A sea breeze ruffled our hair and the waters of Long Island Sound as our tour boat glided away from the Connecticut village of Stony Creek and ushered us toward the Thimble Islands. We passed harbor seals lounging on an outcropping of pink granite — the same stone that forms the islands. There are said to be as many of these remnants of ancient glaciers as there are days in the year, if you count every prominence at low tide. On the larger islets we glimpsed graceful summer homes rising above cedars and pines. As we craned our necks looking for osprey nests, our captain paused a narrative about pirate lore to point out that these waters, where the depths can vary dramatically within short distances, are hardly hospitable to amateur sailors.
The Thimble Islands are far from the only maritime attraction along the coast of New England. From Connecticut to Maine, short cruises of all varieties are pulling up anchor and ready to be added to summer vacation itineraries.
They are popular, though, so plan ahead. For the cruises below, the ticket prices represent the round-trip cost for adults.
From Portland, Maine
The Mailboat Run
A novel way to spend a day on the water is to hop on a working mail delivery boat out of Portland and explore the nearby islands. The Casco Bay Lines Mailboat Run leaves Portland three times a day and stops at Little Diamond and Great Diamond islands, along with Long, Cliff and Chebeague islands. The islands, largely forested and flat, with rocky coasts, are home to fishermen’s cottages and waterfront mansions alike.
For $24, visitors can enjoy the entire mail run, which lasts between 2.5 to 3.5 hours, depending on the route and cargo volume. Because passengers cannot stop to explore individual islands, they sometimes bring picnics to enjoy on board or else grab food and drink at the Cliff Island store while the boat stops briefly there.
“A lot of people just like to watch the crew work,” said Patrick Donovan, a former captain who is now assistant operations manager at Casco Bay Lines. The cargo hauled by the steel-hulled, diesel-powered vessels may be as mundane as residential mail or as exotic as a herd of goats imported to rid a property of invasive bittersweet vines. “You name it, we ship it,” Mr. Donovan said.
Narration is offered for trips of 10 or more passengers; the captain might point out the late-19th-century Fort McKinley on Great Diamond Island, now a residential complex, or the marine creatures in Casco Bay. The Mailboat Run leaves Portland every day year-round at 10 a.m., 12 p.m. and 3 or 3:15 p.m.
From Boothbay Harbor, Maine
Monhegan Island
From Boothbay Harbor, about 60 miles northeast of Portland, art aficionados can take the 12-mile boat journey to Monhegan Island to revel in the landscapes that inspired American artists such as Robert Henri, Rockwell Kent, Edward Hopper, George Bellows, and Andrew and Jamie Wyeth.
Through Oct. 12, Balmy Days Cruises takes up to 130 passengers on a 65-foot fiberglass vessel to Monhegan, which is still an artists’ mecca. Just shy of a square mile in size, the island is home to galleries, studios and the Monhegan Museum of Art & History, as well as cafes, shops, a craft brewery and hiking trails. The Balmy Days II leaves Boothbay Harbor at 9:30 a.m. and returns at 4:15 p.m.
Weather permitting, the boat circumnavigates the island for 30 minutes, offering passengers the occasional whale or seal sighting and dramatic views of Monhegan’s cliffs, which rise as high as 160 feet.
Tickets are $55. Monhegan Island is also accessible by ferries leaving from Boothbay Harbor, New Harbor and Port Clyde.
From Gloucester, Mass.
Whale Watching
Watching a humpback whale approach your boat and do a flipper slap or a breathtaking breach is a magical experience, and whale watches are a summer staple up and down the coast of New England. Sailing out of Gloucester, on the southern shore of Cape Ann, about an hour northeast of Boston by car, 7 Seas Whale Watch goes a step further, touting itself as “the birder’s whale watch.”
The crew points out birds that spend most of their time on the open ocean, such as Wilson’s storm petrels, which sometimes appear to be walking on water, or fast-flying parasitic jaegers, known to divebomb terns until they drop their catch.
