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 that with you Massachusetts sailors two hours sometimes just isn't enough!
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.
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.
“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.”
“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. 👍🏻”
“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 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
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.
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.
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.
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.
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.
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.