Sunset Sail

Feel the ocean breeze. Watch the horizon glow. Let the wind guide you.

Our Locations

Sail in Two Iconic Destinations

Sunset Sail Key West

Sunset Sail Salem

Every sail is unique, shaped by changing skies, ocean rhythms, and unforgettable views. Whether you are seeking relaxation, romance, or a memorable adventure, your perfect sail begins here.

Reviews
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Sunset Sail Salem

5/5
Tripadvisor
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Sunset Sail Salem

5/5
Google

Sail with our exceptional Sunset Cruises, Daysails & Private Charters

We are grateful to have such a supportive and loyal customer base, and we hope you will join them in experiencing the Sunset Sail difference. Find out for yourself why we are at the top of the list of things to do!

Reviews
0 +

Sunset Sail Salem

5/5
Tripadvisor
Reviews
0 +

Sunset Sail Key West

4.89/5
Tripadvisor

WHY CHOOSE US

The Sunset Sail Difference

Sunset Sail blends tradition, experience, and natural beauty to create meaningful ocean experiences. Our professional crew, carefully maintained vessels, and personalized service ensure every sail becomes a lasting memory rather than just a boat ride.

OUR EXPERIENCES

Unforgettable Sailing Experiences &
discover the magic of the sea with a sailing experience designed to inspire & relax.

Shared Sailing

Relax and enjoy scenic day sails or breathtaking sunset cruises while our experienced crew handles everything.

Private Charters

Create a personalized sailing experience tailored for romance, proposals, celebrations, or peaceful escapes on the water.

Our Fleet

When and If

Marrying old-world elegance with racing performance, this classic yacht is steeped in history and brimming with top-of-the-line detail.

In 1939, the spectacular schooner was built for General George S. Patton. As WWII was beginning, he stated,

“When the war is over, and If I return, Bea and I are going to sail her around the world.”

REVIEWS

Our happy customers share their experiences

At Sunset Sail Salem, we pride ourselves on delivering exceptional sailing excursions to our guests. Don’t just take our word for it – read what our satisfied clients have to say about their experiences with us.

“So much fun, and so relaxing. The captain and crew are awesome and really do their best to make your experience amazing. This is a must do.”

Christopher

“Been onboard multiple times for a few day sails & also booked a private charter for my mom & dad’s 30th anniversary last year. Phenomenal experience every time.”

Ashley Skeffington

“We had the best sail we could have hoped for. Captain Eric was fun and informative. Will go again and recommend you all do the same. 👍🏻”

Carin Yasli

Frequently Asked Questions

Helpful information before you sail.

Can I sail the boat?

Weather and traffic permitting, everyone who wants to will get a chance to man the helm and get a taste of what it’s like to sail.

As it reflects off the water, the sun out on the water is brighter than on land. We highly recommend using some sunscreen– a minimum of 30 SPF or higher. Also, if you are prone to sunburn, you may want to wear protective clothing. And nothing reduces the glare off the water as well as polarized sunglasses.

Ocean wildlife, like wildlife everywhere, is diverse and unpredictable. Every trip will offer different species. Key West is filled with dolphins, manatees, tarpon, sharks, barracuda, turtles, and many species of birds. The reefs are brimming with exotic tropical fish and corals. Of course, we can not predict nor guarantee what you will see, our experienced crew will do their best to point out any interesting wildlife that you may encounter during your charter. Keep a camera handy.

Yes. Sunset Sail Key West is kid-friendly. However, all children must be supervised by an adult for the duration of the trip. Children 6 and under will be provided with a lifejacket they are required to wear on-board.

Authentic Sailing, Timeless Experience

Sunset Sail delivers a true sailing experience inspired by tradition, craftsmanship, and the natural beauty of the sea. Our classic schooners and sailing yachts move with the wind, creating a quiet, smooth, and deeply relaxing journey far from crowded and noisy tour boats.

Simple & Easy Booking

Plan Your Perfect Sail

Booking your sailing experience is quick and secure. Choose your location, select your preferred sail, and reserve your spot in minutes.