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Top 10 Best North America Sailing Trips

Found 769 Sailing Trips activities in North America. Sort by Popularity. - Page 4
 

Sunset Sail in Key West with Beverages Included

(4.9 of 973 reviews)

Key West is famous for fabulous sunsets and Floridays is famous for our spectacular uncrowded champagne sunset cruise. Our reputation for personal service and attention to detail on our sunset cruise is legendary. Being out on the... More

Free Cancellation
Start From $79.00
 
Sunset Sail in Key West with Beverages Included

Sunset Sail in Key West with Beverages Included

  • North America
  • Superb973 reviews4.9

Key West is famous for fabulous sunsets and Floridays is famous for our spectacular uncrowded champa....

    Free Cancellation
    Start From $79.00
 
 

Half-Day Luxury Sailing Experience in Tulum with Open Bar

(4.2 of 260 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 Tulum with Open Bar

Half-Day Luxury Sailing Experience in Tulum with Open Bar

  • North America
  • Exellent260 reviews4.2

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
 
 

Honolulu Sunset Sail from Kewalo Harbor Including Drinks

(4.8 of 200 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 ... More

Free Cancellation
Start From $61.50
 
Honolulu Sunset Sail from Kewalo Harbor Including Drinks

Honolulu Sunset Sail from Kewalo Harbor Including Drinks

  • North America
  • Superb200 reviews4.8

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

    Free Cancellation
    Start From $61.50
 
 

2.5-Hour Small-Group Catamaran Sail with Drinks

(5 of 313 reviews)

Experience the ultimate San Diego sailing adventure with a spacious catamaran cruise, offering your choice of a relaxing daytime sail or a breathtaking sunset sail. Designed for comfort and stability, these modern catamarans featu... More

Free Cancellation
Start From $119.00
 
2.5-Hour Small-Group Catamaran Sail with Drinks

2.5-Hour Small-Group Catamaran Sail with Drinks

  • North America
  • Superb313 reviews5

Experience the ultimate San Diego sailing adventure with a spacious catamaran cruise, offering your ....

    Free Cancellation
    Start From $119.00
 
 

Hilton Head Pirate Ship Adventure Sail aboard the Black Dagger

(4.9 of 708 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 Sparrow and set sail in search of treasure! But wait it's no... More

Free Cancellation
Start From $47.99
 
Hilton Head Pirate Ship Adventure Sail aboard the Black Dagger

Hilton Head Pirate Ship Adventure Sail aboard the Black Dagger

  • North America
  • Superb708 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 $47.99
 
 

Newport Sunset Sail on Schooner Adirondack

(4.8 of 120 reviews)

Join us aboard a classic sailboat for a 1.5-hour sunset sail in Newport! Sunset sailing is one of the best evening activities to do during your stay in Newport, RI. Enjoy a relaxing sail around Narragansett Bay on a classic sailbo... More

Free Cancellation
Start From $67.84
 
Newport Sunset Sail on Schooner Adirondack Likely to Sell Out

Newport Sunset Sail on Schooner Adirondack

  • North America
  • Superb120 reviews4.8

Join us aboard a classic sailboat for a 1.5-hour sunset sail in Newport! Sunset sailing is one of th....

    Free Cancellation
    Start From $67.84
 
 

Four Winds Molokini Snorkeling Tour from Maalaea Harbor

(4.7 of 844 reviews)

Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beautiful coral reefs and tropical fish underneath the water, or bask in the warmth of paradise. From the experienced snorkeler to those... More

Free Cancellation
Start From $213.41
 
Four Winds Molokini Snorkeling Tour from Maalaea Harbor Likely to Sell Out

Four Winds Molokini Snorkeling Tour from Maalaea Harbor

  • North America
  • Superb844 reviews4.7

Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beauti....

