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Destination - Boston Harbor Islands

There’s another world to explore just miles off one of the country’s most famous cities

There’s another world to explore just miles off one of the country’s most famous cities

One of the great New England destinations, Boston offers the perfect combination of both an urban setting and the solitude of 30 harbor islands just a few miles from downtown. The city is both a boater’s playground and an active maritime port, offering the best blend of sights and sounds, from interesting vessel traffic to peaceful, protected anchorages.

Boston is a truly revitalized city, having cleaned up its harbor more than a decade ago with the construction of the state-of-the-art Deer Island Wastewater Treatment Facility.


 Boston Light on Little Brewster Island seems a world away from the city skyline.

And with the more recent completion of the project known locally as the Big Dig — a huge federal undertaking that replaced a congested maze of elevated highways with an underground expressway — Boston is a place of parkways, open space and clean water.

“The great thing about coming to Boston is that you have the wonderful harbor islands just a few miles away from the city,” says Bryan Peugh, vice president of Flagship Adventures (www.flagship, a Boston-based educational and charter company focusing on the BostonHarbor islands. “You can eat at a restaurant or tour the waterfront, and yet you can also camp on an island, build a fire, sleep in a tent or swim at the beach. The islands are the string of jewels that decorate the city with miles of biking and hiking trails, beaches, public sailing, history, architecture and lore, all under the jurisdiction of the city and state that maintain it.”

In a real-estate hungry region like metropolitan Boston, what ultimately protects the islands from development is their status on the National Register of Historic Places as an Archeological District, because the oldest skeletal remains ever found in New England were discovered on Peddocks Island and date back 4,200 years. Additionally, Boston and the harbor islands have three National Historic Landmarks, including Boston Light, the country’s oldest continuously used lighthouse site (1716), on Little Brewster Island; Fort Warren, a Union coastal fort used as a training camp and prison on Georges Island; and Long Wharf, the oldest continuously operated wharf in the nation, which is next to such sites as Fanueil Hall marketplace and the Customs House.

“This may sound strange, but one of the greatest spectacles for all of us who spend a lot of time on Boston Harbor — and it doesn’t matter how old you are — is watching the giant passenger planes taking off and landing at nearby Boston [Logan International] Airport right over our heads,” says Peugh, who has spent nearly 20 years working on and around the harbor. “It is truly an awesome sight, and I have watched people of all ages look at the planes with a childlike awe. It is an interesting phenomenon.”

The air traffic in and out of Logan, the eighth-busiest airport in the country, is an accepted part of waterfront life. However, when the airport was expanded in the 1950s, it wasn’t welcomed by one of Boston’s most famous historians, Edward Rowe Snow (1902-1982). Losing what was Governor’s Island and subsequently the ancient FortWinthrop to expand Logan in the 1950s and ’60s fueled Snow and other Bostonians to protect the harbor islands. Snow spent a lifetime teaching, writing, researching, photographing and working to preserve them.

A colorful, classic New England personality, Snow was known as the Flying Santa, because he used his small plane to deliver packages to lighthouse keepers during the 1950s and ’60s, when they were still stationed there. He loved lighthouses and once took an infamous swan dive off the top of Minot’s Ledge Light, much to the horror of his wife. Until an advanced age, he ran tour groups around the islands and lighthouses of BostonHarbor. In the 1930s, he wrote the definitive “The Islands of Boston Harbor,” a book that’s still in print.

After his death in 1982, The Boston Globe commended his support for conservation: “There are many political leaders and environmentalists who can justly share the credit for the preservation of the harbor islands, but among them Mr. Snow will hold a special place as a link to their past and a guide to their present.”

Island appeal

At the BostonHarbor entrance, there is a north channel and a south channel, and either one puts you within minutes of the harbor islands, with options for a day at the beach or exploring a short jaunt away. Getting around the islands is easy, and the seasonal rangers from the Department of Conservation and Recreation — likely the first faces you’ll see when arriving by private boat — can offer guidance. Camping is permitted on many of the islands, though boaters cruising with pets should note that dogs aren’t allowed on any of them.

If you are docked inside the harbor and would rather secure your boat and take it easy, Harbor Island Express ferries ( ) depart frequently from Boston and Quincy, and there is a free interisland shuttle service that connects SpectacleIsland and GeorgesIsland to Lovells, Grape, Peddocks and Bumpkin islands.

