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Top 10 Best North America Sailing Trips

Found 676 Sailing Trips activities in North America. Sort by Popularity. - Page 4
 

Small-Group San Diego Sunset Sailing Excursion

(4.9 of 548 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
Start From $127.00
 
Small-Group San Diego Sunset Sailing Excursion

Small-Group San Diego Sunset Sailing Excursion

  • North America
  • Superb548 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
    Start From $127.00
 
 

Honolulu Sunset Sail from Kewalo Harbor Including Drinks

(4.9 of 100 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
Start From $61.50
 
Honolulu Sunset Sail from Kewalo Harbor Including Drinks

Honolulu Sunset Sail from Kewalo Harbor Including Drinks

  • North America
  • Superb100 reviews4.9

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
 
 

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

(4.5 of 255 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
Start From $79.95
 
Sunset Sip and Sail Key West with Open Bar and Live Music

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

  • North America
  • Exellent255 reviews4.5

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

    Free Cancellation
    Start From $79.95
 
 

Sunset and Manta Ray Snorkel Adventure

(4.9 of 744 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
Start From $148.57
 
Sunset and Manta Ray Snorkel Adventure

Sunset and Manta Ray Snorkel Adventure

  • North America
  • Superb744 reviews4.9

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

    Free Cancellation
    Start From $148.57
 
 

Adults only Sunset Cruise from Key West with Champagne

(4.9 of 872 reviews)

Get out on Key West’s beautiful shallow waters on the Adults Only sunset cruise, to sip Moët & Chandon champagne while enjoying the sunset. Included in the tour price are the house champagne Chandon Brut, 7 premium red and whit... More

Free Cancellation
Start From $108.91
 
Adults only Sunset Cruise from Key West with Champagne

Adults only Sunset Cruise from Key West with Champagne

  • North America
  • Superb872 reviews4.9

Get out on Key West’s beautiful shallow waters on the Adults Only sunset cruise, to sip Moët & Ch....

    Free Cancellation
    Start From $108.91
 
 

Half Day Private Sailing Cruise Puerto Vallarta with Snorkeling

(5 of 47 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 $666.44
 
Half Day Private Sailing Cruise Puerto Vallarta with Snorkeling

Half Day Private Sailing Cruise Puerto Vallarta with Snorkeling

  • North America
  • Superb47 reviews5

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

    Free Cancellation
    Private Tour
    Start From $666.44
 
 

Snorkel with Manta Rays Guaranteed

(4.8 of 660 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
  • Superb660 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
 
 

America's Cup 12-Meter Yacht Afternoon Sail from Hilton Head

(4.6 of 423 reviews)

Only on Hilton Head and only in Harbour Town can you sail aboard the real America's Cup, 12 meter, Stars & Stripes once skippered by the famous Dennis Connor. All trips take place under full sail. We only use our motor to get in a... More

Free Cancellation
Private Tour
Start From $52.95
 
America's Cup 12-Meter Yacht Afternoon Sail from Hilton Head Likely to Sell Out

America's Cup 12-Meter Yacht Afternoon Sail from Hilton Head

  • North America
  • Superb423 reviews4.6

Only on Hilton Head and only in Harbour Town can you sail aboard the real America's Cup, 12 meter, S....

    Free Cancellation
    Private Tour
    Start From $52.95
 
 

Sunset Sail on a Small Charming Hawaiian Catamaran Maalaea Harbor

(4.7 of 50 reviews)

Experience the resilience and spirit of Maui aboard the Winona, a vessel that bravely survived the Lahaina harbor wildfires, moored outside of the harbor breakwall. Now operating from Ma'alaea Harbor, we invite you to join our cap... More

Free Cancellation
Private Tour
Start From $119.00
 
Sunset Sail on a Small Charming Hawaiian Catamaran Maalaea Harbor Likely to Sell Out

Sunset Sail on a Small Charming Hawaiian Catamaran Maalaea Harbor

  • North America
  • Superb50 reviews4.7

Experience the resilience and spirit of Maui aboard the Winona, a vessel that bravely survived the L....

    Free Cancellation
    Private Tour
    Start From $119.00
 
 

Key West Dolphin and Snorkel Experience

(4.4 of 262 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 $64.95
 
Key West Dolphin and Snorkel Experience Likely to Sell Out

Key West Dolphin and Snorkel Experience

  • North America
  • Exellent262 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 $64.95
 
 

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

(4.4 of 346 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
  • Exellent346 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
 
 

Suncoast Sailing's Sunset Sailing Experience!

