First Reef Sailing is a sail training organization located in East Boston, Massachusetts that provides sailing instruction and certifications to sailors at every level. We strive to deliver high-quality sailing courses and experiences in a professional, modern setting in both instruction and equipment. Our mission is to provide sailors with no prior experience a clear pathway to gain the skills necessary to own their own cruising boat or competently skipper a bareboat charter. We pride ourselves in not only offering top-tier instruction but also fostering a sense of community and providing avenues for experience-building and continuing education.

Core Curriculum

Our core curriculum begins with the American Sailing 101 Basic Keelboat Certification and progresses all the way through 106 Advanced Coastal Cruising. We offer American Sailing courses as day courses in East Boston from May to October and as fully immersive week-long live-aboard courses in the Florida Keys and the Caribbean from December to April. All of our courses are taught on modern, high-quality keelboats ranging from 26 to 44 feet. In addition to American Sailing Certification courses, we also offer “mile-building” passages each Spring and Fall to introduce sailors to real-world cruising and offshore sailing as we move our training boats from Boston, MA to the Florida Keys and the Caribbean. If you would like to sail without formal instruction we also offer five and seven-day captained charters in the winter. Bring your family and friends along regardless of experience and enjoy an unforgettable sailing vacation!

Instruction

All of our instructors are professional sailing instructors with US Coast Guard captain’s licenses and years of experience sailing in the Northeast and beyond. However, at First Reef Sailing, our philosophy is to select instructors that are not only excellent sailors but also excellent instructors and teachers. All of our courses are capped at a three-student maximum (plus instructor) to ensure everyone has plenty of time on the helm.

Location

We are located within Boston Harbor Shipyard and Marina in East Boston, an easy drive for students coming from outside Boston while being able to avoid Boston City center (and the traffic that comes with it). Our school is located about a 5-minute drive from Boston’s Logan International Airport as well. We sail in Boston Harbor and surrounding islands with longer trips and courses venturing up and down the east coast.

Land Based Clinics

The learning doesn’t just stop at on-the-water training as we offer land-based clinics and courses throughout the year such as “Intro to Navionics and Electronic Navigation”, Intro to Passage Routing”, “Small Diesel Repair and Maintenance” and “Introduction to Boat Purchasing”.

Pathway to Sailing

As our students become confident and competent sailors we offer many pathways to getting out on the water such as our small boat club, flotillas, and social events, regattas, and our partnerships with larger sailboat clubs. Our goal is not only to produce excellent sailors but to build a robust sailing community in Boston Harbor and beyond.