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Top 10 Best North America Sailing Trips

Found 712 Sailing Trips activities in North America. Sort by Popularity. - Page 14
 

Sunset Cruise with the Whales from Anaeho'omalu Bay

(4.8 of 46 reviews)

Combine unparalleled views of the Hawaiian coastline from a stable and spacious catamaran with the biggest guests of all -- the Humpback Whales -- and you have perfect way to begin your evening in paradise! Cruise along the Kohala... More

Free Cancellation
Start From $165.00
 
Sunset Cruise with the Whales from Anaeho'omalu Bay

Sunset Cruise with the Whales from Anaeho'omalu Bay

  • North America
  • Superb46 reviews4.8

Combine unparalleled views of the Hawaiian coastline from a stable and spacious catamaran with the b....

    Free Cancellation
    Start From $165.00
 
 

Deluxe private Sunset & Day Sail

(5 of 2 reviews)

Set sail on the ultimate San Diego adventure! Departing from 955 Harbor Island Drive, our thrilling voyage takes you through breathtaking waters, past iconic landmarks, and into the heart of coastal paradise. Feel the wind in your... More

Free Cancellation
Private Tour
Start From $714.00
 
Deluxe private Sunset & Day Sail Likely to Sell Out

Deluxe private Sunset & Day Sail

  • North America
  • Superb2 reviews5

Set sail on the ultimate San Diego adventure! Departing from 955 Harbor Island Drive, our thrilling ....

    Free Cancellation
    Private Tour
    Start From $714.00
 
 

Bacalar Lagoon Tour Open Bar With Pick Up

(4.9 of 78 reviews)

What makes our tour unique: • Multilingual captain: English, French and Spanish. • Comfortable pickup from your hotel in van. • Cold drinks and Mexican snacks during the tour. • Snorkeling and water games for children... More

Free Cancellation
Private Tour
Start From $48.14
 
Bacalar Lagoon Tour Open Bar With Pick Up Likely to Sell Out

Bacalar Lagoon Tour Open Bar With Pick Up

  • North America
  • Superb78 reviews4.9

What makes our tour unique: • Multilingual captain: English, French and Spanish. • Comfortabl....

    Free Cancellation
    Private Tour
    Start From $48.14
 
 

Polynesian Canoe Morning Sail

(5 of 18 reviews)

Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) offering a one-of-a-kind native Hawaiian cultural and educational experience. Come sail along the beautiful Waikiki coastline and b... More

Free Cancellation
Private Tour
Start From $200.00
 
Polynesian Canoe Morning Sail Likely to Sell Out

Polynesian Canoe Morning Sail

  • North America
  • Superb18 reviews5

Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) o....

    Free Cancellation
    Private Tour
    Start From $200.00
 
 

Serene Private Sunset Sail on Lake Michigan - Navy Pier, Chicago

(5 of 27 reviews)

Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront. Kick back, relax, and let the US Coast Guard licensed captain treat you to stunning views of Chicago’s spectacular skyline. ... More

Free Cancellation
Private Tour
Start From $507.96
 
Serene Private Sunset Sail on Lake Michigan - Navy Pier, Chicago Likely to Sell Out

Serene Private Sunset Sail on Lake Michigan - Navy Pier, Chicago

  • North America
  • Superb27 reviews5

Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefro....

    Free Cancellation
    Private Tour
    Start From $507.96
 
 

HipHop Catamaran Party from Cancun to Isla Mujeres

(4 of 11 reviews)

Unlike other tours, we combine adventure, relaxation, and an unforgettable party vibe. Start by snorkeling in one of the Caribbean's top reefs, surrounded by vibrant marine life. Then, head to a secluded sandbank—a hidden gem pe... More

Free Cancellation
Private Tour
Start From $42.00
 
HipHop Catamaran Party from Cancun to Isla Mujeres Likely to Sell Out

HipHop Catamaran Party from Cancun to Isla Mujeres

  • North America
  • Very Good11 reviews4

Unlike other tours, we combine adventure, relaxation, and an unforgettable party vibe. Start by snor....

