Menu

Top 10 Best North America Sailing Trips

Found 734 Sailing Trips activities in North America. Sort by Popularity. - Page 3
 

Sunset Sail Along the San Diego Skyline

(4.9 of 605 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

Sunset Sail Along the San Diego Skyline

  • North America
  • Superb605 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
 
 

Luxury Whale Watch Cruise to The Arch Los Cabos

(4.6 of 136 reviews)

Whale season is from mid-December thru mid-April, you can book this tour all year round but to travel only during the Whale Season (Dec 15 thru April 15th). Enjoy 2 hours spectacular adventure looking for whales, who travel thousa... More

Free Cancellation
Start From $95.00
 
Luxury Whale Watch Cruise to The Arch Los Cabos

Luxury Whale Watch Cruise to The Arch Los Cabos

  • North America
  • Superb136 reviews4.6

Whale season is from mid-December thru mid-April, you can book this tour all year round but to trave....

    Free Cancellation
    Start From $95.00
 
 
-12% Waikiki 2-Hour Sunset Sailing Catamaran – Splash & Sail Adventure

Waikiki 2-Hour Sunset Sailing Catamaran – Splash & Sail Adventure

(4.7 of 537 reviews)

There’s no better place to take a dip than the crystal-clear waters of Waikiki—and no better way to experience a Hawaiian sunset than from the ocean, with the iconic Waikiki coastline as your backdrop. As the sun begins to se... More

Special Offer
Free Cancellation
Start From $44.80
(Saving 12% ) $50.71
 
-12% Waikiki 2-Hour Sunset Sailing Catamaran – Splash & Sail Adventure

Waikiki 2-Hour Sunset Sailing Catamaran – Splash & Sail Adventu....

  • North America
  • Superb537 reviews4.7

There’s no better place to take a dip than the crystal-clear waters of Waikiki—and no better way....

    Special Offer
    Free Cancellation
    Start From $44.80
    (Saving 12% ) $50.71
 
 

Key West Sunset Sail Aboard Legendary Schooner Appledore

(5 of 274 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
  • Superb274 reviews5

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

    Free Cancellation
    Start From $89.00
 
 

Cabo San Lucas Sunset Sailing Shared Cruise

(4.9 of 787 reviews)

Enjoy a 2-hour sunset cruise aboard a beautiful luxury sailing boat. Admire the sights illuminated at night, and see the wonderful sunset contrasting with Cabo San Lucas amazing waters. This is a family-friendly tour and includes... More

Free Cancellation
Start From $120.00
 
Cabo San Lucas Sunset Sailing Shared Cruise

Cabo San Lucas Sunset Sailing Shared Cruise

  • North America
  • Superb787 reviews4.9

Enjoy a 2-hour sunset cruise aboard a beautiful luxury sailing boat. Admire the sights illuminated ....

    Free Cancellation
    Start From $120.00
 
 

El Cielo Snorkel by Private Boat

(4.8 of 342 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

El Cielo Snorkel by Private Boat

  • North America
  • Superb342 reviews4.8

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

    Free Cancellation
    Private Tour
    Start From $499.99
 
 

Los Cabos Luxury Sunset Sail with Light Appetizers and Open Bar

(4.8 of 2,282 reviews)

Sail into the sunset along the Cabo coast and enjoy five-star service aboard a luxury yacht. This romantic sunset cruise on Cabo San Lucas Bay includes unlimited drinks from an open bar, accompanied by a delightful menu of small b... More

Free Cancellation
Private Tour
Start From $109.00
 
Los Cabos Luxury Sunset Sail with Light Appetizers and Open Bar Likely to Sell Out

Los Cabos Luxury Sunset Sail with Light Appetizers and Open Bar

  • North America
  • Superb2,282 reviews4.8

Sail into the sunset along the Cabo coast and enjoy five-star service aboard a luxury yacht. This ro....

