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Top 10 Best North America Sailing Trips

Found 755 Sailing Trips activities in North America. Sort by Popularity. - Page 7
 

Monterey Bay Whale Watching

(4.6 of 324 reviews)

Sea Goddess Whale Watching promises a once-in-a-lifetime whale watching experience. Our whale watching tours depart from Moss Landing, right at the mouth of the Monterey Bay Canyon, one of the largest underwater canyons in the wor... More

Free Cancellation
Start From $69.95
 
Monterey Bay Whale Watching Likely to Sell Out

Monterey Bay Whale Watching

  • North America
  • Superb324 reviews4.6

Sea Goddess Whale Watching promises a once-in-a-lifetime whale watching experience. Our whale watchi....

    Free Cancellation
    Start From $69.95
 
 

Private Boat - Snorkeling, Star Island & Dolphin Spotting

(4.5 of 61 reviews)

Step aboard one of the top-rated boat tours in Miami, rated 4.9 stars on Google with over 1.2k reviews. Connect your phone & be your own DJ—bring your own food, drinks & alcohol. Our boat is fully equipped with a Bluetooth sound... More

Free Cancellation
Private Tour
Start From $65.00
 
Private Boat - Snorkeling, Star Island & Dolphin Spotting Likely to Sell Out

Private Boat - Snorkeling, Star Island & Dolphin Spotting

  • North America
  • Exellent61 reviews4.5

Step aboard one of the top-rated boat tours in Miami, rated 4.9 stars on Google with over 1.2k revie....

    Free Cancellation
    Private Tour
    Start From $65.00
 
 

Sunset Sailing Cruise in Monterey Bay

(4.8 of 40 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
Private Tour
Start From $95.00
 
Sunset Sailing Cruise in Monterey Bay Likely to Sell Out

Sunset Sailing Cruise in Monterey Bay

  • North America
  • Superb40 reviews4.8

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

    Free Cancellation
    Private Tour
    Start From $95.00
 
 

Private Sailing Charter on San Diego Bay

(4.9 of 43 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 charter... 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
  • Superb43 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
 
 

Kona Tradewind Catamaran Day Sail

(4.8 of 43 reviews)

Experience the beauty of the Kona Coast from a new perspective aboard the Spirit of Aloha sailing catamaran. Feel the trade winds fill the sails as you glide across the water, taking in panoramic views of volcanic cliffs, sparklin... More

Free Cancellation
Private Tour
Start From $89.00
 
Kona Tradewind Catamaran Day Sail Likely to Sell Out

Kona Tradewind Catamaran Day Sail

  • North America
  • Superb43 reviews4.8

Experience the beauty of the Kona Coast from a new perspective aboard the Spirit of Aloha sailing ca....

    Free Cancellation
    Private Tour
    Start From $89.00
 
 

Amazing Romantic Dinner on a Spanish Galeon with Saxophone Music

(4.6 of 109 reviews)

Have you run out of ideas to celebrate love with your partner? Imagine reconquering your true love. In Cancun, you have an incredible opportunity to fall in love again at the rhythm of the live sax with a sunset as enchanting as t... More

Free Cancellation
Private Tour
Start From $95.00
 
Amazing Romantic Dinner on a Spanish Galeon with Saxophone Music Likely to Sell Out

Amazing Romantic Dinner on a Spanish Galeon with Saxophone Music

  • North America
  • Superb109 reviews4.6

Have you run out of ideas to celebrate love with your partner? Imagine reconquering your true love. ....

    Free Cancellation
    Private Tour
    Start From $95.00
 
 

Premium Isla Mujeres Tour by Private Catamaran

(4.9 of 339 reviews)

We specialize in making this all-day trip unique, a unique and beautiful experience for all our guests. This trip can always be customized as desired, as we offer 2 options to our customers. Our trained team is always there to pro... More

Free Cancellation
Private Tour
Start From $950.00
 
Premium Isla Mujeres Tour by Private Catamaran Likely to Sell Out

Premium Isla Mujeres Tour by Private Catamaran

  • North America
  • Superb339 reviews4.9

We specialize in making this all-day trip unique, a unique and beautiful experience for all our gues....