    Free Cancellation
    Private Tour
    Start From $42.00
 
 

Clear Boat to Cabo Lands End, The Arch and more

(4.4 of 12 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

Special Offer
Free Cancellation
Private Tour
Start From $35.10
(Saving 10% ) $39.00
 
-10% 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
  • Exellent12 reviews4.4

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

    Special Offer
    Free Cancellation
    Private Tour
    Start From $35.10
    (Saving 10% ) $39.00
 
 

Los Cabos Catamaran Cruise with Open Bar & Light Snack

(3.9 of 8 reviews)

Experience Los Cabos from the best seat in the house — aboard a spacious catamaran cruising past its most iconic landmarks. Sail along the dazzling Cabo coastline to The Arch (El Arco), Lover’s Beach, and Divorce Beach, where ... More

Free Cancellation
Private Tour
Start From $75.00
 
Los Cabos Catamaran Cruise with Open Bar & Light Snack Likely to Sell Out

Los Cabos Catamaran Cruise with Open Bar & Light Snack

  • North America
  • Very Good8 reviews3.9

Experience Los Cabos from the best seat in the house — aboard a spacious catamaran cruising past i....

    Free Cancellation
    Private Tour
    Start From $75.00
 
 

Private Sunset Catamaran Sail in Cocoa Beach

(3.9 of 8 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
  • Very Good8 reviews3.9

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
 
 

Private Sunset Sail BYOB Dolphin/History Tours on 43ft Mystique

(5 of 42 reviews)

Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charter company in Charleston's history. #1 activity on Tripadvisor for over 12 years, our sailing yachts are the highest quality and op... More

Free Cancellation
Private Tour
Start From $550.00
 
Private Sunset Sail BYOB Dolphin/History Tours on 43ft Mystique Likely to Sell Out

Private Sunset Sail BYOB Dolphin/History Tours on 43ft Mystique

  • North America
  • Superb42 reviews5

Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charte....

    Free Cancellation
    Private Tour
    Start From $550.00
 
 

Whale-Watching Pirate Ship Cruise in Los Cabos

(4.7 of 98 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 $89.00
 
Whale-Watching Pirate Ship Cruise in Los Cabos Likely to Sell Out

Whale-Watching Pirate Ship Cruise in Los Cabos

  • North America
  • Superb98 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 $89.00
 
 

Private Sunset Sail for Two

(5 of 5 reviews)

Experience intimacy while sailing along the San Diego Bay. Leave your worries behind as you cruise along the vibrant waterfront and marvel at the cityscape. Create a memory of a lifetime while sailing past Downtown, Point Loma, an... More

Free Cancellation
Private Tour
Start From $462.00
 
Private Sunset Sail for Two Likely to Sell Out

Private Sunset Sail for Two

  • North America
  • Superb5 reviews5

Experience intimacy while sailing along the San Diego Bay. Leave your worries behind as you cruise a....

    Free Cancellation
    Private Tour
    Start From $462.00
 
 

Key West Christmas Cruise with Live Band and Drinks

(5 of 3 reviews)

Join us for a family-friendly holiday sail aboard Schooner America 2.0 decorated with festive Christmas lights! Sing along to your favorite Christmas music with our live band and celebrate the holidays and Christmas in Key West. E... More

Free Cancellation
Private Tour
Start From $97.61
 
Key West Christmas Cruise with Live Band and Drinks Likely to Sell Out

Key West Christmas Cruise with Live Band and Drinks

  • North America
  • Superb3 reviews5

Join us for a family-friendly holiday sail aboard Schooner America 2.0 decorated with festive Christ....

    Free Cancellation
    Private Tour
    Start From $97.61
 
 

Vancouver Sailing Experience on a 50 foot Sailboat

(5 of 100 reviews)

I have been living aboard full time for the past 12 years, sailing the Vancouver waterways for over 45 years. I have raced competitively for 20 of those, have extensive sailing and local knowledge, 12 years experience volunteering... More

Free Cancellation
Private Tour
Start From $109.91
 
Vancouver Sailing Experience on a 50 foot Sailboat Likely to Sell Out

Vancouver Sailing Experience on a 50 foot Sailboat

  • North America
  • Superb100 reviews5

I have been living aboard full time for the past 12 years, sailing the Vancouver waterways for over ....