    Free Cancellation
    Private Tour
    Start From $109.00
 
 

Waikoloa Signature Catamaran Sunset Sail

(4.7 of 399 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
  • Superb399 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
 
 

Lands End Luxury Sail and Snorkel Cruise in Cabo San Lucas

(4.9 of 817 reviews)

✨ Discover Los Cabos Like Never Before! Sail the turquoise waters of the Sea of Cortez on an unforgettable snorkeling, sightseeing and sailing adventure. Begin at Pelican’s Rock, dive into crystal-clear waters filled with hun... More

Free Cancellation
Private Tour
Start From $120.00
 
Lands End Luxury Sail and Snorkel Cruise in Cabo San Lucas Likely to Sell Out

Lands End Luxury Sail and Snorkel Cruise in Cabo San Lucas

  • North America
  • Superb817 reviews4.9

✨ Discover Los Cabos Like Never Before! Sail the turquoise waters of the Sea of Cortez on an unfor....

    Free Cancellation
    Private Tour
    Start From $120.00
 
 

2.5-Hour Small-Group Catamaran Sail with Drinks

(4.9 of 227 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
Private Tour
Start From $119.00
 
2.5-Hour Small-Group Catamaran Sail with Drinks Likely to Sell Out

2.5-Hour Small-Group Catamaran Sail with Drinks

  • North America
  • Superb227 reviews4.9

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

    Free Cancellation
    Private Tour
    Start From $119.00
 
 

Small-Group San Diego Sunset Sailing Excursion

(4.9 of 597 reviews)

Set sail from San Diego on this small-group sailing tour on a sunset sail on the open ocean. This three-hour adventure on a Catalina sailboat is limited to six (6) guests allowing you a comfortable, semi-private experience (or, pu... More

Free Cancellation
Private Tour
Start From $127.00
 
Small-Group San Diego Sunset Sailing Excursion Likely to Sell Out

Small-Group San Diego Sunset Sailing Excursion

  • North America
  • Superb597 reviews4.9

Set sail from San Diego on this small-group sailing tour on a sunset sail on the open ocean. This th....

    Free Cancellation
    Private Tour
    Start From $127.00
 
 

Cabo San Lucas Luxury Sailing Yacht and Dinner with a Chef

(4.5 of 295 reviews)

Sail into the sunset on board Tu Enamorado, a beautifully crafted sailing yacht of unsurpassed quality, comfort, and performance. Live the yachting lifestyle, walk barefoot on the deck, feel the sun and breeze on your face, dance ... More

Free Cancellation
Private Tour
Start From $199.00
 
Cabo San Lucas Luxury Sailing Yacht and Dinner with a Chef Likely to Sell Out

Cabo San Lucas Luxury Sailing Yacht and Dinner with a Chef

  • North America
  • Exellent295 reviews4.5

Sail into the sunset on board Tu Enamorado, a beautifully crafted sailing yacht of unsurpassed quali....

    Free Cancellation
    Private Tour
    Start From $199.00
 
 

Southwest Florida Sunset Sail

(4.9 of 481 reviews)

SWFL sunsets are the best, and there is no better place to watch them than from the deck of our 36ft. Sailing Catamaran, "Copacetic". The sunset hours are a magical time to be out on the water. With the winds calm, the sun turns g... More

Free Cancellation
Private Tour
Start From $70.00
 
Southwest Florida Sunset Sail Likely to Sell Out

Southwest Florida Sunset Sail

  • North America
  • Superb481 reviews4.9

SWFL sunsets are the best, and there is no better place to watch them than from the deck of our 36ft....

    Free Cancellation
    Private Tour
    Start From $70.00
 
 

Key West Afternoon Reef Snorkeling with Open Bar

(4.4 of 425 reviews)

Dip and Sip Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip will start a sail to the Key West living reef where you will see coral and tropical fish. All snorkeling equipment is provided an... More

Free Cancellation
Private Tour
Start From $59.95
 
Key West Afternoon Reef Snorkeling with Open Bar Likely to Sell Out

Key West Afternoon Reef Snorkeling with Open Bar

  • North America
  • Exellent425 reviews4.4

Dip and Sip Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip w....

