Sail into adventure! Our upcoming events

Schooner When And If sets sail on a tour of the Great Lakes. Bringing our Historic ship to a port near you. Available for sailaways, corporate functions and specialty private charters in the following ports
Join us in our mission to fulfill General Patton's dream of sailing
When And If around the World!

Coming Soon: Tall Ships Sailing @ Erie, PA Aug 22nd - Aug 24th

August 22, 2025

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Coming Soon: Tall Ships Sailing @ Port Washington, WI Jul 24th - Jul 27th

July 24, 2025

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Tall Ships Sailing @ Sturgeon Bay, WI Jul 31st - Aug 2nd

July 31, 2025

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Tall Ships Sailing @ Duluth, MN Jul 10th - Jul 13th

July 10, 2025

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Coming Soon: Tall Ships Sailing @ Brockville, ON Jun 20th - Jun 22nd

June 20, 2025

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Coming Soon: Tall Ships Sailing @ Chicago, IL Aug 6th - Aug 16th

August 6, 2025

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Sailing in Key West until May 7th 2025

May 5, 2025

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Tall Ships Sailing @ Rochester, NY Jun 25th - Jun 28th

June 25, 2025

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Frequently asked questions

Can we bring alcohol on board?
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Yes. You are welcome to bring any adult beverages of your choice. We have coolers stocked with ice to store your drinks and keep them nice and cold.

Will I get seasick?
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Some people are prone to motion sickness. If you suffer from carsickness, that’s a strong indicator. We do our best to keep our vessels sailing smoothly and make sure everyone is comfortable.

There are over the counter remedies you can take if you think the motion may bother you, just remember to take it at least 45 min before sailing. Some people find wristband products to be helpful, too.

What about weather?
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The captain always checks the weather before sailing. If unfavorable conditions are expected and the charter cannot go out, we offer you the option of rescheduling for another day.

Remember to bring a light jacket or sweater as it can get chilly on the water.

Can I sail the boat?
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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.

Are children welcome?
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Yes. Sunset Sail Salem 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.

Will I get a sunburn?
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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.

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