Vineyard Haven, MA
A six-acre family enclave at 50 Marchant Avenue in Hyannis Port, on Cape Cod's south shore — three connected waterfront houses purchased by Joseph P. Kennedy Sr. starting in 1928 and used by three generations of the Kennedy family. The "Big House" (Joseph and Rose's main residence) was the political nerve center of John F. Kennedy's 1960 presidential campaign: JFK accepted the Democratic nomination from the porch, was elected from the house, and watched the Nixon-Kennedy returns in the basement. The compound also includes the homes Robert Kennedy and JFK each later bought next door. From the compound, Kennedy family members have sailed Nantucket Sound for nearly a century — JFK's 26-foot sloop Victura, on display at the JFK Hyannis Museum in downtown Hyannis, was a familiar sight in the channel. The compound itself remains a private family residence (multiple Kennedys still live there) and is not open to public tours; the JFK Hyannis Museum 1.5 miles inland on Main Street has the photographs and memorabilia. The Kennedy Brothers Memorial sits on a small green at Lewis Bay near the museum, completed 1991 with bronze relief portraits of JFK and RFK.
On Broad Street in downtown Nantucket, in a converted 1847 spermaceti candle factory built by William Hadwen — the museum is the centerpiece interpretation of the period when Nantucket was the whaling capital of the world (roughly 1690 to 1840). At its peak in 1843, Nantucket's whaling fleet numbered 89 ships, more than any other port in the world, harvesting sperm whale oil that fueled streetlamps from London to San Francisco. The fall of the Nantucket fleet came fast: an 1846 fire destroyed the waterfront, sandbars in Nantucket Harbor grew worse, and the discovery of Pennsylvania petroleum in 1859 made whale oil obsolete almost overnight. The museum holds a complete 46-foot sperm whale skeleton (washed ashore on Siasconset Beach 1998), the rudder from the whaleship Essex (rammed and sunk by a sperm whale in 1820 in the South Pacific — the real-life event that Herman Melville built "Moby-Dick" on), Captain George Pollard's logbook from the Essex disaster, scrimshaw, harpoons, and the working 1849 Brown's Patent Lard Press that pressed spermaceti from raw whale oil. The rooftop observation deck gives a 360° view of the harbor and town.
Eleven preserved Gilded Age mansions on Bellevue Avenue and Ochre Point in Newport, Rhode Island — the summer "cottages" of the late 19th-century industrial elite, now operated as museums by The Preservation Society of Newport County. The Breakers (1895, Cornelius Vanderbilt II) is the largest and most-visited: 70 rooms, 65,000 square feet, Italian Renaissance Revival designed by Richard Morris Hunt, built in two years with rare marbles imported from Italy and Africa. Marble House (1892, William K. Vanderbilt) cost $11 million when completed — equivalent to over $400 million today — with $7M spent on the 500,000 cubic feet of white marble alone. Rosecliff (1902) was the setting for The Great Gatsby and True Lies film versions. The Elms (1901, modeled on a French château outside Paris) had elaborate coal tunnels so that servants and supplies were never visible to guests. Cliff Walk, a free 3.5-mile public pedestrian path required by Rhode Island law, runs along the cliff edge between the back lawns of the mansions and the Atlantic. Newport is also the home of the International Tennis Hall of Fame (in the 1880 Newport Casino — the site of the first U.S. National Tennis Championship, 1881).
The fishhook-shaped peninsula curling 65 miles east and north from the Massachusetts mainland, terminating in the curl of Provincetown at its tip. Cape Cod is a glacial deposit — the entire peninsula is essentially a 20,000-year-old sand bar pushed up by the Laurentide Ice Sheet. The Pilgrims made first landfall here in November 1620, in what is now Provincetown Harbor, before continuing to Plymouth. The outer beaches along the National Seashore are the longest unbroken stretch of sandy coast in the eastern US. From altitude the entire fishhook is visible at once — the sandbars, kettle ponds, and salt marshes laid out like a topographic model.