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Top 10 Best North America Sailing Trips

Found 639 Sailing Trips activities in North America. Sort by Popularity. - Page 2
 

Pirate Ship Sunset Dinner and Show in Los Cabos

(4.3 of 527 reviews)

Come back in time, to the days when Cabo was home to pirates, onboard our pirate ships. A fantastic sunset cruise with a show that is the joy for children and grown-ups alike. Our pirates, dance, chant, climb the ropes, while you... More

Free Cancellation
Start From $99.00
 
Pirate Ship Sunset Dinner and Show in Los Cabos

Pirate Ship Sunset Dinner and Show in Los Cabos

  • North America
  • Exellent527 reviews4.3

Come back in time, to the days when Cabo was home to pirates, onboard our pirate ships. A fantastic ....

    Free Cancellation
    Start From $99.00
 
 

Lands End Luxury Sail and Snorkel Cruise in Cabo San Lucas

(4.9 of 729 reviews)

Explore the sparkling turquoise waters of the Sea of Cortez on this sightseeing snorkel adventure of Los Cabos’ Land’s End Arch! First, you’ll enjoy a beautiful sightseeing stop at Pelican’s Rock where you’ll have a cha... More

Free Cancellation
Start From $105.00
 
Lands End Luxury Sail and Snorkel Cruise in Cabo San Lucas

Lands End Luxury Sail and Snorkel Cruise in Cabo San Lucas

  • North America
  • Superb729 reviews4.9

Explore the sparkling turquoise waters of the Sea of Cortez on this sightseeing snorkel adventure of....

    Free Cancellation
    Start From $105.00
 
 

Key West Snorkeling with Breakfast and Unlimited Mimosas

(4.5 of 466 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
  • Exellent466 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
 
 

Los Cabos Luxury Sunset Sail with Light Apetizers and Open Bar

(4.7 of 1,550 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
Start From $109.00
 
Los Cabos Luxury Sunset Sail with Light Apetizers and Open Bar Likely to Sell Out

Los Cabos Luxury Sunset Sail with Light Apetizers and Open Bar

  • North America
  • Superb1,550 reviews4.7

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

    Free Cancellation
    Start From $109.00
 
 

Sunset Boat Cruise: Swim and Cruise Waikiki

(4.7 of 418 reviews)

There is no better place to swim than Waikiki and no better way to watch the sunset than from the Waikiki Coastline. Be amazed by the natural beauty as day turns to night and twilight blankets us with an array of amazing colors ... More

Free Cancellation
Start From $47.00
 
Sunset Boat Cruise: Swim and Cruise Waikiki Likely to Sell Out

Sunset Boat Cruise: Swim and Cruise Waikiki

  • North America
  • Superb418 reviews4.7

There is no better place to swim than Waikiki and no better way to watch the sunset than from the Wa....

    Free Cancellation
    Start From $47.00
 
 

50ft Luxury Yacht Tour in Miami Beach Captain, Champagne & Party!

(4.6 of 36 reviews)

Ready for the party of a lifetime? Hop aboard our luxurious yacht in Miami Beach to party like never before! Perfect for any special occasion, this VIP experience promises unforgettable memories Adventure Highlights Biscayne Bay ... More

Free Cancellation
Private Tour
Start From $599.99
 
50ft Luxury Yacht Tour in Miami Beach Captain, Champagne & Party! Likely to Sell Out

50ft Luxury Yacht Tour in Miami Beach Captain, Champagne & Party!

  • North America
  • Superb36 reviews4.6

Ready for the party of a lifetime? Hop aboard our luxurious yacht in Miami Beach to party like never....