The whales — most are known and named by the crews — are the main event, though. The company’s Privateer IV takes up to 149 passengers about 12 miles out to Stellwagen Bank National Marine Sanctuary, where humpbacks, minkes, sei whales and finbacks feed. Seals, sunfish, sea turtles, sharks and dolphins are also a common sight.
The boat leaves the dock daily through mid-October, weekdays at 10:30 a.m. and weekends at 8:30 a.m. and 1:30 p.m., and the trips last between three and four hours. Tickets are $65.
From Rye Harbor and Portsmouth, N.H.
Star Island
Seven miles from the New Hampshire coast, 46-acre Star Island is the second largest of the nine Isles of Shoals mapped by the British explorer Capt. John Smith in 1614. An established fishing hub by the end of the 17th century, the island incorporated the town of Gosport in 1715. It later became popular as a summer retreat for artists and writers, leading to the construction in 1875 of the Oceanic Hotel, with its wide porch and rocking chairs. Among the island’s landmarks is Gosport Chapel, a stone meeting house on Star Island’s highest point.
Granite State Whale Watch and Island Cruises in Rye Harbor, about seven miles northeast of Portsmouth, has a regular schedule to Star Island aboard Uncle Oscar, a refitted lobster boat that can carry 49 passengers. The season for its Isles of Shoals Tour & Star Island Walkabout trip runs through Sept. 13, with twice-daily cruises available most of the summer. Along the way, the captain identifies marine creatures such as harbor porpoises and seals.
Tickets for the roughly three-hour round trip are $40, and an extended trip allows nearly five hours on Star Island for $45.
Isles of Shoals Steamship Company has a less-regular schedule for its Star Island Walking Tour & Portsmouth Harbor Cruise, but its three-level M/V Thomas Leighton carries 340 passengers.
From Norwalk, Conn.
Lighthouses
That there are plenty of New England cruises catering to lighthouse lovers is no mystery to James Hyland, the president and founder of the Lighthouse Preservation Society. “Lighthouses are to the United States what castles are to Europe,” he said.
About an hour from New York City by train, the Norwalk Seaport Association has a three-hour tour that lets passengers off on 52-acre Sheffield Island, the second largest of the approximately 25 Norwalk Islands, and home to a 19th-century granite lighthouse. As the 45-foot C.J. Toth Catamaran wends its way among the islands, up to 49 passengers are regaled with tales of pirates and Norwalk’s still-thriving oyster industry as well as the history of the area’s lighthouses. The cruises run through the end of August, with tickets at $42.
This year the Norwalk Seaport Association and the Greens Ledge Light Preservation Society is selling $110 tickets for new five-hour cruises to Sheffield Island and the recently opened Greens Ledge Lighthouse on July 11 and Aug. 8. The Greens Ledge Lighthouse, completed in 1902, is one of the 33 metal spark-plug-shaped lighthouses in the United States and is said to be the inspiration for the green light in F. Scott Fitzgerald’s “The Great Gatsby.”
From Stony Creek, Conn.
Thimble Islands
Summer homes on some of the 23 currently inhabited Thimble Islands are the focus of the narrated tours off Stony Creek. The area, known for the pink granite quarries that supplied stone for monuments like the Statue of Liberty, has long been a draw for summer residents. President William Howard Taft used a Newport-style compound on Davis Island as a Summer White House, and Rogers Island has a 27-room privately owned Tudor mansion whose formal gardens, greenhouse, putting green and guesthouse are visible from the boat.
Not all the islands are inhabited. Horse Island, the largest Thimble at 17 acres, is used as an ecological laboratory by Yale University. Outer Island is a five-acre U.S. Fish & Wildlife Services refuge.
We took the 49-passenger Sea Mist, but there are two other boats that give similar tours: The 13-passenger Islander and the 48-passenger Volsunga IV.
Tickets for all are $18 to $20 for 45-to-60 minute tours that are offered several times a day into October. Parking at Stony Creek can be difficult, so arrive early.
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