stunning Kona coastline. This relaxing daytime cruise is perfect for spotting Hawaii’s incredible marine wildlife—keep your eyes peel... More

Special Offer
Free Cancellation
Private Tour
Start From $99.96
(Saving 16% ) $119.00
 
-16% Kona Tradewind Catamaran Day Sail Likely to Sell Out

Kona Tradewind Catamaran Day Sail

  • North America
  • Superb40 reviews4.8

Set sail aboard the spacious Honi Olani catamaran for a scenic 90-minute adventure along the stunnin....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $99.96
    (Saving 16% ) $119.00
 
 

2-Hour Private Sailing Experience in San Diego Bay

(5 of 167 reviews)

Our unique sail displays a peace sign because that is exactly what we share with our customers, peace. Peace is not always an easy thing to obtain in today's world. With all the stress life brings we are happy to provide a peacefu... More

Special Offer
Free Cancellation
Private Tour
Start From $562.50
(Saving 10% ) $625.00
 
-10% 2-Hour Private Sailing Experience in San Diego Bay Likely to Sell Out

2-Hour Private Sailing Experience in San Diego Bay

  • North America
  • Superb167 reviews5

Our unique sail displays a peace sign because that is exactly what we share with our customers, peac....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $562.50
    (Saving 10% ) $625.00
 
 

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
 
 

Discover the Magic of Coral Garden’s Turtle Town - Maalaea Harbor

(4.7 of 158 reviews)

Avoid the over-crowded 50-100 passenger boats. We take 30-40 passengers. Treat yourself and your loved ones to experience a beautiful Snorkeling, Sailing Cruise, and Whale Watching (Dec-Apr) on our Small Charming Hawaiian Catamara... More

Free Cancellation
Private Tour
Start From $159.00
 
Discover the Magic of Coral Garden’s Turtle Town - Maalaea Harbor Likely to Sell Out

Discover the Magic of Coral Garden’s Turtle Town - Maalaea Harb....

  • North America
  • Superb158 reviews4.7

Avoid the over-crowded 50-100 passenger boats. We take 30-40 passengers. Treat yourself and your lov....

    Free Cancellation
    Private Tour
    Start From $159.00
 
 

Deluxe Sail & Snorkel to the Captain Cook Monument

(4.9 of 464 reviews)

Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient lava flows. As you arrive at the "World Famous Captain Cook Monument" your snorkeling adventure will begin in the turquoise waters... More

Free Cancellation
Private Tour
Start From $179.27
 
Deluxe Sail & Snorkel to the Captain Cook Monument Likely to Sell Out

Deluxe Sail & Snorkel to the Captain Cook Monument

  • North America
  • Superb464 reviews4.9

Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient ....

    Free Cancellation
    Private Tour
    Start From $179.27
 
 

Sunset and Manta Ray Snorkel Adventure

(4.9 of 809 reviews)

Our most popular tour!  Watch a legendary Kona sunset from our spacious 50’ catamaran as you sail the Kona coast, followed by the adventure of a lifetime - snorkeling with the majestic manta rays!  Upon arriving, receive an in... More

Free Cancellation
Private Tour
Start From $145.41
 
Sunset and Manta Ray Snorkel Adventure Likely to Sell Out

Sunset and Manta Ray Snorkel Adventure

  • North America
  • Superb809 reviews4.9

Our most popular tour!  Watch a legendary Kona sunset from our spacious 50’ catamaran as you sail....

    Free Cancellation
    Private Tour
    Start From $145.41
 
 

Private Sailing Charter on San Diego Bay

(4.9 of 35 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 private charterÂ... More

Free Cancellation
Private Tour
Start From $475.00
 
Private Sailing Charter on San Diego Bay Likely to Sell Out

Private Sailing Charter on San Diego Bay

  • North America
  • Superb35 reviews4.9

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 $475.00
 
 

Luxury Sailing Tour of San Diego's Bay and Coastal Waterways

(4.9 of 202 reviews)

This is an engaging and unique, small group tour, of San Diego's beautiful bay and coastal waterways. You'll be on a beautiful Catalina 34' Sailboat enjoying the fresh air and best that San Diego has to offer. On your adventure yo... More

Free Cancellation
Private Tour
Start From $119.00
 
Luxury Sailing Tour of San Diego's Bay and Coastal Waterways Likely to Sell Out

Luxury Sailing Tour of San Diego's Bay and Coastal Waterways

  • North America
  • Superb202 reviews4.9

This is an engaging and unique, small group tour, of San Diego's beautiful bay and coastal waterways....

