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Top USA Sailing Trips

376 Results
Fort Lauderdale Sailing Charter

Embark on an unforgettable journey starting in Fort Lauderdale on the iconic New River, often called the “Venice of America.” This scenic waterway offers a …More

Likely to Sell Out
Likely to Sell Out
Fort Lauderdale, USA

Embark on an unforgettable journey starting in Fort Lauderdale on the iconic New River, often called the “Venice of America.” This scenic waterway offers a...

4 hours Free Cancellation
5.0 (401)
from
$95
Sunset Sailing Cruise in Monterey Bay

Looking to impress your date or just treat yourself to something unforgettable? Our Sunset Cruise is the most popular (and most romantic!) way to experience …More

Likely to Sell Out
Likely to Sell Out
Monterey & Carmel, USA

Looking to impress your date or just treat yourself to something unforgettable? Our Sunset Cruise is the most popular (and most romantic!) way to experience...

1 hour 30 minutes Free Cancellation
4.8 (62)
from
$95
Public Sunset Sailing Cruise on Lake Champlain

Witness the captivating Burlington sunset while sailing across Lake Champlain on a classic Friendship Sloop. This two-hour cruise offers an unparalleled view of the Adirondack …More

Likely to Sell Out
Likely to Sell Out
Burlington, USA

Witness the captivating Burlington sunset while sailing across Lake Champlain on a classic Friendship Sloop. This two-hour cruise offers an unparalleled view of the Adirondack...

2 hours
5.0 (23)
from
$95
Public Sunset Picnic Boat Cruise on Lake Champlain

Set sail on Lake Champlain aboard the charming Buttercup for a two-hour sunset picnic cruise. This unique experience invites you to bring your own food …More

Likely to Sell Out
Likely to Sell Out
Burlington, USA

Set sail on Lake Champlain aboard the charming Buttercup for a two-hour sunset picnic cruise. This unique experience invites you to bring your own food...

2 hours Free Cancellation
5.0 (7)
from
$95
Sunset Sail Experience by Catamaran in Waikiki

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 …More

Oahu, USA

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...

2 hours Free Cancellation
4.8 (6)
from
$92
Sail on Tall Ship Windy, join us for our "Chicago Skyline Sail"

Join us for an unforgettable sail on Tall Ship Windy, Chicago's Official Tall Ship Ambassador! This is a relaxing sailing Adventure, that you will enjoy, …More

Likely to Sell Out
Likely to Sell Out
Chicago, USA

Join us for an unforgettable sail on Tall Ship Windy, Chicago's Official Tall Ship Ambassador! This is a relaxing sailing Adventure, that you will enjoy,...

1 hour 15 minutes
4.8 (30)
from
$91
New York Sunset Schooner Cruise on the Hudson River

Experience a New York City sunset from the water on this evening sightseeing sail past many famous waterside landmarks. Step aboard the 80-foot, 2-masted sailboat known …More

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

Experience a New York City sunset from the water on this evening sightseeing sail past many famous waterside landmarks. Step aboard the 80-foot, 2-masted sailboat known...

2 hours Free Cancellation
4.9 (224)
from
$90
New York City Sunset Sail to the Statue of Liberty

Experience a sunset from New York Harbor and enjoy sweeping views of Manhattan's skyline, parts of Brooklyn and Jersey City from Schooner America. This classic …More

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

Experience a sunset from New York Harbor and enjoy sweeping views of Manhattan's skyline, parts of Brooklyn and Jersey City from Schooner America. This classic...

2 hours Free Cancellation
4.9 (75)
from
$90
Waikiki: Fireworks Cruise from Beach & Cocktail Open Bar | Oahu

Set sail with Waikiki’s top-rated fireworks cruise and enjoy the famous Hilton Hawaiian Village display from the best seat on Oahu—the water. Every Friday night, …More

Oahu, USA

Set sail with Waikiki’s top-rated fireworks cruise and enjoy the famous Hilton Hawaiian Village display from the best seat on Oahu—the water. Every Friday night,...

1 hour Free Cancellation
4.8 (62)
from
$90
Waikiki Turtle Snorkeling & 6-in-1 Adventure with Free Pickup

Experience a special turtle snorkeling adventure in Waikiki aboard a smooth and comfortable catamaran. This all-in-one 6-in-1 ocean tour includes snorkeling, kayaking, stand-up paddleboarding (SUP), …More

Honolulu, USA

Experience a special turtle snorkeling adventure in Waikiki aboard a smooth and comfortable catamaran. This all-in-one 6-in-1 ocean tour includes snorkeling, kayaking, stand-up paddleboarding (SUP),...

