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Black Rock Sailing School



Take sailing lessons and earn ASA Sailing Certification with America'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!  We are the ONLY school in New England that owns a catamaran to offer ASA 114 Catamaran Cruising courses and a Catamaran Cruising Club!

02/05/21 News Flash:  A brand new Black Rock website is just over the horizon!  We have recently added online scheduling to this existing website, so whether it is 1pm or 1am, you can click away and register for classes online!  Clicking a "book now" button to register online will start you on your path to acheive your sailing dreams!  We are still available by phone or email if you have specific questions.

02/01/21 News Flash:  It is not to late to join us in the Virgin Islands this winter!!  Our winter Virgin Island ASA certification courses, captained charters, and BRSS graduate adventure sailing weeks are second to none!  Call or email to discuss options and availability through early April!  We have both monohull and catamarans available.

01/20/21 News Flash:  We are accepting 2021 sailing club members!  We have two levels of sailing club membership to choose from - Colgate 26 Daysailing (Colgates in Boston, MA and Warwick, RI), and our Catamaran Cruising (our mint condition 2010 FP Mahe 36!).  Click on the "Membership" button our menu above for pricing and details!

For folks seeking a premier sailing club located in Boston Harbor, check out our sister company, Sailtime Boston, and enjoy a fleet of new Beneteau and Jeanneau Yachts, as well as FP Cruising Catamarans for those discerning sailors!  SailTime Boston's fleet is second to none!!

05/25/2020 Update:  I hope you and your families are staying safe & being socially responsible while we all weather this "storm."  We have finally been allowed to open for the 2020 New England Season!  Certainly, our small class sizes (2 or 3 people at a time), our clean classrooms and boats, a TON of fresh air and sea breezes will be something to look forward to after so many weeks/months stuck at home!  We hope to get out sailing with you this summer!

2/01/20 News Flash:  A HUGE congratulations goes out to my business partner, Captain Paul Sullivan, who earned another "ASA Outstanding Instructor" award for 2019 - keeping up Black Rock's award winning momentum since opening our doors in 2008.  Paul is a truly gifted teacher - and a heck of a lot of fun to hang out with too!  Excellent job Paul!  

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 the country 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.

We take pride in the fact that we do not offer or encourage "Fast Track" or "Zero to Hero" marketing schemes like a lot of our competition.  Unless you already have an extensive sailing background, or live aboard and plan to immediately put your new skills to daily use, you should avoid these "Instant Bareboater" schemes!  If a school attempts to lure you in by promising three, four, or five sailing certifications within a seven day period, they simply do NOT have your best interests in mind!  The amount of material that these schools rush through, skim, or skip entirely is sub-par and dangerous. Reading a book prior to class is no substitution for time on the water with a skilled instructor!  Build confidence and be safer on the water by choosing a school that provides complete and thorough training - choose a school that only provides one or two certifications within a seven or eight day period! "Fast Track" is definitely the WRONG track!! 

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, catamaran cruising, 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 new BRSS 101 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.  Our staff will insure that your boat is clean and ready to sail!  Members enjoy unlimited sailing aboard our fleet of late model Colgate 26's and FP Mahe 36 Catamaran.  Our sister company, SailTime Boston, provides the highest standard for sailing club in all of New England.

If you are serious about learning how to sail, or are looking to join a high quality sailing club in Boston, MA or Narragansett Bay, RI, 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 “stay aboard" 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. All of our staff will rotate between locations.

Our main office is located at the beautiful Charlestown Marina in 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 Safe Harbor Marina 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 and bareboat charter certification - 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!

St. Thomas, US Virgin Islands is our third location.  Our head instructors have been teaching sailing and captaining charter boats in these waters for decades (since 1995)!  We offer a wide range of ASA certification courses, as well as bareboat charters, captained charters, and flotillas. We chose St. Thomas as our base for plenty of reasons - but they all have to do with minimizing cost and maximizing convenience for our customers! Our Virgin Island location has a primary sailing season that runs from December 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 fourth 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 Bahamas location has a primary sailing season that runs from December 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.


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"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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