Friendly Debate: the top Five Sailing Destinations on the East Coast

By Vern Penner 

If you like to be out on the water in Summer, then Springtime is the time to take off the boat covers and paint the bottom, then launch the boat and run up the sails. It also means another year of our favorite old debate: What’s the best sailing destination on the Eastern Seaboard? Five long-time sailing friends, having experienced almost every major port of call on the East Coast, each vouched for their favorite top five sailing destinations. Here’s their breakdown and suggestions to help you decide on your sailing trip for 2015:

Charleston, South Carolina

Charleston Harbor is formed by the convergence of the Ashley and Cooper rivers with a well-marked entrance of sea buoys and channel markers. Less than 10 miles from the ocean, Charleston has provided many a sailor a welcome respite from the Gulf Stream and the capes and shoals of the Eastern Seaboard, as well as a link within the Intracoastal Waterway. The City Marina is a favorite of boaters for its staff of professionals and complete service. It even provides free van transportation to shops and restaurants. The Charleston Harbor Resort & Marina is another full-service yard and plays home to April’s popular Charleston Race Week, which lays claim to being the largest sailing regatta in the U.S. The Maritime Museum is located on nearby Patriot’s Point. Charleston is praised for its southern hospitality, long history and well-preserved architecture of colonial, Civil War, post-bellum and modern styles. Along with its churches, Ft. Sumter, the Battery and the USS Yorktown, the city has some of the most modern-day port operations and dining facilities on the East Coast, making Charleston an excellent port, with or without a storm.


Newport, Rhode Island

Founded nearly 400 years ago in 1639, Newport is among the oldest settlements in the American Colonies. What was once one of the most important commercial and trade hubs on the East Coast in the 17th and 18th centuries is now one of the top tourist destinations across New England and one of the spiritual homes of sailing in the U.S. Rhode Island is called the Ocean State for a reason and Newport is the hub of its maritime culture: shipbuilders, sail makers, marinas, docks and some of the world’s best professional sailors. Sailboat racing is part of its DNA: Newport played host to 12 consecutive America’s Cup races from 1930-1983 before Australia II took the trophy Down Under. In 2015, Newport will be the only North American port for the famous around-the-world Volvo Ocean Race. Seven teams will stop in Newport this year from May 5-17 during their 40,000-nautical mile adventure over nine months. That could be a terrific time to sail up Narragansett Bay, set the anchor and spend a few days exploring on land or around the bay. There are activities, historic sites like Newport’s famous mansions, restaurants, pubs and cafes aplenty. Indeed, few places show off their maritime history quite like Newport does.

 Key West, Florida

If the sailing naturalist who enjoys hiking is drawn to the bays and inlets of Maine, Key West is the nirvana for the cruising mariner who delights in a laid-back “la-la” atmosphere of palm trees and watching ocean sunsets. It lies at the end of a slender necklace of landfalls strung together by 120 miles of highway and causeways, easily approachable from the Gulf or from the northeast via the Florida Straits. Winter from November through February is actually the ideal sailing time with daily sun and breezes and only a rare storm. And for the racing enthusiast, what better way to start the annual season than the Key West Race Week. Watch for that in mid-January 2016. Water temperatures are perfect for swimming and diving among the protected locations forming part of the continental United States’ only living coral barrier reef. The most popular anchorages are southeast and northwest of Wisteria Island just off a corner of Key West, which also hosts a number of excellent marinas such as the Key West Westin or the City Marina in Garrison Bight. Downtown Key West boasts the Hemingway and Truman museums, terrific restaurants and glitzy shops, all within easy walking distance from the historic Key West Bight. If you miss the sunset’s green flash in Mallory Square, you can console yourself people-watching with Bourbon Street-style music and margaritas in virtually every bar on Duval Street.

Penobscot Bay, Maine

You can’t go wrong sailing into Penobscot Bay, located at the top end of the East Coast. It is easily accessible with gorgeous scenery. There are many islands of all sizes offering good anchorages and a number that allow access ashore for picnicking and hiking, some of which are conservation reserves. It is ideal for exploring the many interesting deep-water inlets. And then there are the lobsters and fish, not to mention the mollusks. The annual Maine Lobster Festival runs until the end of July in Rockland, which boasts many fine restaurants, an art museum and the excellent Journey’s End Marina and ship chandlery. The town of Camden is a bustling place with hiking and a state port. Rockport is a gem of a small village with a vibrant arts scene. Castine hosts the Maine Maritime Academy, and the Penobscot Marine Museum is located in Searsport. Yes, there are a few small caveats. Fog can sometimes be a problem, but generally not in July and August. The large tidal range can be a challenge for navigating and anchoring. There are the ever-present lobster buoys to avoid and rocks and shoals are not always well marked. Some might call the swimming a touch cold, but others characterize it as extremely invigorating and ideal for peaking one’s appetite for boiled lobster.


Saving the best for last: This small-town capital city in Maryland is regarded by Annapolitans as the U.S. sailboat capital by virtue of its long sailing season, from March to November, an extensive racing schedule for every class, numerous marinas and service facilities and an easy entrance just south of the Chesapeake Bay Bridge. Yes, it is a long distance of some 150 miles up the Bay from the Atlantic, but as so many residents of this capital city know, Annapolis has something for everyone. It is annually voted the Best on the Bay for families, foodies, history buffs and the party crowd. Sailors looking for repairs can find just about anything in the well-equipped local yards. Almost all major sailboat builders have local representatives or headquarters. There are city-owned slips and dockage that cut right into the center of the town and city moorings have taxi service. To top it off, the annual Annapolis Sailboat Show, which runs four days over Columbus Day weekend, is the largest in the world. What’s not to like, except August’s heat and humidity. So hit the town in late Spring or early Summer when nights and days are a bit cooler.

Vern is a former US ambassador who retired to Annapolis and tries to go sailing as much as possible to avoid garden work. He can be reached at [email protected]



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