First Reef Sailing
| (617) 466-3317 |

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!


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.


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.

American Sailing Certifications Offered

ASA 101, Keelboat Sailing 1
ASA 101, Keelboat Sailing 1
Learn to skipper a 20' - 27' sloop-rigged keelboat by day, in light to moderate winds and sea conditions. Learn basic sailing terminology, parts and functions, helm commands, basic sail trim, points of sail, buoyage, seamanship and safety including basic navigation rules to avoid collisions and hazards.
ASA 103, Basic Coastal Cruising
ASA 103, Basic Coastal Cruising
Learn to skipper a sloop-rigged auxiliary powered 25'-35' keelboat by day in moderate winds and sea conditions. Learn cruising sailboat terminology, basic boat systems, auxiliary engine operation, docking procedures, intermediate sail trim, navigation rules, basic coastal navigation, anchoring, weather, safety and seamanship.
ASA 104, Bareboat Cruising
ASA 104, Bareboat Cruising
Learn how to sail a sloop-rigged, auxiliary powered 30'-45' sailboat during a multi-day cruise upon inland/coastal waters in moderate/heavy winds and sea conditions. Learn about provisioning, boat systems, auxiliary engines, advanced sail trim, coastal navigation, anchoring / mooring, docking, emergency operations, weather, and more.
ASA 106, Advanced Coastal Cruising
ASA 106, Advanced Coastal Cruising
Learn to safely act as skipper and crew of a sailing vessel about 30 to 50 feet in length in coastal and inland waters, in any conditions.
ASA 114, Cruising Catamaran
ASA 114, Cruising Catamaran
Learn to skipper an auxiliary-powered sailing cruising catamaran of approximately 30-45' feet in length during a multi-day liveaboard cruise upon inland or coastal waters in moderate to heavy winds (up to 30 knots) and sea conditions.

Other Services Available

  • Women Only Courses
  • Private Courses
  • Weekday Courses
  • Weekend Courses
  • Corporate Team Building Courses
  • ASA 'Challenges'
  • Day Sail Charters (public)
  • Day Sail Charters (member-only)
  • Vacation Charters
  • Sunset Cruises
  • Sailboat Cruises
  • Sail Trim Courses
  • Spinnaker Courses


ASA Veterans Sailing Education Program - Sign Up Now >>

At ASA we recognize the sacrifices made by the brave men and women who have served or are serving in our country's armed forces. As a token of our appreciation, and our way of saying thank you, we are inviting veterans and active military personnel to share our passion for sailing by offering a discount on our ASA 101 Basic Keelboat Sailing course. First Reef Sailing is offering a minimum of $50.00 or 10% off their ASA 101 Basic Keelboat Sailing course.

Sailing School Reviews / Testimonials

  • First Reef is the best sailing school in Boston hands down From you first experience (ASA 101) to advanced Bareboat certification (ASA 104). Captain Paul and Captain Forest are responsive and super helpful...[read more]

    Colin Raney - ASA 101, Keelboat Sailing 1

  • We have taken classes with both Paul and Forrest, and cannot recommend them highly enough. Extraordinarily patient and willing to review the material as many times as is necessary, and most important, focused on teaching good...[read more]

    Chris Cancian - First Reef Sailing

  • I have had the pleasure of taking my ASA 101 and 103 classes with Forrest; he is an incredibly patient and knowledgeable instructor. I was fortunate enough to further my education by sailing with Forrest from RI to Bermuda...[read more]

    Jeffrey Capobianco - ASA 103, Basic Coastal Cruising

  • Excellent experiences. Sailed with Paul in the USVI/BVI to get my ASA. Could not have asked for a better instructor! A week on a 50' Beneatau, performing all the necessary drills to feel completely comfortable to skipper a barebo...[read more]

    Rob Frimmel - First Reef Sailing

  • Couldn’t ask for a better sailing experience with First Reef Sailing, Captains Forest and Pauls knowledge and experience can’t be beat. I just helped deliver their brand new 42 ft Beneteau to Key West from Miami, if you’re...[read more]

    Phillip Skrabut - First Reef Sailing

  • I can honestly say that learning to sail with Paul changed our lives. Many (many) people have helped us make this dream a reality, but none with the attitude, impact, and confidence of Paul and his fellow captains. My wife...[read more]

    Jeremie Mailloux - First Reef Sailing

  • I have sailed with Forrest twice now: 8 days in the USVI for ASA 103/104, and a 9-day repositioning trip from Charleston to Key West. Forrest has a very impressive amount of experience and skill, and I completely agree that...[read more]

    Chris Petersen - ASA 104, Bareboat Cruising

Contact Information

First Reef Sailing

Address Boston Harbor Shipyard and Marina256 Marginal St. BostonMA02128USA
Phone (617) 466-3317
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