THE CARIBBEAN
Where to Stay A cottage colony on the remote west end, Cambridge Beaches (30 Kings Point Rd., Sandys; 800/468-7300 or 441/234-0331; www.cambridgebeaches.com; doubles from $430) is from another, more charming era. Mandarin Oriental is pouring millions into renovating Elbow Beach (60 S. Shore Rd., Paget Parish; 800/223-7434 or 441/236-3535; www.mandarinoriental.com; doubles from $475). The intimate Reefs Hotel (Southampton; 800/742-2008 or 441/238-0222; www.thereefs.com; doubles from $488) has updated its rooms for a sleeker look.
Where to Eat After a ploughman's lunch at the Lighthouse Tea Room (Southampton; 441/238-8679; lunch for two $25), take in the panoramic view upstairs. For a formal night, the Fourways Inn (1 Middle Rd., Paget; 441/236-6517; dinner for two $130), in an 18th-century residence, delivers.
Insider Tip More fun than the bus (and cheaper than a taxi), the island's ferry system is a great way to mix with the locals—and to avoid driving a moped along the wrong side of Bermuda's notoriously narrow roads.
2. PUERTO RICO
Why This simple-to-reach isle is a rapid remedy for adventure-seekers craving an adrenaline rush. Rappel 250 feet into the prehistoric Camuy Caves, 60 minutes west of San Juan, or hike El Yunque rain forest. Wind down on a tour of Hacienda Buena Vista (Hwy. 123; 787/722-5882; $7), a former coffee plantation near Ponce, about 70 miles south of the capital.
How to Get There Most airlines fly to San Juan from major U.S. cities, including New York (3 1/2 hours), Miami (2 1/2 hours), and Dallas (4 1/2 hours).
Where to Stay Old San Juan makes an ideal base for exploring. Book a room at Chateau Cervantes (329 Recinto Sur, Old San Juan; 787/724-7722; www.cervantespr.com; doubles from $300), a boutique property in a Spanish colonial building with interiors by a local fashion designer.
Where to Eat Grab a porrito (fish taco) and honey-lemon ginger juice at Pure & Natural (1125 Ashford Ave.; 787/725-6104; lunch for two $30), in San Juan's Condado district. At night, dine at the minimalist Marmalade (317 Fortaleza St.; 787/724-3969; dinner for two $90), on a trendy street in Old San Juan.
Insider Tip You can pick up a pound of Puerto Rico's muy fuerte coffee at any market for far less than those beans at Starbucks.
UNITED STATES
Where to Stay The recent multimillion-dollar renovation of the Cloister at Sea Island (800/732-4752 or 912/638-3611; www.seaisland.com; doubles from $725) pays homage to the original Addison Miznerdesigned version. Built in 1887 as a hunting lodge for the likes of the Vanderbilts and Rockefellers, the Jekyll Island Club Hotel (371 Riverview Dr.; 800/535-9547 or 912/635-2600; www.jekyllclub.com; doubles from $179) is a surprisingly affordable hideaway. The 10-room Greyfield Inn (Cumberland Island; 866/410-8051 or 904/261-6408; www.greyfieldinn.com; doubles from $350), a Georgian mansion with a broad front porch, was converted into a guesthouse in 1962 by Andrew Carnegie's grand-niece.
Where to Eat Courtyard at Crane (375 Riverview Dr., Jekyll Island; 912/635-2600; dinner for two $85) offers up local seafood. At Halyards (600 Sea Island Rd., St. Simons; 912/638-9100; dinner for two $110), tables are made of teak from shipwrecked boats.
Insider Tip Check out the golf cartsized tree trunks and limbs scattered along the shores of Driftwood Beach on Jekyll Island.
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