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Black Rock Sailing School




Take sailing lessons and earn ASA Sailing Certification with New England's foremost sailing school & sailing club!  Since 2008, we have become one of the leading ASA sailing schools worldwide and we believe that our sailing courses are second to none.

09/15/17 News Flash:  We are currently taking individual and group reservations for our winter captained charters, graduate weeks, and ASA courses (101/103, 103/104, and 104/114 combo classes) out of our Nassua, Bahamas location!  We will sail the Abacos OR Exuma island chains depending on course levels.  We are targeting December 2 - 9 & 9 - 16, all of January (Sat - Sat), and all of March (Sat - Sat) for these trips.  Other weeks in December and February are being booked by groups of at least four people as well!  Call us for details and/or watch our Facebook page for special announcements.  We will be returning to the Virgin Islands during the 2018/2019 winter season once those islands have a chance to rebuild.

09/01/17 News Flash:  Our NEW Hunter 33 & Hunter 356 charter club has been accepting members!  If we get four more members for 2018, we will buy an additional Hunter 356 and dedicate it to member use!

01/26/17 News Flash:  We just found out that TWO of our instructors, Paul Sullivan & James Ashton, have been awarded "ASA Outstanding Instructor 2016" - breaking Brenton's eight year streak!  Only thirty ASA instructors out of a few thousand earn this recognition.  Huge congrats to these two!  Our staff are the heart and soul of our operation and we are doing something right!  

Providing the highest quality sailing instruction in New England has always been our mission - and it shows! Since opening our doors in 2008, no other sailing school in New England has earned such consistent recognition from the American Sailing Association, and we are ranked within the top 1.5% of all of our competition world-wide! ASA's independent surveys and scoring system have recognized the quality of our instruction, training fleet, curriculum, and overall mission to provide the highest level of sailing instruction.

At Black Rock Sailing School, you will obtain world-class sailing instruction - with a focus on cruising skills, and gain access to New England's youngest fleet of high quality sailing club boats within Massachusetts and Rhode Island.  Our students and annual sailing club members enjoy reciprocity between all of our locations.

We specialize in daysailing, coastal cruising, bareboat charter certification, women's-only courses, docking, navigation, performance cruising, and "adventure cruising" experiences along the New England coastline and beyond.  

Black Rock Sailing School guarantees that you will learn to sail!  We are so confident about our methods, that ALL ASA graduates get up to a 20% discount on our annual sailing club memberships to practice their new skills aboard our boats!

Our small sailing club is designed to provide our customers with inexpensive boat access aboard boats that you will be proud to sail.  You can enjoy day sailors and moderate sized cruising yachts capable of extended trips along the coast - at a fraction of the cost of ownership. Higher levels of membership provide access to all smaller boats as well! Choose to sail a Colgate 26 out of Boston, MA one day, and then take a Hunter 36 for an overnight out of Warwick, RI later that week. Our staff will insure that your boat is clean and ready to sail!

Members enjoy unlimited sailing aboard our fleet of late model Harbor 20's, Colgate 26's, Hunter 33's, and Hunter 36's.  We are confident that our fleet is second to none!  Charter Club members and our ASA 104 graduates also have access to our 2015 Beneteau 41 3-cabin located in the Virgin Islands year-round!

If you are serious about learning how to sail, or are looking to join a high quality sailing club in Boston Harbor, Marblehead Harbor, or Narragansett Bay, we are confident that Black Rock Sailing School should be your choice!  We offer ASA 101 and 103 courses EVERY Monday, Tuesday, Wednesday and Friday, Saturday, Sunday during the season. We would love the opportunity to discuss your goals and set a course for success!

Many people chose to fly in from other states and countries to learn to sail with us! Due to this demand, we offer live-aboard courses and “boat & breakfast” options. We can also assist you with finding local lodging options ashore!

A Winning Formula:

Since 1991, Black Rock's founder has been mentored by sailing school industry leaders, and since 1995, he has managed or owned award winning sailing schools in New England and in the Caribbean year-round. This experience and knowledge is passed along to members of this already talented staff each year.  In 2014 & 2016, two of our three full-time instructors (half of our staff) earned national recognition from the American Sailing Association. Considering that there are over two thousand active ASA instructors worldwide, this places these "ASA Outstanding Instructors" in the top 1.5% of their peers for quality education as judged by their own customers - and we are improving each year!