    Free Cancellation
    Private Tour
    Start From $599.99
 
 

El Cielo Snorkel by Private Boat

(4.9 of 257 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
  • Superb257 reviews4.9

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

    Free Cancellation
    Private Tour
    Start From $499.99
 
 

Four Winds Molokini Snorkeling Tour from Maalaea Harbor

(4.7 of 743 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
Private Tour
Start From $191.78
 
Four Winds Molokini Snorkeling Tour from Maalaea Harbor Likely to Sell Out

Four Winds Molokini Snorkeling Tour from Maalaea Harbor

  • North America
  • Superb743 reviews4.7

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

    Free Cancellation
    Private Tour
    Start From $191.78
 
 

Riviera Maya Luxury Sunset Sailing plus Light Dinner and Open Bar

(4.6 of 372 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 $99.00
 
Riviera Maya Luxury Sunset Sailing plus Light Dinner and Open Bar Likely to Sell Out

Riviera Maya Luxury Sunset Sailing plus Light Dinner and Open Bar

  • North America
  • Superb372 reviews4.6

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

    Free Cancellation
    Private Tour
    Start From $99.00
 
 

Sunset and Manta Ray Snorkel Adventure

(4.9 of 712 reviews)

Our most popular tour!  Watch a legendary Kona sunset from our spacious 50’ catamaran as you sail the Kona coast, followed by the adventure of a lifetime - snorkeling with the majestic manta rays!  Upon arriving, receive an in... More

Free Cancellation
Private Tour
Start From $141.26
 
Sunset and Manta Ray Snorkel Adventure Likely to Sell Out

Sunset and Manta Ray Snorkel Adventure

  • North America
  • Superb712 reviews4.9

Our most popular tour!  Watch a legendary Kona sunset from our spacious 50’ catamaran as you sail....

    Free Cancellation
    Private Tour
    Start From $141.26
 
 

Key West Small-Group Sunset Sail with Wine

(4.9 of 1,108 reviews)

Cruise into the sunset with wines from all around the world, imported and domestic beers as well as hors d'oeuvres. This cruise is great for a romantic evening or just to enjoy time with friends. Please arrive 30 minutes prior to ... More

Special Offer
Free Cancellation
Private Tour
Start From $113.80
(Saving 15% ) $133.89
 
-15% Key West Small-Group Sunset Sail with Wine Likely to Sell Out

Key West Small-Group Sunset Sail with Wine

  • North America
  • Superb1,108 reviews4.9

Cruise into the sunset with wines from all around the world, imported and domestic beers as well as ....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $113.80
    (Saving 15% ) $133.89
 
 

Kona-Kohala Coast Sunset Sail by Catamaran

(4.7 of 311 reviews)

Explore the Waikoloa and Kohala-Kona coastline aboard The Spirit of Aloha, a 54-foot sailing catamaran. Catch the moment the sun slips below the horizon. You may even see the green flash. Board from Anaehoomalu Bay (A-Bay) to sail... More

Free Cancellation
Private Tour
Start From $152.55
 
Kona-Kohala Coast Sunset Sail by Catamaran Likely to Sell Out

Kona-Kohala Coast Sunset Sail by Catamaran

  • North America
  • Superb311 reviews4.7

Explore the Waikoloa and Kohala-Kona coastline aboard The Spirit of Aloha, a 54-foot sailing catamar....

    Free Cancellation
    Private Tour
    Start From $152.55
 
 

Small-Group Sunset Sailing Experience on San Diego Bay

(4.9 of 514 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

Special Offer
Free Cancellation
Private Tour
Start From $98.10
(Saving 10% ) $109.00
 
-10% Small-Group Sunset Sailing Experience on San Diego Bay Likely to Sell Out

Small-Group Sunset Sailing Experience on San Diego Bay

  • North America
  • Superb514 reviews4.9

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

    Special Offer
    Free Cancellation
    Private Tour
    Start From $98.10
    (Saving 10% ) $109.00
 
 

Private Fishing Trip "All Inclusive" in Cabo San Lucas, Mexico

(4.7 of 194 reviews)

Embark on the most exciting fishing adventure in the crystal-clear waters of Cabo San Lucas. Our all-inclusive fishing tour offers you a unique opportunity to immerse yourself in an authentic, action-packed fishing experience, wit... More

Free Cancellation
Private Tour
Start From $586.67
 
Private Fishing Trip Likely to Sell Out

Private Fishing Trip "All Inclusive" in Cabo San Lucas, Mexico

  • North America
  • Superb194 reviews4.7

Embark on the most exciting fishing adventure in the crystal-clear waters of Cabo San Lucas. Our all....

