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Top 10 Best USA Sailing Trips

Found 452 Sailing Trips activities in USA. Sort by Popularity. - Page 13
 

Snorkel, Swim & Dolphin Sightseeing Sail Aboard the Daydreams

(5 of 2 reviews)

This is a luxury Sailboat Excursion for up to 6 guests. Our 47 ft Daydreams Sailboat has a great bow for sunbathing, aft seating area for enjoyment and a luxury salon, galley, cabins and marine head for your use. Get ready for fu... More

Free Cancellation
Start From $120.00
 
Snorkel, Swim & Dolphin Sightseeing Sail Aboard the Daydreams

Snorkel, Swim & Dolphin Sightseeing Sail Aboard the Daydreams

  • USA
  • Superb2 reviews5

This is a luxury Sailboat Excursion for up to 6 guests. Our 47 ft Daydreams Sailboat has a great bow....

    Free Cancellation
    Start From $120.00
 
 

Relaxing Saco River Public Sunset Sail

(5 of 1 review)

Set sail on a memorable 2-hour sunset cruise through the stunning landscapes of Kennebunkport, ME. Glide along the Saco River and take in the picturesque views of Biddeford Pool, Camp Ellis, and the iconic Wood Island Lighthouse. ... More

Free Cancellation
Start From $149.00
 
Relaxing Saco River Public Sunset Sail Likely to Sell Out

Relaxing Saco River Public Sunset Sail

  • USA
  • Superb1 review5

Set sail on a memorable 2-hour sunset cruise through the stunning landscapes of Kennebunkport, ME. G....

    Free Cancellation
    Start From $149.00
 
 

Sailboat Cruise on Chesapeake Bay

(4.8 of 39 reviews)

Enjoy the peaceful sounds of the waves gently breaking off the hull of Eternal Hope as she glides through the waters of the bay, powered only by wind! This cruise sails at 9 am, 12 Noon and 3 pm, Tuesday - Sunday and on Mondays fo... More

Free Cancellation
Start From $116.00
 
Sailboat Cruise on Chesapeake Bay Likely to Sell Out

Sailboat Cruise on Chesapeake Bay

  • USA
  • Superb39 reviews4.8

Enjoy the peaceful sounds of the waves gently breaking off the hull of Eternal Hope as she glides th....

    Free Cancellation
    Start From $116.00
 
 

Key West Ultimate Beach Pass with Parasailing

(4 of 26 reviews)

Join Sunset Watersports, Key West's Original Watersports Company for a day at Smathers Beach. We are the only company offering the Key West Beach Pass.... More

Free Cancellation
Start From $109.95
 
Key West Ultimate Beach Pass with Parasailing Likely to Sell Out

Key West Ultimate Beach Pass with Parasailing

  • USA
  • Very Good26 reviews4

Join Sunset Watersports, Key West's Original Watersports Company for a day at Smathers Beach. We are....

    Free Cancellation
    Start From $109.95
 
 

Waikiki: 2-Hour Whale Watching with Guaranteed Sightings on Oahu

(4.6 of 1,335 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 $53.31
 
Waikiki: 2-Hour Whale Watching with Guaranteed Sightings on Oahu Likely to Sell Out

Waikiki: 2-Hour Whale Watching with Guaranteed Sightings on Oahu

  • USA
  • Superb1,335 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 $53.31
 
 

Private Catamaran Sunset Sail in Waikiki

(5 of 11 reviews)

Established in 2017. As a private charter company, we always cater to your preferences. Our 48-foot catamaran, Hawaiian Style, has a sleek low-profile design which makes it optimal for stability out on the ocean. It has 2 large ... More

Free Cancellation
Private Tour
Start From $900.00
 
Private Catamaran Sunset Sail in Waikiki Likely to Sell Out

Private Catamaran Sunset Sail in Waikiki

  • USA
  • Superb11 reviews5

Established in 2017. As a private charter company, we always cater to your preferences. Our 48-foo....

    Free Cancellation
    Private Tour
    Start From $900.00
 
 

Sunset Sail Experience by Catamaran in Waikiki

(4.8 of 6 reviews)

Enjoy the end of your day on a relaxing 2-hour Waikiki Sunset Sail aboard a 38.6 foot twin-hulled catamaran. Take in the views of Honolulu skyline from offshore Waikiki and feel the warmth of the setting Hawaiian sun and tropical ... More

Free Cancellation
Private Tour
Start From $92.31
 
Sunset Sail Experience by Catamaran in Waikiki Likely to Sell Out

Sunset Sail Experience by Catamaran in Waikiki

  • USA
  • Superb6 reviews4.8

Enjoy the end of your day on a relaxing 2-hour Waikiki Sunset Sail aboard a 38.6 foot twin-hulled ca....

