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Top 10 Best USA Sailing Trips

Found 448 Sailing Trips activities in USA. Sort by Popularity. - Page 17
 

Waikiki Heritage and Diamond Head Wildlife Sail

(4.7 of 32 reviews)

Set sail along the iconic Waikiki coastline for a laid-back 1.5-hour afternoon on the water. This experience emphasizes relaxation, scenic views of Oʻahu’s south shore, and casual wildlife watching—keep an eye out for dolphin... More

Free Cancellation
Start From $79.95
 
Waikiki Heritage and Diamond Head Wildlife Sail Likely to Sell Out

Waikiki Heritage and Diamond Head Wildlife Sail

  • USA
  • Superb32 reviews4.7

Set sail along the iconic Waikiki coastline for a laid-back 1.5-hour afternoon on the water. This ex....

    Free Cancellation
    Start From $79.95
 
 

2 Hour Private Catamaran Charter in Waikiki (7-12 Guests)

(4.7 of 32 reviews)

(IMPORTANT: Make sure you have *over* 6 guests selected to see availability for this activity, or it will show NO AVAILABILITY. If you have 1-6 guests, you can book under our other listing labeled for 1-6 guests.) This 48-foot ca... More

Free Cancellation
Private Tour
Start From $1,200.00
 
2 Hour Private Catamaran Charter in Waikiki (7-12 Guests) Likely to Sell Out

2 Hour Private Catamaran Charter in Waikiki (7-12 Guests)

  • USA
  • Superb32 reviews4.7

(IMPORTANT: Make sure you have *over* 6 guests selected to see availability for this activity, or it....

    Free Cancellation
    Private Tour
    Start From $1,200.00
 
 

Schooner Applejack 2-Hour Day Sail from Boothbay Harbor

(4.3 of 35 reviews)

Welcome Aboard Schooner Lazy Jack in Boothbay Harbor; your Maine Vacation starts here! Join the Schooner crew for a 2hr. day sail on Boothbay Harbor’s oldest windjammer. Help hoist sails or take a turn at the wheel as we set a c... More

Free Cancellation
Private Tour
Start From $54.95
 
Schooner Applejack 2-Hour Day Sail from Boothbay Harbor Likely to Sell Out

Schooner Applejack 2-Hour Day Sail from Boothbay Harbor

  • USA
  • Exellent35 reviews4.3

Welcome Aboard Schooner Lazy Jack in Boothbay Harbor; your Maine Vacation starts here! Join the Scho....

    Free Cancellation
    Private Tour
    Start From $54.95
 
 

Portland Tall Ship Private Charter on Casco Bay

(4.3 of 35 reviews)

What better way to see the delights than in the style of a private charter for you and five friends or family members? Experience the beauty and serenity of the rugged coastline as you gaze upon seabirds, sea houses, and islands. ... More

Free Cancellation
Private Tour
Start From $1,063.46
 
Portland Tall Ship Private Charter on Casco Bay Likely to Sell Out

Portland Tall Ship Private Charter on Casco Bay

  • USA
  • Exellent35 reviews4.3

What better way to see the delights than in the style of a private charter for you and five friends ....

    Free Cancellation
    Private Tour
    Start From $1,063.46
 
 

Wrightsville Beach Day Sail Private Catamaran Charter

(4.3 of 35 reviews)

On this 4hr private charter, you will work with your captain to plan your perfect itinerary of islands and local spots. Upon anchoring, the crew will dinghy you around wherever you'd like to go! The boat is fully equipped with ai... More

Free Cancellation
Private Tour
Start From $1,200.00
 
Wrightsville Beach Day Sail Private Catamaran Charter Likely to Sell Out

Wrightsville Beach Day Sail Private Catamaran Charter

  • USA
  • Exellent35 reviews4.3

On this 4hr private charter, you will work with your captain to plan your perfect itinerary of islan....

    Free Cancellation
    Private Tour
    Start From $1,200.00
 
 

Baltimore Evening Sail on the Summer Wind

(5 of 28 reviews)

Enjoy a beautiful time on the water while you nibble on cheese and sip delicious wine on this 1.5-hour sail. As you sail through beautiful Baltimore Harbor, take in the gorgeous scenery of the skyline as the city lights up. Treat ... More

Free Cancellation
Private Tour
Start From $75.00
 
Baltimore Evening Sail on the Summer Wind Likely to Sell Out

Baltimore Evening Sail on the Summer Wind

  • USA
  • Superb28 reviews5

Enjoy a beautiful time on the water while you nibble on cheese and sip delicious wine on this 1.5-ho....