    Free Cancellation
    Private Tour
    Start From $59.95
 
 

Buccaneer Pirate Cruise in Destin

(4.9 of 96 reviews)

Board a pirate ship in Destin and set out on a swashbuckling adventure perfect for the whole family! Enjoy a fun cruise with interactive pirate-themed activities, entertainment, and treasure hunts. Take in the beauty of the Emeral... More

Free Cancellation
Private Tour
Start From $55.00
 
Buccaneer Pirate Cruise in Destin Likely to Sell Out

Buccaneer Pirate Cruise in Destin

  • North America
  • Superb96 reviews4.9

Board a pirate ship in Destin and set out on a swashbuckling adventure perfect for the whole family!....

    Free Cancellation
    Private Tour
    Start From $55.00
 
 

Sunset Sail Cruise in Key West

(4.9 of 263 reviews)

Sailing on the Rover is an exciting, traditional sailing experience with a Hint of Piracy! Yes - We have cannons! Come sail on Key West's most photographed ship! The Schooner Jolly II Rover is the only squared rigged, topsail scho... More

Free Cancellation
Private Tour
Start From $95.00
 
Sunset Sail Cruise in Key West Likely to Sell Out

Sunset Sail Cruise in Key West

  • North America
  • Superb263 reviews4.9

Sailing on the Rover is an exciting, traditional sailing experience with a Hint of Piracy! Yes - We ....

    Free Cancellation
    Private Tour
    Start From $95.00
 
 

Ft Myers Beach 2 Hour Tiki Pub Fun in the Sun Dolphin Cruise

(4.9 of 94 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 $59.95
 
Ft Myers Beach 2 Hour Tiki Pub Fun in the Sun Dolphin Cruise Likely to Sell Out

Ft Myers Beach 2 Hour Tiki Pub Fun in the Sun Dolphin Cruise

  • North America
  • Superb94 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 $59.95
 
 

Whale-Watching Pirate Ship Cruise in Los Cabos

(4.7 of 117 reviews)

Go whale-watching in Cabo San Lucas aboard a real pirate ship called the Bucaneer Queen. Sail the Pacific Ocean and the Sea of Cortez in search of these amazing creatures. You will be accompanied by an experienced bilingual guide ... More

Free Cancellation
Private Tour
Start From $99.00
 
Whale-Watching Pirate Ship Cruise in Los Cabos Likely to Sell Out

Whale-Watching Pirate Ship Cruise in Los Cabos

  • North America
  • Superb117 reviews4.7

Go whale-watching in Cabo San Lucas aboard a real pirate ship called the Bucaneer Queen. Sail the Pa....

    Free Cancellation
    Private Tour
    Start From $99.00
 
 

Private Luxury Yacht Charters, BYOB & Dolphins

(5 of 397 reviews)

We are a family owned luxury yacht charter business. Come enjoy a BYOB day of sailing and seeing the historic sites of Charleston from the water on one of our sailboats. We offer hourly, daily, or customized tours according to you... More

Free Cancellation
Private Tour
Start From $499.00
 
Private Luxury Yacht Charters, BYOB & Dolphins Likely to Sell Out

Private Luxury Yacht Charters, BYOB & Dolphins

  • North America
  • Superb397 reviews5

We are a family owned luxury yacht charter business. Come enjoy a BYOB day of sailing and seeing the....

    Free Cancellation
    Private Tour
    Start From $499.00
 
 

Isla Mujeres Day Tour with Catamaran, Snorkeling & Beach Club

(4.5 of 158 reviews)

Embark on a full-day adventure to Isla Mujeres, Cancun's most popular island getaway. Snorkel among vibrant tropical fish, then relax on Playa Norte, one of Mexico's finest beaches. Departing from the pier, begin with a 30-minut... More

Free Cancellation
Private Tour
Start From $89.00
 
Isla Mujeres Day Tour with Catamaran, Snorkeling & Beach Club Likely to Sell Out

Isla Mujeres Day Tour with Catamaran, Snorkeling & Beach Club

  • North America
  • Exellent158 reviews4.5

Embark on a full-day adventure to Isla Mujeres, Cancun's most popular island getaway. Snorkel among ....

    Free Cancellation
    Private Tour
    Start From $89.00
 
1 2 3 4 5
Booking.com
Booking.com
Booking.com