    Free Cancellation
    Private Tour
    Start From $586.67
 
 

Sunset Sip and Sail Key West with Open Bar and Live Music

(4.5 of 242 reviews)

Sunset Sip & Sail: Come see the legendary Key West Sunset on a Brand New Catamaran Sail Boat. • Open bar • Live Music • Great Appetizers Welcome aboard Key West's newest catamaran, the "Sandie Cat" as we literally... More

Free Cancellation
Private Tour
Start From $79.95
 
Sunset Sip and Sail Key West with Open Bar and Live Music Likely to Sell Out

Sunset Sip and Sail Key West with Open Bar and Live Music

  • North America
  • Exellent242 reviews4.5

Sunset Sip & Sail: Come see the legendary Key West Sunset on a Brand New Catamaran Sail Boat. â€....

    Free Cancellation
    Private Tour
    Start From $79.95
 
 

Key West Afternoon Reef Snorkeling with Open Bar

(4.5 of 299 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
  • Exellent299 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
 
 

Cabo San Lucas Private catamaran Tour for Six People

(4.9 of 282 reviews)

Have your own private boat  to cruise, snorkel, relax at the beach or swim in different places of the beautiful bay of Cabo San Lucas. Visit all landmarks such as the arch, sea lion colony, neptunes finger, lovers beach, divorc... More

Free Cancellation
Private Tour
Start From $549.00
 
Cabo San Lucas Private catamaran Tour for Six People Likely to Sell Out

Cabo San Lucas Private catamaran Tour for Six People

  • North America
  • Superb282 reviews4.9

Have your own private boat  to cruise, snorkel, relax at the beach or swim in different places of t....

    Free Cancellation
    Private Tour
    Start From $549.00
 
 

Sunset Sail Experience at Kona from Honokohau

(4.8 of 125 reviews)

Explore the beautiful Kona coastline from while aboard the Honi Olani, a 53-foot sailing catamaran. Catch the moment the sun slips below the horizon...you may even see the green flash. Enjoy the blue Pacific Ocean and maybe catch ... More

Free Cancellation
Private Tour
Start From $152.55
 
Sunset Sail Experience at Kona from Honokohau Likely to Sell Out

Sunset Sail Experience at Kona from Honokohau

  • North America
  • Superb125 reviews4.8

Explore the beautiful Kona coastline from while aboard the Honi Olani, a 53-foot sailing catamaran. ....

    Free Cancellation
    Private Tour
    Start From $152.55
 
 

Shell Island Snorkel and Dolphin Catamaran Cruise with Island Time

(4.8 of 3,274 reviews)

The 3-Hr Shell Island Snorkel & Dolphin Cruise aboard the Island Time Sailing Catamaran is a great way to have fun in the sun and enjoy the best of what Panama City Beach has to offer! Cruise over to Shell Island where you and the... More

Free Cancellation
Private Tour
Start From $52.43
 
Shell Island Snorkel and Dolphin Catamaran Cruise with Island Time Likely to Sell Out

Shell Island Snorkel and Dolphin Catamaran Cruise with Island Tim....

  • North America
  • Superb3,274 reviews4.8

The 3-Hr Shell Island Snorkel & Dolphin Cruise aboard the Island Time Sailing Catamaran is a great w....

    Free Cancellation
    Private Tour
    Start From $52.43
 
 

Waikiki Sunset Sail on Hawea Catamaran

(4.8 of 139 reviews)

Our rainbow sails can be spotted from miles away. While on board you may capture such nice photos with the rainbow sails and also the beautiful scenery with Diamond head in the background. The net is also a fun ride and you’ll g... More

Free Cancellation
Private Tour
Start From $72.96
 
Waikiki Sunset Sail on Hawea Catamaran Likely to Sell Out

Waikiki Sunset Sail on Hawea Catamaran

  • North America
  • Superb139 reviews4.8

Our rainbow sails can be spotted from miles away. While on board you may capture such nice photos wi....

    Free Cancellation
    Private Tour
    Start From $72.96
 
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