    Free Cancellation
    Private Tour
    Start From $75.00
 
 

San Salvador Spanish Galleon Adventure Day Sail with General Admission

(4.8 of 5 reviews)

Your 4-hour San Salvador Adventure Day Sail is your opportunity to step back into time as you step on board this 16th century Spanish galleon. The San Salvador is a replica of Juan Rodriguez Cabrillo’s ship that arrived at the ... More

Free Cancellation
Private Tour
Start From $85.00
 
San Salvador Spanish Galleon Adventure Day Sail with General Admission Likely to Sell Out

San Salvador Spanish Galleon Adventure Day Sail with General Admi....

  • USA
  • Superb5 reviews4.8

Your 4-hour San Salvador Adventure Day Sail is your opportunity to step back into time as you step o....

    Free Cancellation
    Private Tour
    Start From $85.00
 
 

Midday Whale Watch: Mā’alaea Harbor

(4.9 of 104 reviews)

Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from Alaska, and although you can see them throughout Hawaii, the ‘Au ‘au channel off the coast of Maui boasts the greatest number. ... More

Free Cancellation
Private Tour
Start From $100.22
 
Midday Whale Watch: Mā’alaea Harbor Likely to Sell Out

Midday Whale Watch: Mā’alaea Harbor

  • USA
  • Superb104 reviews4.9

Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from A....

    Free Cancellation
    Private Tour
    Start From $100.22
 
 

2.5 hr Sailboat Tour aboard Orion's Child

(5 of 90 reviews)

TripAdvisor Special Sail. SEE OUR WEBSITE for other options and availability. Since 2009, we offer the cleanest, safest, and best maintained sailing vessel. Multiple daily sails that include a quarter day and sunset sail aboard a ... More

Free Cancellation
Private Tour
Start From $130.00
 
2.5 hr Sailboat Tour aboard Orion's Child Likely to Sell Out

2.5 hr Sailboat Tour aboard Orion's Child

  • USA
  • Superb90 reviews5

TripAdvisor Special Sail. SEE OUR WEBSITE for other options and availability. Since 2009, we offer t....

    Free Cancellation
    Private Tour
    Start From $130.00
 
 

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
 
 

Day Sailing Adventure in the Florida Marine Sanctuary

(5 of 41 reviews)

Escape the ordinary and embark on an unforgettable journey aboard our 50 foot sailboat, “Chao Lay”. Choose our popular 3-hour Day Sail through the Florida Keys Marine Sanctuary in Marathon, Florida. Our sailboat rides feature ... More

Free Cancellation
Private Tour
Start From $120.00
 
Day Sailing Adventure in the Florida Marine Sanctuary Likely to Sell Out

Day Sailing Adventure in the Florida Marine Sanctuary

  • USA
  • Superb41 reviews5

Escape the ordinary and embark on an unforgettable journey aboard our 50 foot sailboat, “Chao Lay....

    Free Cancellation
    Private Tour
    Start From $120.00
 
 

Waikiki Sail and Snorkel Adventure Best of Hawaii 2023

(4 of 4 reviews)

Immerse yourself in a vibrant underwater wonderland as you snorkel through coral reefs teeming with an array of tropical fish. The clear waters of Turtle Canyons reveal a kaleidoscope of colors, from dazzling schools of fish to vi... More

Free Cancellation
Private Tour
Start From $695.00
 
Waikiki Sail and Snorkel Adventure Best of Hawaii 2023 Likely to Sell Out

Waikiki Sail and Snorkel Adventure Best of Hawaii 2023

  • USA
  • Very Good4 reviews4

Immerse yourself in a vibrant underwater wonderland as you snorkel through coral reefs teeming with ....

    Free Cancellation
    Private Tour
    Start From $695.00
 
 

Tall Ship Adventure aboard the Schooner Californian with General Admission

(4.3 of 6 reviews)

Californian was built from the ground up in 1984 at Spanish Landing in San Diego Bay. She was launched with great fanfare for the 1984 Summer Olympic Games in Los Angeles. In July 2003, the Governor signed a bill into law designat... More

Free Cancellation
Private Tour
Start From $85.00
 
Tall Ship Adventure aboard the Schooner Californian with General Admission Likely to Sell Out

Tall Ship Adventure aboard the Schooner Californian with General ....

  • USA
  • Exellent6 reviews4.3

Californian was built from the ground up in 1984 at Spanish Landing in San Diego Bay. She was launch....

    Free Cancellation
    Private Tour
    Start From $85.00
 
 

Private Sailing Tour -2 Hour (Up to 12 Passengers)

(4.3 of 6 reviews)

Christened in 1934, Cloudia is a beautifully restored, rare example of a classic Norwegian double ended ketch. Inspired by the original designs of famed naval architect Colin Archer (1832-1921), from Larvik, Norway, the Cloudia is... More

Free Cancellation
Private Tour
Start From $1,200.00
 
Private Sailing Tour -2 Hour (Up to 12 Passengers) Likely to Sell Out

Private Sailing Tour -2 Hour (Up to 12 Passengers)

  • USA
  • Exellent6 reviews4.3

Christened in 1934, Cloudia is a beautifully restored, rare example of a classic Norwegian double en....

