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Top 10 Best North America Sailing Trips

Found 687 Sailing Trips activities in North America. Sort by Popularity. - Page 6
 

Half Day Luxury Sailing Experience in Riviera Maya with Open Bar

(4.4 of 60 reviews)

This is a luxury sailing catamaran and it's just 30 minutes away from Tulum. When you sail you can see different colors of blue so that makes the experience better. The snorkeling is amazing, as you will see much colorful fish, st... More

Free Cancellation
Start From $149.00
 
Half Day Luxury Sailing Experience in Riviera Maya with Open Bar

Half Day Luxury Sailing Experience in Riviera Maya with Open Bar

  • North America
  • Exellent60 reviews4.4

This is a luxury sailing catamaran and it's just 30 minutes away from Tulum. When you sail you can s....

    Free Cancellation
    Start From $149.00
 
 

Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)

(4.8 of 20 reviews)

Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui sunset begin to paint the sky. As you step aboard, you're greeted by the friendly crew who welcome you with warm aloha spirit. The c... More

Free Cancellation
Start From $289.00
 
Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)

Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)

  • North America
  • Superb20 reviews4.8

Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui su....

    Free Cancellation
    Start From $289.00
 
 

Key West Morning Snorkel Sail with Mimosas and Gourmet Breakfast

(4.8 of 23 reviews)

Embark on an adventure off the shores of Key West, where the turquiose waters of the Gulf of Mexico and the Atlantic Ocean meet in a symphony of beauty and tranquility. Your day begins as you board a luxurious catamaran, your vess... More

Free Cancellation
Start From $49.00
 
Key West Morning Snorkel Sail with Mimosas and Gourmet Breakfast

Key West Morning Snorkel Sail with Mimosas and Gourmet Breakfast

  • North America
  • Superb23 reviews4.8

Embark on an adventure off the shores of Key West, where the turquiose waters of the Gulf of Mexico ....

    Free Cancellation
    Start From $49.00
 
 

4-Hour Fort Lauderdale Sailing Charter

(4.9 of 287 reviews)

Enjoy some time on the water with this 4-Hour Half Day Sailing Charter located in Fort Lauderdale. Your sail is entirely customizable, and travelers have the option(PRIVATE CRUISES) to use their time docked or sailing out to sea. ... More

Free Cancellation
Start From $165.00
 
4-Hour Fort Lauderdale Sailing Charter Likely to Sell Out

4-Hour Fort Lauderdale Sailing Charter

  • North America
  • Superb287 reviews4.9

Enjoy some time on the water with this 4-Hour Half Day Sailing Charter located in Fort Lauderdale. Y....

    Free Cancellation
    Start From $165.00
 
 

2.5 Hours of Fun: Catamaran Sunset Sail

(4.9 of 148 reviews)

Catamarans really are more fun to sail with the special bow nets designed for sunbathing, and lounging around watching sea life, and water rush by. The swift and stable ocean design ensures a comfortable, and exhilarating ride wit... More

Free Cancellation
Start From $119.00
 
2.5 Hours of Fun: Catamaran Sunset Sail Likely to Sell Out

2.5 Hours of Fun: Catamaran Sunset Sail

  • North America
  • Superb148 reviews4.9

Catamarans really are more fun to sail with the special bow nets designed for sunbathing, and loungi....

    Free Cancellation
    Start From $119.00
 
 

2-Hour Maalaea Luxury Powerboat Sunset Cruise for up to 6 Guests

(4.9 of 10 reviews)

Experience “Amore” a 42-foot Boston Whaler with unmatched state-of-the-art features make the flagship 420 Outrage a boat like no other. From the expansive bow with innovative seating galore, to the beautifully designed convert... More

Free Cancellation
Start From $284.09
 
2-Hour Maalaea Luxury Powerboat Sunset Cruise for up to 6 Guests Likely to Sell Out

2-Hour Maalaea Luxury Powerboat Sunset Cruise for up to 6 Guests

  • North America
  • Superb10 reviews4.9

Experience “Amore” a 42-foot Boston Whaler with unmatched state-of-the-art features make the fla....

