This Indian Ocean island off the coast of Kenya is “gypset to the core,” particularly amid the coral-walled houses of Shela village, a 15-minute dhow ride from Lamu Town. “The center of the action is the Peponi Hotel (doubles from US$281), where everyone from Princess Caroline to penniless poets gather for cocktails on the harbor-side terrace.” To fit in, Chaplin suggests picking up an embroidered caftan or a flamingo-feather-trimmed scarf from nearby boutique Aman (254-733/455-821).
Montauk, United States
Ditch Plains Beach is the center of the summer scene at this working-class resort town turned surfer/fashion-designer playground at the tip of Long Island, New York. “In the evenings, the gypset crowd migrates to the restaurant at the Crow’s Nest Inn, which serves terrific local seafood amid beachy-tribal decor.”
North Goa, India
“There’s a hotel to suit every mood” in the northern half of India’s legendary hippie state. For rest and relaxation, Chaplin recommends Elsewhere (tents from US$483 per week), an enclave of colonial beach houses and luxury tents. Nearby, Sur La Mer (doubles from US$206) caters to party-hunters with villa-style digs centered on a courtyard swimming pool. And for a quirky, no-frills experience, book one of the grass-thatched “domes” at Yab Yum (doubles from US$54) on Ash-vem Beach—“They look like half-buried coconuts.”
Originally appeared in the December 2012/January 2013 print issue of DestinAsian magazine (“Ready, Set, Go”)