When & If

Private Charter Daysail on When and If

February 25, 2023

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!

Sailing on When and If

When And If sails all year round: out of Key West, FL in the Winter and Salem, MA in the Summer. With our wide range of custom private charter options as well as our a la carte shared sailing availabilities, you’re sure to find your dream sail on this beautiful classic schooner yacht.

Whether it’s a morning excursion, an afternoon on the water or a sunset sail, When And If offers an unparalleled sailing experience on a gorgeous historic schooner; see and be seen as you sail in style.

When and If
When and If
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Our happy customers share their experiences

At When and If, we pride ourselves on delivering exceptional sail trips to our customers. Don't just take our word for it - read what our satisfied clients have to say about their experiences with us.

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

Ashley Skeffington
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“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
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“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.”


Book your next trip on When and If

Book your next adventure of a lifetime on the historic When and If charter sailing vessel. Experience the beauty of the open water while being transported back in time on our fully restored and maintained ship. Don't miss out, book now and make memories to last forever.

Book Now

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.