    Free Cancellation
    Start From $213.41
 
 

Sailing on Historic Schooner Yacht in Salem, MA

(4.9 of 198 reviews)

Set Sail in beautiful Salem, Massachusetts on an incredible and historic schooner yacht. Experience the majesty aboard John G. Alden's personal schooner yacht Malabar X. Winner of the 1930 and 1932 Newport to Bermuda race and open... More

Free Cancellation
Start From $55.00
 
Sailing on Historic Schooner Yacht in Salem, MA Likely to Sell Out

Sailing on Historic Schooner Yacht in Salem, MA

  • North America
  • Superb198 reviews4.9

Set Sail in beautiful Salem, Massachusetts on an incredible and historic schooner yacht. Experience ....

    Free Cancellation
    Start From $55.00
 
 

Kauai’s Na Pali Coast Snorkel and Sail Tour

(4.8 of 569 reviews)

Set sail for a once-in-a-lifetime adventure along Kauai’s iconic Na Pali Coast. This five-hour catamaran journey combines spectacular sightseeing, exciting snorkeling, and all-inclusive comfort, making it the top choice for fami... More

Free Cancellation
Start From $292.48
 
Kauai’s Na Pali Coast Snorkel and Sail Tour Likely to Sell Out

Kauai’s Na Pali Coast Snorkel and Sail Tour

  • North America
  • Superb569 reviews4.8

Set sail for a once-in-a-lifetime adventure along Kauai’s iconic Na Pali Coast. This five-hour cat....

    Free Cancellation
    Start From $292.48
 
 

2-Hour Sunset Sail on the San Francisco Bay

(4.7 of 418 reviews)

Whether you want to kick off a fabulous date night or wrap up an enjoyable afternoon, this two-hour sunset sail is just the ticket. Step aboard the gorgeous traditional vessel to take in the sights at the most bewitching time of d... More

Free Cancellation
Start From $129.00
 
2-Hour Sunset Sail on the San Francisco Bay Likely to Sell Out

2-Hour Sunset Sail on the San Francisco Bay

  • North America
  • Superb418 reviews4.7

Whether you want to kick off a fabulous date night or wrap up an enjoyable afternoon, this two-hour ....

    Free Cancellation
    Start From $129.00
 
 

Sunset Sail Along the San Diego Skyline

(4.9 of 637 reviews)

Enjoy an evening sailing under the sunset on a relaxing sailing cruise with a unique perspective on San Diego that you can only get from the water.  Our San Diego Bay Sunset Sailing Cruises provide an up-close and personal view o... More

Free Cancellation
Start From $109.00
 
Sunset Sail Along the San Diego Skyline Likely to Sell Out

Sunset Sail Along the San Diego Skyline

  • North America
  • Superb637 reviews4.9

Enjoy an evening sailing under the sunset on a relaxing sailing cruise with a unique perspective on ....

    Free Cancellation
    Start From $109.00
 
 

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

(4.4 of 383 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
Start From $57.32
 
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
  • Exellent383 reviews4.4

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

    Free Cancellation
    Start From $57.32
 
 

Best of Halifax Harbour Boat Tour

(4.9 of 90 reviews)

This 45' luxury boat is the perfect venue to learn about the history of Halifax. You are alongside our Captain and Deckhand throughout the relaxed harbour tour as they share Halifax's history and present day facts!... More

Free Cancellation
Start From $43.03
 
Best of Halifax Harbour Boat Tour Likely to Sell Out

Best of Halifax Harbour Boat Tour

  • North America
  • Superb90 reviews4.9

This 45' luxury boat is the perfect venue to learn about the history of Halifax. You are alongside ....

    Free Cancellation
    Start From $43.03
 
 

Key West's Favorite Afternoon Dolphin Sail

(4.6 of 209 reviews)

Our afternoon dolphin watch is limited to an intimate number of passengers to optimize your views! Enjoy sailing aboard a 60' catamaran to the dolphin playground to view wild dolphins play and frolic in their natural habitat. Atla... More

Free Cancellation
Start From $59.00
 
Key West's Favorite Afternoon Dolphin Sail Likely to Sell Out

Key West's Favorite Afternoon Dolphin Sail

  • North America
  • Superb209 reviews4.6

Our afternoon dolphin watch is limited to an intimate number of passengers to optimize your views! E....