(4.9 of 215 reviews)

Set sail aboard the iconic schooner Suncoast Horizon as we set sail in the picturesque waters of Treasure Island, Florida! You’ll set sail about an hour before sunset to give you plenty of time to catch the full range of hues p... More

Free Cancellation
Private Tour
Start From $64.99
 
Suncoast Sailing's Sunset Sailing Experience! Likely to Sell Out

Suncoast Sailing's Sunset Sailing Experience!

  • North America
  • Superb215 reviews4.9

Set sail aboard the iconic schooner Suncoast Horizon as we set sail in the picturesque waters of Tre....

    Free Cancellation
    Private Tour
    Start From $64.99
 
 

2 hour Tiki Pub Sensational Sunset Cruise (Adults only)

(4.9 of 53 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 $69.95
 
2 hour Tiki Pub Sensational Sunset Cruise (Adults only) Likely to Sell Out

2 hour Tiki Pub Sensational Sunset Cruise (Adults only)

  • North America
  • Superb53 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 $69.95
 
 

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

(4.8 of 256 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 $625.00
 
Private Fishing Trip Likely to Sell Out

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

  • North America
  • Superb256 reviews4.8

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

    Free Cancellation
    Private Tour
    Start From $625.00
 
 

El Cielo Cozumel and Turtle Bay Snorkeling by Catamaran

(4.4 of 276 reviews)

TRAVELER’S FAVORITE TRIP! Get in the mood for fun aboard your Catamaran in a fun sail to magnificent reefs and great snorkeling and after, head back to a secluded Beach to relax and enjoy the beauty of Cozumel turquoise waters.... More

Special Offer
Free Cancellation
Private Tour
Start From $99.00
(Saving 10% ) $110.00
 
-10% El Cielo Cozumel and Turtle Bay Snorkeling by Catamaran Likely to Sell Out

El Cielo Cozumel and Turtle Bay Snorkeling by Catamaran

  • North America
  • Exellent276 reviews4.4

TRAVELER’S FAVORITE TRIP! Get in the mood for fun aboard your Catamaran in a fun sail to magnific....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $99.00
    (Saving 10% ) $110.00
 
 

Cancun Adults Only Party Cruise to Isla Mujeres with Open Bar

(3.7 of 200 reviews)

Take a Party Cruise Adult Only from Cancun to Isla Mujeres. Make a stop to snorkel at one of the best reefs and see beautiful tropical fish. Enjoy a delicious buffet lunch on our private beach club, and then tour Isla Mujeres to s... More

Free Cancellation
Private Tour
Start From $69.99
 
Cancun Adults Only Party Cruise to Isla Mujeres with Open Bar Likely to Sell Out

Cancun Adults Only Party Cruise to Isla Mujeres with Open Bar

  • North America
  • Very Good200 reviews3.7

Take a Party Cruise Adult Only from Cancun to Isla Mujeres. Make a stop to snorkel at one of the bes....

    Free Cancellation
    Private Tour
    Start From $69.99
 
 

Private Sailing Charter with Captain, BYOB

(5 of 45 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 Likely to Sell Out

Private Sailing Charter with Captain, BYOB

  • North America
  • Superb45 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
 
 

2-Hour Private Sailing Experience in San Diego Bay

(5 of 147 reviews)

Our unique sail displays a peace sign because that is exactly what we share with our customers, peace. Peace is not always an easy thing to obtain in today's world. With all the stress life brings we are happy to provide a peacefu... More

Free Cancellation
Private Tour
Start From $585.00
 
2-Hour Private Sailing Experience in San Diego Bay Likely to Sell Out

2-Hour Private Sailing Experience in San Diego Bay

  • North America
  • Superb147 reviews5

Our unique sail displays a peace sign because that is exactly what we share with our customers, peac....

    Free Cancellation
    Private Tour
    Start From $585.00
 
 

4-Hour Fort Lauderdale Sailing Charter

(4.9 of 280 reviews)

Enjoy some time on the water with this 4-Hour Half Day Sailing Charter located in Fort Lauderdale. Your sail is entirely customizable, and travelers have the option(PRIVATE CRUISES) to use their time docked or sailing out to sea. ... More

Free Cancellation
Private Tour
Start From $165.00
 
4-Hour Fort Lauderdale Sailing Charter Likely to Sell Out

4-Hour Fort Lauderdale Sailing Charter

  • North America
  • Superb280 reviews4.9

Enjoy some time on the water with this 4-Hour Half Day Sailing Charter located in Fort Lauderdale. Y....

    Free Cancellation
    Private Tour
    Start From $165.00
 
 

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

(5 of 493 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

Free Cancellation
Private Tour
Start From $2,200.00
 
Lagoon 39ft Private Catamaran 5hr - El Cielo Full Experience Likely to Sell Out

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

  • North America
  • Superb493 reviews5

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

    Free Cancellation
    Private Tour
    Start From $2,200.00
 
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