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Top 10 Best USA Sailing Trips

Found 410 Sailing Trips activities in USA. Sort by Popularity.
 

Shell Island Snorkel and Dolphin Catamaran Cruise with Island Time

(4.8 of 2,596 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
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....

  • USA
  • Superb2,596 reviews4.8

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

    Free Cancellation
    Start From $52.43
 
 

Key West Sunset Sail with Full Bar, Live Music and Hors D'oeuvres

(4.7 of 2,712 reviews)

Admire an exquisitely painted sky during this premium sunset cruise in Key West. Create fantastic memories as you set sail on one of Sebago's modern sailing catamarans while sipping sparkling wine or your favorite cocktail and fea... More

Free Cancellation
Start From $79.00
 
Key West Sunset Sail with Full Bar, Live Music and Hors D'oeuvres Likely to Sell Out

Key West Sunset Sail with Full Bar, Live Music and Hors D'oeuvres

  • USA
  • Superb2,712 reviews4.7

Admire an exquisitely painted sky during this premium sunset cruise in Key West. Create fantastic me....

    Free Cancellation
    Start From $79.00
 
 

Deluxe Na Pali Sunset Tour on the Lucky Lady

(4.7 of 992 reviews)

Tour the Na Pali coast aboard a Luxury Catamaran, Lucky Lady for an afternoon that features incredible scenery topped off with a spectacular sunset. Look for dolphins, whales, and other marine critters as you sip a drink, snap som... More

Free Cancellation
Start From $206.55
 
Deluxe Na Pali Sunset Tour on the Lucky Lady Likely to Sell Out

Deluxe Na Pali Sunset Tour on the Lucky Lady

  • USA
  • Superb992 reviews4.7

Tour the Na Pali coast aboard a Luxury Catamaran, Lucky Lady for an afternoon that features incredib....

    Free Cancellation
    Start From $206.55
 
 

Sunset & Dolphin Catamaran Cruise with Island Time

(4.9 of 1,188 reviews)

The Dolphin Watching & Sunset Sail is a 2 hour cruise aboard the Island Time Sailing Catamaran which departs from the Lagoon Pontoons Marina in Panama City Beach, FL. Enjoy a rum punch while cruising along the beautiful Gulf Coa... More

Free Cancellation
Start From $41.73
 
Sunset & Dolphin Catamaran Cruise with Island Time Likely to Sell Out

Sunset & Dolphin Catamaran Cruise with Island Time

  • USA
  • Superb1,188 reviews4.9

The Dolphin Watching & Sunset Sail is a 2 hour cruise aboard the Island Time Sailing Catamaran which....

    Free Cancellation
    Start From $41.73
 
 

Moana’s Sunset Cocktail Sail along Oahu's Waikiki Coast

(4.9 of 1,263 reviews)

All aboard! There is no better place to be during Oahu’s magnificent golden sunsets than on our Waikiki Sunset Cruise, an unmatched experience complete with premium drinks, indescribable views, and music. As we sail alongside Oa... More

Free Cancellation
Start From $69.99
 
Moana’s Sunset Cocktail Sail along Oahu's Waikiki Coast Likely to Sell Out

Moana’s Sunset Cocktail Sail along Oahu's Waikiki Coast

  • USA
  • Superb1,263 reviews4.9

All aboard! There is no better place to be during Oahu’s magnificent golden sunsets than on our Wa....

    Free Cancellation
    Start From $69.99
 
 

Deluxe Sail & Snorkel to the Captain Cook Monument

(4.9 of 326 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 a... More

Free Cancellation
Start From $177.72
 
Deluxe Sail & Snorkel to the Captain Cook Monument Likely to Sell Out

Deluxe Sail & Snorkel to the Captain Cook Monument

  • USA
  • Superb326 reviews4.9

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

    Free Cancellation
    Start From $177.72
 
 

Afternoon Sail & Snorkel to the Captain Cook Monument

(4.9 of 588 reviews)

A three hour tour you won't want to miss! 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 a... More

Free Cancellation
Start From $134.64
 
Afternoon Sail & Snorkel to the Captain Cook Monument Likely to Sell Out

Afternoon Sail & Snorkel to the Captain Cook Monument

  • USA
  • Superb588 reviews4.9

A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathta....

