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Top 10 Best North America Sailing Trips

Found 735 Sailing Trips activities in North America. Sort by Popularity. - Page 32
 

Chesapeake Bay Private Cruise

(4.4 of 7 reviews)

This private cruise for up to 6 persons is great for family outings, friends in town, a girls or guys day out on the water, or just to have the cruise to yourself! Enjoy the peaceful sounds of the waves gently breaking off the hul... More

Free Cancellation
Private Tour
Start From $651.00
 
Chesapeake Bay Private Cruise

Chesapeake Bay Private Cruise

  • North America
  • Exellent7 reviews4.4

This private cruise for up to 6 persons is great for family outings, friends in town, a girls or guy....

    Free Cancellation
    Private Tour
    Start From $651.00
 
 

Private Sailing Experience along the Southern Maine Coastline

(5 of 1 review)

Indulge in a private sailing experience along the serene Saco River and Saco Bay. With a maximum of six guests, this exclusive journey allows you to soak in the stunning scenery while learning about the rich history of the area, i... More

Free Cancellation
Private Tour
Start From $747.00
 
Private Sailing Experience along the Southern Maine Coastline

Private Sailing Experience along the Southern Maine Coastline

  • North America
  • Superb1 review5

Indulge in a private sailing experience along the serene Saco River and Saco Bay. With a maximum of ....

    Free Cancellation
    Private Tour
    Start From $747.00
 
 

Full-Day Sailing Adventure to Isla Mujeres

(3.5 of 4 reviews)

This 7-hour tour is the best way to enjoy "the life aquatic" of the Cancun coast. Sail from Cancun to Isla Mujeres aboard a wind-powered catamaran with an experienced and friendly captain and crew. Lounge, swim, eat, and drink at ... More

Free Cancellation
Private Tour
Start From $69.99
 
Full-Day Sailing Adventure to Isla Mujeres

Full-Day Sailing Adventure to Isla Mujeres

  • North America
  • Good4 reviews3.5

This 7-hour tour is the best way to enjoy "the life aquatic" of the Cancun coast. Sail from Cancun t....

    Free Cancellation
    Private Tour
    Start From $69.99
 
 

Luxury Sailboat 50 feet in Private for up to 9 People 4 hrs

(3.5 of 4 reviews)

Welcome to the coast of Puerto Vallarta, a luxury destination known for its variety of exciting nautical activities! If you are looking to live a unique and unforgettable experience with family or friends, this is the perfect plac... More

Free Cancellation
Private Tour
Start From $3,708.00
 
Luxury Sailboat 50 feet in Private for up to 9 People 4 hrs

Luxury Sailboat 50 feet in Private for up to 9 People 4 hrs

  • North America
  • Good4 reviews3.5

Welcome to the coast of Puerto Vallarta, a luxury destination known for its variety of exciting naut....

    Free Cancellation
    Private Tour
    Start From $3,708.00
 
 

Pirate Ship by Day

(3.4 of 5 reviews)

Start the day enjoying a delicious and complete breakfast Under the Sea, in our Pirate Tavern, aboard an incredible 700-ton Galleon, full of adventure and fun. Let yourself be pampered by nature on Majahuitas Island (Ecological R... More

Free Cancellation
Private Tour
Start From $280.00
 
Pirate Ship by Day

Pirate Ship by Day

  • North America
  • Good5 reviews3.4

Start the day enjoying a delicious and complete breakfast Under the Sea, in our Pirate Tavern, aboar....

    Free Cancellation
    Private Tour
    Start From $280.00
 
 

Los Cabos Private Catamaran Sunset Cruise with Snacks & Open Bar

(5 of 1 review)

Experience Cabo San Lucas like never before on your private catamaran at sunset. Unlike crowded group tours, this 2-hour cruise is exclusive to your party, giving you space to relax, celebrate, and enjoy the views in privacy. Sai... More

Free Cancellation
Private Tour
Start From $999.00
 
Los Cabos Private Catamaran Sunset Cruise with Snacks & Open Bar

Los Cabos Private Catamaran Sunset Cruise with Snacks & Open Bar

  • North America
  • Superb1 review5

Experience Cabo San Lucas like never before on your private catamaran at sunset. Unlike crowded grou....

    Free Cancellation
    Private Tour
    Start From $999.00
 
 

Private Snorkeling and Sightseeing Catamaran Boat Tour Deluxe 36 passengers

(5 of 1 review)

Embark on a breathtaking sailing adventure from Cancun to Isla Mujeres. Feel the excitement as you explore stunning sites and Caribbean reefs. Experience the magic of the Mexican Caribbean, snorkeling in Isla Mujeres and Cancun's ... More

Free Cancellation
Private Tour
Start From $5,900.00
 
Private Snorkeling and Sightseeing Catamaran Boat Tour Deluxe 36 passengers

Private Snorkeling and Sightseeing Catamaran Boat Tour Deluxe 36 ....

