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Annapolis, America’s Sailing Capital

Jul 02, 2015 11:00AM ● By Cate Reynolds

The Wednesday Night Sailing races in Annapolis are a summer tradition, as are the U.S. Naval Academy offshore sailing teams practicing. Photo courtesy of

Is our state capital truly deserving of this locally ingrained moniker?

By Gary Jobson

Referring to Annapolis, as “America’s Sailing Capital” might be considered a bold declaration. I always smile when sailors outside of Annapolis question our unofficial moniker. Initially, the slogan was a play on words. The theory behind the slogan is, Annapolis is the capital of the state of Maryland, and therefore it is easy to say that, Annapolis is America’s Sailing “capital.” At one time a sign with this message was posted on Rowe Boulevard as a greeting to visitors. About ten years ago some spoil-sport in the state government decided the space was too valuable and removed the sign in favor of the current sign that simply reads, “1649 Annapolis, Maryland’s Capital.” The original (now fading) sign sits on the east side of the Spa Creek Bridge. It would be nice to see the original sign back on Rowe Blvd.

Some prominent international cities use similar names to promote sailing. For example, Auckland, New Zealand, is “The City of Sails” and China’s 2008 Olympic sailing host city, Qingdao, is known as “Sailing City.” Can Annapolis truly be considered America’s Sailing Capital? Certainly, the debate will be spirited if the topic comes up here, or in any other waterfront town like Newport, Rhode Island or San Diego, California. As a longtime resident of Annapolis, I am comfortable about making the case, that our slogan is accurate.

Members of the U.S. Naval Academy varsity and junior varsity offshore sailing teams practice in the Santee Basin near the academy campus for the Fall Keelboat Invitational Regatta and the McMillan Cup Intercollegiate Regatta. Photo by Petty Officer 2nd Class Chad Runge.

Recently, while returning from a trip, I flew over Annapolis aboard a Southwest Airlines jet. We approached BWI airport from the south. While sitting by a window I was able to get a perfect view of Annapolis, the Chesapeake Bay, and the Severn River. There were hundreds of boats stretching in every direction. Happily, most of the craft were sailboats. The great English artist, JMW Turner would have found inspiration in the aerial scene. It was a Wednesday evening, with a steady breeze blowing in from the south. Throughout the warm months of the year, commerce shuts down each Wednesday as a few thousand sailors head for the waterfront for the weekly evening races. Boats of all shapes and sizes are crewed by people of every age. When the boats cross the finish line, that is set right next to the Spa Creek Bridge, you can see wide smiles on the faces of the crews. In fact, racing takes place on most nights in Annapolis on a wide variety of one-design class boats. Weekend sailing tends to be more serious, and attracts many out-of-town sailors. There is always something going on around the waterfront. It is no accident that more than 3,000 boats are located in our town.

Annapolis is a favorite stop for most mariners cruising up or down the Chesapeake. And, it is easy to understand why. The harbor is sheltered, there are many boatyards, countless moorings, anchorages with good holding ground, a historic city to explore, a lively waterfront for the thirsty and hungry, and a convenient place near an international airport. Annapolis makes a handy rendezvous point. As I travel around the world and mention that I am from Annapolis, the response I receive is often, “Oh, we went there for the boat show.”

The sign that once greeted visitors to Annapolis via Rowe Boulevard now sits on the Eastport side of the Spa Creek Bridge.

A historical review helps us understand how Annapolis became an important port. Since the earliest settlers reached Annapolis there has been a vibrant waterfront. The formative years centered on commercial trade, fishing, naval military activity, transport of passengers, and a robust industry to support the diverse vessels that worked out of the port or visited Annapolis. There were few roads and no railroads in the 17th and 18th centuries. Travel by water was the most efficient method of moving goods and people. There was considerable naval activity under sail during the Revolutionary War. Sail training became an important addition to Annapolis when the United States Naval Academy moved here from Philadelphia in 1845. Even the yacht America was located here after the Civil War. She won the trophy that became known as the America’s Cup in 1851. She was used in battle for both the Union and the South during the Civil War. She was a training vessel for the Academy for many years, and finally collapsed in Eastport during a winter storm.

After World War II, the Naval Academy used yachting for small boat qualifications and racing to prepare Midshipmen for their naval careers. Famous yachtsman, DeCoursey Fales established a committee to advise the academy on waterfront activities, and to encourage boat owners to donate their yachts for Midshipmen training. During the spring and fall semesters, dozens of large and small boats practice in the afternoon for upcoming regattas. The Naval Academy is consistently one of the top ranked college sailing teams in the country. The coaching staff features many champion racers including Ian Burman, Jon Tihansky, three-time America’s Cup winning crew Jon Wright, Olympian Nancy Haberland, around-the-world racer Renee Mehl, and Adams Cup winner Joni Palmer. Later in life, many naval officers will retire in the Annapolis area with the goal of spending time on the water.