    Free Cancellation
    Start From $134.64
 
 

2 Hour Sailing Cruise on Lake Tahoe

(4.9 of 495 reviews)

Sail Tahoe Blue is the premier sailing charter in South Lake Tahoe. We offer a unique sailing adventure and include complementary local beer and wine, as well as non-alcoholic beverages on all of our daily cruises. Unlike other t... More

Free Cancellation
Start From $140.00
 
2 Hour Sailing Cruise on Lake Tahoe Likely to Sell Out

2 Hour Sailing Cruise on Lake Tahoe

  • USA
  • Superb495 reviews4.9

Sail Tahoe Blue is the premier sailing charter in South Lake Tahoe. We offer a unique sailing advent....

    Free Cancellation
    Start From $140.00
 
 

Evening Colors Sunset Sail Tour in Seattle

(4.8 of 285 reviews)

Sailing aboard Seattle's premier tall ship is the best way to see our city from the water. Help hoist the sails, then we will shut the engine down and enjoy the quiet of our beautiful schooner cutting through the tranquil Puget So... More

Free Cancellation
Start From $65.00
 
Evening Colors Sunset Sail Tour in Seattle Likely to Sell Out

Evening Colors Sunset Sail Tour in Seattle

  • USA
  • Superb285 reviews4.8

Sailing aboard Seattle's premier tall ship is the best way to see our city from the water. Help hois....

    Free Cancellation
    Start From $65.00
 
 

Hawaiian Sea Turtle Snorkel Sail from Waikiki with Lunch Included

(4.7 of 1,931 reviews)

Welcome aboard Hawaii Nautical, you're invited to observe, learn, and experience Hawaiian Green Sea Turtles firsthand! Guests will learn about the life cycle, behaviors, and threats to the Hawaiian Sea Turtles "Honu" (Learning pr... More

Free Cancellation
Start From $125.43
 
Hawaiian Sea Turtle Snorkel Sail from Waikiki with Lunch Included Likely to Sell Out

Hawaiian Sea Turtle Snorkel Sail from Waikiki with Lunch Included

  • USA
  • Superb1,931 reviews4.7

Welcome aboard Hawaii Nautical, you're invited to observe, learn, and experience Hawaiian Green Sea ....

    Free Cancellation
    Start From $125.43
 
 

Key West Sunset Sail: Dolphin Watching, Wine, and Tapas

(4.6 of 518 reviews)

Our Captain’s Choice Dolphin Watch Sunset Sail is the ultimate VIP sailing experience! Limited to an intimate number of passengers, this 2.5 hour sail is more like a private cruise than a group tour and is one of the top things ... More

Free Cancellation
Start From $89.00
 
Key West Sunset Sail: Dolphin Watching, Wine, and Tapas Likely to Sell Out

Key West Sunset Sail: Dolphin Watching, Wine, and Tapas

  • USA
  • Superb518 reviews4.6

Our Captain’s Choice Dolphin Watch Sunset Sail is the ultimate VIP sailing experience! Limited to ....

    Free Cancellation
    Start From $89.00
 
 

Chicago Skyline Tall Ship Sightseeing Cruise

(4.5 of 441 reviews)

Leave the hustle and bustle behind! Explore Chicago's shores with a leisurely trip around Lake Michigan. Take in the world-famous skyline, enjoy spectacular views, and discover the Windy City from the water. Windy is the Official ... More

Free Cancellation
Start From $59.00
 
Chicago Skyline Tall Ship Sightseeing Cruise Likely to Sell Out

Chicago Skyline Tall Ship Sightseeing Cruise

  • USA
  • Exellent441 reviews4.5

Leave the hustle and bustle behind! Explore Chicago's shores with a leisurely trip around Lake Michi....

    Free Cancellation
    Start From $59.00
 
 

Key West Snorkeling with Breakfast and Unlimited Mimosas

(4.5 of 397 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 Likely to Sell Out

Key West Snorkeling with Breakfast and Unlimited Mimosas

  • USA
  • Exellent397 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
 
 

OAHU CATAMARANS Sunset Tour on a 40 Foot Catamaran FOOD & BYOB!!!

