What I miss most about summer

It’s 5°F here in Somerville, MA and we’re about halfway through a week-long, post-holiday cold snap. It’s not all that unusual for this time of year, but it makes me think back to some of the gorgeous afternoons we enjoyed just six months ago.

This summer I decided, among other things, that I wanted to learn how to sail a boat.

I made an attempt or two during my freshman year of college, puttering about Dorchester Bay in a tiny centerboard boat called a Cape Cod Mercury. UMass Boston, situated right on the ocean, provides free sailing lessons to all eager student ID-holders.

A group of us tried it out one day:  some were successful, one boat capsized, another was piloted by someone who spent his gap year crewing a ship across the globe. All in all, it was a fun, wet, and intriguing afternoon. Sailing a boat required a lot more thought, coordination, and energy than I had imagined.

As a busy teenager and an undergrad, my ambition to set sail soon fell by the wayside, swiftly replaced by classes, parties, work, and exploring the city with friends.

It took me over ten years to get back on the ocean.

When I decided to revive my sailing aspirations, I had a lot of questions. How do I choose a sailing school? Do I sail on the Charles (River) or Boston Harbor? What’s the difference between ASA and U.S. Sailing Certifications?

I searched on Google and Yelp for a couple of days in search of a facility. Boston, given its proximity to water, offers an overabundance of options, ranging from the Black Rock Sailing School in South Boston to Community Boating on the Charles.

I landed on Boston Sailing Center in the North End. As I learned by reading through their website, the school offers a wide range of American Sailing Association (ASA) certified classes throughout the year. In addition, the center provides yearly memberships at tiered pricing levels, providing access to their fleet of sailboats ranging from small daysailers to full-size cruising yachts. By coincidence, a coworker of mine has been a member for several years and raves about the club.

I signed up for their Learn to Sail (ASA 101) course, which is offered both on weekdays and weekends. In my case, over the course of two full weekends, I embarked on a fun group learning experience with a bunch of new faces and began to grasp the fundamentals of sailing on Boston’s Inner Harbor.

I chose sailing on the harbor instead of the river due to my gravitation towards cruising versus racing. I wanted to make progress towards an eventual goal of sailing larger boats in the open ocean, and BSC offers a number of key steps along that path.

On the morning of my first class, I punched in “54 Lewis Wharf, Boston, MA” in Google Maps and was promptly guided to a parking lot in the North End.

Boston Sailing Center runs their entire operation from a riverboat berthed right in the harbor. Their fleet of boats rests along the docks and moorings nearby and their main office greets you immediately as you walk in the door.


It was a warm, sunny June Saturday and I strolled in right on time, iced coffee in hand. The classroom was already packed and filled to the brim with about fifteen other students.

We met our instructor Chris Allen (there are two of them at BSC) and dove right into the basics, following along in our textbooks and looking at a miniature sailboat as a guide. In our first two classroom sessions we covered many of the essentials:

  • Parts of the sailboat
  • Basic sailing physics and principles of lift
  • Points of sail
  • Tacking and jibing (maneuvering)
  • Safety and man overboard drills

Each morning we spent a few hours in a lecture and watched instructional film. We were given written quizzes to cover the prior day’s material. Every class was taught by a different instructor, which allowed us to learn new techniques, styles, and terminology.

While it was definitely a lot to take in within a short period of time, I have come to realize that sailing is not always an exact science. There are a few different ways to accomplish the same tasks and a number of divergent schools of thought, all of which can be appropriate in the right circumstances.

The real learning happened when we got out on the water.

After our lectures, we took a brief lunch break and then split up into small groups led by a single instructor per sailboat. Our boat class of choice was the Soling, a former Olympic class keelboat that holds a crew of two to four.


The Soling is a quick and responsive racing boat that provides students instant feedback and easy maneuvering. It’s a bit larger and more stable than the Cape Cod Mercury that I sailed at UMass.

Much of our first day was spent learning about the sails, the rigging, and how to prepare the boat before setting sail. Our boat crew was clumsy and disorganized at first, but by the fourth day, we worked together like a well-oiled machine to raise those sails and get off the mooring ball. I quickly learned that teamwork plays an important role in sailing.

Once underway, we took turns at the helm (the rear of the boat by the rudder) and tacked and jibed our way through Boston’s busy inner harbor. Since sailboats cannot sail directly into the wind, they must always approach the wind at an angle, which requires some coordinated zig-zagging (tacking) and hopping from one side of the boat to the other. The timing and quick handling required a good amount of trial-and-error, and our patient instructors guided us through each pass.

