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Top USA Sailing Trips

375 Results
Waikiki Best Whale Watching in Honolulu: Whales Guaranteed

Guaranteed whale sightings* Spacious and modern Trimaran with unobstructed open air views as well as ample seating and shade on board. Knowledgeable staff with plenty …More

Honolulu, USA

Guaranteed whale sightings* Spacious and modern Trimaran with unobstructed open air views as well as ample seating and shade on board. Knowledgeable staff with plenty...

2 hours Free Cancellation
4.7 (242)
from
$79
Escape from the Rock! Cruise around Alcatraz

Embark on a 90-minute cruise along the San Francisco waterfront, under the Golden Gate Bridge and past Angel Island State Park before circling Alcatraz Island for an …More

San Francisco, USA

Embark on a 90-minute cruise along the San Francisco waterfront, under the Golden Gate Bridge and past Angel Island State Park before circling Alcatraz Island for an...

1 hour 30 minutes Free Cancellation
4.5 (146)
from
$48
Baltimore Inner Harbor Sail on Summer Wind

Enjoy the beautiful Inner Harbor of Baltimore on this 1.5-hour sailing experience. Relax on an authentic schooner and see the gorgeous views of the bustling …More

Baltimore, USA

Enjoy the beautiful Inner Harbor of Baltimore on this 1.5-hour sailing experience. Relax on an authentic schooner and see the gorgeous views of the bustling...

1 hour 30 minutes Free Cancellation
4.7 (118)
from
$65
Ka'anapali Luxury Sunset Cocktail Sail with Open Bar in Maui

Set sail on a luxurious journey along West Maui's stunning coastline with the Holo Holo Sunset Cocktail Sail. Departing from Ka’anapali Beach, this 2-hour experience …More

Likely to Sell Out
Likely to Sell Out
Maui, USA

Set sail on a luxurious journey along West Maui's stunning coastline with the Holo Holo Sunset Cocktail Sail. Departing from Ka’anapali Beach, this 2-hour experience...

2 hours Free Cancellation
4.7 (89)
from
$148
Waikiki 2 Hour Sunset Whale Watching Cruise Sightings Guaranteed

Experience the breathtaking beauty of nature with our Sunset Whale Watch excursion. Join us for an unforgettable journey as we set sail into the golden …More

Oahu, USA

Experience the breathtaking beauty of nature with our Sunset Whale Watch excursion. Join us for an unforgettable journey as we set sail into the golden...

2 hours Free Cancellation
4.6 (87)
from
$68
Half Day Oahu Combo Adventure: Bike, Sail and Snorkel

Join our Honolulu bike tour on the Bike, Sail & Snorkel adventure. This exhilarating Oahu combo tour from rainforest to reef combines views high above …More

Honolulu, USA

Join our Honolulu bike tour on the Bike, Sail & Snorkel adventure. This exhilarating Oahu combo tour from rainforest to reef combines views high above...

5 hours 30 minutes Hotel pickup offered Free Cancellation
4.7 (67)
from
$197
Miami Private Yacht Celebration Cruise with Captain

Ready for the party of a lifetime? Step aboard our luxurious Yacht Tour in Miami Beach and celebrate like never before. This VIP experience is …More

Miami, USA

Ready for the party of a lifetime? Step aboard our luxurious Yacht Tour in Miami Beach and celebrate like never before. This VIP experience is...

4 hours Free Cancellation
4.7 (52)
from
$799
Hilton Hawaiian Village Turtle Snorkel with Optional Lunch

Swim with turtles and fish, while enjoying the crystal blue topical waters. Sail the scenic Waikiki coastline and snorkel at Turtle Canyon. Our eco-conscious cruise …More

Oahu, USA

Swim with turtles and fish, while enjoying the crystal blue topical waters. Sail the scenic Waikiki coastline and snorkel at Turtle Canyon. Our eco-conscious cruise...

