July 11, 2026
Join us as we set sail from the dock Boston Harbour to enjoy an hour and a half daysail or a two hour sunset sail on the historic schooner Harvey Gammage. Harvey Gamage was built in 1973 at the Harvey F. Gamage Shipyard in South Bristol, Maine. Designed by naval architect McCurdy & Rhodes, she represents the finest traditions of Maine wooden boat building with a 50 year tradition in sail training.
Named after one of Maine’s legendary shipbuilders, Harvey Gamage carries forward the tradition of using the sea as a classroom. The schooner was specifically designed for educational purposes, with accommodations for students and crew, classroom space, and facilities for marine science research.
Boston Harbor itself is spectacular sailing ground; enjoy the view of the harbor islands and Boston's iconic skyline as we head out to sea to enjoy some bluewater cruising before returning to the dock.
Daysails are 90 minutes from Boston Harbor. Sunsets are two hours.
Book NowAt 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.”
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.