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Top 10 Best North America Sailing Trips

Found 713 Sailing Trips activities in North America. Sort by Popularity. - Page 13
 

Windjammer Classic Sunset Sail from Camden, Maine

(4.9 of 525 reviews)

Maine sunsets are best appreciated from the water aboard the romantic Appledore II! This tall ship is limited to 49 passengers for an intimate sailing experience. She is a modern windjammer with luxurious accommodations and plent... More

Free Cancellation
Start From $74.95
 
Windjammer Classic Sunset Sail from Camden, Maine

Windjammer Classic Sunset Sail from Camden, Maine

  • North America
  • Superb525 reviews4.9

Maine sunsets are best appreciated from the water aboard the romantic Appledore II! This tall ship ....

    Free Cancellation
    Start From $74.95
 
 

Public Daytime Sailing Cruise

(5 of 50 reviews)

Experience the beauty of Lake Champlain from a unique perspective aboard classic Friendship Sloops, Friend Ship and Wild Rose. With a maximum of 10 guests, this intimate sailing adventure is perfect for anyone looking to escape th... More

Free Cancellation
Start From $85.00
 
Public Daytime Sailing Cruise

Public Daytime Sailing Cruise

  • North America
  • Superb50 reviews5

Experience the beauty of Lake Champlain from a unique perspective aboard classic Friendship Sloops, ....

    Free Cancellation
    Start From $85.00
 
 

Sunset Catamaran Sail in Cocoa Beach

(4.9 of 198 reviews)

Experience a Magical Sunset in Cocoa Beach! 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 beauty of Floridaâ... More

Free Cancellation
Start From $56.49
 
Sunset Catamaran Sail in Cocoa Beach

Sunset Catamaran Sail in Cocoa Beach

  • North America
  • Superb198 reviews4.9

Experience a Magical Sunset in Cocoa Beach! Set sail into the golden hour and enjoy a stunning eveni....

    Free Cancellation
    Start From $56.49
 
 

Private sailing tour of Bacalar Lagoon

(5 of 495 reviews)

Enjoy a private Sailboat with the comforts and attention you deserve. Relax and let our team pamper you. During the tour, you can enjoy a delicious fruit cocktail, water and beer. Our certified guides will make this tour an unfo... More

Free Cancellation
Private Tour
Start From $240.00
 
Private sailing tour of Bacalar Lagoon

Private sailing tour of Bacalar Lagoon

  • North America
  • Superb495 reviews5

Enjoy a private Sailboat with the comforts and attention you deserve. Relax and let our team pamper ....

    Free Cancellation
    Private Tour
    Start From $240.00
 
 

Luxury Camden Sailing Experience

(4.9 of 19 reviews)

Small groups of up to six. Two staff members to take care of you. Cushioned seating for all. Fastest boat in the harbor... More

Free Cancellation
Private Tour
Start From $125.00
 
Luxury Camden Sailing Experience

Luxury Camden Sailing Experience

  • North America
  • Superb19 reviews4.9

Small groups of up to six. Two staff members to take care of you. Cushioned seating for all. Faste....

    Free Cancellation
    Private Tour
    Start From $125.00
 
 

Dolphin Adventure Sail in Cocoa Beach

(4.9 of 238 reviews)

Experience the Magic of Cocoa Beach with Our Dolphin Adventure Sail! Join Cocoa Beach Catamaran for an unforgettable journey through the Banana River Lagoon! Glide across calm waters on our spacious catamaran as you encounter pla... More

Free Cancellation
Private Tour
Start From $50.85
 
Dolphin Adventure Sail in Cocoa Beach

Dolphin Adventure Sail in Cocoa Beach

  • North America
  • Superb238 reviews4.9

Experience the Magic of Cocoa Beach with Our Dolphin Adventure Sail! Join Cocoa Beach Catamaran for....

    Free Cancellation
    Private Tour
    Start From $50.85
 
 

Bacalar Private Sailing Boat Tour with Pick up

(5 of 35 reviews)

Discover the beauty of Bacalar’s Lagoon of Seven Colors on an unforgettable private sailing adventure, with convenient hotel pick-up and drop-off included. Explore some of the lagoon’s most beautiful spots, including Piratesâ... More

Free Cancellation
Private Tour
Start From $203.25
 
Bacalar Private Sailing Boat Tour with Pick up

Bacalar Private Sailing Boat Tour with Pick up

  • North America
  • Superb35 reviews5

Discover the beauty of Bacalar’s Lagoon of Seven Colors on an unforgettable private sailing advent....

