Discover the charm of New England as you sail across scenic Salem Sound surrounded by islands, lighthouses, and coastal beauty. Morning, afternoon, and sunset sails offer a peaceful escape into one of America’s most historic maritime regions.
Sunset Sail Salem
Get inspired with our most popular trips!
Sunset Sail On When And If
- 2 Hours
- From $58.30
- 10 Blaney St. Salem, MA
Enjoy the sunset from the water aboard the gorgeous 1939 wooden schooner built for General George S. Patton. Built with the dream to sail around the world 'When the war is over, and If I live through it," When and If is over 80 years young with her destiny as yet unfulfilled.
Sunset Sail On Malabar X
- 2 Hours
- From $58.44
- 10 Blaney St. Salem, MA
Set sail on John Alden’s greatest creation! His personal yacht and 1930 and 1932 Bermuda Race winner. Enjoy a 2 hr sunset sail in elegance and style. Rum punch, select beers and wine available for purchase with complementary bottled water.
Private Sunset Sail On When And If
- 2 Hours
- From $1163.44
- 10 Blaney St. Salem, MA
Sail into the Summer Sunset on your own private classic yacht. With capacity for up to 32 guests, When And If is the last word in comfort and elegance for cruising away those long balmy evenings or catching the breeze for a little seafaring adventure.
Private Day Sail On When And If
- 2 Hours
- From $1163.44
- 10 Blaney St. Salem, MA
Take to the glorious waters on the North Shore on your own private Classic. When And If is ready to take you and your party sailing as an exclusive group and whether you'd like to do our a-la-carte trip or customise it by adding hours, we're here to make your dream sail come true!
Private Charter Sunset Sail On Malabar X
- 2 Hours
- From $1902.70
- 10 Blaney St. Salem, MA
This elegant 1930s John Alden-designed yacht offers a perfect blend of history, comfort, and adventure as the experienced crew hoists sails and glides you past lighthouses, islands, and scenic New England coastline.
Private Charter Daysail On Malabar X
- 2 Hours
- From $950.94
- 10 Blaney St. Salem, MA
Have the ship to yourself for a summer afternoon of yachting in style as the captain and crew cater to your every needs. Perfect for any special occasion. Elegant. Sublime. Affordable.
Day Sail On When And If
- 2 Hours
- From $47.70
- 10 Blaney St. Salem, MA
Sail away on the gorgeous 1939 wooden schooner built for General George S. Patton. Built with the dream to sail around the world 'When the war is over, and If I live through it," When and If is over 80 years young with her destiny as yet unfulfilled.
Trips
Sunset Sail offers both shared sailing trips and private
charter experiences designed for couples, families, & small groups. Each journey blends natural beauty, comfort, and authentic sailing tradition.
Private Charters
Discover Your Perfect Private Charter
Set out on a snorkeling, stargazing, or sunset sail, or build your own custom trip. Romance, relax or unwind from the privacy of your own chartered sailboat.
Shared Trips
Daysails & Sunset Sails
Rise above the crush of the crowds and set sail on a unique sunset sail experience, with a few friends you haven’t met yet. A personable local crew and captain will treat you to a stunning sunset view from the deck of an unforgettable vessel– General Patton’s elegant, private schooner When and If.
Special Events
4th of July Cruise
Leave the crowds behind and experience the Fourth of July from the water. Enjoy stunning views, fresh ocean air, and a memorable evening with family and friends.
Sunset Sail Salem
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.
Malabar X
A true classic, this 1930 wooden schooner yacht was built to win the Newport Bermuda races of her time - which she did, smashing records in 1930 and 1932.
Schooner When And If
launched in 1939 for General George S. Patton
American naval architect John Alden possessed an extraordinary talent for designing yachts that exquisitely combined traditional elegance with exceptional sailing performance. Commissioned for General George S. Patton and launched in 1939, this transoceanic wooden yacht was named after Patton’s dream: “When the war is over, and if I live through it, Bea and I are going to sail her around the world.”
Featuring a traditional wooden hull and a gorgeous rig with tall masts, When And If is known worldwide for her beauty and speed. Before World War II, Patton made just one voyage aboard, sailing from Maine to the Chesapeake Bay. General Patton returned briefly in the summer of 1945 for a final week of sailing out of Manchester, MA, before tragically losing his life in Europe shortly after.
The schooner spent much of her long life in the waters of the North Shore, first as part of the Patton estate through the 1960s, then with the Landmark School in the 70s and 80s, and later as the darling of Vineyard Haven. In 2012, the yacht was meticulously restored to her original lines by Doug Hazlitt and current owner Captain Seth Salzmann.
