Menu

Top 10 Best North America Sailing Trips

Found 755 Sailing Trips activities in North America. Sort by Popularity. - Page 18
 

Private Sailing Tour through the Ten Thousands Islands

(4.9 of 152 reviews)

If you like to sail but have never been on a stiletto catamaran then are missing out! The stilettos where built in the early 80s and are known through out the sailing community as the fastest, driest, beachable catamaran on the ma... More

Private Tour
Start From $450.00
 
Private Sailing Tour through the Ten Thousands Islands Likely to Sell Out

Private Sailing Tour through the Ten Thousands Islands

  • North America
  • Superb152 reviews4.9

If you like to sail but have never been on a stiletto catamaran then are missing out! The stilettos ....

    Private Tour
    Start From $450.00
 
 

Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure

(5 of 705 reviews)

Join us aboard our luxurious 50’ catamaran “Kona Style”, as we sail the Kona coast. Scan the horizon for dolphins and whales (seasonal) from our shaded cabin or sunny splash nets. Snorkel calm waters and lush coral gardens u... More

Free Cancellation
Private Tour
Start From $189.00
 
Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure Likely to Sell Out

Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure

  • North America
  • Superb705 reviews5

Join us aboard our luxurious 50’ catamaran “Kona Style”, as we sail the Kona coast. Scan the h....

    Free Cancellation
    Private Tour
    Start From $189.00
 
 

Okanagan Lake Sailing Tour from Penticton & Naramata BC

(5 of 48 reviews)

Sailing is a life changing experience! In four hours, you will help sail a large sailing yacht into the sunny waters of Okanagan Lake. We provide hands on instruction and lots of opportunities to learn or just relax. And it is ... More

Free Cancellation
Private Tour
Start From $186.94
 
Okanagan Lake Sailing Tour from Penticton & Naramata BC Likely to Sell Out

Okanagan Lake Sailing Tour from Penticton & Naramata BC

  • North America
  • Superb48 reviews5

Sailing is a life changing experience! In four hours, you will help sail a large sailing yacht int....

    Free Cancellation
    Private Tour
    Start From $186.94
 
 

Sunset & Dolphin Sightseeing Sail Aboard the Lazy Daze Catamaran

(5 of 1 review)

Your 90 minute sunset sail on 41ft, 32 passenger Lazy Daze Catamaran will include a scenic trip through Grand Lagoon and along the coast of Shell Island. Enjoy a relaxing sail in the Gulf of Mexico and look for dolphins along the ... More

Free Cancellation
Private Tour
Start From $40.00
 
Sunset & Dolphin Sightseeing Sail Aboard the Lazy Daze Catamaran Likely to Sell Out

Sunset & Dolphin Sightseeing Sail Aboard the Lazy Daze Catamaran

  • North America
  • Superb1 review5

Your 90 minute sunset sail on 41ft, 32 passenger Lazy Daze Catamaran will include a scenic trip thro....

    Free Cancellation
    Private Tour
    Start From $40.00
 
 

Sunrise by Paddle or Kayak with Floating Picnic

(5 of 367 reviews)

Dare to live a new experience! During this activity you will connect with your ecological SELF as you paddle towards sunrise. Enjoy a delicious picnic in a natural environment while you immerse yourself in warm and crystal clear w... More

Free Cancellation
Private Tour
Start From $29.57
 
Sunrise by Paddle or Kayak with Floating Picnic Likely to Sell Out

Sunrise by Paddle or Kayak with Floating Picnic

  • North America
  • Superb367 reviews5

Dare to live a new experience! During this activity you will connect with your ecological SELF as yo....

    Free Cancellation
    Private Tour
    Start From $29.57
 
 

Sail Seattle's Iconic Lake Union All Year Around

(5 of 367 reviews)

Relax, take in the views, and discover why Lake Union, in the very heart of Seattle, is one of the city's most fascinating—and beautiful—places to explore. Your captain, Grant, born and raised in the great Northwest, has bee... More

Special Offer
Free Cancellation
Private Tour
Start From $100.00
(Saving 20% ) $125.00
 
-20% Sail Seattle's Iconic Lake Union All Year Around Likely to Sell Out

Sail Seattle's Iconic Lake Union All Year Around

  • North America
  • Superb367 reviews5

Relax, take in the views, and discover why Lake Union, in the very heart of Seattle, is one of the c....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $100.00
    (Saving 20% ) $125.00
 
 

Pirate Ship Yo Ho! Sunset Show and BBQ Dinner in Cabo San Lucas

(2.7 of 3 reviews)

The Yo Ho Show pirate cruise in Los Cabos offers an unforgettable experience full of action and entertainment. Two boats face off in the bay, presenting a vibrant show with jugglers, aerial acrobats and fire dances. Enjoy a delici... More

Free Cancellation
Private Tour
Start From $127.78
 
Pirate Ship Yo Ho! Sunset Show and BBQ Dinner in Cabo San Lucas Likely to Sell Out

Pirate Ship Yo Ho! Sunset Show and BBQ Dinner in Cabo San Lucas

  • North America

The Yo Ho Show pirate cruise in Los Cabos offers an unforgettable experience full of action and ente....

