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Top 10 Best North America Sailing Trips

Found 676 Sailing Trips activities in North America. Sort by Popularity. - Page 3
 

Key West Snorkeling with Breakfast and Unlimited Mimosas

(4.5 of 494 reviews)

Rise and Reef Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip will start with a Light Breakfast and sail to the Key West living reef where you will see coral and tropical fish. All snorkeling... More

Free Cancellation
Start From $46.94
 
Key West Snorkeling with Breakfast and Unlimited Mimosas

Key West Snorkeling with Breakfast and Unlimited Mimosas

  • North America
  • Exellent494 reviews4.5

Rise and Reef Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip....

    Free Cancellation
    Start From $46.94
 
 

Sunset Sail from Ma'alaea Harbor

(4.6 of 203 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 ex... More

Free Cancellation
Start From $133.05
 
Sunset Sail from Ma'alaea Harbor

Sunset Sail from Ma'alaea Harbor

  • North America
  • Superb203 reviews4.6

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

    Free Cancellation
    Start From $133.05
 
 

El Cielo Snorkel by Private Boat

(4.8 of 293 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
  • Superb293 reviews4.8

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

    Free Cancellation
    Private Tour
    Start From $499.99
 
 

Waikiki Sunset Cocktail Sail with Open Bar

(4.7 of 459 reviews)

This is our most popular sail for the fun-loving crowd! All drinks are included on this lively cruise! Strangers become fast friends on this one regardless if your cruising solo or with a crew! We provide juice, soda, bottled wate... More

Free Cancellation
Private Tour
Start From $85.00
 
Waikiki Sunset Cocktail Sail with Open Bar

Waikiki Sunset Cocktail Sail with Open Bar

  • North America
  • Superb459 reviews4.7

This is our most popular sail for the fun-loving crowd! All drinks are included on this lively cruis....

    Free Cancellation
    Private Tour
    Start From $85.00
 
 

Small-Group Sunset Sailing Experience on San Diego Bay

(4.9 of 531 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
Private Tour
Start From $125.00
 
Small-Group Sunset Sailing Experience on San Diego Bay

Small-Group Sunset Sailing Experience on San Diego Bay

  • North America
  • Superb531 reviews4.9

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

    Free Cancellation
    Private Tour
    Start From $125.00
 
 

Deluxe Sunset & Day Sail Small Group

(5 of 110 reviews)

Experience the breathtaking beauty of San Diego Bay at sunset aboard our mono-hull sailboat, perfect for up to six passengers. Glide through calm waters as the sky transforms into a masterpiece of color. Keep an eye out for playfu... More

Free Cancellation
Private Tour
Start From $119.00
 
Deluxe Sunset & Day Sail Small Group

Deluxe Sunset & Day Sail Small Group

  • North America
  • Superb110 reviews5

Experience the breathtaking beauty of San Diego Bay at sunset aboard our mono-hull sailboat, perfect....

    Free Cancellation
    Private Tour
    Start From $119.00
 
 

Key West Reef Snorkel & Sail Adventure

(4.7 of 501 reviews)

Join us for a snorkel adventure to the only living coral reef in North America. We have several fantastic reefs to choose from on both the north and south sides of Key West, each offering a unique experience. It’s about an hour ... More

Free Cancellation
Private Tour
Start From $79.00
 
Key West Reef Snorkel & Sail Adventure

Key West Reef Snorkel & Sail Adventure

  • North America
  • Superb501 reviews4.7

Join us for a snorkel adventure to the only living coral reef in North America. We have several fant....

    Free Cancellation
    Private Tour
    Start From $79.00
 
 

Riviera Maya Luxury Sunset Sailing plus Light Dinner and Open Bar

(4.6 of 387 reviews)

Experience the sunset like never before on this fabulous Sunset Sailing excursion. You’ll sail along the stunning coastline of the Riviera Maya aboard a luxurious catamaran, while Mother Nature prepares for her nightly performan... More

Free Cancellation
Private Tour
Start From $109.00
 
Riviera Maya Luxury Sunset Sailing plus Light Dinner and Open Bar

Riviera Maya Luxury Sunset Sailing plus Light Dinner and Open Bar

  • North America
  • Superb387 reviews4.6

Experience the sunset like never before on this fabulous Sunset Sailing excursion. You’ll sail alo....

    Free Cancellation
    Private Tour
    Start From $109.00
 
 

Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure

(4.7 of 891 reviews)

Snorkel Turtle Canyon on the Largest Luxury Catamaran! Top Quality Gear, Certified Crew & Premium On Board Bar. When you trust Moana Sailing Co. for your snorkel adventure, you’re choosing the tour with the most professionalis... More

Free Cancellation
Private Tour
Start From $84.99
 
Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure

Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventu....

  • North America
  • Superb891 reviews4.7

Snorkel Turtle Canyon on the Largest Luxury Catamaran! Top Quality Gear, Certified Crew & Premium On....