    Free Cancellation
    Private Tour
    Start From $203.25
 
 

Key West Wreckers Race Aboard Schooner America 2.0

(4.9 of 15 reviews)

Join in on the annual Wreckers Race and take part in a fast pace race toward Sand Key Lighthouse aboard Schooner America 2.0! Back in the day, pirate ships from afar often ran aground on Sand Key Reef, nine miles off the southern ... More

Free Cancellation
Private Tour
Start From $116.10
 
Key West Wreckers Race Aboard Schooner America 2.0

Key West Wreckers Race Aboard Schooner America 2.0

  • North America
  • Superb15 reviews4.9

Join in on the annual Wreckers Race and take part in a fast pace race toward Sand Key Lighthouse abo....

    Free Cancellation
    Private Tour
    Start From $116.10
 
 

Sunset Sailboat Cruise on Winyah Bay

(5 of 2 reviews)

As the sun lowers over the bay, the water softens and the sky comes alive. This is a favorite for couples, relaxed evenings, and anyone who wants to end the day on the water. Step aboard for an unforgettable evening on the water ... More

Free Cancellation
Private Tour
Start From $145.00
 
Sunset Sailboat Cruise on Winyah Bay

Sunset Sailboat Cruise on Winyah Bay

  • North America
  • Superb2 reviews5

As the sun lowers over the bay, the water softens and the sky comes alive. This is a favorite for co....

    Free Cancellation
    Private Tour
    Start From $145.00
 
 

Isla Mujeres Plus by Albatros Catamarans

(4.1 of 341 reviews)

Delight all your senses aboard a boat that will take you to one of the best islands in the world, swim in the impressive turquoise of the Mexican Caribbean, enjoy the delicacies of Mexican food, dance to Latin rhythms and forget a... More

Free Cancellation
Private Tour
Start From $89.00
 
Isla Mujeres Plus by Albatros Catamarans

Isla Mujeres Plus by Albatros Catamarans

  • North America
  • Exellent341 reviews4.1

Delight all your senses aboard a boat that will take you to one of the best islands in the world, sw....

    Free Cancellation
    Private Tour
    Start From $89.00
 
 

Waikiki Beach Whale Watching: Catamaran Sail & Open Bar

(5 of 15 reviews)

Observe the majestic humpback whales during their migration from December to March on this 1.5-hour sail in Honolulu. Experience the beauty of Oahu's coastline while searching for dolphins and sea turtles in their natural habitat.... More

Free Cancellation
Private Tour
Start From $53.36
 
Waikiki Beach Whale Watching: Catamaran Sail & Open Bar

Waikiki Beach Whale Watching: Catamaran Sail & Open Bar

  • North America
  • Superb15 reviews5

Observe the majestic humpback whales during their migration from December to March on this 1.5-hour ....

    Free Cancellation
    Private Tour
    Start From $53.36
 
 

Catamaran to Isla Mujeres

(3.4 of 8 reviews)

Enjoy the sun and to sail in the Caribean ocean just to discover the amazing Isla Mujeres you will snorkel and spend time in the exclusive beach club where you will have a delicious buffet.... More

Free Cancellation
Private Tour
Start From $59.00
 
Catamaran to Isla Mujeres

Catamaran to Isla Mujeres

  • North America
  • Good8 reviews3.4

Enjoy the sun and to sail in the Caribean ocean just to discover the amazing Isla Mujeres you will s....

    Free Cancellation
    Private Tour
    Start From $59.00
 
 

3 Hours Ultimate Watersports Excursion in Miami

(3.4 of 8 reviews)

All-Inclusive Catamaran Adventure in Miami: 3 Hours of Adrenaline and Party! Board your comfortable and stable Catamaran for an unforgettable all-inclusive water experience. Highlights: - Extreme Watersports: Feel the thrill wi... More

Free Cancellation
Private Tour
Start From $139.00
 
3 Hours Ultimate Watersports Excursion in Miami

3 Hours Ultimate Watersports Excursion in Miami

  • North America
  • Good8 reviews3.4

All-Inclusive Catamaran Adventure in Miami: 3 Hours of Adrenaline and Party! Board your comfortable....

