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Black Rock Sailing School



Our small sailing club provides our members with unlimited access to the highest quality sailing club fleet in New England – at a fraction of the cost of ownership!  We have a variety of membership options designed to cover a range of budgets and needs, and our members enjoy reciprocity between all of our Massachusetts and Rhode Island locations.

We only accept late model designs that are modern, fast, and fun – yet safe, extremely comfortable, and impossible to capsize. Our fleet ranges from 20ft. day sailors to 36ft. coastal cruising and daysailing/racing yachts.  Higher level of memberships include all smaller boat usage too!

Our club is the perfect transition between learning to sail and taking on the responsibility and cost of owning a boat of your own, and is the ideal solution to your busy schedule.

Our club manager oversees all club operations & online scheduling, meets & greets our members, and assists with all of their needs.  We try and offer social events throughout the season, to give a sense of “community” and provide opportunities to meet others whom they may want to sail with.


Boston, MA

This location provides amazing views of the city skyline and historic waterfront, as well as a maze of naturally rugged islands that make you feel as if you are hundreds of miles away from any city.  

West and Northwest winds can be shifty near the city, but our location provides the most immediate access to the protected waters of the outer harbor and harbor islands.  Most summer days, a sea breeze fills in from the southeast – providing absolutely perfect sailing conditions and natural “air conditioning.”  There is moderate tide and current, and usually a lot of boat traffic to work with.

Boston Harbor is truly a unique place to sail, and one of our favorite places to sail out of!

Daysailing members are able to explore Boston Harbor, Dorchester Bay, Hingham Bay, the outer Boston Harbor Islands.  

Cruising members are able to do overnights out to Scituate, Marblehead, Salem, Beverly, Manchester, Gloucester, and Rockport Harbors. Make a three day trip and visit Provincetown (view whales along the way!).

Marblehead, MA

This location provides scenic views of the New England coastline.  Magnificent homes appear amongst the granite rocks and wooded shoreline.  Winds are sometimes less consistent than Boston or Warwick, but all of our boats have auxiliary power, and navigation skills are a bit more important when sailing these waters, therefore, ASA 103 is required to sail here.

Daysailing members are able to explore all of Salem Sound and the outer waters between Tinker’s Island and Halfway Rock.  This area includes Marblehead, Salem, Beverly, Beverly Farms, Manchester By The Sea, and all of the various islands (and rocks) scattered about.

Cruising members are able to head up toward Gloucester and Rockport Harbors – or possibly an extended trip up to Newburyport and/or the Isles of Shoals.

Warwick, RI

This location is a cruising paradise!  At least a dozen world-class harbors are within a few hours of our base.  Winds tend to be lighter in the morning, and then pick up to around 15 knots in the early afternoon due to a reliable southwest sea breeze.  Unlike our northern locations, these waters are warm and are a pleasure to swim in!  

Daysailing members are able to explore the protected waters of Greenwich Bay and upper Narragansett Bay.  

Cruising members are able to do overnights in the many gorgeous harbors of Narragansett Bay, or plan an extended trip out to Block Island, Buzzard’s Bay, or Martha’s Vineyard.  


Choose a location that you intend to sail the most out of – this will be your “home port.”  You can add additional ports for a one time fee of $350 per location (this fee includes a four hour chart briefing, location orientation, and on-water training session)!

Clients new to our program must have ASA or US Sailing Certifications will need to pass a skill assessment and complete a boat orientation/club policy/training session for EACH location that they wish to sail out of.

Returning members pay a discounted orientation/re-training fee each year to start the season right.

Our sailing club provides members with guaranteed sailing time each month aboard the highest quality sailing club boats in the area. Anyone with ASA or US Sailing Basic Keelboat certification can join. Higher levels of certification expand your sailing range and/or provide larger boat membership access.

Membership is good for one year from the date of registration, and is for our sailing season which runs May 1 through October 15 each year.  In certain instances, we can pro-rate until the end of a particular season, but this is more expensive per month.  Discounts and promotions over 10% are only good when members pay in full by cash or check.

When you join, you split the cost of boating with up to six other families; leaving all of the planning and maintenance worries to us. This enables you to sail a boat that could be more expensive than you might want to own alone, AND allows you to focus your limited free time on what is fun – sailing. Members can invite friends and family along!


