Newport, Rhode Island, winked into life in 1639 as a working town. It was crucial to shipping and seafaring before and well after the Revolutionary War, and it’s still home to the United States Naval War College. It didn’t remain the sole province of sailors, however. Around the mid-19th century, the well-heeled began fleeing the high-summer swelter of the cities to bask in the sea breezes and sapphire skies of Newport. The Gilded Age transformed the “cottage” into an ironic moniker applied to absurdly lavish million-dollar mansions that were occupied only 10 weeks a year.

The arrival of the income tax and air-conditioning ended Newport’s reign as the seasonal home of America’s wealthiest and most powerful, but it has never completely fallen from favor. Hosting the country’s earliest tennis tournaments, the first U.S. Open golf tournament and the America’s Cup race for the better part of the 20th century helped maintain its reputation. Presidents Dwight D. Eisenhower and John F. Kennedy looked to Newport as the destination for their summer White House, and Kennedy married Jacqueline Bouvier at St. Mary’s Church in the city in 1953. Gilded Age glamour remains a draw, but so too do forms of music that probably would have scandalized the high society of old — the Newport Jazz Festival and the Newport Folk Festival draw crowds every summer.

Early Morning

The day begins at the Hideaway Report-recommended Castle Hill Inn, situated on its own peninsula near the end of Ocean Drive. Built in 1874 by marine scientist Alexander Agassiz as a summer home, the 33-room property serves breakfast in the Agassiz Mansion. Maine lobster hash, smoked salmon toast and omelettes made with spinach, tomatoes and goat cheese provide the kickoff to a fully packed day.