    Free Cancellation
    Private Tour
    Start From $92.31
 
 

Sunday Brunch Sail in Greenport

(5 of 9 reviews)

You haven't truly visited the North Fork if you haven't been on the water! A sailing trip is hands down the best ways to see the East End of Long Island, and sailing aboard our unique schooner makes the experience extra special. U... More

Free Cancellation
Private Tour
Start From $175.00
 
Sunday Brunch Sail in Greenport Likely to Sell Out

Sunday Brunch Sail in Greenport

  • USA
  • Superb9 reviews5

You haven't truly visited the North Fork if you haven't been on the water! A sailing trip is hands d....

    Free Cancellation
    Private Tour
    Start From $175.00
 
 

Sunday Mimosa Brunch Charleston Harbor Sail - Food Included

(5 of 8 reviews)

Kick back and soak up the ultimate Sunday vibes on our Sunday Funday Mimosa Bar Sail. Step aboard our a spacious and stylish 50-foot catamaran, and set sail for a relaxing and refreshing 2-hour cruise through Charleston’s histor... More

Free Cancellation
Private Tour
Start From $75.00
 
Sunday Mimosa Brunch Charleston Harbor Sail - Food Included Likely to Sell Out

Sunday Mimosa Brunch Charleston Harbor Sail - Food Included

  • USA
  • Superb8 reviews5

Kick back and soak up the ultimate Sunday vibes on our Sunday Funday Mimosa Bar Sail. Step aboard ou....

    Free Cancellation
    Private Tour
    Start From $75.00
 
 

South Shore Open Sail from Kewalo Harbor Including Drinks

(4.7 of 27 reviews)

Join us for a 90-minute daytime sailing experience from Kewalo Basin Harbor on one of the most iconic catamarans in Honolulu! Our sails always have complimentary drinks (alcoholic beverages available for adults 21+ with valid ID o... More

Free Cancellation
Private Tour
Start From $47.50
 
South Shore Open Sail from Kewalo Harbor Including Drinks Likely to Sell Out

South Shore Open Sail from Kewalo Harbor Including Drinks

  • USA
  • Superb27 reviews4.7

Join us for a 90-minute daytime sailing experience from Kewalo Basin Harbor on one of the most iconi....

    Free Cancellation
    Private Tour
    Start From $47.50
 
 

Private Sailboat Charter from San Pedro: Port of Los Angeles

(4.7 of 27 reviews)

Experience the beauty of the Pacific Ocean with a private yacht charter in San Pedro, CA. Enjoy a sunset sailing adventure on a Beneteau Oceanis (39ft) sailing yacht, perfect for couples or small groups looking for a memorable out... More

Free Cancellation
Private Tour
Start From $380.00
 
Private Sailboat Charter from San Pedro: Port of Los Angeles Likely to Sell Out

Private Sailboat Charter from San Pedro: Port of Los Angeles

  • USA
  • Superb27 reviews4.7

Experience the beauty of the Pacific Ocean with a private yacht charter in San Pedro, CA. Enjoy a su....

    Free Cancellation
    Private Tour
    Start From $380.00
 
 

Condor Sailing Fun, Relaxing Public Dolphin & Sightseeing Cruise

(4.9 of 73 reviews)

Perfect for kids to grandparents, and perfect for couples! Always fun, relaxing, and uncrowded. Chill out in comfy seats, with beautiful views of the bay and National Seashore. Or explore the Condor: walk around, do the Titanic po... More

Free Cancellation
Private Tour
Start From $114.00
 
Condor Sailing Fun, Relaxing Public Dolphin & Sightseeing Cruise Likely to Sell Out

Condor Sailing Fun, Relaxing Public Dolphin & Sightseeing Cruise

  • USA
  • Superb73 reviews4.9

Perfect for kids to grandparents, and perfect for couples! Always fun, relaxing, and uncrowded. Chil....

    Free Cancellation
    Private Tour
    Start From $114.00
 
 

Detroit Sunset Sail on the River

(4.9 of 73 reviews)

Our sunset sail is designed to feel effortless, intimate, and elevated from the moment you step aboard. This is not a crowded cruise. It’s a small group sailing experience where guests can truly relax, connect, and take in Detro... More

Free Cancellation
Private Tour
Start From $115.00
 
Detroit Sunset Sail on the River Likely to Sell Out

Detroit Sunset Sail on the River

  • USA
  • Superb73 reviews4.9

Our sunset sail is designed to feel effortless, intimate, and elevated from the moment you step aboa....

