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Top 10 Best USA Sailing Trips

Found 395 Sailing Trips activities in USA. Sort by Popularity.
 

2-Hour Whale Watching from Oahu

(4.6 of 877 reviews)

Humpback whales visit Hawaii each year and give birth in our warm tropical waters, it's a once in a lifetime experience that you will never forget to see this amazing creature. If you are lucky enough, you might see dolphins, sea ... More

Free Cancellation
Start From $50.71
 
2-Hour Whale Watching from Oahu

2-Hour Whale Watching from Oahu

  • USA
  • Superb877 reviews4.6

Humpback whales visit Hawaii each year and give birth in our warm tropical waters, it's a once in a ....

    Free Cancellation
    Start From $50.71
 
 

Shell Island Snorkel and Dolphin Catamaran Cruise with Island Time

(4.8 of 3,323 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
  • Superb3,323 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 3,105 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
  • Superb3,105 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 1,263 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 $219.42
 
Deluxe Na Pali Sunset Tour on the Lucky Lady Likely to Sell Out

Deluxe Na Pali Sunset Tour on the Lucky Lady

  • USA
  • Superb1,263 reviews4.7

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

    Free Cancellation
    Start From $219.42
 
 

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

(4.9 of 1,882 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 $84.99
 
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
  • Superb1,882 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 $84.99
 
 

Waikiki Turtle Snorkel & Sail combo on Hawea Catamaran

(4.8 of 1,421 reviews)

This is the best way to start your day on Oahu! Come snorkel with us at Turtle Canyon, a green sea turtle cleaning station. Our crew shows you not only turtles but also hidden creatures such as he’e (octopus) and ka hoku kai (st... More

Free Cancellation
Start From $84.77
 
Waikiki Turtle Snorkel & Sail combo on Hawea Catamaran Likely to Sell Out

Waikiki Turtle Snorkel & Sail combo on Hawea Catamaran

  • USA
  • Superb1,421 reviews4.8

This is the best way to start your day on Oahu! Come snorkel with us at Turtle Canyon, a green sea t....

    Free Cancellation
    Start From $84.77
 
 

Waikiki Catamaran Adventure: Snorkel with Sea Turtles

(4.7 of 2,050 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 $108.62
 
Waikiki Catamaran Adventure: Snorkel with Sea Turtles Likely to Sell Out

Waikiki Catamaran Adventure: Snorkel with Sea Turtles

  • USA
  • Superb2,050 reviews4.7

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

    Free Cancellation
    Start From $108.62
 
 

Sunset & Dolphin Catamaran Cruise with Island Time

(4.9 of 1,493 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 $52.43
 
Sunset & Dolphin Catamaran Cruise with Island Time Likely to Sell Out

Sunset & Dolphin Catamaran Cruise with Island Time

  • USA
  • Superb1,493 reviews4.9

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

    Free Cancellation
    Start From $52.43
 
 

Live Music Sunset Sail with Drinks Included

(4.8 of 107 reviews)

Come aboard our spacious state-of-the-art catamaran on St. Augustine's only all inclusive sunset sail! Indulge in complimentary beer, wine, soda, water, margaritas, champagne, and a snack, while enjoying live performances by some ... More

Free Cancellation
Start From $63.85
 
Live Music Sunset Sail with Drinks Included Likely to Sell Out

Live Music Sunset Sail with Drinks Included

  • USA
  • Superb107 reviews4.8

Come aboard our spacious state-of-the-art catamaran on St. Augustine's only all inclusive sunset sai....

    Free Cancellation
    Start From $63.85
 
 

Discover the Magic of Coral Garden’s Turtle Town - Maalaea Harbor

(4.6 of 134 reviews)

Avoid the over-crowded 50-100 passenger boats. We take 30-40 passengers. Treat yourself and your loved ones to experience a beautiful Snorkeling, Sailing Cruise, and Whale Watching (Dec-Apr) on our Small Charming Hawaiian Catamara... More

Free Cancellation
Start From $139.00
 
Discover the Magic of Coral Garden’s Turtle Town - Maalaea Harbor Likely to Sell Out

Discover the Magic of Coral Garden’s Turtle Town - Maalaea Harb....

  • USA
  • Superb134 reviews4.6

Avoid the over-crowded 50-100 passenger boats. We take 30-40 passengers. Treat yourself and your lov....

    Free Cancellation
    Start From $139.00
 
 

Sunset Catamaran Cruise in Ft. Lauderdale

(4.8 of 629 reviews)

A perfect way to end the day, with a relaxing sail upon the Atlantic Ocean. Imagine taking in the breathtaking views of FT. Lauderdale beach as the sun slips slowly behind the lights of the city. This evening cruise calls for sun ... More

Free Cancellation
Start From $89.00
 
Sunset Catamaran Cruise in Ft. Lauderdale Likely to Sell Out

Sunset Catamaran Cruise in Ft. Lauderdale

  • USA
  • Superb629 reviews4.8

A perfect way to end the day, with a relaxing sail upon the Atlantic Ocean. Imagine taking in the br....

