When and If

Take a morning trip on our shared charter

Up to 32 people • Price includes 12 people

From the colorful fall foliage to the warm summer sun, each trip on our boat is a unique and unforgettable experience, tailored to the time of year. Whether you're planning a romantic getaway or an adventurous excursion, we have something for every season. Take a look and start planning your next journey with us!

About morning trips

Blow away those cobwebs and start your day right with a morning sail on When And If. Saturday mornings are Mimosa Mornings, so let our crew tell you about today’s signature cocktail with a twist, or enjoy a soft drink as we sail into the morning sun.

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 morning trip today

Join the Morning Sail for the thrilling Key West Wreckers Race series - a must-attend event for sailing enthusiasts. Experience the beauty of the Florida Keys and test your skills against the best sailors in the game. Don't miss out on the action and sign up today!

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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.