    Free Cancellation
    Start From $59.00
 
 

El Cielo Snorkel by Private Boat

(4.8 of 366 reviews)

- Private and comfortable vessels - Snorkel at world famous reefs - Spectacular marine life and coral formations - Stop over at a secluded pristine white sandy beach away from the crowds - Taste a delicious fish ceviche and co... More

Free Cancellation
Private Tour
Start From $499.99
 
El Cielo Snorkel by Private Boat Likely to Sell Out

El Cielo Snorkel by Private Boat

  • North America
  • Superb366 reviews4.8

- Private and comfortable vessels - Snorkel at world famous reefs - Spectacular marine life and co....

    Free Cancellation
    Private Tour
    Start From $499.99
 
 

Waikoloa Signature Catamaran Sunset Sail

(4.7 of 413 reviews)

End your day in paradise with a relaxing sunset cruise along Waikoloa’s beautiful Kohala Coast. Departing from Anaeho‘omalu Bay, the Spirit of Aloha catamaran offers a smooth, comfortable ride with panoramic views of Mauna Kea... More

Free Cancellation
Private Tour
Start From $159.00
 
Waikoloa Signature Catamaran Sunset Sail Likely to Sell Out

Waikoloa Signature Catamaran Sunset Sail

  • North America
  • Superb413 reviews4.7

End your day in paradise with a relaxing sunset cruise along Waikoloa’s beautiful Kohala Coast. De....

    Free Cancellation
    Private Tour
    Start From $159.00
 
 

San Francisco Bay Sailing Cruise

(4.9 of 649 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
Private Tour
Start From $65.00
 
San Francisco Bay Sailing Cruise Likely to Sell Out

San Francisco Bay Sailing Cruise

  • North America
  • Superb649 reviews4.9

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

    Free Cancellation
    Private Tour
    Start From $65.00
 
 

Windjammer Classic Sunset Sail from Camden, Maine

(4.9 of 456 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
Private Tour
Start From $64.95
 
Windjammer Classic Sunset Sail from Camden, Maine Likely to Sell Out

Windjammer Classic Sunset Sail from Camden, Maine

  • North America
  • Superb456 reviews4.9

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

    Free Cancellation
    Private Tour
    Start From $64.95
 
 

Lagoon 39ft Private Catamaran 5hr - El Cielo Full Experience

(5 of 655 reviews)

Our 5 Hrs private charter delivers the ultimate all-inclusive vacation on the water aboard your own private catamaran. Complete with a professional captain & crew , your group will enjoy spacious accommodations and a premium, pers... More

Special Offer
Free Cancellation
Private Tour
Start From $2,090.00
(Saving 5% ) $2,200.00
 
-5% Lagoon 39ft Private Catamaran 5hr - El Cielo Full Experience Likely to Sell Out

Lagoon 39ft Private Catamaran 5hr - El Cielo Full Experience

  • North America
  • Superb655 reviews5

Our 5 Hrs private charter delivers the ultimate all-inclusive vacation on the water aboard your own ....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $2,090.00
    (Saving 5% ) $2,200.00
 
 

Small-Group San Diego Afternoon Sailing Excursion

(4.9 of 556 reviews)

This three-hour adventure on a a beautiful modern-day sailboat is limited to just 6 people, allowing you a comfortable, semi-private experience (or, grab five friends and fill up the whole boat!). Sit back, relax and enjoy the com... More

Special Offer
Free Cancellation
Private Tour
Start From $116.00
(Saving inf% ) $0.00
 
-inf% Small-Group San Diego Afternoon Sailing Excursion Likely to Sell Out

Small-Group San Diego Afternoon Sailing Excursion

  • North America
  • Superb556 reviews4.9

This three-hour adventure on a a beautiful modern-day sailboat is limited to just 6 people, allowing....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $116.00
    (Saving inf% ) $0.00
 
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