Sailing downwind (with the wind coming from behind the boat) requires a bit less acrobatics, but one must always be wary of the boom during a jibe maneuver, which will swing quickly and with force as the helm of the boat passes through the wind. Luckily, no one was hit in the head and knocked overboard.

Boston Harbor offers an excellent testing ground, with its combination of recreational, commercial, and municipal traffic, as well as low-flying jets from Logan International Airport. Sailboats compete with yachts, ferries, tankers, and lobster boats, so quick navigation skills and situational awareness come into play in the busy inner harbor.

There were quite a few encounters with Codzilla, whale watching excursions, and the occasional pirate ship.

After a few days of practice, we spent our final water session exploring the Outer Harbor and the Boston Harbor Islands.


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We were lucky to delight in such a beautiful day for our final sail and the views were wonderful. The outer harbor is a bit less hectic than the inner harbor but with noticeably choppier water and more natural hazards.

Part of our course included basic navigation and chart reading, which is especially important in Boston. We learned how to read buoys and day markers and to be aware of the shallow spots and hidden rocks scattered between the islands. It’s common for boats to run aground in the precarious waters and shifting tides.

At the completion of Learn to Sail, BSC offers students a free month-long day sailing membership.

Our class was fairly tight-knit by the end of our weekend adventure, and my friend and fellow sailor Lynne volunteered to start an email chain after the class. We kept in touch and arranged days and times to enjoy some summer sailing.

I took advantage of the free membership and tried to get out on a Soling once a week with different members. Not only was this advantageous from a financial standpoint, but it provided me valuable practice and experience. In fact, I was even brave enough to take a few friends out for a pleasure cruise one afternoon and thankfully no one got (too) wet.

By the early fall, I was craving more time on the water, so I signed up for Boston Sailing Center’s Advanced Course (ASA 103).

This time, our class consisted of only three students and a single instructor. In a similar weekend format, we spent our mornings in lectures and afternoons out on the water. Due to the smaller class size, the course felt much more detailed and intimate.

We received a new textbook and learned about more advanced techniques, regulations, and procedures. The boats for this course included the J-24 and J-27 class, which offer a small cabin and outboard motor. We learned how to motorsail, utilizing the engine and sails simultaneously. We also raised a spinnaker sail for the first time, an unwieldy but elegant, parachute-like sail that rides towards the bow of the boat.

Given the time of the year, the weather was a bit less forgiving and we faced some cold and rainy days for our water sessions. I enjoyed the exposure though, as the class felt more genuine and authentic to the challenges a sailor might face at sea.


With a larger boat, we gained a bit more real estate on and below deck, which allowed us to roam freely and assume different roles on the boat. I felt much more like a crew member than I did on the Soling (and we had the luxury of bench seats and a dry cabin to hide out in).

I really enjoyed this next level of excitement out on the ocean and my classmates and instructor were a pleasure to work with. I remember on our final sail, our instructor Brad brought an assortment of meats, cheeses, and a cutting board for lunch. Learning to cut salami on a windy day on a heeling sailboat proved nearly as challenging as the sailing itself!


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ASA Certifications are offered at the completion of each course at BSC.

The American Sailing Association offers a number of different levels of sailing certifications, which demonstrates a certain degree of sailing proficiency and knowledge. While these certs are not a license, they are recognized internationally and I feel that they add structure to my learning path. There are alternatives to ASA, like U.S. Sailing, which offers a similar certification program and is taught at many schools throughout the world.

At the end of each of my two courses, I had a chance to read through the ASA textbook(s) and take a short written exam. Upon completion of the exam, you can sign up for an ASA membership and track your progress online and in a passbook. While I know that most of my learning will happen out on the water, it’s a great way to wrap up each course at BSC and be more prepared for the next level.

This winter, during the off-season, I have begun reading the Chapman Piloting & Seamanship guide, which provides further detailed information about the history, techniques, regulations, and necessary safety precautions for sailing and motoring. It’s nearly nine hundred pages in length, so not a quick read by a long-shot, but I’m willing to give it a go.

The book is not required reading but was recommended by our last instructor Brad during the Advanced Course.


Next month, I’m headed to the French Antilles with BSC to tackle my Caribbean Cruising Course (ASA 104)!

I’ll be living aboard a forty-six foot cruiser with a few new students and an instructor for a week-long voyage around the Caribbean island of Martinique. We’ll be learning the basics of bareboat cruising in a much warmer climate. More to come after the trip!


I plan on continuing my learning through 2018 and hopefully get some more time out in Boston Harbor and beyond. Like some of the other activities I’ve tried out this year, sailing has opened up an entire new network of enthusiastic and supportive people with an eye for adventure.

I can’t wait for those long summer days ahead!

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