By far the most visited island is 39-acre Georges, which sits about seven miles from downtown Boston and is considered the gateway to the BostonHarbor islands. It is the site of FortWarren, which was constructed in 1833. Like many of the harbor islands, Georges is filled with wonderful and sometimes tragic historical anecdotes, tales and stories. One of the most famous stories that characterizes the lore of the harbor islands is that of the Lady in Black.

According to Snow’s account, the Lady in Black was a Southerner whose husband was imprisoned at FortWarren during the Civil War. He sent word to his young wife through the Underground Railroad that he was on GeorgesIsland. She traveled from the South to Hull, Mass., where she rowed a skiff across to the beach. Slipping past the guards and into the fort, she was reunited with her husband. When their plot to escape was discovered, he was killed and she was sentenced to hang, accused of treason. On the day she was hanged, her only request was to wear widow’s black.

After her death, her presence haunted men stationed at the fort. There are records of men who shot at ghost-like figures while on sentry duty, heard voices, saw footprints — one man deserted his post, claiming he had been chased by the Lady in Black. In later years, it may have been Snow himself; it is well-known he was theatrical and liked to scare visitors with his Lady in Black routine.

Each island has a story that adds to its appeal. At nearby GrapeIsland, Snow writes that pirates (or vagrants) lived and prospered there just after the Civil War, and it is believed that gold is buried on the island. The islands have been used as military camps during World War II, as a hospital and as prisons during the last 400 years. Other legends include the hermit on SlateIsland, the shipwrecks and treasure on Lovell’s Island, and the Woman in Scarlet on Long Island. Most intriguing is the alleged sea serpents at CastleIsland spotted in 1818, which no doubt fueled the imagination of a young sentry by the name of Edgar Allan Poe, who was stationed there in 1827.

Islands and then some

Approximately 50 moorings serve BostonHarborIslandsNational Park ( ). Located in safe anchorages off Long, Peddocks, Gallops, Georges and Rainsford islands, the moorings are available for four hours, by the night or for the season. Reservations are suggested, especially for weekends and peak summer holiday periods.

For information about marina reservations, moorings on the harbor islands or anchoring, contact either the Constitution Marina — , (617) 241-9640 — or Spectacle Island Marina — (857) 452-7221 and channel 69.

In Boston proper, landing near Charlestown at Constitution Marina gives visitors a chance to tour the Charlestown Navy Yard, home of the USS Constitution. Additionally, the HarborWalk (, which includes Long Wharf, Rowe’s Wharf and T-Wharf — once a huge part of Boston’s maritime activity — can be reached via the Boston Harbor Sailing Club, which also has rental moorings. The club mooring facility is located in Federal Anchorage A at BostonInnerHarbor. It’s the only mooring basin offering regular launch service from May 1 through Oct. 31 ( ).

Walking toward Rowe’s Wharf, you’ll pass the New England Aquarium and the staging point for harbor cruises, whale watches and a stroll along HarborWalk, which leads to the elegant Boston Harbor Hotel. Additional marinas along the historic Boston waterfront include the Boston Waterboat Marina ( on LongWharf, which can be reached on VHF channel 9. Fuel is available here and at Constitution Marina.

All of this is within close proximity of Boston’s famous North End, which boasts not only great Italian restaurants and coffee shops but also is the neighborhood where the OldNorthChurch and Paul Revere’s house are located.

Nearby Hull Gut is the gateway to additional cruising, including the Cape Cod Canal farther down the coast. Or cruise across Massachusetts Bay to Provincetown at the tip of Cape Cod, passing through the feeding grounds of whales at Stellwagen Bank. Getting to the open waters of Massachusetts Bay from BostonHarbor, you can pass through the picturesque and sometimes tricky Hull Gut. This route passes by the historic HullLifesavingMuseum ( ) on shore, which is worth a visit. It’s considered the museum of Boston Harbor’s heritage, and through its open-water rowing programs, young people can learn the traditions and ethics of 19th century coastal lifesavers, who were vital to mariners in distress.