Now owned by Captain Seth, this stunning vessel is open to the public for the first time in her storied history. Operated by Sunset Sail Salem in the summer and Sunset Sail Key West in the winter, When And If is available for private charters and public sails. Step aboard to experience how classic yachting truly thrives in the modern age!
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!
Sunset Sail Salem
5/5
Tripadvisor
Sunset Sail Salem
5/5
Sunset Sail Salem
5/5
Tripadvisor
WHY CHOOSE US
Sunset Sail Salem
Salem and the North Shore are home to some of loveliest sailing in New England. We offer daily sailing and private charters on the beautiful Salem Sound.
Come sail on our unique historic yacht and take in the views of Boston’s North Shore, the scenic islands, picturesque lighthouses and abundant wildlife as wind fills the sails, the rigging tightens and the boat leans into her element.
This summer marks our eighth season sailing the beautiful classic schooners from the Salem landing. Hop onboard as we gracefully sail by up to 5 of Salem Sound’s majestic lighthouses while sipping on your favorite cocktail in comfort and style!
A beautiful classic
The Historic Schooner Malabar
X was built in 1930 for her designer, John G Alden to win the Newport-Bermuda race.
American naval architect John G. Alden (1884 – 1962) possessed an extraordinary talent for designing yachts which exquisitely combined spectacular elegance and record-breaking performance.
A passionate offshore racer, Alden designed a series of winning yachts for the Newport – Bermuda races. Those designed for his personal use he named the Malabar series. The 1930-built Malabar X was the magnum opus of his schooner portfolio, winning her class in 1930 and smashing records in 1932 to take first place overall ahead of 3 other schooners of Alden’s design.
Malabar X was built by Hodgdon yachts in East Boothbay, ME in 1930. Following extensive damage during Hurricane Bob in 1991 she was rebuilt in 2003 with silver bali planking over an angelique backbone and white oak frames on her original iron keel.
The elegant classic schooner yacht now takes up residence with Sunset Sail Salem under the care of owner and Captain Seth Salzmann. This vessel is your chance to enjoy truly glorious sailing with room for up to 28 guests on private charters and 25 guests on saysails and sunset sails. Set sail in class and style on this stunning example of the golden years in American yachting under sail!
Love our Salem sailing excursions?
If you’ve enjoyed our Salem sailing excursions, you’ll definitely want to check out our sister sailing companies!
Key West
Sunset Sail Key West is more than just a private sailing charter, it is the culmination of decades of experience and a lifetime of passion for sailing, and for Key West.
When and If
A beautifully restored 1939 John Alden schooner, When and If was designed for American General George S. Patton to sail around the world.
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.
Will I get a sunburn?
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.
What wildlife will I see?
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.
Are children welcome?
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.
Explore Boston's beautiful surrounding waters with our upcoming events.
Join us as we set sail and explore the stunning coastline surrounding Boston. Check out our events to see what’s coming up and sign up today for an unforgettable adventure sailing Boston’s eclectic North Shore with its scenic islands, historic lighthouses and myriad local wildlife.
4th of July Fireworks Cruise
Enjoy an extended sail on our gorgoeus classic schooner before returning to the dock for a front row seat to Salem's 4th of July firework display.
Classic schooner Sunset Sail
Set sail on a classic sailing yacht, gliding through the calm waters while the evening breeze fills the sails. The experience of sailing during the sunset is a memory that will last a lifetime
Private Charter on Malabar X
Charter the beautiful Malabar X exclusively for your guests for a private sail on Boston's North Shore. With 5 lighthouses in our range, numerous islands and myriad wildlife from Cape Ann to Boston to Marblehead Neck, a private sailing trip aboard this historic schooner yacht is an opportunity not to be missed.
Private Sunset Sail
An excellent option for those seeking a unique, unforgettable and exclusive experience. Fully customizable with extra hours, catering, live music or decoration, our Private Sunset Sail can accommodate up to 28 guests for your perfect evening.
Perfect sailing
Escape the crowds and take to the sea for an experience unlike any other. Watch as your experienced captain and crew cast off lines and the yacht glides out of the harbor.
Sit back and relax or lend a hand as we raise sail and turn off the engine. You’ll experience the thrill of the sails catching the wind and the schooner picking up speed as we sail past majestic lighthouse, beautiful beaches, rocky shores and numerous islands in the well protected waters of Salem Sound.
Enjoy from our selction of boutique wines, select beers and RTD cocktails as our Captain and crew share stories of the history of the ship and nautical tales of Salem Sound’s storied landmarks and out islands. Misery island, Bakers island, Children’s Island and Marblehead neck are among the many sights to be seen on a regular basis.
We go where the wind takes us and no two trips are the same!
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. 👍🏻”
