Celebrity Travel

Gossip

Hyannis Port Has Been the Kennedy Family's Summer Address Since Joseph Kennedy Bought a Cottage in 1928

The Kennedy Compound in Hyannis Port, Massachusetts, three adjoining waterfront properties bought by the family from the late 1920s onward, served as John F. Kennedy's 'Summer White House' and remains Cape Cod's most storied old-money enclave.

Gossip

Napa Valley Is Where Old Wine Money and New Hollywood Money Finally Agree

Since the 1976 'Judgment of Paris' put its wines on the map, Napa Valley has drawn old vintner families and famous newcomers alike to buy into its hillside estates, led by Francis Ford Coppola's restoration of the historic Inglenook winery.

Gossip

Le Touquet Has Been the Discreet Coast for Paris and London's Old Money Since the 1900s

Built from pine forest into a resort at the turn of the twentieth century, Le Touquet-Paris-Plage drew British and French aristocracy between the wars and remains a low-key second-home coast for Paris's establishment today, including France's own political families.

Gossip

Block Island Is the New England Retreat Old Families Picked Precisely Because It Wasn't Newport

Nine miles off the Rhode Island coast, Block Island built its own Victorian-era grand-hotel era in the 1870s and 1880s, then spent the following century staying deliberately less developed than Newport or Nantucket, a reputation it has guarded ever since.

Gossip

Round Hill Has Been Jamaica's Old-Money Address Since 1953, Built as a Colony of Private Villas

West of Montego Bay in Hopewell, Round Hill Hotel and Villas has drawn transatlantic society since it opened in 1953 as a cottage colony of individually owned villas, a structure that still shapes the resort and its long-running association with Ralph Lauren.

Gossip

Newport Is Where America's Old Astor Money Lost a Very Public Fight to the Vanderbilts

Rhode Island's Gilded Age summer colony turned a rivalry between old Astor money and Vanderbilt new money into a run of stone 'cottages' along the Atlantic, several of which still stand open to the public today.

Gossip

Mackinac Island Banned Cars in 1898, and Old Midwest Money Has Summered There Ever Since

Reachable only by ferry or small aircraft, Mackinac Island has banned motor vehicles since 1898 and has quietly drawn Midwest industrial money, from the Ford to the Wrigley families, to its Victorian summer cottages for generations.

Gossip

Greenwich Is Where Wall Street's Hedge Fund Money Went Home

A 45-minute train ride from Grand Central, Greenwich, Connecticut has moved from Gilded Age railroad fortunes to one of the most concentrated hedge fund addresses in the United States, without losing its gated, low-key character.

Gossip

Park City Turned a Dying Silver Town Into Robert Redford's Sundance and an Olympic Ski Resort

A former silver-mining town in Utah's Wasatch Mountains, Park City now hosts the Sundance Film Festival each January and America's largest single ski resort, drawing a part-time celebrity population alongside Hollywood's annual arrival.

Gossip

Point Piper Holds Australia's Three Most Expensive House Sales, All on One Small Peninsula

A single harbourside peninsula east of Sydney's centre, Point Piper holds the country's record for its three most expensive residential sales and a street regularly ranked Australia's costliest.

Gossip

Sag Harbor Was Once America's Fourth-Busiest Port, Built Entirely on Whale Oil

A former whaling port that once rivalled New Bedford, Sag Harbor has spent the last few decades quietly filling with writers, artists and, increasingly, the same wealthy weekenders who colonised the rest of the Hamptons, without losing its working-village look.

Gossip

Highlands, North Carolina Was Founded on a Hunch About Where Two Lines Would Cross

A 4,000-foot-high plateau town founded in 1875 on a speculative hunch, Highlands has spent over a century as a low-profile summer retreat for old Southern money and, later, Tom Fazio-designed golf estates.