(4.9 of 414 reviews)

Join us for a beautiful Hawaiian sunset!! We have been sailing the Pacific waters off of the Island of Oahu since 1985 and are proud to boast a perfect safety record. Passengers are limited to 50% of Coast Guard rated capacity for... More

Free Cancellation
Start From $49.99
 
OAHU CATAMARANS Sunset Tour on a 40 Foot Catamaran FOOD & BYOB!!! Likely to Sell Out

OAHU CATAMARANS Sunset Tour on a 40 Foot Catamaran FOOD & BYOB!!!

  • USA
  • Superb414 reviews4.9

Join us for a beautiful Hawaiian sunset!! We have been sailing the Pacific waters off of the Island ....

    Free Cancellation
    Start From $49.99
 
 

Small-Group Sunset Sailing Experience on San Diego Bay

(4.9 of 437 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 $119.00
 
Small-Group Sunset Sailing Experience on San Diego Bay Likely to Sell Out

Small-Group Sunset Sailing Experience on San Diego Bay

  • USA
  • Superb437 reviews4.9

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

    Free Cancellation
    Start From $119.00
 
 

Four Winds II Molokini Snorkeling Tour from Maalaea Harbor

(4.7 of 697 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
Start From $191.78
 
Four Winds II Molokini Snorkeling Tour from Maalaea Harbor Likely to Sell Out

Four Winds II Molokini Snorkeling Tour from Maalaea Harbor

  • USA
  • Superb697 reviews4.7

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

    Free Cancellation
    Start From $191.78
 
 

Panama City Beach Sunset Catamaran Sail on The Privateer

(4.8 of 542 reviews)

If you are looking to unwind before dinner or a night out on the town, come take a romantic Sunset Sail on the SV Privateer, our 78-passenger catamaran, with Paradise Adventures! This breathtaking sunset sail along the Gulf of Mex... More

Free Cancellation
Start From $40.00
 
Panama City Beach Sunset Catamaran Sail on The Privateer Likely to Sell Out

Panama City Beach Sunset Catamaran Sail on The Privateer

  • USA
  • Superb542 reviews4.8

If you are looking to unwind before dinner or a night out on the town, come take a romantic Sunset S....

    Free Cancellation
    Start From $40.00
 
 

Moana’s Guided Turtle Snorkel & Sailing Adventure at Waikiki

(4.7 of 783 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
Start From $69.99
 
Moana’s Guided Turtle Snorkel & Sailing Adventure at Waikiki Likely to Sell Out

Moana’s Guided Turtle Snorkel & Sailing Adventure at Waikiki

  • USA
  • Superb783 reviews4.7

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

    Free Cancellation
    Start From $69.99
 
 

Sightseeing Day Sail around Boston Harbor

(4.7 of 250 reviews)

Choose between either a 1.5 or 2-hour sail around Boston Harbor aboard one of our beautiful schooner Adirondack sailboats! These classic boats are reminiscent of the sailboats from the 1890s. Sail past the seaport district, Castle... More

Free Cancellation
Start From $58.45
 
Sightseeing Day Sail around Boston Harbor Likely to Sell Out

Sightseeing Day Sail around Boston Harbor

  • USA
  • Superb250 reviews4.7

Choose between either a 1.5 or 2-hour sail around Boston Harbor aboard one of our beautiful schooner....

    Free Cancellation
    Start From $58.45
 
 

2-Hour Windjammer Sailing Trip in Maine with Licensed Captain

(4 of 189 reviews)

Enjoy a leisurely sail on Frenchman Bay that includes narration about historical and geographical points of interest. View wildlife including eagles, seals and porpoises.... More

Free Cancellation
Start From $79.00
 
2-Hour Windjammer Sailing Trip in Maine with Licensed Captain Likely to Sell Out

2-Hour Windjammer Sailing Trip in Maine with Licensed Captain

  • USA
  • Very Good189 reviews4

Enjoy a leisurely sail on Frenchman Bay that includes narration about historical and geographical po....

    Free Cancellation
    Start From $79.00
 
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