Photo courtesy of

Frequent recreational boating did not get started around Annapolis until after the Civil War. In 1886, a former oyster shack at the foot of Compromise Street was leased from the Redemptorist Fathers of St. Mary’s Church to a group of boating enthusiasts. Two years later, the property was renamed the Severn Boat Club. The modest building and pier provided access to the water, a home for social events, and a center for boating. The club endured hurricanes, and the Great Depression. By 1937 the club was renamed Annapolis Yacht Club. Over the years, several buildings were constructed on the property. The current AYC building was opened in 1962.

Racing took off after World War II. Many members distinguished themselves on long-distance races and in one-design championships. The list of sailing heroes of Annapolis is long. Here is a partial honor roll: Carlton Mitchell, won the Bermuda Race a record three times. Al Van Metre successfully raced his 60-footer, Running Tide with distinction. The legendary Arnie Gay, was a boat broker and champion offshore sailor. Clayton Ewing broke the rudder on his yacht, Dyna, in the 1963 Transatlantic Race, and yet, still reached the finish line using his sails to steer. It was an extraordinary feat of seamanship. Gaither Scott was a highly respected international race officer. Severn Sailing Association’s Stuart Walker and the late Sam Merrick won countless small boat titles. Yacht designers, Bruce Farr and Russell Bowler were recognized as the best in world for many years. Authors James Michener, Richard Henderson, Admiral Bob McNitt, and the editor of Skipper Magazine, Bunny Riggs; all were Annapolis ambassadors. Considerable publishing continues in Annapolis with titles like Spin Sheet, Prop Talk, and Chesapeake Bay Magazine. Singer Burl Ives enjoyed his time on the water here, as did television news anchor, Walter Cronkite. More recent champion and professional sailors include Terry Hutchinson, Chris Larsen, Jim Allsopp, Larry Leonard, and Scott Allan. Big boat owners like Jim Muldoon, Peter Gordon, the late Jack King, George Collins, and Kevin McNeill are well-respected on the international racing circuit.

In 1963, President John F. Kennedy spoke at the Academy and toured the waterfront. He and his brother won the collegiate McMillan Cup for Harvard in 1936. The McMillan Cup is now hosted by the Naval Academy.

Jerry Wood, recognized a need for sailing instruction and founded the Annapolis Sailing School in 1959. Twelve years later he founded the U.S. Sailboat Show. Ownership of the boat show has changed in recent years, and continues to be one of the best in-the-water shows in the world. Today, Annapolis is a center for sailing instruction and boat chartering. Anyone looking to buy a new boat will find it easy by working any of the many brokerage companies in our town.

There are many boating organizations located in Annapolis. In 2005, then Governor Robert Ehrlich announced the establishment of the National Sailing Hall of Fame, which is located on City Dock. The Hall of Fame plans to construct a building within the next few years. The Annapolis Maritime Museum is located in the old McNasby Oyster factory on Back Creek. Annapolis Community Boating gets hundreds of young people on the water each year.

Three strong yacht clubs, Annapolis YC, Severn Sailing Association, and Eastport Yacht Club host hundreds of races each year. The junior sailing programs in Annapolis are among the best in the USA. There are six high schools with active sailing teams that practice in all weather conditions throughout the year. Happily, the sailors in our town are philanthropically minded. The Leukemia Cup and Hospice Cup, as just two examples, are well-attended and both raise funds well over six figures each year.

Annapolis has hosted many major sailing events. The Whitbread Round the World Race visited in 1998. The new owners of the Whitbread, renamed the race The Volvo Ocean Race and returned in 2002 and 2006. In 1990 the America’s Cup challengers from the 1930s Endeavour and Shamrock V raced off Annapolis. There were thousands of spectator boats on hand for all of these events. In 2003, two America’s Cup winning 12 meters, Courageous and Freedom scrimmaged off Annapolis. Every year Sailing World magazine and the Annapolis Yacht Club co-host America’s largest National Offshore One-Design Championship. The event has a clever acronym—NOOD. This is just a small sample of the many regattas that take place on our waters every year.

Racing is only a fraction of the sailing activity that takes place. Cruising is vibrant year around. Sailors venture from Annapolis in all directions during the summer months. There are an equal amount of boats that seem to visit our harbor every day during the sailing season.

It is fair to note that Annapolis requires a long sail to reach ocean waters. But, our rivers, creeks, and beloved bay provide a huge area for sailing. The wind can usually be counted on, (at least most of the time, I write with a smile).

Calling Annapolis, “America’s Sailing Capital” seems appropriate when considering the vibrant sailing scene that thrives here year-around.


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.