Top activities
Top landmarks
Trip ideas
Nearby places
Port schedule

Top USA Sailing Trips

376 Results
Key West Backcountry Safari

Spend an unforgettable day sailing emerald waters, kayaking mangrove-shaded channels and snorkeling coral gardens in an unspoiled marine wilderness. …More

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

Spend an unforgettable day sailing emerald waters, kayaking mangrove-shaded channels and snorkeling coral gardens in an unspoiled marine wilderness....

4.5 or 6.5 hours (approx.) Free Cancellation
4.9 (2,739)
from
$105
Sunset Sail Cruise in Key West

Sailing on the Rover is an exciting, traditional sailing experience with a Hint of Piracy! Yes - We have cannons! Come sail on Key West's …More

Key West, USA

Sailing on the Rover is an exciting, traditional sailing experience with a Hint of Piracy! Yes - We have cannons! Come sail on Key West's...

2 hours Free Cancellation
5.0 (292)
from
$102
Lahaina Maui Afternoon Whale Watch Sail in Humpback Sanctuary

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, …More

Maui, USA

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,...

2 hours Free Cancellation
5.0 (1)
from
$102
Portland Tall Ship Cruise on Casco Bay

What better way to see the delights of Portland than from the sea in one of the famous schooner tall ships. Join us for this …More

Portland, USA

What better way to see the delights of Portland than from the sea in one of the famous schooner tall ships. Join us for this...

2 hours Free Cancellation
4.6 (242)
from
$101
Sail Biscayne Bay: An Intimate Eco-Adventure with Snorkeling

This tour is an intimate experience, our groups are 3-5 people per boat maximum. We have two boats. We have been sailing the Biscayne Bay …More

Miami, USA

This tour is an intimate experience, our groups are 3-5 people per boat maximum. We have two boats. We have been sailing the Biscayne Bay...

3 hours 30 minutes Free Cancellation
4.9 (458)
from
$101
Waikiki Turtle Snorkeling Adventure(8am)

Discover an all-in-one Waikiki ocean adventure with our Turtle Snorkeling Tour. Cruise aboard our spacious and comfortable catamaran to Turtle Canyon, where you’ll have the …More

Likely to Sell Out
Likely to Sell Out
Honolulu, USA

Discover an all-in-one Waikiki ocean adventure with our Turtle Snorkeling Tour. Cruise aboard our spacious and comfortable catamaran to Turtle Canyon, where you’ll have the...

3 hours Hotel pickup offered Free Cancellation
4.9 (141)
from
$100
The Boat People Cruise Private Harbor Cruises

Join us for an hour and a half picnic cruise with a coastal ambiance on the bow of our sailboat. We strive to create an …More

Newport Beach, USA

Join us for an hour and a half picnic cruise with a coastal ambiance on the bow of our sailboat. We strive to create an...

1 hour 30 minutes
5.0 (53)
from
$100
Key West Schooner Sunset Sail with Hors D'oeuvres and Full Bar

Meet for this Key West Sunset Sail at the Key West Historic Harbor. Board a beautiful bugeye schooner, and get acquainted with your captain and …More

Key West, USA

Meet for this Key West Sunset Sail at the Key West Historic Harbor. Board a beautiful bugeye schooner, and get acquainted with your captain and...

2 hours (approx.) Free Cancellation
4.9 (1,703)
from
$100
Private Sunset Sail in San Diego Up to 6 guests

Join Sea Monkey Adventures for a 2-hour sailing tour on San Diego Bay. This small-group sail is perfect for solo travelers, couples, or friends looking …More

La Jolla, USA

Join Sea Monkey Adventures for a 2-hour sailing tour on San Diego Bay. This small-group sail is perfect for solo travelers, couples, or friends looking...

2 hours Free Cancellation
5.0 (74)
from
$99
Key West Wind & Wine Sunset Sail

Wind & Wine has been the #1 rated sunset sail on Cool Shore Excursions for over a decade. In our opinion, this is the best …More

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

Wind & Wine has been the #1 rated sunset sail on Cool Shore Excursions for over a decade. In our opinion, this is the best...