    Free Cancellation
    Start From $284.09
 
 

9am Turtle Canyon Snorkel Adventure

(4.9 of 243 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

Free Cancellation
Start From $96.30
 
9am Turtle Canyon Snorkel Adventure Likely to Sell Out

9am Turtle Canyon Snorkel Adventure

  • North America
  • Superb243 reviews4.9

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

    Free Cancellation
    Start From $96.30
 
 

Portland Tall Ship Cruise on Casco Bay

(4.5 of 222 reviews)

What better way to see the delights of Portland than from the sea in one of the famous schooner tall ships. Join us for this mid morning cruise that will make your visit to Portland live long in the memory.... More

Free Cancellation
Start From $99.11
 
Portland Tall Ship Cruise on Casco Bay Likely to Sell Out

Portland Tall Ship Cruise on Casco Bay

  • North America
  • Exellent222 reviews4.5

What better way to see the delights of Portland than from the sea in one of the famous schooner tall....

    Free Cancellation
    Start From $99.11
 
 

Deluxe Sail & Snorkel to the Captain Cook Monument

(4.9 of 433 reviews)

Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient lava flows. As you arrive at the "World Famous Captain Cook Monument" your snorkeling adventure will begin in the turquoise waters... More

Free Cancellation
Start From $179.27
 
Deluxe Sail & Snorkel to the Captain Cook Monument Likely to Sell Out

Deluxe Sail & Snorkel to the Captain Cook Monument

  • North America
  • Superb433 reviews4.9

Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient ....

    Free Cancellation
    Start From $179.27
 
 

2 hour Tiki Pub Sensational Sunset Cruise (Adults only)

(4.9 of 62 reviews)

Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages (BYOB), take pics, get some sun, make friends, play party games and have a blast! With a cozy capacity for 25, choose between mingling with new pal... More

Free Cancellation
Start From $69.00
 
2 hour Tiki Pub Sensational Sunset Cruise (Adults only) Likely to Sell Out

2 hour Tiki Pub Sensational Sunset Cruise (Adults only)

  • North America
  • Superb62 reviews4.9

Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages (BYOB), take pics,....

    Free Cancellation
    Start From $69.00
 
 

Hilton Head Pirate Ship Adventure Sail aboard the Black Dagger

(4.9 of 634 reviews)

The fun starts at the dock as we transform your little one with pirate gear, face paint and tattoos. Learn how to walk and talk like a pirate then climb aboard the Black Dagger and set sail in search of treasure! But wait it's not... More

Free Cancellation
Start From $41.99
 
Hilton Head Pirate Ship Adventure Sail aboard the Black Dagger Likely to Sell Out

Hilton Head Pirate Ship Adventure Sail aboard the Black Dagger

  • North America
  • Superb634 reviews4.9

The fun starts at the dock as we transform your little one with pirate gear, face paint and tattoos.....

    Free Cancellation
    Start From $41.99
 
 

Monterey Bay Whale Watching

(4.7 of 276 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
  • Superb276 reviews4.7

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

    Free Cancellation
    Start From $69.95
 
 

FROM FLORIDA: Bimini Bahamas Day Trip By Fast Ferry

(3.9 of 9 reviews)

Take advantage of the vicinity of the Bahamas Islands during your Florida visit to experience the world's best beaches. The ocean crossing is provided with our comfortable Express-Ferry featuring restrooms, comfortable seats, air ... More

Special Offer
Free Cancellation
Start From $284.05
(Saving 5% ) $299.00
 
-5% FROM FLORIDA: Bimini Bahamas Day Trip By Fast Ferry Likely to Sell Out

FROM FLORIDA: Bimini Bahamas Day Trip By Fast Ferry

  • North America
  • Very Good9 reviews3.9

Take advantage of the vicinity of the Bahamas Islands during your Florida visit to experience the wo....

    Special Offer
    Free Cancellation
    Start From $284.05
    (Saving 5% ) $299.00
 
 

Dolphin Adventure Sail in Cocoa Beach

(5 of 131 reviews)

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

Free Cancellation
Start From $50.85
 
Dolphin Adventure Sail in Cocoa Beach Likely to Sell Out

Dolphin Adventure Sail in Cocoa Beach

  • North America
  • Superb131 reviews5

Experience the Magic of Cocoa Beach with Our Dolphin Tour! Join Cocoa Beach Catamaran for an unforg....