2 hours 30 minutes Free Cancellation
4.5 (50)
from
$110
Waikiki Sunset Cocktail Cruise - Hilton Hawaiian Village

Explore the Waikiki coastline aboard the new Spirit of Aloha, a 65-foot sailing catamaran custom-built for the Hilton Hawaiian Village Waikiki Beach Resort. See the …More

Likely to Sell Out
Likely to Sell Out
Oahu, USA

Explore the Waikiki coastline aboard the new Spirit of Aloha, a 65-foot sailing catamaran custom-built for the Hilton Hawaiian Village Waikiki Beach Resort. See the...

1 hour 30 minutes Free Cancellation
4.5 (44)
from
$120
Schooner Applejack 2-Hour Day Sail from Boothbay Harbor

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 …More

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...

2 hours Free Cancellation
4.5 (41)
from
$65
Waikiki Friday Night Fireworks Cruise NYE SPECIAL CRUISE!

Experience authentic aloha vibes with us. Our knowledgeable guides and crew are ready to share insights on local culture, marine life, and island tips. Bring …More

Oahu, USA

Experience authentic aloha vibes with us. Our knowledgeable guides and crew are ready to share insights on local culture, marine life, and island tips. Bring...

1 hour Free Cancellation
4.7 (30)
from
$60
Key West Ultimate Beach Pass with Parasailing

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

Key West, USA

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....

8 hours Free Cancellation
4.7 (19)
from
$107
New York Fall Foliage Sail up the Hudson River

Enjoy a 3.5-hour scenic sail up the Hudson River to the Palisades aboard Schooner Adirondack or Schooner America 2.0, both 1800s-style sailboats. Bordering the Hudson …More

Likely to Sell Out
Likely to Sell Out
New York City, USA

Enjoy a 3.5-hour scenic sail up the Hudson River to the Palisades aboard Schooner Adirondack or Schooner America 2.0, both 1800s-style sailboats. Bordering the Hudson...

3 hours 30 minutes Free Cancellation
4.6 (11)
from
$143
Daytime Charleston Harbor Sail - Lux Catamatan w/Bar

Sail aboard the Palmetto Breeze for a serene and scenic Afternoon Sail through Charleston’s historic harbor. This 55-foot catamaran offers the perfect vantage point to …More

Mount Pleasant, USA

Sail aboard the Palmetto Breeze for a serene and scenic Afternoon Sail through Charleston’s historic harbor. This 55-foot catamaran offers the perfect vantage point to...

2 hours Free Cancellation
4.7 (11)
from
$56
Waikiki Fireworks Cocktail Cruise

Majestic provides a intimate ambiance and exceptional service. We provide a romantic setting on a beautiful fireworks cruise that will give you a night to …More

Oahu, USA

Majestic provides a intimate ambiance and exceptional service. We provide a romantic setting on a beautiful fireworks cruise that will give you a night to...

1 hour 30 minutes Free Cancellation
4.6 (10)
from
$85
LA: Yacht Private Trip -1 hour (1 ticket covers 1-6 ppl

You may bring 1-6 people on this activity. One ticket covers you and your guests, you have the Yacht to yourselves, just your group and …More

Long Beach, USA

You may bring 1-6 people on this activity. One ticket covers you and your guests, you have the Yacht to yourselves, just your group and...

1 hour
4.6 (8)
from
$255
Sunset Sail on the Black Pearl

Come experience the tranquility of gliding through the water under sail on the Black Pearl while appreciating our beautiful Lake Erie sunsets. See Cedar Point …More

Sandusky, USA

Come experience the tranquility of gliding through the water under sail on the Black Pearl while appreciating our beautiful Lake Erie sunsets. See Cedar Point...

2 hours Free Cancellation
4.4 (7)
from
$595
Tall Ship Adventure aboard the Schooner Californian with General Admission

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 …More

San Diego, USA

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...

4 hours
4.3 (6)
from
$85
Baltimore Harbor Evening Sail on the Unforgettable

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 …More

Baltimore, USA

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...

1 hour 30 minutes Free Cancellation
4.6 (5)
from
$75
90 Minute Sailing Tour of Portland

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 …More

Portland, USA

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...

1 hour 30 minutes Free Cancellation
4.5 (4)
from
$99

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