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Top 10 Best North America Sailing Trips

Found 668 Sailing Trips activities in North America. Sort by Popularity. - Page 5
 

San Francisco Bay Sailing Cruise

(4.9 of 591 reviews)

Experience the beauty of San Francisco during a 1.5-hour catamaran cruise over San Francisco Bay. Sail away from bustling city and enjoy photo ops from the vantage point of the water. You’ll coast past the city skyline, the Gold... More

Free Cancellation
Start From $69.00
 
San Francisco Bay Sailing Cruise

San Francisco Bay Sailing Cruise

  • North America
  • Superb591 reviews4.9

Experience the beauty of San Francisco during a 1.5-hour catamaran cruise over San Francisco Bay. Sa....

    Free Cancellation
    Start From $69.00
 
 
-5% FROM FLORIDA: Bimini Bahamas Day Trip By Fast Ferry

FROM FLORIDA: Bimini Bahamas Day Trip By Fast Ferry

(3.6 of 10 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

FROM FLORIDA: Bimini Bahamas Day Trip By Fast Ferry

  • North America
  • Very Good10 reviews3.6

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
 
 

Key West Sunset Sail Aboard Legendary Schooner Appledore

(5 of 181 reviews)

Experience sailing Key West on a majestic 2-masted schooner, just like adventurers from the 19th century, while enjoying the luxurious state-of-the-art accommodations of a modern passenger schooner. Her decks are spacious and comf... More

Free Cancellation
Start From $89.00
 
Key West Sunset Sail Aboard Legendary Schooner Appledore

Key West Sunset Sail Aboard Legendary Schooner Appledore

  • North America
  • Superb181 reviews5

Experience sailing Key West on a majestic 2-masted schooner, just like adventurers from the 19th cen....

    Free Cancellation
    Start From $89.00
 
 

Private Sailing Charter with Captain, BYOB

(5 of 49 reviews)

Embark on an exclusive sailing adventure on board "Esprit de Joy," tailor-made for groups of up to 6 guests for a 2.5-hour charter embracing Charleston's scenic Harbor. The golden hour of sunset is our prime booking time, offering... More

Free Cancellation
Private Tour
Start From $500.00
 
Private Sailing Charter with Captain, BYOB

Private Sailing Charter with Captain, BYOB

  • North America
  • Superb49 reviews5

Embark on an exclusive sailing adventure on board "Esprit de Joy," tailor-made for groups of up to 6....

    Free Cancellation
    Private Tour
    Start From $500.00
 
 

Half Day Private Sailing Cruise Puerto Vallarta with Snorkeling

(5 of 56 reviews)

Experience the beauty of Puerto Vallarta’s stunning bay on an exclusive, half-day private sailing cruise. Explore pristine beaches and beautiful sights while savoring fresh guacamole and a selection of delicious snacks. This pe... More

Free Cancellation
Private Tour
Start From $654.02
 
Half Day Private Sailing Cruise Puerto Vallarta with Snorkeling

Half Day Private Sailing Cruise Puerto Vallarta with Snorkeling

  • North America
  • Superb56 reviews5

Experience the beauty of Puerto Vallarta’s stunning bay on an exclusive, half-day private sailing ....

    Free Cancellation
    Private Tour
    Start From $654.02
 
 

2.5 Hours of Fun: Catamaran Sunset Sail

(4.9 of 149 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
Private Tour
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
  • Superb149 reviews4.9

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

    Free Cancellation
    Private Tour
    Start From $119.00
 
 

Snorkel with Manta Rays Guaranteed

(4.8 of 680 reviews)

Join us aboard our luxurious catamaran, Hoku Nui, as we coast to the world famous Manta Ray Village. Travel Channel says “its one of the top ten things to do in your life time”, and Sea Paradise has been offering its guests th... More

Free Cancellation
Private Tour
Start From $141.57
 
Snorkel with Manta Rays Guaranteed Likely to Sell Out

Snorkel with Manta Rays Guaranteed

  • North America
  • Superb680 reviews4.8

Join us aboard our luxurious catamaran, Hoku Nui, as we coast to the world famous Manta Ray Village.....

    Free Cancellation
    Private Tour
    Start From $141.57
 
 

Kealakekua Snorkel and Sail Adventure

(5 of 631 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 garde... More

Free Cancellation
Private Tour
Start From $177.65
 
Kealakekua Snorkel and Sail Adventure Likely to Sell Out

Kealakekua Snorkel and Sail Adventure

  • North America
  • Superb631 reviews5

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

    Free Cancellation
    Private Tour
    Start From $177.65
 
 

9am Turtle Canyon Snorkel Adventure

(4.9 of 248 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 $77.04
(Saving 20% ) $96.30
 
-20% 9am Turtle Canyon Snorkel Adventure Likely to Sell Out

9am Turtle Canyon Snorkel Adventure

  • North America
  • Superb248 reviews4.9

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 $77.04
    (Saving 20% ) $96.30
 
 

Key West Dolphin and Snorkel Experience

(4.4 of 274 reviews)

The Sunset Watersports Dolphin watch triple combo is the best way to watch Dolphins, Snorkel the Key West tropical waters, and see the world famous Key West Sunset all in one trip.... More

Free Cancellation
Private Tour
Start From $69.95
 
Key West Dolphin and Snorkel Experience Likely to Sell Out

Key West Dolphin and Snorkel Experience

  • North America
  • Exellent274 reviews4.4

The Sunset Watersports Dolphin watch triple combo is the best way to watch Dolphins, Snorkel the Key....

