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Getting Started

First Reef Sailing was founded in order to provide a clear and cohesive pathway for students to learn the skills and gain the experience necessary to be competent and qualified skippers and sailboat owners!  

Scroll through the entire page to see the curriculum and timeline of a typical First Reef Sailing student as they go from no sailing experience to owning their own boat! 

A big question for many new sailors is what does a typical pathway to confidently skippering a cruising boat look like? Below we outline a typical progression of sailing classes and experiences from no sailing experience at all to owning your own boat.

Year One: Establishing Your Sailing Education

Try it out! There are many ways to dip your toes into the world of sailing without signing up for a formal course.

Kid on a Sailboat

Discover Sailing Classes

3 Hours

Join us on one of our 26-foot sailboats for a 3 hour harbor cruise where you will be introduced to the world of sailing and basic sailing concepts. Take the helm and experience the thrill of driving your own sailboat under the watchful eye of a professional sailing instructor!


Attend One of Our Sailing School Open Houses

45 minutes

We host Open Houses a couple of times a year where you can go out for a sail on any of our sailing school boats for absolutely free! Try sailing on our smaller 26-foot Colgate 26 or head straight to the big boats on our 36-foot Beneteau First 36.7.


Develop Sailing Skills and Go Sailing With Friends

We are always happy to connect eager sailors with boat owners who are looking for crew!


ASA 101 - Basic Keelboat

Our first American Sailing certification course, no sailing experience necessary! Learn how to competently and safely sail a small keelboat!

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Sailing Trip

ASA 103 - Basic Cruising

ASA 103 Basic Cruising picks up where ASA 101 left off and is designed to transfer the basic sailing skills you have learned on our smaller keelboat and transfer them to a larger cruising sailboat. It also covers basic cruising skills such as navigation, docking, anchoring and more!

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Keep sailing and gain experience!


Join our Small Boat Club

We only require ASA 101 to join our small boat club, where you can pay an annual fee and sail our Colgate 26's all around Boston Harbor.  With each further ASA certification, your sailing area grows larger until you have the run of all of Boston Harbor and surrounding islands!


Sunset Sailboats

Enjoy a fun day of sailing in one of our flotillas

First Reef Sailing holds flotillas throughout the summer where we sail our school boats, invite all of our former students and sailing club members and sail to a specific destination. This coming May we are planning to sail to Peddocks island in Boston Harbor where we will BBQ and enjoy some fun activities! Come along with us and meet fellow local sailors!


Sailing Race

Join our race crew

On Wednesday nights we typically race our Beneteau First 36.7 in the Boston Harbor Racing series. We are not a hardcore racing team, there is a strict no yelling policy aboard our boats. We race because we like to sail and it’s exciting to sail with other boats!


Find sailing partners

We have a large network of sailing friends and former students who are always looking for crew and sailing partners! We are always happy to connect sailors together, to help everyone get out on the water. Shoot us an email, give us a call or join our Facebook group to get connected! There are also plenty of websites and apps such as and the ASA Go Sailing app meant to connect sailors with opportunities to sail.

Year Two

So you’ve got the sailing bug, some experience and are ready to take your sailing career to the next level!

Sailboat Top View

Sail with us in the Caribbean

Each winter we offer 7 day courses and captained charters in warm locations such as the Virgin Islands and the Florida keys! You can choose to do a single class in a more relaxed, vacation format over 7 days, or really get into it and join one of our combination courses and attain two certifications in a single week!



ASA 104 - Bareboat Cruising

ASA 104 Bareboat Cruising is our first “live-aboard” course where students board our training boat on Thursday morning and spend the next four days and three nights sailing up and down the coast, anchoring or mooring in a different harbor each night. The goal of the course is to provide the skills and real world knowledge to the students so that they can safely and competently plan and sail a multi-day voyage in a cruising sailboat from 36 to 45 feet in length!

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Keep sailing!


Join a cruising sailboat club

First Reef Sailing partners closely with SailTime Boston, a fractional ownership sailing club. For an annual fee you can become a member on a SailTime boat. The fleet consists of brand new boats ranging from 35 to 45 feet, monohulls and catamarans!


Join a Yacht Club

There are many yacht clubs throughout the United States that own their own fleet of boats and allow members use of them.

Year Three

You’re well on your way to being a confident, experienced sailor whether inshore or coastal! Keep building those skills!


Join a "Mile Building" Passage

Each Spring and Fall we move our training boats from Boston, MA down to the Florida Keys. Join a 5 day leg where we cover up to 500 nautical miles of inshore, coastal and offshore sailing. Experience what the true cruising dream is all about as we sail our boat to new locales. Read about past passages in our “Debrief Series” on our First Reef Sailing Blog.

Coastal Navigation Sailing Course

ASA 105 - Coastal Navigation

ASA 105 is a classroom based course that teaches students to apply the navigational theory and practices for safe navigation in coastal and inland waters. We practice charting and passage routing using compasses, parallel rules and dividers. 

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Sunset on the Coast

ASA 106 Advanced Coastal Cruising

ASA 106 Advanced Coastal Cruising is the most advanced ASA course we teach here at First Reef Sailing! The goal of the course is to provide students with the knowledge and skills to safely and confidently plan, navigate and sail a multi-day coastal offshore passage. We practice night sailing, watchkeeping, safety at sea, emergency maneuvers, heavy weather sailing and so much more during this 5 day, 4 night live aboard course.

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Year Four

You have realized that sailing is going to be a life-long passion and that the world of sailing knowledge is endless! You’re able, willing and ready to be the skipper of your own yacht whether it be bareboat chartering in the Caribbean or buying your own boat!

Fishing Boat

Buy a boat

We at First Reef Sailing are more than happy to help you with the boat purchasing process whether it’s providing advice, acting as your very own boat broker or helping you purchase a new boat and place it in a sailing club program such as SailTime.

Join us for continuing education clinics, classes and seminars

We offer clinics and seminars year-round aimed at addressing specific areas of the sailing world whether its Navigation Apps and Marine Electronics, The Boat Purchasing Process, Marine Diesel Maintenance, Sail Care and Repair. Our offerings are continuously changing and improving as we strive to stay on the cutting edge of the sailing industry!

Sailing Time

Private Lessons on your own boat

We offer private lessons on your own boat to work on skills and maneuvers specific to your vessel. We can also help you move your new boat from where it was purchased to its homeport in the form of a shakedown and training cruise.


Live the dream!

Just be sure to wave when you see a First Reef boat sailing by!

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