Tenant Spotlight: First Reef Sailing School

Every sailor starts somewhere.

For Boston-area folks, look no further than First Reef Sailing School, located right here in Boston Harbor Shipyard and Marina. 

First Reef is a comprehensive sailing school that offers American Sailing Association certification courses, charters, mile building passages, and more. It was founded in 2022 by Forrest Hardy and Paul Sullivan, two avid sailors with years of experience under their belts.

Forrest and Paul of First Reef Sailing School

First Reef Sailing School was born when Paul and Forrest noticed the need for adult sailing education in Boston. They observed other sailing schools and clubs in the area, but many were focused on youth education and smaller vessels, and some of the clubs required existing certifications to join. The two wanted to create a pathway for those with little to no experience to get on a large vessel and receive formal instruction. 

“First Reef” gets its name from Paul and Forrest’s ideal sailing conditions. The “F” of the sailing school’s logo is represented by a wind barb signaling twenty knots, a speed where one may “reef” their sails, or make them smaller. These wind conditions are “sporty, but not scary” according to Paul and Forrest, which is why they enjoy sailing in twenty knots of wind.

Both Paul and Forrest are lifelong sailors who have worked a number of jobs over the years, but always came back to sailing. They feel that professional sailing instructors can be hard to come by. From what they have found, many are college students or retired adults who are great sailors, but do not always have extensive teaching experience. The key to being a good sailing instructor according to the First Reef team? Being a good instructor, period. You must “get good at teaching first, sailing is second,” says Forrest, “you have to be a good instructor to be a good sailing instructor.”

And both agree that teaching sailing has made them better sailors. Paul describes it as a “sixth sense that comes from experience and repetition,” and reflects on his strengthened ability to size up a situation quickly. Teaching sailing requires them to be several seconds ahead of what is happening, and this skill is transferable to their own sailing experience aboard different vessels. 

Paul of First Reef Sailing School teaching lessons

First Reef’s classroom is located within Boston Harbor Shipyard and Marina where they conduct lectures with students before heading out on the water. The team loves being located on Boston Harbor because “if you can sail on Boston Harbor, you can sail anywhere,” says Paul. Within the harbor, you will find large ships, tugboats, barges, ferries, tour boats, fishing boats, as well as other recreational boats to navigate around. There is also the unique tidal range in Boston and of course, the New England weather that is known for being able to change quickly. They also love the proximity to the Boston Harbor Islands. The islands are just a short sail away from the inner harbor and they provide lots to explore. “There are islands I haven’t been to and I’ve been here for decades,” says Forrest.

Classes offered at First Reef Sailing School range from “Discover Sailing Classes” for when you are just starting out, to basic cruising, to bareboat cruising, to even coastal navigation and mile building passages for experienced sailors. In the winters, First Reef sails to the Virgin Islands and offers additional courses and charter experiences. Forrest, who spent some time living in Saint Thomas full-time in the past, enjoys the opportunity to bring upper-level students along and have them experience offshore sailing for the first time. More information on classes offered and how to register can be found on First Reef’s website.

When heading out on long passages, there are some things Forrest and Paul cannot live without. For Paul, a sailing essential is ice. “I like to have a cooler full of ice for my coffee and my sundowners in the evening!” Forrest is always sure to pack a pair of slippers. “I have a pair of what look like moon boot slippers – everyone laughs but they’re really warm!” When spending long periods of time in the cockpit, he likes to be comfortable. Some of the songs you may hear on their sailing playlist include “Sail” by AWOLNATION, the “Pirates of the Caribbean” theme song, and of course, plenty of reggae and Jimmy Buffett music. When they are not sailing, you can likely find Forrest and Paul either skiing or playing with their dogs.

First Reef’s best tip for a first-time sailor? “Just go sailing!” They advise new sailors to not have too many expectations or worry about getting everything right on the first try. Learning to sail is a process, and repetition is key. But with practice, it is an attainable skill. “You just have to get out there and keep doing it.”


Start on your sailing journey with First Reef Sailing School