    Free Cancellation
    Private Tour
    Start From $84.99
 
 

Deluxe Sail & Snorkel to the Captain Cook Monument

(4.9 of 432 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
Private Tour
Start From $179.27
 
Deluxe Sail & Snorkel to the Captain Cook Monument

Deluxe Sail & Snorkel to the Captain Cook Monument

  • North America
  • Superb432 reviews4.9

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

    Free Cancellation
    Private Tour
    Start From $179.27
 
 

El Cielo, Palancar Snorkel & Beach Party Experience

(4.8 of 474 reviews)

El Cielo is an unspoiled, natural marvel of cobalt crystal clear shallow waters, sand bottom, and Cozumel's jungle in the background; we will relax here after snorkeling at the world famous Palancar Reef offers to snorkelers a col... More

Free Cancellation
Private Tour
Start From $79.00
 
El Cielo, Palancar Snorkel & Beach Party Experience Likely to Sell Out

El Cielo, Palancar Snorkel & Beach Party Experience

  • North America
  • Superb474 reviews4.8

El Cielo is an unspoiled, natural marvel of cobalt crystal clear shallow waters, sand bottom, and Co....

    Free Cancellation
    Private Tour
    Start From $79.00
 
 

Southwest Florida Sunset Sail

(4.9 of 399 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
  • Superb399 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
 
 

Small-Group San Diego Afternoon Sailing Excursion

(5 of 486 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

Free Cancellation
Private Tour
Start From $116.00
 
Small-Group San Diego Afternoon Sailing Excursion Likely to Sell Out

Small-Group San Diego Afternoon Sailing Excursion

  • North America
  • Superb486 reviews5

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

    Free Cancellation
    Private Tour
    Start From $116.00
 
 

Key West's Favorite Afternoon Dolphin Sail

(4.8 of 44 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
Private Tour
Start From $59.00
 
Key West's Favorite Afternoon Dolphin Sail Likely to Sell Out

Key West's Favorite Afternoon Dolphin Sail

  • North America
  • Superb44 reviews4.8

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

    Free Cancellation
    Private Tour
    Start From $59.00
 
 

Puerto Vallarta Luxury Sailing with Premium Open bar & lunch

(4.8 of 282 reviews)

Sail across Banderas Bay in luxury aboard our exclusive Leopard and Beneteau yachts, taking in breathtaking views of Puerto Vallarta’s coastline and the majestic Sierra Madre mountains. This small-group experience offers a perfe... More

Free Cancellation
Private Tour
Start From $129.00
 
Puerto Vallarta Luxury Sailing with Premium Open bar & lunch Likely to Sell Out

Puerto Vallarta Luxury Sailing with Premium Open bar & lunch

  • North America
  • Superb282 reviews4.8

Sail across Banderas Bay in luxury aboard our exclusive Leopard and Beneteau yachts, taking in breat....

    Free Cancellation
    Private Tour
    Start From $129.00
 
 

Kealakekua Snorkel and Sail Adventure

(5 of 615 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
  • Superb615 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
 
 

Catamaran Day Sail Shelling Excursion 42ft. Mainecat Cool Beans

(4.9 of 113 reviews)

Create memories that lasts a lifetime with a day on the Gulf of Mexico sailing to a private island for some swimming and shelling (weather permitting) while taking in the sun and spectacular views. Our beautifully, well appointed ... More

Free Cancellation
Private Tour
Start From $70.00
 
Catamaran Day Sail Shelling Excursion 42ft. Mainecat Cool Beans Likely to Sell Out

Catamaran Day Sail Shelling Excursion 42ft. Mainecat Cool Beans

  • North America
  • Superb113 reviews4.9

Create memories that lasts a lifetime with a day on the Gulf of Mexico sailing to a private island f....

    Free Cancellation
    Private Tour
    Start From $70.00
 
 

Luxury Catamaran Whale Watch

(5 of 32 reviews)

Come join us to observe the playful habits of Maui's most consistent return visitor - the humpback whale. The waters off West Maui have long been the favored vacation spot of these massive marine mammals. The Alii Class Yachts pro... More

Free Cancellation
Private Tour
Start From $159.00
 
Luxury Catamaran Whale Watch Likely to Sell Out

Luxury Catamaran Whale Watch

  • North America
  • Superb32 reviews5

Come join us to observe the playful habits of Maui's most consistent return visitor - the humpback w....

    Free Cancellation
    Private Tour
    Start From $159.00
 
 

Na Pali Coast Kauai Snorkel and Sail

(4.8 of 506 reviews)

Families and groups-- say YES to an action-packed, five-hour ocean adventure aboard our gorgeous and comfortable 50’ Kauai-built sailing catamaran, Leila. Let’s explore the cliffs, valleys, sea caves and wildlife of the Napali... More

Free Cancellation
Private Tour
Start From $275.28
 
Na Pali Coast Kauai Snorkel and Sail Likely to Sell Out

Na Pali Coast Kauai Snorkel and Sail

  • North America
  • Superb506 reviews4.8

Families and groups-- say YES to an action-packed, five-hour ocean adventure aboard our gorgeous and....

    Free Cancellation
    Private Tour
    Start From $275.28
 
 

Key West Afternoon Reef Snorkeling with Open Bar

(4.5 of 328 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 $54.95
 
Key West Afternoon Reef Snorkeling with Open Bar Likely to Sell Out

Key West Afternoon Reef Snorkeling with Open Bar

  • North America
  • Exellent328 reviews4.5

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 $54.95
 
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