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Let’s Go Sailing: Navigating How to Enjoy and Participate in this Nautical Sport

Aug 13, 2015 11:27AM ● By Cate Reynolds
By Gary Jobson

Take a walk down to City Dock, and look out toward the water. There will likely be many sailboats passing by. It is an idyllic scene. For someone who rarely gets to be on a boat, the thought of actually sailing may never cross their mind. Unfortunately, sailing has long had a reputation of being a “rich man’s sport,” and not being very accessible. But, I have good news, learning to sail in Annapolis is easy. There are many opportunities for anyone who wants to spend time on the water.

When asked why an experienced sailor likes to be on the water, the answer begins with the freedom of being away from land. Sailing, as a sport, has many attributes: it is an environmentally clean sport, it lasts a lifetime, connects generations, and provides a wide range of experience levels, from the casual day sailor to the long distance cruiser, and, for the most motivated, the Olympic Games. There is something available for people of all ages.

The first step for the beginner is to be comfortable on the water. I suggest simply taking a ride on one of the many tour boats available around Annapolis harbor. The Woodwind schooners are a nice way to start sailing. The crew will let you steer, and give you an overview of what it takes to sail. Everything looks different from the water. The weather and the views are always changing. Knowing how to swim gives the new sailor confidence. You will learn that many professional sailors wear a lifejacket anytime they are on the water. A PFD (personal flotation device) is an important piece of equipment for every sailor.

There are many good books available on basic sailing. Interestingly, author John Rousmaniere named his comprehensive book on boating, The Annapolis Book of Seamanship. I suggest reading about sailing and exploring videos on YouTube as an introduction. There is no substitute, however, for spending time on the water. Taking a sailing course is a good idea for even the intermediate sailor.

The next step is to sign up for a sailing school. (Note the list of sailing schools below.) I recommend a three- or four-day course so there is plenty of time to absorb the lessons from class room and the practical experience on the water. It is important to try every job on the boat from steering to trimming sails. You will be amazed how easy the fundamentals are to understand.

Learning to read the wind can be challenging at first because you cannot see the wind, but you can observe how the wind affects objects like flags, sails, and ripples on the water. There are three elements to make a boat sail efficiently and in the desired direction. Namely, steering, sail trim, and weight placement. The instructors will show you how to work on each of these fundamentals.

One of my great joys in life is taking friends sailing for the first time. When the boat first heels over most people will scramble toward the windward side. Within an hour the novice will be comfortable. It is important for a veteran sailor to explain what is about to happen. This puts the crew at ease. A few years ago I took a group of medical workers out for a sail. Not one of them had been on a sailboat before. Throughout the afternoon I made sure that everyone had a chance to steer and trim the sails. Crews are happiest when they have a job while on board. You learn quickly when you are assigned specific tasks. My medical group took lots of pictures and talked about the sail for months. I hope some of them were inspired to sail more often.

Like any sport the best time to learn is at a young age. There are excellent junior sailing programs run by local yacht clubs including Annapolis Yacht Club and Severn Sailing Association. Kidship Sailing is a commercial company based in Annapolis that specializes in young people, as young as five years old, and families. Everyone can learn together at Kidship. Womanship has focused on the female sailor since 1984. More recently lessons are available for couples and families. The company offers cruising destinations worldwide. Many people are attracted to sailing well after college or later in life. There is no reason to be intimated with good instruction available.

Since 1959, the Annapolis Sailing School has helped many thousands of people become sailors. The program includes classroom time followed by sailing with an instructor. It is an easy routine that has been fine-tuned over many years.

 Gary Jobson’s Whirlwind can accommodate six guests comfortably for a day sail.


After being certified by a sailing school or organization, the next step is to charter a boat for a day or longer. There are many charter companies around Annapolis. Most offer instruction. After a year or so of chartering, it might be time to purchase a boat. Take your time defining what kind of sailing you want to do. I recently purchased a new boat. My goal is to spend time sailing with friends and family. I wanted a boat that would easily fit six people in the cockpit. I wanted a small engine. My new boat has a small electric motor that can be charged by the sun. The boat had to sail well, and look good. I named her Whirlwind after my lifestyle of traveling around the world.

New sailors often ask me, “What do you do on the water?” I have the same routine, whether I am racing, cruising, or day sailing. The first step is to decide on a plan. How many hours do I want to be on the water? It is important that everyone on board brings the appropriate clothing, which includes clean deck shoes, a hat, sunglasses, and foul weather gear. Be sure to have enough drinks to keep everyone hydrated. The wind and sun can dry you out quickly out on the water. Before leaving the dock I always give a brief safety lesson, explain where safety gear is stowed, and explain where we will be sailing. I also make sure someone on shore knows our estimated time of arrival back at the dock. Each crew is given an assignment so they feel part of the action once underway.

Out on the water conversation flows easily. As mentioned there is something new to see every few moments. I like to keep the boat sailing fast. Speed always builds morale on a boat. Sometimes I even set up pretend races with other boats that are nearby. This gives the voyage a purpose. It is great fun. The evolution of the day sail is a weeklong charter. The first charters can be done on the Bay, but with experience can be taken anywhere in the world.

When you return from your sail everyone on board will feel good. Make sure that everyone is engaged in putting the boat away. The old adage, “many hands, make light work” is true on a sailboat. After a good day on the water, the inevitable question will be, “When can we go sailing again.” The answer? “Soon!”

Gary Jobson is a world class sailor, television commentator, and author based in Annapolis. He is the pre-eminent ambassador for sailing in the U.S.

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List of sailing organizations that feature instruction or boat charters:

Annapolis Sailtime: sailtime.com/annapolis
Maryland School of Sailing & Seamanship: mdschool.com
Annapolis Community Boating: annapolisboating.org
Kidship Sailing: kidshipsailing.com
Annapolis Sailing School: annapolissailing.com
The Sailing Academy Chesapeake Bay: thesailingacademy.com
Annapolis Bay Charters: annapolisbaycharters.net/school
Annapolis Naval Academy Sailing Associationansa.org
Womanship: womanship.com
Horizon Yacht Charters: horizonyachtcharters.com
Schooner Woodwind: schoonerwoodwind.com
J World Annapolis: jworldannapolis.com
Severn Sailing Association: juniors.severnsailing.org
Eastport Yacht Clubeastportyc.org
Annapolis Yacht Club: annapolisyc.org/juniors/programs
Cruise Annapolis Charters: cruise-annapolis.com
National Sailing Hall of Fame: nshof.org