Frequently Asked Questions

1. May I bring a small child?

This type of sailing cruise on Boston Harbor is mostly an adult activity. We occasionally have families or a single parent and child. We provide adult life jackets only. ALL guests must fit properly in an adult life jacket provided or bring your own child size life jacket. Children must be 7 years or older and must stay in the assigned seat. For the safety of all passengers allowing a child onboard is the sole decision of the Captain. 

2. I noticed you have dog on board, may I bring my pet?

No. Ensign is the resident boat dog. She is very well behaved. Often she will sit and sail her ears. She's the only full-time crew. She is not good with other dogs onboard.

3. What if it rains or bad weather?

Please review our complete Weather Policy

4. If I purchase 3 groupons may I reserve the whole boat?

Yes. Check the Availability to find a cruise with 6 seats available.

5. Is fishing permited?

No. This is a sailing cruise.

6. How far do you go? Do you sail in the Charles River?

This is an ocean sail. We sail from Boston. Depending on the wind and weather we ussually go out around the first island. We sometimes cruise to Charleston and view Old Ironsides. We don't sail in the Charles River.

5. I was thinking of taking my girlfriend's, brother's, wife but neither of us know anything about sailing, will we be out of place?

Well, you might when we see your girlfriend.. but otherwise, No sailing knowledge is needed. You are welcome to sit back and relax or pull on a line or crank on winch with direction from the Captain.

If you have a question that is not answered here or elsewhere on this site Submit a Question.

Things you should know when you come along for a sail..

• You are welcome to bring your own food, snacks, and drinks including your favorite alcoholic beverage. You may want to keep it simple and have everything already prepared. Non-glass wine glasses and a bottle opener are available for your use. A foam cozy is available for your beer bottles. Excessive drinking is not allowed.

• You are welcome to sit back and relax; or pull on the lines, crank on the winch, and help with the sailing. We will make every effort to exceed your expectations. A gratuity is appreciated.

• Remember your camera and sunscreen. Also it may be colder on the water. You may want to bring an extra sweater or light coat. We sail rain or shine. Be prepared for any foul weather. Check our Weather Policy for more information.

• If in doubt about anything, please ask. Whatever you bring on board will need to be stowed below while we are underway. Your cooperation in keeping a clean and safe boat is expected. Smoking is not allowed on board.

• Ensign is the resident Cocker Spaniel. She is a very well behaved boat dog. She's the full-time crew.

• The pickup location is subject to change. Please be sure to provide your mobile phone number upon RSVP or payment. It may be needed in case of any last minute pickup changes. Please also have my phone number with you (617-510-6767.) Please call if you are running late or need directions. An additional docking fee would apply for a late pickup.

• The property around the docks is private property. Please respect their rights. Please wait at the TOP of the gangway. DO NOT enter the gangway and docks until s/v Hestia is fully docked and you are asked to proceed. You will receive instructions for safe boarding.

Still have questions? Check our Frequently Asked Questions

"A SMILE is mandatory! Money can't buy happiness.. but it sure can rent it for a while."

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