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Top 10 Best USA Sailing Trips

Found 430 Sailing Trips activities in USA. Sort by Popularity. - Page 3
 

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
Start From $59.95
 
Key West Afternoon Reef Snorkeling with Open Bar

Key West Afternoon Reef Snorkeling with Open Bar

  • USA
  • 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
    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
Start From $55.00
 
Buccaneer Pirate Cruise in Destin

Buccaneer Pirate Cruise in Destin

  • USA
  • Superb96 reviews4.9

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

    Free Cancellation
    Start From $55.00
 
 

Sunset Sail Cruise in Key West

(4.9 of 264 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
Start From $95.00
 
Sunset Sail Cruise in Key West

Sunset Sail Cruise in Key West

  • USA
  • Superb264 reviews4.9

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

    Free Cancellation
    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
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

  • USA
  • Superb94 reviews4.9

Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages (BYOB), take pics,....

    Free Cancellation
    Start From $59.95
 
 

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

  • USA
  • 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
 
 

Small Group Key West Adult Sunset & Moët Sail & Amazing Cheeses

(4.9 of 960 reviews)

Avoid the crowds and Sail on Key West’s beautiful shallow waters on this Adults Only Sunset & Moët cruise, to sip Moët & Chandon champagne and indulge your palate while being washed in the colors of the Key West sunset! Incl... More

Free Cancellation
Private Tour
Start From $108.91
 
Small Group Key West Adult Sunset & Moët Sail & Amazing Cheeses Likely to Sell Out

Small Group Key West Adult Sunset & Moët Sail & Amazing Cheeses

  • USA
  • Superb960 reviews4.9

Avoid the crowds and Sail on Key West’s beautiful shallow waters on this Adults Only Sunset & Moë....

    Free Cancellation
    Private Tour
    Start From $108.91
 
 

Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)

(4.8 of 46 reviews)

Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui sunset begin to paint the sky. As you step aboard, you're greeted by the friendly crew who welcome you with warm aloha spirit. The c... More

Free Cancellation
Private Tour
Start From $289.00
 
Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only) Likely to Sell Out

Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)

  • USA
  • Superb46 reviews4.8

Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui su....

    Free Cancellation
    Private Tour
    Start From $289.00
 
 

Key West Sailing & Snorkeling: A Reef Adventure

(4.8 of 186 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 Sailing & Snorkeling: A Reef Adventure Likely to Sell Out

Key West Sailing & Snorkeling: A Reef Adventure

  • USA
  • Superb186 reviews4.8

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
 
 

Molokini Snorkel and Performance Sail: Mā’alaea Harbor

(4.8 of 215 reviews)

Sail Maui is proud to offer a destination snorkel sail to Molokini, one of Maui’s most incredible snorkeling destinations. The unique, crescent shaped crater is a natural marine preserve, and is home to over 250 species of t... More

Free Cancellation
Private Tour
Start From $200.00
 
Molokini Snorkel and Performance Sail: Mā’alaea Harbor Likely to Sell Out

Molokini Snorkel and Performance Sail: Mā’alaea Harbor

  • USA
  • Superb215 reviews4.8

Sail Maui is proud to offer a destination snorkel sail to Molokini, one of Maui’s most incredib....

    Free Cancellation
    Private Tour
    Start From $200.00
 
 

Deluxe Sunset & Day Sail Small Group

(5 of 247 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

Special Offer
Free Cancellation
Private Tour
Start From $101.15
(Saving 15% ) $119.00
 
-15% Deluxe Sunset & Day Sail Small Group Likely to Sell Out

Deluxe Sunset & Day Sail Small Group

  • USA
  • Superb247 reviews5

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

    Special Offer
    Free Cancellation
    Private Tour
    Start From $101.15
    (Saving 15% ) $119.00
 
 

Two Hour Coastal Sailing Cruise

(5 of 26 reviews)

What makes this tour unique is the custom experience aboard our 43-foot, 27-foot wide trimaran—one of the largest and most stable sailing vessels in Savannah. Unlike crowded tour boats, our open-deck layout offers plenty of room... More

Free Cancellation
Private Tour
Start From $124.99
 
Two Hour Coastal Sailing Cruise Likely to Sell Out

Two Hour Coastal Sailing Cruise

  • USA
  • Superb26 reviews5

What makes this tour unique is the custom experience aboard our 43-foot, 27-foot wide trimaran—one....

