Tall Ships Twilight Cruise @ Rochester, NY

Lake Ontario Sunset Sailaways at Rochester, NY

June 25, 2025

Join us as we set sail from the dock at Port Of Rochester Marina to enjoy a two hour sunset sail on the historic schooner When And If. Built in 1939 for General George Patton to sail around the world "When the war is over, and if I live through it," When and If is a beautiful transoceanic cruising yacht with remarkable sailing provenance.

Come be a part of her story; take a turn at the helm, help raise sail or simply relax and enjoy the ride as a cloud of ivory canvas blossoms above the sprung teak deck, the wind fills the sails and the boat leans into her element.

A short journey out of the mouth of the Genesee river rings us onto the gorgeous open waters of Lake Ontario where we will set sail and enjoy a cruise wherever the wind blows us, returning to the dock 2 hours later.

A truly unique and delightful experience awaits you!

When and If
When and If
No items found.

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.

StarsLogo TripadvisorGoogle LogoFacebook Logo

“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
StarsLogo TripadvisorGoogle LogoFacebook Logo

“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
StarsLogo TripadvisorGoogle LogoFacebook Logo

“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

Book your Rochester, NY Sunset Sail on When And If here!

Click to choose your timeslot and date for your beautiful Summer Lake Ontario sail

Book Now

Frequently asked questions

Can we bring alcohol on board?
Down Arrow Icon

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?
Down Arrow Icon

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?
Down Arrow Icon

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?
Down Arrow Icon

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?
Down Arrow Icon

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?
Down Arrow Icon

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.