2 hours (approx.) Free Cancellation
5.0 (1,717)
$115
$99
Sunset Sail Along the San Diego Skyline

Enjoy an evening sailing under the sunset on a relaxing sailing cruise with a unique perspective on San Diego that you can only get from …More

Likely to Sell Out
Likely to Sell Out
San Diego, USA

Enjoy an evening sailing under the sunset on a relaxing sailing cruise with a unique perspective on San Diego that you can only get from...

2 hours Free Cancellation
4.9 (658)
from
$99
Key West Sunset Sail Aboard Legendary Schooner Appledore

Experience sailing Key West on a majestic 2-masted schooner, just like adventurers from the 19th century, while enjoying the luxurious state-of-the-art accommodations of a modern …More

Key West, USA

Experience sailing Key West on a majestic 2-masted schooner, just like adventurers from the 19th century, while enjoying the luxurious state-of-the-art accommodations of a modern...

2 hours Free Cancellation
5.0 (369)
from
$99
1.5-Hour San Francisco Bay Sailing Tour

For a relaxing afternoon on the water, hop aboard the Privateer, a truly traditional sailboat, for a semi-private 90-minute cruise of the bay, complete with …More

San Francisco, USA

For a relaxing afternoon on the water, hop aboard the Privateer, a truly traditional sailboat, for a semi-private 90-minute cruise of the bay, complete with...

1 hour 30 minutes Free Cancellation
4.8 (396)
from
$99
Small Group Waikiki Sunset Sailing Tour

Hawaii is well known for its majestic sunsets, and there is truly no better way to experience it than on our boat, The Universe. Come …More

Likely to Sell Out
Likely to Sell Out
Oahu, USA

Hawaii is well known for its majestic sunsets, and there is truly no better way to experience it than on our boat, The Universe. Come...

2 hours Free Cancellation
4.9 (121)
from
$99
Waikiki small group turtle snorkeling & sailing

Witness the brilliant colors of a sunrise over Diamond Head crater. Ideal for early birds, couples or families who are up at the crack of …More

Likely to Sell Out
Likely to Sell Out
Oahu, USA

Witness the brilliant colors of a sunrise over Diamond Head crater. Ideal for early birds, couples or families who are up at the crack of...

2 hours Free Cancellation
5.0 (109)
from
$99
Daytime Sailing Along San Diego's Skyline

Set sail with your Captain aboard our sail yacht and see some of San Diego's finest highlights on thisfamily-friendly sailing experience. We'll set sail from Safeharbor …More

Likely to Sell Out
Likely to Sell Out
San Diego, USA

Set sail with your Captain aboard our sail yacht and see some of San Diego's finest highlights on thisfamily-friendly sailing experience. We'll set sail from Safeharbor...

2 hours Free Cancellation
5.0 (161)
from
$99
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
Marina Del Rey Luxury Yacht Experience

Discover the perfect blend of relaxation, fun, and local insight on the water with our exclusive Marina del Rey yacht experience, hosted by our friendly …More

Santa Monica, USA

Discover the perfect blend of relaxation, fun, and local insight on the water with our exclusive Marina del Rey yacht experience, hosted by our friendly...

1 hour 15 minutes Free Cancellation
4.7 (3)
from
$99
Key West Christmas Cruise with Live Band and Drinks

Join us for a family-friendly holiday sail aboard Schooner America 2.0 decorated with festive Christmas lights! Sing along to your favorite Christmas music with our …More

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

Join us for a family-friendly holiday sail aboard Schooner America 2.0 decorated with festive Christmas lights! Sing along to your favorite Christmas music with our...

1 hour 30 minutes Free Cancellation
5.0 (5)
from
$98
Let's Go Sail the York River in Gloucester Point Virginia

Couples and families enjoy a unique opportunity to sail their own 32-foot sloop with all the modern conveniences. Or sit back and relax in the …More

Likely to Sell Out
Likely to Sell Out

Couples and families enjoy a unique opportunity to sail their own 32-foot sloop with all the modern conveniences. Or sit back and relax in the...

2 hours 30 minutes Free Cancellation
5.0 (168)
from
$96

Frequently Asked Questions

These answers are based on answers previously given to Cool Shore Excursions customers' questions.

Recent tour reviews
Activity name

Discover USA