    Free Cancellation
    Private Tour
    Start From $124.99
 
 

Sail Biscayne Bay: An Intimate Eco-Adventure with Snorkeling

(4.9 of 446 reviews)

This tour is an intimate experience, our groups are 3-5 people per boat maximum. We have two boats. We have been sailing the Biscayne Bay for over 15 years, just for the fun of it. We started this eco-tour in 2018 to share the ama... More

Free Cancellation
Private Tour
Start From $129.00
 
Sail Biscayne Bay: An Intimate Eco-Adventure with Snorkeling Likely to Sell Out

Sail Biscayne Bay: An Intimate Eco-Adventure with Snorkeling

  • USA
  • Superb446 reviews4.9

This tour is an intimate experience, our groups are 3-5 people per boat maximum. We have two boats. ....

    Free Cancellation
    Private Tour
    Start From $129.00
 
 

Waikiki Sunset Boat Cruise

(4.9 of 104 reviews)

No vacation is complete without experiencing a vibrant Hawaiian sunset from the water. Unobstructed views create the best photo opportunities! Listen to great music as we cruise the Waikiki coastline with views of Diamond head cra... More

Free Cancellation
Private Tour
Start From $50.00
 
Waikiki Sunset Boat Cruise Likely to Sell Out

Waikiki Sunset Boat Cruise

  • USA
  • Superb104 reviews4.9

No vacation is complete without experiencing a vibrant Hawaiian sunset from the water. Unobstructed ....

    Free Cancellation
    Private Tour
    Start From $50.00
 
 

Key West Reef Snorkel & Sail Adventure

(4.7 of 542 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 Likely to Sell Out

Key West Reef Snorkel & Sail Adventure

  • USA
  • Superb542 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
 
 

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

(4.4 of 373 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 $59.95
 
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

  • USA
  • Exellent373 reviews4.4

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

    Free Cancellation
    Private Tour
    Start From $59.95
 
 

Honolulu Sunset Sail from Kewalo Harbor Including Drinks

(4.8 of 173 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
Private Tour
Start From $61.50
 
Honolulu Sunset Sail from Kewalo Harbor Including Drinks Likely to Sell Out

Honolulu Sunset Sail from Kewalo Harbor Including Drinks

  • USA
  • Superb173 reviews4.8

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

    Free Cancellation
    Private Tour
    Start From $61.50
 
 

2 hour Tiki Pub Sensational Dolphin Sunset Cruise (Adults only)

(5 of 112 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 $69.00
 
2 hour Tiki Pub Sensational Dolphin Sunset Cruise (Adults only) Likely to Sell Out

2 hour Tiki Pub Sensational Dolphin Sunset Cruise (Adults only)

  • USA
  • Superb112 reviews5

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 $69.00
 
 

Catamaran Day Sail Shelling Excursion 42ft. Mainecat Cool Beans

(4.9 of 167 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 $79.50
 
Catamaran Day Sail Shelling Excursion 42ft. Mainecat Cool Beans Likely to Sell Out

Catamaran Day Sail Shelling Excursion 42ft. Mainecat Cool Beans

  • USA
  • Superb167 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 $79.50
 
 

Akialoa Mā’alaea Sunset Sail

(4.6 of 9 reviews)

Witness the stunning sunsets of Maui from the comfort of a luxury sailing catamaran. The Akialoa Sunset Sail offers a two-hour journey through the picturesque inter-island channel, showcasing the beauty of Maui, Lāna‘i, and Kah... More

Free Cancellation
Private Tour
Start From $108.11
 
Akialoa Mā’alaea Sunset Sail Likely to Sell Out

Akialoa Mā’alaea Sunset Sail

  • USA
  • Superb9 reviews4.6

Witness the stunning sunsets of Maui from the comfort of a luxury sailing catamaran. The Akialoa Sun....

    Free Cancellation
    Private Tour
    Start From $108.11
 
 

Snorkel with Manta Rays Guaranteed

(4.8 of 740 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

  • USA
  • Superb740 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
 
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