Beneath the boutiques and Botox, Colombia’s flashy coastal hangout is a swirling mix of coffee-stained cobblestones and urban panache. In the Centro Histórico, watch Afro-Caribbean dancers perform for tips in front of Las Bovedas, an arcade of onetime prison cells, now candy stalls. Take a meal at La Cevicheria on Calle Stuart, a hole-in-the-wall slinging ceviches of every sort. Swing by Gelateria Paradiso on Calle del Estanco del Tabaco, where a leggy, onetime political scientist from Venezuela churns out artisanal ice creams in flavors like curuba and hibiscus-basil-thyme. Leave your pride at the door of the open-sided Chiva tour bus (cartagenamastertours.com), which drunkenly crawls its way, with unlimited rum, to salsa spots and drinking dens before finally stopping at a packed discoteca.
Where to Stay
The modern, 32nd-floor Marbella Beach Loft floats above the beach and has a balcony Jacuzzi (from $199; vrbo.com/358789).
This Old City Penthouse is a 2,000-square-foot three-bed, three-bath duplex and has Colonial architecture, terraces, colorful tiles, and a spa-quality shower (from $135; airbnb.com/rooms/116127).
The ultrahip Casa Lola offers a rooftop pool, ten snug rooms, and globally sourced art and furniture (from $155; casalola.com.co).
Culebra, Puerto Rico
Unplugged castaways on the four-by-seven-mile island, a half-hour puddle-jump from San Juan or an hour ferry ride from Fajardo (though recent service cutbacks have reportedly made the journey longer), seem perfectly happy to leave the piña-colada-sipping scenesters to neighbor Vieques and its recently opened W hotel. BYOB—as in boat—or take a diving lesson (culebradivers.com) to discover the coves of Luis Peña and Cayo Norte. Hike to the sands of Carlos Rosario, Resaca, or Brava, or kayak to Soldiers Point for views stretching to St. Thomas and the British Virgin Islands. Do the most untrendy thing imaginable and watch birds (some 50,000 fliers of thirteen species dwell here), then brag about your species list over fresh grouper and hogfish at El Eden (eledenculebra.com).
Where to Stay
The Singing House comes with two bedrooms, a wraparound porch, and a private dock for sunbathing in solitude (from $275; allvacationreservations.com).
A massive great room and 1,500-square-foot terrace mark this spacious three-bedroom, three-bath house (above) near Zoni Beach(from $1,000 per week; vrbo.com/151448).
The quaint cottages at Club Seabourne, a full-service boutique hotel, are equidistant from town and beach (from $175; clubseabourne.com).