Black Rock Sailing School

Black Rock Sailing School

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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

Photos from Black Rock Sailing School's post 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!

Photos from Black Rock Sailing School's post 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.

Photos from Black Rock Sailing School's post 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!

SV Magic Bus Offshore Incident Report: Key Analysis and Learnings 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!

FULL REPORT HERE:

SV Magic Bus Offshore Incident Report: Key Analysis and Learnings Explore the detailed offshore incident report of SV Magic Bus, covering crew survival, key lessons learned, and rescue operations.

Photos from Black Rock Sailing School's post 12/21/2025

We are having another AMAZING ASA 103/104 combo week a with a really fun crew!!

Suddenly, there are other boats cruising around the USVI! We’ve had the place to ourselves the past two months!

Photos from Black Rock Sailing School's post 12/11/2025

…and here we have an extremely rare “Quadrimaran!” The ferry between St Thomas and St Croix!

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Location

Telephone

Address


1 Masthead Drive
Boston, MA
02886

Opening Hours

Monday 10am - 6pm
Tuesday 10am - 6pm
Wednesday 10am - 6pm
Thursday 10am - 6pm
Friday 10am - 6pm
Saturday 10am - 6pm
Sunday 10am - 6pm