    Free Cancellation
    Private Tour
    Start From $127.78
 
 

Clear Boat to Cabo Lands End, The Arch and more

(4.5 of 15 reviews)

Are you ready for an unforgettable experience? Come to visit the spectacular sea of Los Cabos, most uniquely, in a clear boat. You will take a tour just where the Pacific Ocean meets the Sea of Cortez, the famous Lands End. In our... More

Free Cancellation
Private Tour
Start From $39.00
 
Clear Boat to Cabo Lands End, The Arch and more Likely to Sell Out

Clear Boat to Cabo Lands End, The Arch and more

  • North America
  • Exellent15 reviews4.5

Are you ready for an unforgettable experience? Come to visit the spectacular sea of Los Cabos, most ....

    Free Cancellation
    Private Tour
    Start From $39.00
 
 

Safari Sea of Cortes al Natural

(4.5 of 15 reviews)

What makes this experience unique is the combination of specialized guidance, authentic encounters with marine life and a focused operation in small groups, in one of the most impressive ecosystems in the world. We include round ... More

Free Cancellation
Private Tour
Start From $224.76
 
Safari Sea of Cortes al Natural Likely to Sell Out

Safari Sea of Cortes al Natural

  • North America
  • Exellent15 reviews4.5

What makes this experience unique is the combination of specialized guidance, authentic encounters w....

    Free Cancellation
    Private Tour
    Start From $224.76
 
 

Key West Dolphin Watch and Sunset Sail on Catamaran

(4.7 of 39 reviews)

Aboard our spacious 42-foot sailing catamaran, you'll experience the pure joy of sailing as the lightweight boat glides across the water, catching every gust of wind. This tour is perfect for all ages and offers a wide-open, unobs... More

Free Cancellation
Private Tour
Start From $117.17
 
Key West Dolphin Watch and Sunset Sail on Catamaran Likely to Sell Out

Key West Dolphin Watch and Sunset Sail on Catamaran

  • North America
  • Superb39 reviews4.7

Aboard our spacious 42-foot sailing catamaran, you'll experience the pure joy of sailing as the ligh....

    Free Cancellation
    Private Tour
    Start From $117.17
 
 

6hrs of Sailing in Bacalar Lagoon: discover Cenotes, Islands and Stromatolites.

(5 of 20 reviews)

Ideal for adventurers and sailing lovers! Explore the most emblematic points of the lagoon, or modify the route to discover areas far from tourism. 6 hours of deep exploration and adventure where you can get to know: The Pirate Ch... More

Free Cancellation
Private Tour
Start From $467.26
 
6hrs of Sailing in Bacalar Lagoon: discover Cenotes, Islands and Stromatolites. Likely to Sell Out

6hrs of Sailing in Bacalar Lagoon: discover Cenotes, Islands and ....

  • North America
  • Superb20 reviews5

Ideal for adventurers and sailing lovers! Explore the most emblematic points of the lagoon, or modif....

    Free Cancellation
    Private Tour
    Start From $467.26
 
 

Sailing Snorkel Adventure

(4.5 of 6 reviews)

Interactive Sailing Adventure, Snorkeling, Surf Up Paddle, Premium Bar and Incredible views. This Sailing Boat Adventure is unbeatable Value.... More

Free Cancellation
Private Tour
Start From $149.00
 
Sailing Snorkel Adventure Likely to Sell Out

Sailing Snorkel Adventure

  • North America
  • Exellent6 reviews4.5

Interactive Sailing Adventure, Snorkeling, Surf Up Paddle, Premium Bar and Incredible views. This Sa....

    Free Cancellation
    Private Tour
    Start From $149.00
 
 

Sunset Dolphin Sail Aboard the Daydreams Sailboat

(4.9 of 34 reviews)

Your 2 hour sunset charter on our 47-foot sailboat Daydreams will include a scenic trip through Grand Lagoon and along the coast of Shell Island. Enjoy a relaxing sail in the Gulf of Mexico and look for dolphins along the way. Wit... More

Free Cancellation
Private Tour
Start From $99.00
 
Sunset Dolphin Sail Aboard the Daydreams Sailboat Likely to Sell Out

Sunset Dolphin Sail Aboard the Daydreams Sailboat

  • North America
  • Superb34 reviews4.9

Your 2 hour sunset charter on our 47-foot sailboat Daydreams will include a scenic trip through Gran....

    Free Cancellation
    Private Tour
    Start From $99.00
 
 

JFarwell Adventure Yacht Sailing in the Halifax Harbour

(5 of 147 reviews)

Halifax's only wind powered sailing experience! This 45' Oceanis Beneteau handles beautifully on the water, and offers a great introduction to sailing. Guests are encouraged to be as hands on with the sailing process as they would... More

Free Cancellation
Private Tour
Start From $82.25
 
JFarwell Adventure Yacht Sailing in the Halifax Harbour Likely to Sell Out

JFarwell Adventure Yacht Sailing in the Halifax Harbour

  • North America
  • Superb147 reviews5

Halifax's only wind powered sailing experience! This 45' Oceanis Beneteau handles beautifully on the....