    Free Cancellation
    Start From $50.85
 
 

Sail and Turtle Snorkeling Tour in Waikiki

(4.9 of 235 reviews)

Experience the Best boat tour in Waikiki with our Turtle Canyon Snorkeling Tour Get ready for an epic 2-hour boat adventure that combines the thrill of sailing past Diamond Head with the magic of snorkeling with turtles in their ... More

Free Cancellation
Start From $99.00
 
Sail and Turtle Snorkeling Tour in Waikiki Likely to Sell Out

Sail and Turtle Snorkeling Tour in Waikiki

  • North America
  • Superb235 reviews4.9

Experience the Best boat tour in Waikiki with our Turtle Canyon Snorkeling Tour Get ready for an ep....

    Free Cancellation
    Start From $99.00
 
 

6 hours on a Private Yacht in Puerto Vallarta - Snorkeling & Beaches

(5 of 11 reviews)

Sail on a private trip aboard our 50-foot private yacht, ideal for up to 18 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... More

Free Cancellation
Private Tour
Start From $1,341.73
 
6 hours on a Private Yacht in Puerto Vallarta - Snorkeling & Beaches Likely to Sell Out

6 hours on a Private Yacht in Puerto Vallarta - Snorkeling & Beac....

  • North America
  • Superb11 reviews5

Sail on a private trip aboard our 50-foot private yacht, ideal for up to 18 passengers. We are sure ....

    Free Cancellation
    Private Tour
    Start From $1,341.73
 
 

Sail Biscayne Bay: An Intimate Eco-Adventure

(4.9 of 412 reviews)

This tour is an intimate experience, our groups are 3-5 people per boat maximum. We have two boats. We have been sailing the Biscayne Bay for over 15 years, just for the fun of it. We started this eco-tour in 2018 to share the ama... More

Free Cancellation
Private Tour
Start From $129.00
 
Sail Biscayne Bay: An Intimate Eco-Adventure Likely to Sell Out

Sail Biscayne Bay: An Intimate Eco-Adventure

  • North America
  • Superb412 reviews4.9

This tour is an intimate experience, our groups are 3-5 people per boat maximum. We have two boats. ....

    Free Cancellation
    Private Tour
    Start From $129.00
 
 

Cozumel Luxury Sailing & Snorkeling with Lunch and Open Bar Onboard

(4.8 of 217 reviews)

• Enjoy the turquoise waters of Cozumel aboard one of our luxury sailing catamarans. • Snorkel and marvel at the wide array of tropical fish and rich marine life that inhabit the colorful reefs of the island. • Paddleboard a... More

Free Cancellation
Private Tour
Start From $139.00
 
Cozumel Luxury Sailing & Snorkeling with Lunch and Open Bar Onboard Likely to Sell Out

Cozumel Luxury Sailing & Snorkeling with Lunch and Open Bar Onboa....

  • North America
  • Superb217 reviews4.8

• Enjoy the turquoise waters of Cozumel aboard one of our luxury sailing catamarans. • Snorkel a....

    Free Cancellation
    Private Tour
    Start From $139.00
 
 

Private Guided Sunset and Dolphin Cruise up to 6 Passengers

(5 of 57 reviews)

Our cruise is a private tour to see Destin's sunset as you want to see it. We can look for Dolphins, or watch the sunset from classic Destin Locations Crab Island and Norriego Point. Our boat includes a cooler with bottled water a... More

Free Cancellation
Private Tour
Start From $249.99
 
Private Guided Sunset and Dolphin Cruise up to 6 Passengers Likely to Sell Out

Private Guided Sunset and Dolphin Cruise up to 6 Passengers

  • North America
  • Superb57 reviews5

Our cruise is a private tour to see Destin's sunset as you want to see it. We can look for Dolphins,....

    Free Cancellation
    Private Tour
    Start From $249.99
 
 

2-Hour Windjammer Sailing Trip in Maine with Licensed Captain

(4 of 390 reviews)

Enjoy a leisurely sail on Frenchman Bay that includes narration about historical and geographical points of interest. View wildlife including eagles, seals and porpoises.... More

Free Cancellation
Private Tour
Start From $70.00
 
2-Hour Windjammer Sailing Trip in Maine with Licensed Captain Likely to Sell Out

2-Hour Windjammer Sailing Trip in Maine with Licensed Captain

  • North America
  • Very Good390 reviews4

Enjoy a leisurely sail on Frenchman Bay that includes narration about historical and geographical po....

    Free Cancellation
    Private Tour
    Start From $70.00
 
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