    Free Cancellation
    Private Tour
    Start From $139.00
 
 

Waikiki small group turtle snorkeling & sailing

(5 of 109 reviews)

Witness the brilliant colors of a sunrise over Diamond Head crater. Ideal for early birds, couples or families who are up at the crack of dawn during their Hawaiian vacation due to time zone changes. As we start out our tour from ... More

Free Cancellation
Private Tour
Start From $99.00
 
Waikiki small group turtle snorkeling & sailing

Waikiki small group turtle snorkeling & sailing

  • North America
  • Superb109 reviews5

Witness the brilliant colors of a sunrise over Diamond Head crater. Ideal for early birds, couples o....

    Free Cancellation
    Private Tour
    Start From $99.00
 
 

Maui Sunset Sail

(4.6 of 225 reviews)

Enjoy tantalizing pupus (appetizers) and island-style music against the backdrop of a stunning sunset over the Pacific Ocean.This relaxing cruise is aboard our luxury sailing catamaran, Ocean Spirit. It’s the perfect way to expe... More

Free Cancellation
Private Tour
Start From $137.82
 
Maui Sunset Sail

Maui Sunset Sail

  • North America
  • Superb225 reviews4.6

Enjoy tantalizing pupus (appetizers) and island-style music against the backdrop of a stunning sunse....

    Free Cancellation
    Private Tour
    Start From $137.82
 
 

Afternoon Sightseeing and Sailing Tour

(4.8 of 37 reviews)

Kick back and relax on this beautiful 53' sailing catamaran that can accommodate up to 44 passengers. Cruise through the prestigious Port Royal neighborhood in Naples Bay and then set sail into the Gulf of Mexico. Cruises are narr... More

Free Cancellation
Private Tour
Start From $43.46
 
Afternoon Sightseeing and Sailing Tour

Afternoon Sightseeing and Sailing Tour

  • North America
  • Superb37 reviews4.8

Kick back and relax on this beautiful 53' sailing catamaran that can accommodate up to 44 passengers....

    Free Cancellation
    Private Tour
    Start From $43.46
 
 

Waikiki Turtle Snorkeling Adventure(8am)

(5 of 141 reviews)

Discover an all-in-one Waikiki ocean adventure with our Turtle Snorkeling Tour. Cruise aboard our spacious and comfortable catamaran to Turtle Canyon, where you’ll have the opportunity to snorkel with Hawaiian green sea turtles ... More

Free Cancellation
Private Tour
Start From $100.00
 
Waikiki Turtle Snorkeling Adventure(8am)

Waikiki Turtle Snorkeling Adventure(8am)

  • North America
  • Superb141 reviews5

Discover an all-in-one Waikiki ocean adventure with our Turtle Snorkeling Tour. Cruise aboard our sp....

    Free Cancellation
    Private Tour
    Start From $100.00
 
 

Private Therapy Sailing Adventure

(4.8 of 49 reviews)

Old Plank Adventures: Sail into Deep Tranquility LUXURY SAILING | THERAPEUTIC ESCAPES | GOURMET CUISINE | INTIMATE WILDLIFE ENCOUNTERS Immerse yourself in the timeless Mediterranean elegance along Southern California’s glitteri... More

Free Cancellation
Private Tour
Start From $400.00
 
Private Therapy Sailing Adventure

Private Therapy Sailing Adventure

  • North America
  • Superb49 reviews4.8

Old Plank Adventures: Sail into Deep Tranquility LUXURY SAILING | THERAPEUTIC ESCAPES | GOURMET CUIS....

    Free Cancellation
    Private Tour
    Start From $400.00
 
 

Fort Myers: Tiki Pub VIP Private Dolphin & Sunset Cruise

(5 of 4 reviews)

Spend the most amazing time of day in the best place to enjoy it. Our custom tiki boat has it all. Whether you want to dance, sing Tiki-Oki, slip down the on board water slide, or just relax and enjoy the sunset, this cruise will ... More

Free Cancellation
Private Tour
Start From $449.00
 
Fort Myers: Tiki Pub VIP Private Dolphin & Sunset Cruise Likely to Sell Out

Fort Myers: Tiki Pub VIP Private Dolphin & Sunset Cruise

  • North America
  • Superb4 reviews5

Spend the most amazing time of day in the best place to enjoy it. Our custom tiki boat has it all. W....

    Free Cancellation
    Private Tour
    Start From $449.00
 
 

Tiki Pub Amazing Dolphin Eco Adventure

(4.5 of 11 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 $59.95
 
Tiki Pub Amazing Dolphin Eco Adventure Likely to Sell Out

Tiki Pub Amazing Dolphin Eco Adventure

  • North America
  • Exellent11 reviews4.5

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

    Free Cancellation
    Private Tour
    Start From $59.95
 
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