Have the sea to yourself with a private charter

Do you dream of the wind in your hair, the sky above, and the sea below? We get it. And we’ve got you.

When and If

Private charter day sail on When and If

Up to 32 people • Price includes 12 people
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!
Book Now
When and If

Private charter sunset sail on When And If

Private sunset sailing on the North Shore
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!
Book Now

Frequently asked questions

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.

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.

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.

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.

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.

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.

Subscribe to the latest news & offers