BRSS is New England’s premier sailing school, having become one of American Sailing’s most awarded schools since opening in 2008. Quality, Not Quantity!
We offer world class training & certifications aboard our boats in RI, or your boat anywhere along the entire US East Coast! As a student at Black Rock Sailing School in Boston Harbor, 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 sp
ecialize 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 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! Since opening our doors in 2008, we have won national recognition by the American Sailing Association. Their 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. 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 a majority of their time out on the water, 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 Massachusetts and our design choices are second to none. We are located at the Fan Pier Marina in South Boston, Massachusetts, in the heart of historic Boston Harbor. 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. See our “News” section to read why learning to sail on Boston Harbor is such a great experience! 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, Boston, to help them reach their goals. Do your homework, and then call or email us with your questions. We would love the opportunity to discuss your goals and set a course for your 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 other local lodging options ashore! Black Rock Sailing Vacations provide anyone the chance to sail exotic locals throughout the world.
03/02/2026
What an absolutely incredible night we are having! Sunset, moonrise, and then an epic full moon!
Three weeks down, five more to go on this round of classes and charters!
Book your class or captained charter with Captain Brenton today!
01/15/2026
2026 is off to a magical start, as I wrap up another week down in paradise! After 35yrs cruising these islands, I have become incredibly familiar with the area, enabling me to provide my students and charter guests with a highly customized experience and world class learning experiences!
01/11/2026
The air quality over the past month or so has been superb down here in paradise! Here, you can see St Croix in its entirety! Vieques, Culebra, and Puerto Rico are in perfect view to the west once over in St Thomas waters.
Can anyone tell me where I shot this video from?? Three weeks ago, two of my students got engaged right here!
01/11/2026
I will NEVER get sick of the amazing sunsets, and the color and clarity of the water down here!
Join me in the Caribbean for captained charters, adventure weeks, and American Sailing certification courses, available in the Caribbean and New England all year round!
01/05/2026
Today kicks off the official start of Black Rock Sailing School’s 2026 sailing season, with a week long American Sailing 104/114 catamaran course! Join me in 2026!
12/30/2025
See you next year/week St Thomas! It has been fabulous!
12/29/2025
The air has been so incredibly clear and dry. This is the eastern most point of Vieques under the sunset. We’ve seen Puerto Rico, Culebra, and St Croix in the not so far distance the past few days.
12/27/2025
One minute I am on a monohull, and the next minute I am on a cat! A new crew for a new course!
Join me in paradise all winter, every year!
12/25/2025
Merry Christmas to all! We are currently in Christmas Cove, USVI! Join me down in paradise every winter!
Be well, and be merry!
12/24/2025
Here is an interesting read about the back story of the abandoned catamaran that I crossed paths with south of the gulfstream last month! Apparently my photographs that I emailed to the USCG helped determine some of the cause of the flooding!
Thank you Lisa Batchelor Frailey for finding and sharing this with me!