    Free Cancellation
    Private Tour
    Start From $115.00
 
 

Luxury Catamaran Whale Watch

(4.9 of 89 reviews)

From December through April, the waters off Maui come alive with the sights and sounds of the majestic humpback whales, and there’s no better way to witness the wonder than from the deck of our 65’ catamaran. This two-hour ex... More

Free Cancellation
Private Tour
Start From $119.00
 
Luxury Catamaran Whale Watch Likely to Sell Out

Luxury Catamaran Whale Watch

  • USA
  • Superb89 reviews4.9

From December through April, the waters off Maui come alive with the sights and sounds of the majest....

    Free Cancellation
    Private Tour
    Start From $119.00
 
 

Afternoon Schooner Clearwater Beach Cruise Sailing

(5 of 2 reviews)

Whether you are a seasoned sailor or if this is your first time sailing, this will be a memorable visit!!! ;) *Children under age 5-not permitted to sail. *Not Suitable for Guests with mobility issues. *Participants must weigh l... More

Free Cancellation
Private Tour
Start From $65.00
 
Afternoon Schooner Clearwater Beach Cruise Sailing Likely to Sell Out

Afternoon Schooner Clearwater Beach Cruise Sailing

  • USA
  • Superb2 reviews5

Whether you are a seasoned sailor or if this is your first time sailing, this will be a memorable vi....

    Free Cancellation
    Private Tour
    Start From $65.00
 
 

Polynesian Canoe Day Sail

(4.9 of 29 reviews)

Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) offering a one-of-a-kind native Hawaiian cultural and educational experience. Come sail along the beautiful Waikiki coastline and b... More

Special Offer
Free Cancellation
Private Tour
Start From $180.00
(Saving 10% ) $200.00
 
-10% Polynesian Canoe Day Sail Likely to Sell Out

Polynesian Canoe Day Sail

  • USA
  • Superb29 reviews4.9

Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) o....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $180.00
    (Saving 10% ) $200.00
 
 

90 Minute Sailing Tour of Portland

(3.8 of 5 reviews)

Our tour begins with a cruise across the river to the most expensive floating homes on the Willamette. We then usually head down the historic Holgate channel on Portland's own "Jungle Cruise" to the spectacular city riverfront wh... More

Special Offer
Free Cancellation
Private Tour
Start From $99.00
(Saving inf% ) $0.00
 
-inf% 90 Minute Sailing Tour of Portland Likely to Sell Out

90 Minute Sailing Tour of Portland

  • USA
  • Very Good5 reviews3.8

Our tour begins with a cruise across the river to the most expensive floating homes on the Willamet....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $99.00
    (Saving inf% ) $0.00
 
 

Experience Maalaea Harbor Sailing Snorkeling Adventure

(3.8 of 5 reviews)

Spend a leisurely afternoon sailing aboard the widest and most stable and luxurious catamaran in Maui, where your adventure takes you to the stunning waters of Molokini or a secret turtle sanctuary. Enjoy hand-shaken Mai Tais and ... More

Special Offer
Free Cancellation
Private Tour
Start From $149.00
(Saving inf% ) $0.00
 
-inf% Experience Maalaea Harbor Sailing Snorkeling Adventure Likely to Sell Out

Experience Maalaea Harbor Sailing Snorkeling Adventure

  • USA
  • Very Good5 reviews3.8

Spend a leisurely afternoon sailing aboard the widest and most stable and luxurious catamaran in Mau....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $149.00
    (Saving inf% ) $0.00
 
 

Seattle Golden Gardens Sunset Sail 70ft Boat Tour

(5 of 2 reviews)

Experience a beautiful Seattle evening on this 2-hour sunset sailing cruise departing from Shilshole Bay Marina near the iconic Golden Gardens Park. Step aboard a classic 70-foot former ocean racing yacht and head out onto Puget S... More

Special Offer
Free Cancellation
Private Tour
Start From $76.00
(Saving inf% ) $0.00
 
-inf% Seattle Golden Gardens Sunset Sail 70ft Boat Tour Likely to Sell Out

Seattle Golden Gardens Sunset Sail 70ft Boat Tour

  • USA
  • Superb2 reviews5

Experience a beautiful Seattle evening on this 2-hour sunset sailing cruise departing from Shilshole....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $76.00
    (Saving inf% ) $0.00
 
 

New York City Skyline Lights Sail

(4.6 of 14 reviews)

Experience New York City from the water on classic Schooner Adirondack. Gaze at the city lights from the water and enjoy a peaceful setting as you escape the city and take to a quiet harbor at night. Key points about this activ... More

Special Offer
Free Cancellation
Private Tour
Start From $67.01
(Saving inf% ) $0.00
 
-inf% New York City Skyline Lights Sail Likely to Sell Out

New York City Skyline Lights Sail

  • USA
  • Superb14 reviews4.6

Experience New York City from the water on classic Schooner Adirondack. Gaze at the city lights fro....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $67.01
    (Saving inf% ) $0.00
 
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