    Free Cancellation
    Private Tour
    Start From $82.25
 
 

Waikiki Sunset Cruise Catamaran Boat Tour on Oahu

(4.7 of 17 reviews)

Our tour offers a plethora of beautiful views such as Waikiki bay itself, Diamond head crater (Lē‘ahi), crystal blue waters, a gorgeous sunset, and from December-March, of course, the annual humpback whales!... More

Free Cancellation
Private Tour
Start From $70.00
 
Waikiki Sunset Cruise Catamaran Boat Tour on Oahu Likely to Sell Out

Waikiki Sunset Cruise Catamaran Boat Tour on Oahu

  • North America
  • Superb17 reviews4.7

Our tour offers a plethora of beautiful views such as Waikiki bay itself, Diamond head crater (Lē....

    Free Cancellation
    Private Tour
    Start From $70.00
 
 

Private Sunset Catamaran Sail in Cocoa Beach

(4.7 of 17 reviews)

Experience a magical sunset in with Cocoa Beach Catamaran Set sail into the golden hour and enjoy a stunning evening on the serene waters of the Banana River Lagoon. Our Sunset Sail is the perfect way to relax and take in the bea... More

Free Cancellation
Private Tour
Start From $337.87
 
Private Sunset Catamaran Sail in Cocoa Beach Likely to Sell Out

Private Sunset Catamaran Sail in Cocoa Beach

  • North America
  • Superb17 reviews4.7

Experience a magical sunset in with Cocoa Beach Catamaran Set sail into the golden hour and enjoy a....

    Free Cancellation
    Private Tour
    Start From $337.87
 
 

Fins Up - Dolphin & Island Sandbar Adventure in Clearwater Beach

(4.6 of 55 reviews)

Guaranteed Dolphin Siting! Set Sail for Adventure. Explore Clearwater Beach on an Unforgettable Dolphin, Island Swim & Sunset Cruises. Enjoy your Island Sandbar stop at One Tree Island, where you can enjoy the beautiful waters... More

Free Cancellation
Private Tour
Start From $34.95
 
Fins Up - Dolphin & Island Sandbar Adventure in Clearwater Beach Likely to Sell Out

Fins Up - Dolphin & Island Sandbar Adventure in Clearwater Beach

  • North America
  • Superb55 reviews4.6

Guaranteed Dolphin Siting! Set Sail for Adventure. Explore Clearwater Beach on an Unforgettable Do....

    Free Cancellation
    Private Tour
    Start From $34.95
 
 

All Inclusive Beach Club, Water Sports, Horse Ride, Food & Drinks

(3.8 of 13 reviews)

Introducing the ultimate beach getaway - Stone Island! This all-inclusive package offers an unbeatable experience with unlimited drinks, mouth-watering lunch, and your choice of two exciting activities. Whether you want to ride ho... More

Free Cancellation
Private Tour
Start From $59.00
 
All Inclusive Beach Club, Water Sports, Horse Ride, Food & Drinks Likely to Sell Out

All Inclusive Beach Club, Water Sports, Horse Ride, Food & Drinks

  • North America
  • Very Good13 reviews3.8

Introducing the ultimate beach getaway - Stone Island! This all-inclusive package offers an unbeatab....

    Free Cancellation
    Private Tour
    Start From $59.00
 
 

Tiki Pub Amazing Dolphin Eco Adventure

(4.8 of 5 reviews)

Join us for an Environmentalist led Adventure! Go to Sandbars and Beaches to see our shallow water inhabitants, cruise the bay for Dolphins, Manatee, and a myriad of sea creatures and incredible Birds! The best part is that then y... More

Free Cancellation
Private Tour
Start From $49.95
 
Tiki Pub Amazing Dolphin Eco Adventure Likely to Sell Out

Tiki Pub Amazing Dolphin Eco Adventure

  • North America
  • Superb5 reviews4.8

Join us for an Environmentalist led Adventure! Go to Sandbars and Beaches to see our shallow water i....

    Free Cancellation
    Private Tour
    Start From $49.95
 
 

Escape from the Rock! Cruise around Alcatraz

(4.2 of 157 reviews)

Embark on a 90-minute cruise along the San Francisco waterfront, under the Golden Gate Bridge and past Angel Island State Park before circling Alcatraz Island for an in-depth view of the prison. Take in the sights and sounds of ... More

Free Cancellation
Private Tour
Start From $48.00
 
Escape from the Rock! Cruise around Alcatraz Likely to Sell Out

Escape from the Rock! Cruise around Alcatraz

  • North America
  • Exellent157 reviews4.2

Embark on a 90-minute cruise along the San Francisco waterfront, under the Golden Gate Bridge and ....

    Free Cancellation
    Private Tour
    Start From $48.00
 
Booking.com
Booking.com
Booking.com