  • North America
  • Superb1 review5

Embark on a breathtaking sailing adventure from Cancun to Isla Mujeres. Feel the excitement as you e....

    Free Cancellation
    Private Tour
    Start From $5,900.00
 
 

San Diego Bay Private Sailing Experience Aboard Classic Yacht

(5 of 4 reviews)

Our private afternoon and sunset cruises offer an exclusive adventure for up to six individuals. Immerse your family and friends in the many sights of San Diego Bay, while enjoying the personalized touch of a family-owned venture.... More

Free Cancellation
Private Tour
Start From $625.00
 
 San Diego Bay Private Sailing Experience Aboard Classic Yacht Likely to Sell Out

San Diego Bay Private Sailing Experience Aboard Classic Yacht

  • North America
  • Superb4 reviews5

Our private afternoon and sunset cruises offer an exclusive adventure for up to six individuals. Imm....

    Free Cancellation
    Private Tour
    Start From $625.00
 
 

Sail into Serenity Tropical Jazz & Wine Aboard a Catamaran

(5 of 4 reviews)

Step aboard the elegant Tropicat and escape into a world of tranquility and beauty. As we gently sail through the stunning waters of Los Cabos, immerse yourself in breathtaking views at every turn — from the iconic Lover’s Bea... More

Free Cancellation
Private Tour
Start From $135.00
 
Sail into Serenity Tropical Jazz & Wine Aboard a Catamaran Likely to Sell Out

Sail into Serenity Tropical Jazz & Wine Aboard a Catamaran

  • North America
  • Superb4 reviews5

Step aboard the elegant Tropicat and escape into a world of tranquility and beauty. As we gently sai....

    Free Cancellation
    Private Tour
    Start From $135.00
 
 

Morning Charleston Harbor Sail Lux Catamaran Shade and Seating

(3.7 of 3 reviews)

Ready to escape the everyday and experience Charleston from a whole new perspective? Step aboard the Charleston's premier 50-foot catamaran. Designed for stunning views in the South's picturesque setting, this 2-hour sail gives yo... More

Free Cancellation
Private Tour
Start From $38.00
 
Morning Charleston Harbor Sail Lux Catamaran Shade and Seating Likely to Sell Out

Morning Charleston Harbor Sail Lux Catamaran Shade and Seating

  • North America
  • Very Good3 reviews3.7

Ready to escape the everyday and experience Charleston from a whole new perspective? Step aboard the....

    Free Cancellation
    Private Tour
    Start From $38.00
 
 

Waikiki private Day Tour and Sunset sail for couples

(5 of 17 reviews)

Why go with an overcrowded catamaran, when you can enjoy the privacy with your love one .This private tour was specifically created for Newlywed couples on their honeymoon, celebrating an Anniversary, or just in love, celebrating ... More

Free Cancellation
Private Tour
Start From $300.00
 
Waikiki private Day Tour and Sunset sail for couples Likely to Sell Out

Waikiki private Day Tour and Sunset sail for couples

  • North America
  • Superb17 reviews5

Why go with an overcrowded catamaran, when you can enjoy the privacy with your love one .This privat....

    Free Cancellation
    Private Tour
    Start From $300.00
 
 

JFarwell Private Yacht Wine & Cheese Sunset Sail

(4.9 of 18 reviews)

This sunset sail is a stunning opportunity to see how Halifax's urban and nature connect. Guests will be greeting with their first Nova Scotia wine upon boarding, and then set sail. With the engines off and fully under wind power,... More

Free Cancellation
Private Tour
Start From $149.63
 
JFarwell Private Yacht Wine & Cheese Sunset Sail Likely to Sell Out

JFarwell Private Yacht Wine & Cheese Sunset Sail

  • North America
  • Superb18 reviews4.9

This sunset sail is a stunning opportunity to see how Halifax's urban and nature connect. Guests wil....

    Free Cancellation
    Private Tour
    Start From $149.63
 
 

Private 43' Azimut Yacht 4h – Drinks & Food Included

(5 of 6 reviews)

What truly sets this tour apart is the level of privacy and customization we offer. Whether you're celebrating a special occasion or simply seeking a luxurious escape, our crew tailors every detail to your preferences — from the... More

Free Cancellation
Private Tour
Start From $1,705.00
 
Private 43' Azimut Yacht 4h – Drinks & Food Included Likely to Sell Out

Private 43' Azimut Yacht 4h – Drinks & Food Included

  • North America
  • Superb6 reviews5

What truly sets this tour apart is the level of privacy and customization we offer. Whether you're c....