    Free Cancellation
    Private Tour
    Start From $1,200.00
 
 

Private Sail New York with Brooklyn Sail (Reserve the entire boat)

(5 of 125 reviews)

2.5 hour sails for private groups up to six passengers from Pier 5 in Brooklyn Bridge Park, One15 Brooklyn Marina, 159 Bridge Park Drive. Views of the Brooklyn Bridge, Statue of Liberty, World Trade Center, Ellis Island, Governor... More

Free Cancellation
Private Tour
Start From $895.00
 
Private Sail New York with Brooklyn Sail (Reserve the entire boat) Likely to Sell Out

Private Sail New York with Brooklyn Sail (Reserve the entire boat....

  • USA
  • Superb125 reviews5

2.5 hour sails for private groups up to six passengers from Pier 5 in Brooklyn Bridge Park, One15 Br....

    Free Cancellation
    Private Tour
    Start From $895.00
 
 

4 hours Sailboat Tour for 2 people along the Los Angeles Coastline

(3.7 of 3 reviews)

The coastal line of Los Angeles. You will see Marina Del Rey, head for Santa Monica, sail past Venice Beach, Airport, Malibu beach, go into the open ocean, anchor (if desired) and return back to Marina Del Rey.... More

Free Cancellation
Private Tour
Start From $599.00
 
4 hours Sailboat Tour for 2 people along the Los Angeles Coastline Likely to Sell Out

4 hours Sailboat Tour for 2 people along the Los Angeles Coastlin....

  • USA
  • Very Good3 reviews3.7

The coastal line of Los Angeles. You will see Marina Del Rey, head for Santa Monica, sail past Venic....

    Free Cancellation
    Private Tour
    Start From $599.00
 
 

Private Day Sailing Experience in San Diego up to 12 guests

(5 of 67 reviews)

This private day sail, is a excellent if you are looking for a more exciting sail! Day sailing is best to go see our San Diego landmarks along downtown where we will see the US Midway, Sea port Village, the Rady shell and we might... More

Free Cancellation
Private Tour
Start From $235.00
 
Private Day Sailing Experience in San Diego up to 12 guests Likely to Sell Out

Private Day Sailing Experience in San Diego up to 12 guests

  • USA
  • Superb67 reviews5

This private day sail, is a excellent if you are looking for a more exciting sail! Day sailing is be....

    Free Cancellation
    Private Tour
    Start From $235.00
 
 

Baltimore Harbor Evening Sail on the Unforgettable

(4.6 of 5 reviews)

Enjoy a beautiful time on the water as you sail through beautiful Baltimore Harbor, take in the gorgeous scenery of the skyline as the city lights up. Treat yourself and a loved one on this elegant sailing experience.  It's BYOB,... More

Free Cancellation
Private Tour
Start From $75.00
 
Baltimore Harbor Evening Sail on the Unforgettable Likely to Sell Out

Baltimore Harbor Evening Sail on the Unforgettable

  • USA
  • Superb5 reviews4.6

Enjoy a beautiful time on the water as you sail through beautiful Baltimore Harbor, take in the gorg....

    Free Cancellation
    Private Tour
    Start From $75.00
 
 

#1 eFoil 1.25 hr or 2 hr wing foil or windsurf or kayak lesson

(5 of 4 reviews)

You will receive special Ocean Safety training prior to your adventure. Our two way radio helmets help us to give precise specific info as needed so you learn faster and safer. We will share with you the best locations to launch f... More

Free Cancellation
Private Tour
Start From $450.00
 
#1 eFoil 1.25 hr or 2 hr wing foil or windsurf or kayak lesson Likely to Sell Out

#1 eFoil 1.25 hr or 2 hr wing foil or windsurf or kayak lesson

  • USA
  • Superb4 reviews5

You will receive special Ocean Safety training prior to your adventure. Our two way radio helmets he....

    Free Cancellation
    Private Tour
    Start From $450.00
 
 

Discover Maine's Coastal Charms: Half-Day Scenic Sail

(5 of 3 reviews)

Set sail with us and immerse yourself in the unparalleled beauty of coastal Maine on our half-day excursion. Traverse the serene waters of the Saco River and Saco Bay with its eight gorgeous islands as you uncover their hidden sec... More

Free Cancellation
Private Tour
Start From $259.00
 
Discover Maine's Coastal Charms: Half-Day Scenic Sail Likely to Sell Out

Discover Maine's Coastal Charms: Half-Day Scenic Sail

  • USA
  • Superb3 reviews5

Set sail with us and immerse yourself in the unparalleled beauty of coastal Maine on our half-day ex....

    Free Cancellation
    Private Tour
    Start From $259.00
 
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