We Found These Experiences For You (16)
Sunset Sail Salem
2hr Sunset Sail on Malabar X
Schooner Malabar X Sunset Sail
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. Sit back and relax or lend a hand as the crew sets sail for ...
Private Charter Sunset Sail on Malabar X
Classic Schooner Yacht Private Charter Day Sail
Set sail on a 2-hour private Daysail aboard the classic Schooner Malabar X and enjoy a truly unforgettable sailing experience on Salem Sound. 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 ...
Salem
2hrs with option to add more time!
Private Tours
Sailing
Sunset Sail Salem
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2hr Day Sail on Malabar X
Classic Schooner Yacht Day Sail on Salem Sound
Step aboard our stunning classic schooner Malabar X (10). Built in 1930 for the private use of her designer, the famed John G. Alden of Boston, MA. Embark on a 2 hour sail through Salem sound under billowing canvas as we pass by up to 5 of the areas most beautiful lighthouses. Take in the sights of the ...
Salem
2 hours
Private Tours
Sailing
Sunset Sail Salem
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Private Charter Daysail on Malabar X
From $950.94 • Classic Schooner Yacht Day Sail Private Charter on Salem Sound
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.
Salem
2 Hour minimum
Private Tours
Sailing
Sunset Sail Salem
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Morning Mimosa Sail
Gourmet Yacht Mimosas!
What better way to start a Summer morning than with fully instagramable Mimosas and sailing on a classic yacht? Our star garnishes change from week to week so whether it's Elderflower and Mint, Blood Orange and Thyme or cheeky tropical Mango Basil, get ready to start your Sunday in style with Sunset ...
Bloody Mary Sunday Sail
Special Bloody Marys on Sunday Mornings!
Summer Sundays are for sailing with Bloody Marys! Depart the dock with a well-stocked bar and Bloody Marys are on special all morning long! (credit card preferred, please.) Our star garnishes change from week to week so whether it's local pickles, a gourmet cheese skewer or an artisan olive selection, ...
Gloucester Schooner Festival on Malabar X
August 31st, 2025
Gloucester Schooner race onboard the historic racing schooner Malabar X. Lead the pack aboard this elegant Newport-Bermuda record breaker and enjoy the spectacular views of the Parade Of Sail and the Mayor's Cup race at Gloucester 2026! BOARD AND DISEMBARK AT GLOUCESTER, MA. Gloucester Schooner ...
Gift Certificate
Give the gift of sailing!
Give them a memory they can cherish forever A gift certificate from Sunset Sail Salem is the perfect way to give the gift of sailing: Freedom, adventure, luxury, escape. You've found a winning gift for friends or loved ones while supporting a small family company and the preservation of an iconic ...
Salem
Gift Card
Sunset Sail Salem
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2hr Sunset Sail on When And If
Summer Sunsets on a Stunning Classic Schooner
2 HR. Sunset sail departing daily. 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 ...
2hr Day Sail on When And If
A Beautiful Sail on a Classic Yacht
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. Come and be part of her story! Take a turn ...
Private Charter Sunset Sail on When And If
From $1,163.44 • Private Sunset Sailing on the North Shore
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. Call to talk about extending your trip - we know ...
Salem
Private Tours
Sailing
Sunset Sail Salem
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Private Charter Daysail on When and If
From $950.94 • Up to 32 People • Price includes 12 people
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!
Salem
Private Tours
Sailing
Sunset Sail Salem
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Gloucester Schooner Festival on When And If
September 6th, 2026
Gloucester Schooner race onboard the legendary Schooner When And If BOARD AND DISEMBARK AT GLOUCESTER, MA. Gloucester Schooner Festival is a vibrant, informative place for people of like schooning mind to get together and admire one another's traditional boats, before the Annual Gloucester Schooner ...
Gloucester Schooner Festival on Harvey Gamage
September 6th, 2026
Gloucester Schooner race onboard the 131ft gaff rigged wooden sail training vessel Harvey Gamage. Experience the event from one of the larger vessels in the fleet and enjoy the view from the heart of the action as we take to the water for Gloucester's legendary Parade Of Sail and Mayor's Cup ...
Gloucester Sailaway On Malabar X
Step aboard the magnificent 1930 John Alden Schooner Malabar X for an unforgettable sail from historic Gloucester, Massachusetts. Feel the wind in the sails as you cruise the spectacular waters of Cape Ann and the North Shore. Get hands-on with the experience—help raise the sails, learn the ropes, ...
Gloucester Sailaway On Harvey Gamage
Step aboard the 131-foot gaff-rigged wooden schooner Harvey Gamage for an unforgettable sailing adventure from Gloucester, Massachusetts. Built in 1973 at the Gamage Shipyard in South Bristol, Maine, she was designed by McCurdy & Rhodes alongside Frederick W. Bates and serves as a premier, U.S. Coast ...