    Free Cancellation
    Start From $89.00
 
 

Key West Schooner Sunset Sail with Bar & Hors d'oeuvres

(4.9 of 667 reviews)

Enjoy an exquisite 2-hour sunset sailing adventure aboard a stunning modern-built schooner! Take in the sights aboard Schooner America 2.0, the most elegant schooner in Key West, as you sail by Mallory Square, Sunset Pier, Sand K... More

Free Cancellation
Start From $116.10
 
Key West Schooner Sunset Sail with Bar & Hors d'oeuvres Likely to Sell Out

Key West Schooner Sunset Sail with Bar & Hors d'oeuvres

  • USA
  • Superb667 reviews4.9

Enjoy an exquisite 2-hour sunset sailing adventure aboard a stunning modern-built schooner! Take in....

    Free Cancellation
    Start From $116.10
 
 

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

(4.5 of 39 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!

  • USA
  • Exellent39 reviews4.5

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
 
 

Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbor

(4.5 of 425 reviews)

Meet us at Aquarium Wharf near Concord St. and Calhoun St. in Charleston SC as you experience historic Charleston Harbor aboard our classic 84-foot Tall Ship for a unique sailing experience. There is no better way to witness all o... More

Free Cancellation
Private Tour
Start From $54.50
 
Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbor Likely to Sell Out

Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbo....

  • USA
  • Exellent425 reviews4.5

Meet us at Aquarium Wharf near Concord St. and Calhoun St. in Charleston SC as you experience histor....

    Free Cancellation
    Private Tour
    Start From $54.50
 
 

Leila Na Pali Sunset Dinner Sail

(4.7 of 453 reviews)

Let us wine & dine you as we sail off into the sunset along Kauai’s spectacular Napali Coast. Enjoy appetizers, craft beer, wine, and Koloa Rum Mai-Tais aboard our sleek and spacious sailing catamaran, Leila. Your captain will s... More

Free Cancellation
Private Tour
Start From $240.86
 
Leila Na Pali Sunset Dinner Sail Likely to Sell Out

Leila Na Pali Sunset Dinner Sail

  • USA
  • Superb453 reviews4.7

Let us wine & dine you as we sail off into the sunset along Kauai’s spectacular Napali Coast. Enjo....

    Free Cancellation
    Private Tour
    Start From $240.86
 
 

Oahu Sunset Tour on a 40 Foot Catamaran: Food and BYOB

(4.9 of 608 reviews)

AFTER 36 DAYS THE KAHALA KAI IS BACK IN THE WATER AFTER A FULL AND COMPLETE REFURBURSHMENT! PLEASE COME SEE OUR COMPLETELY REIMAGINED VESSEL! Join us for a beautiful Hawaiian sunset!! We have been sailing the Pacific waters off o... More

Free Cancellation
Private Tour
Start From $54.95
 
Oahu Sunset Tour on a 40 Foot Catamaran: Food and BYOB Likely to Sell Out

Oahu Sunset Tour on a 40 Foot Catamaran: Food and BYOB

  • USA
  • Superb608 reviews4.9

AFTER 36 DAYS THE KAHALA KAI IS BACK IN THE WATER AFTER A FULL AND COMPLETE REFURBURSHMENT! PLEASE C....

    Free Cancellation
    Private Tour
    Start From $54.95
 
 

Deluxe Sail & Snorkel to the Captain Cook Monument

(4.9 of 453 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
Private Tour
Start From $177.73
 
Deluxe Sail & Snorkel to the Captain Cook Monument Likely to Sell Out

Deluxe Sail & Snorkel to the Captain Cook Monument

  • USA
  • Superb453 reviews4.9

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

    Free Cancellation
    Private Tour
    Start From $177.73
 
 

Four Winds Molokini Snorkeling Tour from Maalaea Harbor

(4.7 of 778 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 $202.59
 
Four Winds Molokini Snorkeling Tour from Maalaea Harbor Likely to Sell Out

Four Winds Molokini Snorkeling Tour from Maalaea Harbor

  • USA
  • Superb778 reviews4.7

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

    Free Cancellation
    Private Tour
    Start From $202.59
 
 

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

(4.6 of 614 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
Private Tour
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
  • Superb614 reviews4.6

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

    Free Cancellation
    Private Tour
    Start From $89.00
 
 

Key West Snorkeling with Breakfast and Unlimited Mimosas

(4.5 of 499 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
Private Tour
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
  • Exellent499 reviews4.5

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

    Free Cancellation
    Private Tour
    Start From $46.94
 
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