    Free Cancellation
    Private Tour
    Start From $950.00
 
 

Sunset and Manta Ray Snorkel Adventure

(4.9 of 854 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 $154.51
 
Sunset and Manta Ray Snorkel Adventure Likely to Sell Out

Sunset and Manta Ray Snorkel Adventure

  • North America
  • Superb854 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 $154.51
 
 

'Alihilani Golden Hour Sail

(4.9 of 86 reviews)

We pride ourselves on sailing, so enjoy the natural sounds as we turn of our motors and raise our sails. Our spacious catamarans make for a luxurious experience, allowing for incredible views of Maui and the inter islands from the... More

Free Cancellation
Private Tour
Start From $107.10
 
'Alihilani Golden Hour Sail Likely to Sell Out

'Alihilani Golden Hour Sail

  • North America
  • Superb86 reviews4.9

We pride ourselves on sailing, so enjoy the natural sounds as we turn of our motors and raise our sa....

    Free Cancellation
    Private Tour
    Start From $107.10
 
 

2-Hour Oahu Sunset Catamaran Sail

(4.8 of 127 reviews)

Relax, sit back and delight in our 2-hour sunset sailing cruise on a gorgeous, 53' foot catamaran from the beautiful Ko Olina Marina on Oahu. Sip a cocktail and enjoy warm wind in your hair as you scan for dolphins and listen for ... More

Free Cancellation
Private Tour
Start From $130.00
 
2-Hour Oahu Sunset Catamaran Sail Likely to Sell Out

2-Hour Oahu Sunset Catamaran Sail

  • North America
  • Superb127 reviews4.8

Relax, sit back and delight in our 2-hour sunset sailing cruise on a gorgeous, 53' foot catamaran fr....

    Free Cancellation
    Private Tour
    Start From $130.00
 
 

Key West Historic Schooner When And If Sunset Cruise

(4.9 of 129 reviews)

Historic Schooner. Champagne Sunset Toast. Elegant and Exclusive. Step aboard the historic schooner When And If, commissioned by General George Patton in the late 1930s, and sail into a breathtaking Key West sunset. Raise a champ... More

Free Cancellation
Private Tour
Start From $109.00
 
Key West Historic Schooner When And If Sunset Cruise Likely to Sell Out

Key West Historic Schooner When And If Sunset Cruise

  • North America
  • Superb129 reviews4.9

Historic Schooner. Champagne Sunset Toast. Elegant and Exclusive. Step aboard the historic schooner....

    Free Cancellation
    Private Tour
    Start From $109.00
 
 

Newport Sunset Sail on Classic Sailboat

(4.8 of 42 reviews)

Sunset sailing is one of the best evening activities to do during your stay in Newport, RI. Enjoy a relaxing sail around Narragansett Bay on a classic sailboat and see all of Newport's iconic sights from the water including histor... More

Free Cancellation
Private Tour
Start From $67.84
 
Newport Sunset Sail on Classic Sailboat Likely to Sell Out

Newport Sunset Sail on Classic Sailboat

  • North America
  • Superb42 reviews4.8

Sunset sailing is one of the best evening activities to do during your stay in Newport, RI. Enjoy a ....

    Free Cancellation
    Private Tour
    Start From $67.84
 
 

Cancun Adults Only Party Cruise to Isla Mujeres with Open Bar

(3.7 of 208 reviews)

Take a Party Cruise Adult Only from Cancun to Isla Mujeres. Make a stop to snorkel at one of the best reefs and see beautiful tropical fish. Enjoy a delicious buffet lunch on our private beach club, and then tour Isla Mujeres to s... More

Free Cancellation
Private Tour
Start From $69.99
 
Cancun Adults Only Party Cruise to Isla Mujeres with Open Bar Likely to Sell Out

Cancun Adults Only Party Cruise to Isla Mujeres with Open Bar

  • North America
  • Very Good208 reviews3.7

Take a Party Cruise Adult Only from Cancun to Isla Mujeres. Make a stop to snorkel at one of the bes....

    Free Cancellation
    Private Tour
    Start From $69.99
 
 

Whale-Watching Pirate Ship Cruise in Los Cabos

(4.7 of 119 reviews)

Go whale-watching in Cabo San Lucas aboard a real pirate ship called the Bucaneer Queen. Sail the Pacific Ocean and the Sea of Cortez in search of these amazing creatures. You will be accompanied by an experienced bilingual guide ... More

Free Cancellation
Private Tour
Start From $99.00
 
Whale-Watching Pirate Ship Cruise in Los Cabos Likely to Sell Out

Whale-Watching Pirate Ship Cruise in Los Cabos

  • North America
  • Superb119 reviews4.7

Go whale-watching in Cabo San Lucas aboard a real pirate ship called the Bucaneer Queen. Sail the Pa....