A growing sailing legacy

Not only has the harbor cleanup and the focus on the islands improved the choices for area boaters and visitors alike, it has begun to transform Boston into a true sailing city. With the BostonSailingCenter ( ), CourageousSailingCenter ( ), PiersParkSailingCenter ( ) and the boatbuilding and facility of Boston BoatWorks in East Boston ( ), the area is becoming a destination for international regattas and competitions.

In 2004, the city hosted its first single-handed trans-Atlantic race, the Transat, from Plymouth, England, to Boston. It finished just off RowesWharf and featured Boston’s own Rich Wilson, who placed second in his division. Four years later, in June 2008, the Transat race returned to Boston, and a new tradition was set. Additionally, next May, the Volvo Ocean Race will make Boston its U.S. stopover, putting the city in international yachting headlines. With racing yachts staying up to three weeks, the Volvo stopover will be one of the biggest and most important sailing events to come to Boston. It will feature the Puma Racing Team, the syndicate headed by Ken Read of Rhode Island and sponsored by a Boston-area company.

Wilson, one of Boston’s most famous sailing sons, will be racing in the 2008-’09 single-handed non-stop Vendee Globe. He hopes to use Newspaper in Education programs ( ) and his sitesAlive Foundation Web site ( to educate Americans about the race, which isn’t that well-known in the United States, but is followed closely by millions of sailing fans elsewhere. Wilson has made some demanding voyages in his time, setting speed records for passages from New York to Australia, Hong Kong to New York, and San Francisco to Boston.

“I will never forget the reception I received when I finished my San Francisco to Boston voyage, and hundreds of schoolkids and boats came out to give me a hero’s welcome in BostonHarbor,” says Wilson. “It was unforgettable for me.”

With the city’s long history of philanthropy, Bostonians — regional sailors in particular — are very proud of the CourageousSailingCenter at the Charlestown Navy Yard. It was established in a joint effort between the City of Boston Parks and Recreation Department and the late South Boston sailing enthusiast Harry McDonough, whose dream was to create a sailing center that would teach sailing for free to children from all economic and ethnic backgrounds.

“We have the use of about 80 boats altogether to teach inner city kids how to sail,” says John Maconga, executive director of the center. “This is a free outreach program, and over the years we have given youth who would never have had the chance to sail the opportunity to get on the water and also explore the islands.”

As the program has gained support and interest, the center tends to have children who come to the program as students and stay on to teach and volunteer as they get older. The center currently has one “graduate” who is pursuing a dream to sail in the Olympics.

“Sailing does change the lives of these young people, and it influences them in a powerful way,” says Maconga. “I think there are many key moments for these kids, and one of them is when they are able to sail without an instructor. I have seen how this changes them, and it becomes an empowering experience that stays with them.”

CourageousSailingCenter also offers one-day memberships so a visitor can use a sailboat for the day. It is the site of the annual Flip Flop Regatta held in memory of Alexandra Nicole Zapp, a 30-year-old sailor who was murdered by a sex offender in Massachusetts in 2002. The event benefits the ALLY Foundation, which was established to “prevent opportunities for violent sex offenses, to educate the public, and to advocate for necessary changes in culture, attitude and policy” ( ).

The regatta includes first-time racers from the CourageousSailingCenter, where Zapp spent much time volunteering, wearing her trademark pink-and-green colors and flip-flops. “This is really the only big-boat regatta in Boston,” says Scott Akerman, one of the event organizers and a good friend of Ally Zapp’s. “The event has grown, and with the spectator fleet, non-sailors are able to get out on the water and participate, too.”

With its growing status as a destination for world-class events and sailors, Boston also remains a favorite for powerboaters, who have the flexibility to run up to the city or out to the islands with ease. And keep in mind that ferries run between the islands for day visits and run to Quincy, Salem, Provincetown and Hull. There also are harbor cruises, whale-watching and duck-boat tours.

Boston is a great harbor to visit, a great waterfront to walk along and a great jumping-off point to explore the islands. “Sailing in Boston and around the harbor islands is a very different experience for many sailors and boaters because you have the commercial traffic, fishermen, crabbing and everything that is tied to the maritime industry,” CourageousSailingCenter’s Maconga says. “With the harbor cleanup and depression of the central artery, the harbor is more vibrant, the islands look greener, and this place just opens up a world of possibilities on the water.”