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Sailboat Rental

Social Sail

Adult Sailboat Rental: 3 Options

Ages: 19+ Prerequisites: DBMS qualification test Requirements: Competent Swimmer

Do you love sailing? Does the cost and time required of owning your own boat keep you from getting out on the water? Looking for a cheaper alternative? DBMS is here to help you feel the salt on your face once again. We have Marshall 15s and Flying Scots that are ready and waiting for you to take them out.

Sailboat rentals are based around tides and are 3 hours long. Roundtrip launch service included to our Snug Harbor moorings, prepaid passes valid for 2017 only.

As a safety precaution we require all renters to pass a short, one-time, on-water qualification test. Please contact us to schedule yours.

Option I

Reserve your boat type and pick a time.

Book for 3 hours $105

Option II

Purchase a Prepaid Package of three outings on our fleet of Marshall Cat & Flying Scot sailboats.

Purchase 3 pack for $299

Option III

10% Discount if purchased before June 1st

Unlimited Rentals for $899

Skipper & Mate


2 hrs / 1 day / $35 per person

Ages: 4-5 and an adult Prerequisites: None Requirements: None

If you’ve ever dreamed about taking your little one for a sail around Duxbury Bay, then this 2 hour class is for you. Join one of our instructors aboard a 23ft O’day sailboat for a relaxed cruise with your first mate. Class price is per person.

Parent Sail and Sea

Junior sailing 2
Sign Up

Parent sails during child's lesson $25

Parent Sail and Sea is designed for the parent who is eager to see on-the-water programs in action – and maybe has an interest to learn how to sail themselves! This 1 hour, light on learning, sail will take place every Tuesday and Wednesday throughout the summer. We strive to sail you near the classes you wish to see, however we are sometimes restricted by the tide and wind. Come prepared to have fun, talk sailing basics and take advantage of the photo opportunities…With the added bonus of knowing what your junior sailor is talking about at the dinner table later that night.

Sailing Basics


3hrs / 2 days / $275

Ages: 19+ Prerequisites: None Requirements: Competent Swimmer

Students will be introduced to sailing terms, wind awareness, weather, tides, rigging, points of sail, tacking and jibing and general boating safety. Lessons will consist of ‘chalk talks’ on land, and hands on learning on the water. Class is taught in Flying Scots or Marshall 15 catboats. Includes US Sailing Book ‘Learn Sailing Right’. 3 Hours each day.

Sunset Sail

Adult sailing classes on Duxbury Bay.


Pricing: $25 1st Adult / $15 Add l Adult / $10 Add l Child)

Ages: 19+ Prerequisites: None Requirements: Competent Swimmer

Come be whisked away on a 2 hour cruise with friends or family as you watch the sun set on the beautiful Duxbury Bay. Sunset Sails will be on a Marshall 15 that will be skippered by a DBMS instructor. Feel free just sit back, relax and enjoy the sail along with any refreshments and snacks you may bring along with you for the ride.

Sunset Sails are suitable for up to four people. For dates and sign up, please check online.