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The Sailing Pathway: From Novice to Boat Owner

Updated: Mar 28

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

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

Discover Sailing

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 Open Houses

We host Open Houses a couple 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.

Go Sailing With Friends

We are always happy to connect eager sailors to current boat owners looking for sailing partners!


So you think that sailing might be for you, its time to start your formal training!

This is sailing 101, no prior experience required! The goal of the course is to take a student with no prior sailing experience to a level where they feel comfortable sailing a 20 to 28 foot sailboat as skipper (sailor in charge) in favorable conditions. This 3 day course runs from 9am to 5pm each day. We start each day in the classroom, spending about two hours of lecture where we incorporate video, whiteboard diagrams and sailboat models to explain the fundamentals of sailing and to teach skills that we will be practicing on the water. We typically break for lunch from 11:45 am to 12:30 pm and then the rest of the day is spent sailing our Colgate 26 (our 26 foot sailboat designed specifically for sailing instruction) practicing all of the necessary skills and maneuvers to competently sail a keelboat of this size. This means you will be spending at minimum 4 and half hours a day gaining sailing experience and practicing maneuvers! At the end of the course there is a brief examination and each student receives an American Sailing 101 Basic Keelboat certification.

Topics covered in ASA 101 - Basic Keelboat

Parts of the boat/Terminology

Basic Sailing Maneuvers (Tacking and Gybing)

Basic Sail Trim

Sail theory and the physics of sailing

Sailing Strategy and Wind shifts

Safety Maneuvers (Heaving to, Crew Overboard Recovery)

Returning to a mooring ball under sail

Rules of the road/Right of Way

Sound Signals

Light Signals

International Collision Regulations

Aids to Navigation


And more!


Pre-requisites: ASA 101

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 and heavier sailboat, our Beneteau First 36.7. The goal of the course is to take a student with some prior sailing experience and train them to the point where they feel comfortable skippering a keelboat from 30 to 40 feet in mild to moderate conditions. This course focuses on the many different skills needed to “cruise” in a larger sailboat including navigation, anchoring, equipment handling, docking and so much more. Each day begins with a couple hours of lecture in the classroom followed by a lunch break and then at least 4 hours sailing around Boston Harbor and surrounding islands on our cruising sailboat. On the water, we practice many of the skills you have learned in 101 like Crew Overboard Recovery and Heaving to, focusing on applying them to a larger and heavier boat. We also spend an entire afternoon practicing docking! At the end of the course, there is a written examination and upon successful completion each student receives their American Sailing 103 Basic Cruising certification.

Topics covered in ASA 103 Basic Cruising

Parts of the boat/terminology

Safety Systems

Required and Recommended Equipment

Hypothermia and Heat Exhaustion



Visual Navigation

Safety Maneuvers (Heaving to and Crew Overboard Recoveries)

Dive Flags

Duties of the Skipper and Crew



Maneuvering under power and docking

And more!


Time to go 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 bigger and bigger until you have the run of all of Boston Harbor and surrounding islands.

If First Reef Sailing’s club doesn’t do it for you, there are plenty of other sailing clubs locally and across the U.S. that recognize American Sailing certifications!

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!

Have a day of fun 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!

Find Sailing Buddies

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 2

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

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!


Take ASA 104 - Bareboat Cruising in Boston

Prerequisite: ASA 103

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! Even though we are spending the majority of the time onboard we still follow a similar format to ASA 101 and ASA 103 where we spend a couple hours each morning doing a classroom lecture followed by a long sailing session in the afternoon. We typically depart East Boston on Thursday afternoon and spend the next three days sailing between Scituate, Salem/Marblehead and the Boston Harbor islands depending on conditions. This is as real world experience as it gets! On the final day there is a written examination and upon completion, students receive an American Sailing 104 Bareboat Cruising certification. (ASA 104 certification is equivalent to the International Certificate of Proficiency that is required in order to bareboat anywhere in the Mediterranean!)

Topics Covered in ASA 104 - Bareboat Cruising

Provisioning and Preparation

Fuel Consumption and Planning


Entering a Foreign Port

Weather and Fog

Advanced Sail Trim

Compass Fixes and Dead Reckoning

Tides and Currents

Advanced Emergencies

Advanced Anchoring

Dinghy Operations

Yacht Systems and Troubleshooting

Advanced Docking

And more!


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 3

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. Each leg consists of a couple port calls, at least a 48 hour continuous offshore passage and plenty of navigation practice! 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.


Enroll in 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. Students learn the intricacies of tides and currents and how to adjust their projected courses to account for these differences.

Topics Covered in ASA 105 - Coastal Navigation

Dead Reckoning and Estimated Positions

Taking Compass Fixes

Tides and Currents

Calculating Set and Drift

Taking Running Fixes

Danger Bearings

Navigation Instruments

Important Navigation Publications

Converting courses and bearings between True, Magnetic and Compass North

And More!


Take 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 cover serious miles in our ASA 106 courses, typically averaging 200 nautical miles. 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.

Topics Covered in ASA 106 - Advanced Coastal Cruising

Passage Planning

Night Sailing


Heavy Weather Sailing

Emergencies at Sea

Mechanical Problems and Repairs

Advanced Weather

And More!


Year 4

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!

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!

Enroll in 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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