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Nantucket’s Whaling Museum tells the tale of the Quaker whalers who made Nantucket prosperous in the 19th century. The island has shed its Quaker past and now boasts trophy beach houses and million-dollar yachts. For sports, there’s kayaking, casting for striped bass from Surfside Beach, or cycling to the former fishing village of Sconset with its rose-covered clifftop cottages.

In the 19th century, Newburyport was a prosperous seaport. The grand three-story mansions along the High Street present a virtual case study in Federal architecture, while boutiques and antiques shops line downtown Merrimac, Water, and State streets. The Parker River National Wildlife Refuge on the adjacent Plum Island is one of the US’s top bird-watching sanctuaries.

The Other Side enjoys a loyal following of health-conscious hipsters who melt at the sight of its brie, apple, and pear sandwich. Its intimate outdoor patio is highly coveted real estate.

Here you’ll find some of the area’s best beaches. The 40-mile (64-km) National Seashore offers great surfing at Coast Guard and Nauset Light, and the beaches of Marconi, Head of the Meadow, and Race Point all have dramatic dunes and great ocean swimming. The artist colonies of Wellfleet and Truro are worth a visit as is Provincetown, a fishing village turned gay resort.

This split-level café with a patio has a lovely view onto the Public Garden (see Boston Common & Public Garden) and an inspired menu of delicious and wildly creative sandwiches (see Parish Café).

Jaw-dropping panoramic views from a 50th-floor observatory. (see Prudential Skywalk).

North End’s Puopolo Park boasts supreme frontage on the harbor, looking out toward Charlestown. On warm days, the neighborhood’s old guard enjoy a game of bocce (bowls). Nearby, kids play baseball or splash around in the outdoor pool.

Established in 1896, Revere Beach was the first public beach in the US. Thanks to a centennial restoration, it’s also one of the best, with nearly 3 miles (4.5 km) of clean white sand and clear blue water.

Home to the imposing Boston Harbor Hotel (see Boston Harbor), Rowes Wharf is a popular docking spot for high-end harbor cruise outfits. Framed by the hotel’s colossal courtyard-atrium, with its grand arches and copper dome, the wharf is a luxurious contrast to the city’s grittier, saltier working docks.