HARBOR 20 CLUB: (Our basic level of membership)
ONE-TIME INITIATION/TRAINING FEE:  $700 (BRSS graduates get 50% off this fee)
7-DAY ACCESS SEASONAL FEE:  $1,999 up front
WEEKDAY ONLY ACCESS (Mon-Thurs): $1,599.20 up front

COLGATE 26 & J/80 CLUB: (Includes access to the Harbor 20s too!)
ONE-TIME INITIATION/TRAINING FEE:  $700 (BRSS graduates get 50% off this fee)
7-DAY ACCESS SEASONAL FEE:  $3,199 up front
WEEKDAY ONLY ACCESS (Mon-Thurs): $2,559.20 up front


NEW in 2017!  Call for details on how program works!  This is a different format than our Charter Club found below!

PRE-PAY for the season and receive 20+% OFF per-diem rates!  Pre-pay $5,999 and we will deduct your per-diem usage at at a 20+% discount!

HUNTER 33/Hunter 356 CLUB: (Includes access to the Harbor 20s, Colgate 26s, and J80s too!)
ONE-TIME INITIATION/TRAINING FEE:  $1,200 (BRSS ASA 104 graduates get 50% off this fee)
7-DAY ACCESS SEASONAL FEE:  $5,999 (a payment plan is available over the winter months)
WEEKDAY ONLY ACCESS (Mon-Thurs): $5,199 (a payment plan is available over the winter months)

Owner/member opportunities may exist for those looking for incredible savings and an attractive package that covers ownership costs for up to five years.  Call for details!


The Charter Club is for those who intend to sail less than a dozen days throughout the entire season AND only want multi-day sailing blocks. If you don’t fit this criteria, see annual membership options listed above.

Joining our Charter Club provides access to our Hunter 33 & Hunter 356 cruising yachts.

ASA 104 and orientation/check out is required.  We will be adding new boats to our charter fleet as opportunities arise.


Membership costs $1,000 and includes your orientation/training session. Get a 50% discount on your annual membership if you have graduated from BRSS within the past year OR were a Charter Club member the year prior!

Members get access to charter our boats for three, four, or seven day extended sailing trips at additional cost per charter.

Hunter 33/Hunter 356 peak season rates are $400 – $425 per day.

PRE-PAY for the season and receive 20+% OFF per-diem rates!  Pre-pay $5,999 and we will deduct your per-diem usage at at a 20+% discount!  (See Annual Cruising Club above!)

We have placed a 2015 Beneteau 41 3-cabin into the CYOA Yacht Charter fleet in the Virgin Islands year-round!  Receive a 10% discount IF you book your charter directly through Black Rock Sailing School.



We have placed a 2015 Beneteau 41 3-cabin into the CYOA Yacht Charter fleet in the Virgin Islands year-round AND are official charter brokers for the entire CYOA fleet of late model catamarans and monohulls!  Receive a 10% discount off of any CYOA charter IF you book your charter directly through Black Rock Sailing School!

Black Rock Sailing School offers bareboat and captained charters via. CYOA Yacht Charters in St. Thomas!  The British Virgin Islands are only fifteen miles to the east, and the Spanish Virgin Islands are only fifteen miles to the west!  Inexpensive, direct flights are available from Boston Logan!


Our ASA 101 graduates get a free 30 day limited membership in our Harbor 20 club to practice their newly acquired skills aboard our boats.  Upgrade to an annual club membership during your 30 day trial period and receive a 20% discount!

Boston 101 graduates are restricted to the inner harbor (waters south of the Tobin Bridge and north of the airport runway light pier across to the containership docks) and Warwick 101 graduates are restricted to Greenwich Bay waters (out to Prudence Island, in view of our marina).  ASA 101 graduates are only able to utilize our boats only on days when winds are forecast to be below 20 knots or less.

Our club manager will instruct you on how to reserve boats on your last day of class and assist you with rigging and de-rigging the first few times you go out.


We are required to collect MA and RI sales tax on the membership fee portion and/or charters only.  All one-time initiation/training fees and/or additional location orientation fees are non-taxable.

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