We have always sacrificed growth for high standards, and waiting to hire only the best instructor candidates has been paying off. Black Rock Sailing School is the place to go if you would like to learn how to sail - at any level! We keep our program small so that we can focus on quality - not quantity. We are not a sailing school "factory" like our larger competitors who must feed their huge sailing clubs and racing programs, and we are not a yacht brokerage firm and/or charter company disguised as a sailing school trying to ultimately sell more boats. We have never lost our focus, and will always be a sailing school first.

Our formula is simple:

  1. Hire only the most experienced and talented instructors who are knowledgable and fun.  Then, provide extensive in-house training that is based on over twenty five years of experience, and have our staff teach more classes per year than most other instructors in the country so they can become a true professional.
  2. Purchase only late model boats that are exciting to sail and are packed with safety and comfort features.  Teach aboard high quality, purpose-built training boats that have also been selected by the US Navy, US Coast Guard, and Merchant Marine Academies for their training needs.
  3. Utilize the most effective curriculum that has been improved upon for over twenty five years, and use the latest technologies to help deliver your message.
  4. Sail out of beautiful locations known for favorable sailing conditions
  5. Stick with what you love and know best
  6. Sacrifice growth for quality

Our staff is there for you every step of the way, offering ongoing advice to our graduates as they enjoy our sailing club, sail with friends, bareboat charter on their own, purchase boats themselves, and in many cases, sail south and follow their dreams.

Quality - Not Quantity!

As a student at Black Rock Sailing School, you will receive world class sailing instruction on the best training boats available and receive internationally recognized American Sailing Association (ASA) certifications upon successful course completion. We specialize in training our students at the highest level; whether they dream of bareboat chartering a yacht in exotic locations around the world, or wish to simply explore their local cruising grounds. We offer year round instruction with a full spectrum of sailing courses in Boston, MA, Warwick, RI, and advanced live-aboard courses held in the Caribbean all winter.

Black Rock Sailing School offers comprehensive, hands-on instruction. Our program is purposefully small, allowing us to focus on a few students at a time, providing unprecedented support before, during, and after their graduation. Our proven curriculum is both fun and rigorous, providing you with the skills, knowledge, and confidence to take command of a boat on your own – guaranteed!

By keeping our program small, we can afford to have some of the most rigorous hiring standards in the industry, and only need to hire the very best career instructors.  Our team has proven themselves in the sailing world and in the classroom.  They have been carefully selected to ensure that they have the personality, experience, and ability to pass along their knowledge in a safe and relaxed manner.  All of our instructors are American Sailing Association Instructor Certified and hold their U.S. Coast Guard Captain’s license.  Read our instructor bios to learn more about their backgrounds and accomplishments.

During our courses, students spend two hours in the classroom, followed by five or six hours out on the water each day, so we insist on teaching aboard the best sailboat designs which provide an ideal combination of safety, stability, comfort, performance, and speed. We have the youngest, most reliable fleet of any major sailing school in New England and our design choices are second to none.

Reciprocity Between All Of Our Locations!

Students and sailing club members can sail out of any of our locations to enjoy a new experience and get a change of scenery if they wish. Our fleet is constantly growing, and various boat types will be added in locations where there is demand. Half of our staff will rotate between locations.

Our main office is located at the beautiful Fan Pier Marina in South Boston, Massachusetts - in the heart of historic Boston Harbor. This full-service location offers a wide range of sailing courses, sailing club access to a bulk of our fleet, charter access to our larger cruising yachts, and yacht brokerage/delivery services.

Entry level classes are taught within the protected waters of Boston Harbor and Hingham Bay, while our more advanced courses will take you to distant ports within Massachusetts Bay, Cape Cod Bay, and beyond.

Learning how to sail on Boston Harbor is truly a unique experience. Only a few harbors around the country can offer the same amount of commercial and recreational boat traffic, tides/current, aids to navigation, maze of pristine islands to explore, and city skyline to enjoy!

Our Boston, MA location has a sailing season that runs from May 1st - October 1st, although we frequently extend the season as needed.

Our second full-service location is at Brewer Yacht Yard, Cowesett in Warwick, Rhode Island - in the heart of picturesque Narragansett Bay. We have been sailing in and around Narragansett Bay since 1994. Warwick is a fantastic location to sail out of, and we are thrilled to have opened our doors here in 2015.

Unlike our competition, this location is only seven minutes off of I-95, twenty minutes from the Connecticut border, and provides instant access to sailable waters - providing our customers with at least thirty minutes of additional sailing time per day!