    Free Cancellation
    Private Tour
    Start From $99.00
 
 

Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea

(4.8 of 292 reviews)

Our rainbow sails can be spotted from miles away. While on board you may capture such nice photos with the rainbow sails and also the beautiful scenery with Diamond head in the background. The net is also a fun ride and you’ll g... More

Free Cancellation
Private Tour
Start From $72.96
 
Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea Likely to Sell Out

Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea

  • North America
  • Superb292 reviews4.8

Our rainbow sails can be spotted from miles away. While on board you may capture such nice photos wi....

    Free Cancellation
    Private Tour
    Start From $72.96
 
 

El Cielo Cozumel Snorkeling trip by Catamaran

(4.4 of 281 reviews)

TRAVELER’S FAVORITE TRIP! Get in the mood for fun aboard your Catamaran in a fun sail to magnificent reefs and great snorkeling and after, head back to a secluded Beach to relax and enjoy the beauty of Cozumel turquoise waters.... More

Free Cancellation
Private Tour
Start From $95.00
 
El Cielo Cozumel Snorkeling trip by Catamaran Likely to Sell Out

El Cielo Cozumel Snorkeling trip by Catamaran

  • North America
  • Exellent281 reviews4.4

TRAVELER’S FAVORITE TRIP! Get in the mood for fun aboard your Catamaran in a fun sail to magnific....

    Free Cancellation
    Private Tour
    Start From $95.00
 
 

Snorkel & Millionaire Row - Private Miami Boat Rental w/ Drinks

(4.8 of 269 reviews)

Step aboard one of the top-rated boat tours in Miami, rated 4.9 stars on Google with over 1.2k reviews. Connect your phone & be your own DJ—bring your own food, drinks & alcohol. Our boat is fully equipped with a Bluetooth sound... More

Free Cancellation
Private Tour
Start From $150.00
 
Snorkel & Millionaire Row - Private Miami Boat Rental w/ Drinks Likely to Sell Out

Snorkel & Millionaire Row - Private Miami Boat Rental w/ Drinks

  • North America
  • Superb269 reviews4.8

Step aboard one of the top-rated boat tours in Miami, rated 4.9 stars on Google with over 1.2k revie....

    Free Cancellation
    Private Tour
    Start From $150.00
 
 

Lagoon 39ft Private Catamaran 5hr - El Cielo Full Experience

(5 of 632 reviews)

Our 5 Hrs private charter delivers the ultimate all-inclusive vacation on the water aboard your own private catamaran. Complete with a professional captain & crew , your group will enjoy spacious accommodations and a premium, pers... More

Free Cancellation
Private Tour
Start From $2,200.00
 
Lagoon 39ft Private Catamaran 5hr - El Cielo Full Experience Likely to Sell Out

Lagoon 39ft Private Catamaran 5hr - El Cielo Full Experience

  • North America
  • Superb632 reviews5

Our 5 Hrs private charter delivers the ultimate all-inclusive vacation on the water aboard your own ....

    Free Cancellation
    Private Tour
    Start From $2,200.00
 
 

Deluxe Day Sail in San Diego

(5 of 67 reviews)

Set sail with San Diego Sailing Excursions and discover what sets us apart from the rest. Our personalized day sailing experiences on the San Diego Bay offer a perfect blend of adventure and relaxation. With our passionate and kno... More

Free Cancellation
Private Tour
Start From $119.00
 
Deluxe Day Sail in San Diego Likely to Sell Out

Deluxe Day Sail in San Diego

  • North America
  • Superb67 reviews5

Set sail with San Diego Sailing Excursions and discover what sets us apart from the rest. Our person....

    Free Cancellation
    Private Tour
    Start From $119.00
 
 

New York Sunset Schooner Cruise on the Hudson River

(4.9 of 222 reviews)

Experience a New York City sunset from the water on this evening sightseeing sail past many famous waterside landmarks. Step aboard the 80-foot, 2-masted sailboat known as Schooner Adirondack - inspired by the pilot schooners of... More

Free Cancellation
Private Tour
Start From $90.12
 
New York Sunset Schooner Cruise on the Hudson River Likely to Sell Out

New York Sunset Schooner Cruise on the Hudson River

  • North America
  • Superb222 reviews4.9

Experience a New York City sunset from the water on this evening sightseeing sail past many famous w....

    Free Cancellation
    Private Tour
    Start From $90.12
 
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