    Free Cancellation
    Private Tour
    Start From $119.00
 
 

Statue of Liberty Sunset Cruise and New York City Sky Line

(3.1 of 41 reviews)

New York City Sightseeing Scenic cruise. Enjoy the Statue of Liberty and Ellis Island up close. View of the Manhattan skyline, One World Trade Center and the Empire State Building.Enjoy a panoramic view of lower Manhattan as you p... More

Free Cancellation
Private Tour
Start From $35.99
 
Statue of Liberty Sunset Cruise and New York City Sky Line Likely to Sell Out

Statue of Liberty Sunset Cruise and New York City Sky Line

  • North America
  • Good41 reviews3.1

New York City Sightseeing Scenic cruise. Enjoy the Statue of Liberty and Ellis Island up close. View....

    Free Cancellation
    Private Tour
    Start From $35.99
 
 

Schooner Eastwind 2 Hour Day Sail in Boothbay Harbor

(4.6 of 125 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
  • Superb125 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
 
 

Sail Biscayne Bay: An Intimate Eco-Adventure with Snorkeling

(4.9 of 432 reviews)

This tour is an intimate experience, our groups are 3-5 people per boat maximum. We have two boats. We have been sailing the Biscayne Bay for over 15 years, just for the fun of it. We started this eco-tour in 2018 to share the ama... More

Free Cancellation
Private Tour
Start From $129.00
 
Sail Biscayne Bay: An Intimate Eco-Adventure with Snorkeling Likely to Sell Out

Sail Biscayne Bay: An Intimate Eco-Adventure with Snorkeling

  • North America
  • Superb432 reviews4.9

This tour is an intimate experience, our groups are 3-5 people per boat maximum. We have two boats. ....

    Free Cancellation
    Private Tour
    Start From $129.00
 
 

Panama City Beach Dolphin Sightseeing Sail

(4.8 of 116 reviews)

This cruise along the Gulf Coastline and Bay area offers a great opportunity to photograph local wildlife and scenery. At our onboard bar we have snacks and beverages available for purchase. Enjoy a variety of cocktails, including... More

Free Cancellation
Private Tour
Start From $35.00
 
Panama City Beach Dolphin Sightseeing Sail Likely to Sell Out

Panama City Beach Dolphin Sightseeing Sail

  • North America
  • Superb116 reviews4.8

This cruise along the Gulf Coastline and Bay area offers a great opportunity to photograph local wil....

    Free Cancellation
    Private Tour
    Start From $35.00
 
 

Sail on Tall Ship Windy, join us for our "Chicago Skyline Sail"

(4.8 of 20 reviews)

Join us for an unforgettable sail on Tall Ship Windy, Chicago's Official Tall Ship Ambassador! This is a relaxing sailing Adventure, that you will enjoy, on Lake Michigan, while enjoying the views, and the fresh air! Fun for all ... More

Free Cancellation
Private Tour
Start From $91.23
 
Sail on Tall Ship Windy, join us for our Likely to Sell Out

Sail on Tall Ship Windy, join us for our "Chicago Skyline Sail"

  • North America
  • Superb20 reviews4.8

Join us for an unforgettable sail on Tall Ship Windy, Chicago's Official Tall Ship Ambassador! This ....

    Free Cancellation
    Private Tour
    Start From $91.23
 
 

2 hour Tiki Pub Sensational Dolphin Sunset Cruise (Adults only)

(5 of 83 reviews)

Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages (BYOB), take pics, get some sun, make friends, play party games and have a blast! With a cozy capacity for 25, choose between mingling with new pal... More

Free Cancellation
Private Tour
Start From $69.00
 
2 hour Tiki Pub Sensational Dolphin Sunset Cruise (Adults only) Likely to Sell Out

2 hour Tiki Pub Sensational Dolphin Sunset Cruise (Adults only)

  • North America
  • Superb83 reviews5

Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages (BYOB), take pics,....

    Free Cancellation
    Private Tour
    Start From $69.00
 
 

Sunset Sail on a Small Charming Hawaiian Catamaran Maalaea Harbor

(4.8 of 82 reviews)

Experience the resilience and spirit of Maui aboard the Winona, a vessel that bravely survived the Lahaina harbor wildfires, moored outside of the harbor breakwall. Now operating from Ma'alaea Harbor, we invite you to join our cap... More

Free Cancellation
Private Tour
Start From $119.00
 
Sunset Sail on a Small Charming Hawaiian Catamaran Maalaea Harbor Likely to Sell Out

Sunset Sail on a Small Charming Hawaiian Catamaran Maalaea Harbor

  • North America
  • Superb82 reviews4.8

Experience the resilience and spirit of Maui aboard the Winona, a vessel that bravely survived the L....

    Free Cancellation
    Private Tour
    Start From $119.00
 
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