Our Warwick, RI location has a summer sailing season that runs from the third Friday in April through October 1st, although we frequently extend the season as needed.  Note:  If you are looking for a sailing school in Rhode Island (or even Connecticut!) that focuses on coastal cruising - look no further!  We are 100% confident that no other school in this area is better prepared to help you reach your goals than us!

Marblehead, MA is our third location, offering sailing club access out of the town docks at the west end of Village Street.  Salem Sound and the surrounding waters are simply stunning!

Marblehead still is a sailing mecca, but not what it was decades ago before much of the industry moved down to Rhode Island.

Our Marblehead, MA location has a sailing season that runs from May 15 through October 1st.

St. Thomas, US Virgin Islands is our fourth location.  Our head instructors have been teaching sailing and captaining charter boats in these waters for decades (since 1995)!  In 2014, Black Rock Sailing School partnered up with CYOA Yacht Charters to offer a wide range of ASA certification courses aboard our lead boat - a 2015 Beneteau 41, as well as bareboat charters, captained charters, flotillas, and instruction aboard CYOA's fleet of late model monohulls and catamarans. We chose St. Thomas as our base for plenty of reasons - but they all have to do with minimizing cost and maximum convenience for our customers! Our Virgin Island location has a primary sailing season that runs from November 1st - the second Sunday in April. For more information on each of our locations, click "Locations" on the upper menu bar.

Nassau, Bahamas, (Exuma and Abaco Island Chains) is our fifth location.  In 2016, Black Rock Sailing School began sailing out of New Providence, Bahamas (Nassau).  We specialize in liveaboard cruising courses (101/103, 103/104, and 104/114) and captained charters.  Our local knowledge of the area will insure you get to explore some of the most exciting snorkel and hiking spots, and walk along some of the most pristine and isolated beaches that we have ever seen!  Our more advanced 105/106 courses will most likely transit between the east coast of Florida and the Bahamas - including a gulf stream crossing!  Our Bahamas location has a primary sailing season that runs from November 1st - the second Sunday in April. For more information on each of our locations, click "Instruction" on the upper menu bar and click on "Caribbean Winter Courses."

Compare Us To Others!

Use the following link, “Why Choose Black Rock Sailing School,” to compare us to others!  There are many reasons why more and more people choose Black Rock Sailing School to help them reach their goals.  Do your homework, and then call or email us with your questions - you will always speak directly with the owner, and he would love the opportunity to discuss your goals and set a course for your success!

Black Rock Sailing Vacations provide anyone the chance to sail exotic locations throughout the world.

ASA 101 & 103 Online Registration

To register online for our Boston location, select the button or call 617-639-3061

Register Now!

For Rhode Island Registrations, please call 401-773-9990


Certified Training Facility


The weather in New England sucks right now! Capt. Paul and his crew found a way to navigate themselves down to the incredibly warm and beautiful Virgins Islands this week! You should find a way too! We have a few 101/103 and 103/104 openings in February and March! Take these courses for the first time, or take them as a refresher down in paradise! The Bahamas and Virgin Islands are calling me - and I bet that they are calling you too! ... See MoreSee Less

In late October, my dear "Learning Curve" took a fatal blow during a short, yet intense, wind storm that caused havoc around our town and marina. Despite our efforts to strip and secure her properly, our neighbor's huge powerboat broke free from it's slip and literally crushed her under load. "LC" never let me down. She was a good boat. She is on her way to "boat heaven," leaving an interesting opportunity for greater things to come in 2018. I hope the New Year brings new life and opportunity to your world. Black Rock is really looking forward to the 2018 season, and we have been hard at work assessing where we can improve so that we can stay on top of our game. Happy New Year everyone!! Thank you for your support! ... See MoreSee Less


"I have wanted to sail for a very long time. After my husband took the ASA 105 course with Brenton, he came home and immediately said, “Honey, I found your teacher! I just learned more in one day than I have in five years.”
- - M.R. - Boston

"Brenton has been a tremendous resource to me over the years in all things sailing. Having been a sailing instructor in the past, I like to know when I see I real pro. Brenton is on a whole other level. He possesses that rare talent of knowing what works when it comes to instruction, whether to a 7 yr old or a 70 yr old, and places a huge emphasis on safety."
- - J.C. – Manchester By The Sea

“Ultimate, quintessential, ideal, perfect...you can choose any superlative and stick it in front of “Sailing Instructor.”  Brenton has the DNA for the job!”
 - -D.C. Norwalk, CT

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