    Free Cancellation
    Private Tour
    Start From $1,705.00
 
 

Land’s End Sunset Cruise – Open Bar & Tacos Included

(5 of 6 reviews)

Embark on a serene journey aboard the CaboMar Catamaran, where each moment unfolds in tranquility, with approximately 40 minutes spent at each captivating point along the route. As you glide through the stunning landscapes of Cab... More

Free Cancellation
Private Tour
Start From $140.00
 
Land’s End Sunset Cruise – Open Bar & Tacos Included Likely to Sell Out

Land’s End Sunset Cruise – Open Bar & Tacos Included

  • North America
  • Superb6 reviews5

Embark on a serene journey aboard the CaboMar Catamaran, where each moment unfolds in tranquility, w....

    Free Cancellation
    Private Tour
    Start From $140.00
 
 

Daily Swim, Snorkel & Sail (Kewalo Harbor)

(5 of 6 reviews)

A beautiful swim and boat ride along the south shore of Oahu, potentially viewing sea turtles, dolphins, fish, and whales (seasonal). Our snorkel, swim and sail is the perfect combination of warm sun, refreshing salty water, and b... More

Free Cancellation
Private Tour
Start From $70.00
 
Daily Swim, Snorkel & Sail (Kewalo Harbor) Likely to Sell Out

Daily Swim, Snorkel & Sail (Kewalo Harbor)

  • North America
  • Superb6 reviews5

A beautiful swim and boat ride along the south shore of Oahu, potentially viewing sea turtles, dolph....

    Free Cancellation
    Private Tour
    Start From $70.00
 
 

Afternoon Kealakekua Snorkel and Sail

(5 of 12 reviews)

Join us for a sensational 3.5 hour coastal sail, which includes snorkeling in the marine sanctuary of Kealakekua Bay (home of the Captain Cook Monument). Explore the incredible world under the water with its abundance of marine li... More

Free Cancellation
Private Tour
Start From $189.00
 
Afternoon Kealakekua Snorkel and Sail Likely to Sell Out

Afternoon Kealakekua Snorkel and Sail

  • North America
  • Superb12 reviews5

Join us for a sensational 3.5 hour coastal sail, which includes snorkeling in the marine sanctuary o....

    Free Cancellation
    Private Tour
    Start From $189.00
 
 

Private Morning Ceremony Sailing Charter

(5 of 12 reviews)

This is a 90-minute sailing trip to attend to ceremonies, ash scatterings, organization charters, and more. We offer this experience at a discounted rate to accommodate groups wanting to do private charters in the morning to celeb... More

Free Cancellation
Private Tour
Start From $1,000.00
 
Private Morning Ceremony Sailing Charter Likely to Sell Out

Private Morning Ceremony Sailing Charter

  • North America
  • Superb12 reviews5

This is a 90-minute sailing trip to attend to ceremonies, ash scatterings, organization charters, an....

    Free Cancellation
    Private Tour
    Start From $1,000.00
 
 

Bacalar Private Sailing Tour Open Bar with Pick Up

(5 of 6 reviews)

Discover Bacalar Lagoon like no other tour. Our experiences are responsibly crafted to offer a truly unique adventure. Visit hidden, less-explored spots and enjoy the lagoon with skilled captains and crew fluent in Spanish, Englis... More

Free Cancellation
Private Tour
Start From $250.03
 
Bacalar Private Sailing Tour Open Bar with Pick Up Likely to Sell Out

Bacalar Private Sailing Tour Open Bar with Pick Up

  • North America
  • Superb6 reviews5

Discover Bacalar Lagoon like no other tour. Our experiences are responsibly crafted to offer a truly....

    Free Cancellation
    Private Tour
    Start From $250.03
 
 

Adults-Only Sunset Catamaran Cruise to Isla Mujeres

(5 of 6 reviews)

Adults-Only Atmosphere Unlike typical family catamaran tours, this is exclusively for adults, creating a relaxed yet lively vibe perfect for couples, friends, and groups looking to unwind or celebrate. Stylish, Spacious Catamaran... More

Free Cancellation
Private Tour
Start From $119.00
 
Adults-Only Sunset Catamaran Cruise to Isla Mujeres Likely to Sell Out

Adults-Only Sunset Catamaran Cruise to Isla Mujeres

  • North America
  • Superb6 reviews5

Adults-Only Atmosphere Unlike typical family catamaran tours, this is exclusively for adults, creati....

    Free Cancellation
    Private Tour
    Start From $119.00
 
 

2 hour Catamaran Sailing Cruise on Lake Tahoe

(5 of 6 reviews)

Enjoy the stunning views of Lake Tahoe on a two-hour sailing cruise aboard the 50-foot catamaran, "Blue Zephyr". Perfect for couples, families, or groups, this adventure promises a memorable experience on the water. Relax and take... More

Free Cancellation
Private Tour
Start From $130.00
 
2 hour Catamaran Sailing Cruise on Lake Tahoe Likely to Sell Out

2 hour Catamaran Sailing Cruise on Lake Tahoe

  • North America
  • Superb6 reviews5

Enjoy the stunning views of Lake Tahoe on a two-hour sailing cruise aboard the 50-foot catamaran, "B....

    Free Cancellation
    Private Tour
    Start From $130.00
 
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