    Free Cancellation
    Private Tour
    Start From $109.91
 
 

12pm Turtle Canyon Snorkel Adventure

(4.8 of 300 reviews)

What better way to start your day than to slip into the refreshing waters of Turtle Canyon and swim with amazing green sea turtles, beautiful tropical fish, and other incredible marine life? Our snorkel guides help you feel confid... More

Special Offer
Free Cancellation
Private Tour
Start From $72.05
(Saving 15% ) $84.77
 
-15% 12pm Turtle Canyon Snorkel Adventure Likely to Sell Out

12pm Turtle Canyon Snorkel Adventure

  • North America
  • Superb300 reviews4.8

What better way to start your day than to slip into the refreshing waters of Turtle Canyon and swim ....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $72.05
    (Saving 15% ) $84.77
 
 

Private boat for 6 hours with snorkeling & beaches in Puerto Vallarta

(5 of 2 reviews)

Sail on a private trip aboard our 26-foot boat. Ideal for up to 8 passengers. We are sure that with us you will know the best part of our beautiful bay of Puerto Vallarta. Do not miss the opportunity we offer you to make this rese... More

Free Cancellation
Private Tour
Start From $953.79
 
Private boat for 6 hours with snorkeling & beaches in Puerto Vallarta Likely to Sell Out

Private boat for 6 hours with snorkeling & beaches in Puerto Vall....

  • North America
  • Superb2 reviews5

Sail on a private trip aboard our 26-foot boat. Ideal for up to 8 passengers. We are sure that with ....

    Free Cancellation
    Private Tour
    Start From $953.79
 
 

Cancun: 4-Hour All Inclusive Luxury Yacht – 50' Cranchi

(5 of 30 reviews)

An incredible 4 hours experience in an exclusive yacht, tasting exquisite dishes and enjoying a day just for you and your family. You can visit different exclusive places... More

Free Cancellation
Private Tour
Start From $2,100.00
 
Cancun: 4-Hour All Inclusive Luxury Yacht – 50' Cranchi Likely to Sell Out

Cancun: 4-Hour All Inclusive Luxury Yacht – 50' Cranchi

  • North America
  • Superb30 reviews5

An incredible 4 hours experience in an exclusive yacht, tasting exquisite dishes and enjoying a day ....

    Free Cancellation
    Private Tour
    Start From $2,100.00
 
 

Private Family Catamaran From Isla Mujeres

(5 of 1 review)

Enjoy our “Lite Sailing Charters” Sail through the wonderful Bay of Isla Mujeres! Why invest all day when you can do it in less time? Affordable Private Catamaran, avoid crowded vessels Half-day fun catamaran, with a guided sn... More

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

Private Family Catamaran From Isla Mujeres

  • North America
  • Superb1 review5

Enjoy our “Lite Sailing Charters” Sail through the wonderful Bay of Isla Mujeres! Why invest all....

    Free Cancellation
    Private Tour
    Start From $950.00
 
 

Diamond Head Sunset Sail

(4.7 of 15 reviews)

Hawaii’s Best Sunset Cruise is the experience you don’t want to miss. Our Diamond Head Sunset Sail features a two hour cruise aboard a private luxury yacht. Immerse yourself in a gorgeous Hawaiian sunset the only way, from the... More

Free Cancellation
Private Tour
Start From $695.00
 
Diamond Head Sunset Sail Likely to Sell Out

Diamond Head Sunset Sail

  • North America
  • Superb15 reviews4.7

Hawaii’s Best Sunset Cruise is the experience you don’t want to miss. Our Diamond Head Sunset Sa....

    Free Cancellation
    Private Tour
    Start From $695.00
 
 

Private Luxury Sunset Sail on the 50ft Sailing Yacht Fate BYOB

(4.9 of 55 reviews)

Sail the Charleston Harbor, see dolphins, amazing sunsets or even participate in real sailing yacht regattas. Fate is not only the most demanded but also the largest and nicest sailing yacht available for Charter in Charleston, kn... More

Free Cancellation
Private Tour
Start From $660.00
 
Private Luxury Sunset Sail on the 50ft Sailing Yacht Fate BYOB Likely to Sell Out

Private Luxury Sunset Sail on the 50ft Sailing Yacht Fate BYOB

  • North America
  • Superb55 reviews4.9

Sail the Charleston Harbor, see dolphins, amazing sunsets or even participate in real sailing yacht ....

    Free Cancellation
    Private Tour
    Start From $660.00
 
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