3 hours Hotel pickup offered Free Cancellation
4.9 (684)
from
$90
Waikiki Sunset Cocktail Sail on the Moana Catamaran

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 …More

Likely to Sell Out
Likely to Sell Out
Oahu, USA

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...

2 hours Free Cancellation
4.9 (2,419)
from
$90
Key West Catamaran Dolphin Watch & Sunset Sail

Set sail from Key West's Historic Seaport for a thrilling dolphin watch and famous Key West sunset sail aboard a luxury catamaran with premium wines …More

Key West, USA

Set sail from Key West's Historic Seaport for a thrilling dolphin watch and famous Key West sunset sail aboard a luxury catamaran with premium wines...

2 hours 30 minutes (approx.) Free Cancellation
4.8 (750)
from
$90
Tiki Pub Glow Party Cruise (Adults only)

Light up the night on Fort Myers! Sail the backwaters of Fort Myers Beach under shimmering stars, sipping on your BYOB drinks. Experience the magic …More

Likely to Sell Out
Likely to Sell Out
Fort Myers, USA

Light up the night on Fort Myers! Sail the backwaters of Fort Myers Beach under shimmering stars, sipping on your BYOB drinks. Experience the magic...

2 hours Free Cancellation
4.9 (18)
from
$90
Waikiki Turtle Snorkel and Sail on Hawea Catamaran

Experience the best of Waikiki on a Turtle Snorkel & Sail combo aboard the Hawea Catamaran. This popular Oahu tour blends marine exploration and island …More

Oahu, USA

Experience the best of Waikiki on a Turtle Snorkel & Sail combo aboard the Hawea Catamaran. This popular Oahu tour blends marine exploration and island...

2 hours 30 minutes Free Cancellation
4.8 (1,757)
from
$90
Sailing Charters in Wilmington

After a successful first three seasons I am happy to be here for a fourth season!!! Sail in style on the historic Wilmington river walk. …More

Wilmington, USA

After a successful first three seasons I am happy to be here for a fourth season!!! Sail in style on the historic Wilmington river walk....

2 hours Free Cancellation
5.0 (218)
from
$89
Ft Myers Beach 3 Hour Tiki Pub Tropical Sandbar Getaway Cruise

Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages, take pics, get some sun, make friends, play party …More

Likely to Sell Out
Likely to Sell Out
Fort Myers, USA

Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages, take pics, get some sun, make friends, play party...

3 hours Free Cancellation
4.9 (59)
from
$89
Kona Tradewind Catamaran Day Sail

Experience the beauty of the Kona Coast from a new perspective aboard the Spirit of Aloha sailing catamaran. Feel the trade winds fill the sails …More

Big Island of Hawaii, USA

Experience the beauty of the Kona Coast from a new perspective aboard the Spirit of Aloha sailing catamaran. Feel the trade winds fill the sails...

1 hour 30 minutes Free Cancellation
4.8 (51)
from
$89
Original Cruisin Tikis Snorkeling Safari

The Snorkeling Safari is a must-do when visiting Destin. Pop open your favorite drinks and let your professional, USCG-licensed captain cruise you through the heart …More

Likely to Sell Out
Likely to Sell Out
Destin, USA

The Snorkeling Safari is a must-do when visiting Destin. Pop open your favorite drinks and let your professional, USCG-licensed captain cruise you through the heart...

3 hours
5.0 (1)
from
$89
Sunset Sail Aboard the Liberty Clipper

Set sail into the golden hues of sunset on the 125' Schooner Liberty Clipper. This 2-hour adventure lets you glide through the tranquil waters while …More

Long Island, USA

Set sail into the golden hues of sunset on the 125' Schooner Liberty Clipper. This 2-hour adventure lets you glide through the tranquil waters while...

2 hours Free Cancellation
5.0 (18)
from
$89
Key West Night Cruise aboard Schooner America 2.0

Join us aboard Schooner America 2.0 in Key West for a fun night time experience. During this night cruise in Key West, guests can enjoy …More

Likely to Sell Out
Likely to Sell Out
Key West, USA

Join us aboard Schooner America 2.0 in Key West for a fun night time experience. During this night cruise in Key West, guests can enjoy...

1 hour 45 minutes Free Cancellation
5.0 (5)
from
$89

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