    Free Cancellation
    Private Tour
    Start From $69.95
 
 

Private Guided Sunset and Dolphin Cruise up to 6 Passengers

(5 of 58 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
  • Superb58 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
 
 

Panama City Beach Sunset Sail on The Footloose Catamaran

(4.8 of 394 reviews)

If you are looking to unwind before dinner or a night out on the town, come take a romantic Sunset Sail on SV Footloose, our 38 passenger catamaran, with Paradise Adventures! This breathtaking sunset sail along the Gulf of Mexico ... More

Free Cancellation
Private Tour
Start From $45.00
 
Panama City Beach Sunset Sail on The Footloose Catamaran Likely to Sell Out

Panama City Beach Sunset Sail on The Footloose Catamaran

  • North America
  • Superb394 reviews4.8

If you are looking to unwind before dinner or a night out on the town, come take a romantic Sunset S....

    Free Cancellation
    Private Tour
    Start From $45.00
 
 

Dolphin Adventure Sail in Cocoa Beach

(5 of 134 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 Likely to Sell Out

Dolphin Adventure Sail in Cocoa Beach

  • North America
  • Superb134 reviews5

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

    Free Cancellation
    Private Tour
    Start From $50.85
 
 

Key West Rum and Reggae: Reef Snorkel Adventure and Sunset Sail

(4.4 of 348 reviews)

Fury’s Snorkel Adventure is unique for its combination of thrilling snorkeling and a vibrant sailing experience. Guests board a spacious Fury Catamaran, part of the largest luxury fleet in the Florida Keys, and sail to North Ame... More

Free Cancellation
Private Tour
Start From $59.07
 
Key West Rum and Reggae: Reef Snorkel Adventure and Sunset Sail Likely to Sell Out

Key West Rum and Reggae: Reef Snorkel Adventure and Sunset Sail

  • North America
  • Exellent348 reviews4.4

Fury’s Snorkel Adventure is unique for its combination of thrilling snorkeling and a vibrant saili....

    Free Cancellation
    Private Tour
    Start From $59.07
 
 

Sightseeing Day Sail around Boston Harbor

(4.7 of 382 reviews)

Choose between either a 1.5 or 2-hour sail around Boston Harbor aboard one of our beautiful schooner Adirondack sailboats! These classic boats are reminiscent of the sailboats from the 1890s. Sail past the seaport district, Castle... More

Free Cancellation
Private Tour
Start From $66.54
 
Sightseeing Day Sail around Boston Harbor Likely to Sell Out

Sightseeing Day Sail around Boston Harbor

  • North America
  • Superb382 reviews4.7

Choose between either a 1.5 or 2-hour sail around Boston Harbor aboard one of our beautiful schooner....

    Free Cancellation
    Private Tour
    Start From $66.54
 
 

NYC Statue of Liberty Tall Ship Sail aboard Clipper City

(4.3 of 253 reviews)

Step aboard a historic sailing ship and cruise around New York Harbor, taking in magnificent views of this grand city by day. You will enjoy breathtaking views of New York City and see the Statue of Liberty, Ellis Island, the Manh... More

Free Cancellation
Private Tour
Start From $68.00
 
NYC Statue of Liberty Tall Ship Sail aboard Clipper City Likely to Sell Out

NYC Statue of Liberty Tall Ship Sail aboard Clipper City

  • North America
  • Exellent253 reviews4.3

Step aboard a historic sailing ship and cruise around New York Harbor, taking in magnificent views o....

    Free Cancellation
    Private Tour
    Start From $68.00
 
 

Sail and Turtle Snorkeling Tour in Waikiki

(4.9 of 236 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
Private Tour
Start From $99.00
 
Sail and Turtle Snorkeling Tour in Waikiki Likely to Sell Out

Sail and Turtle Snorkeling Tour in Waikiki

  • North America
  • Superb236 reviews4.9

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

    Free Cancellation
    Private Tour
    Start From $99.00
 
 

Honolulu Sunset Sail from Kewalo Harbor Including Drinks

(4.8 of 106 reviews)

Our Sunset Sail tour is a fun and wild 90-minute sail where all drinks are complimentary! (Must be 21+ with valid ID to consume alcoholic beverages). Sail the south shore from Kaka'ako Waterfront to Waikiki, with beautiful views o... More

Free Cancellation
Private Tour
Start From $61.50
 
Honolulu Sunset Sail from Kewalo Harbor Including Drinks Likely to Sell Out

Honolulu Sunset Sail from Kewalo Harbor Including Drinks

  • North America
  • Superb106 reviews4.8

Our Sunset Sail tour is a fun and wild 90-minute sail where all drinks are complimentary! (Must be 2....

    Free Cancellation
    Private Tour
    Start From $61.50
 
 

2-Hour Windjammer Sailing Trip in Maine with Licensed Captain

(4 of 391 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 Good391 reviews4

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

    Free Cancellation
    Private Tour
    Start From $70.00
 
 

Ft Myers Beach Tiki Pub Fun in the Sun Dolphin Cruise

(4.9 of 57 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
Private Tour
Start From $59.00
 
Ft Myers Beach Tiki Pub Fun in the Sun Dolphin Cruise Likely to Sell Out

Ft Myers Beach Tiki Pub Fun in the Sun Dolphin Cruise

  • North America
  • Superb57 reviews4.9

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

    Free Cancellation
    Private Tour
    Start From $59.00
 
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