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.

Sailing Basics


2 Class Options

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

Enjoy a 2 hour cruise with friends or family as you watch the sun set on beautiful Duxbury Bay. Sunset Sails are on Marshall 15’s skippered by a DBMS instructor. Relax and enjoy the sail along with any refreshments and snacks you may bring along.

Sunset Sails, for up to four people, may be scheduled on weekdays. Contact Jim Flynn to schedule:

Private Lesson

Book A Private Lesson

Private lessons are a great opportunity for students to rapidly improve their skills one on one with an instructor. Private lessons can be taken in addition to a sailing class, as recurring private instruction, or as a way to learn to sail for the first time.

Private lessons can be taught by instructor of your choice or we can match you with someone that will fit your sailing goals. Private lessons are scheduled on an individual basis, DBMS is able to accommodate most schedules. Lessons are 1 ½ hours or more. Depending on the lesson, the coach will be in the boat with you or in a powerboat beside you the whole time.

Already booked a pre-paid package?

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 2018 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

HALF SEASON PACKAGE – 10% Discount if purchased before June 1st

Unlimited Rentals for $499

Option IV

FULL SEASON PACKAGE – 10% Discount if purchased before June 1st

Unlimited Rentals for $999