Why Among the wealthiest isles on earth, this land of coral walls, pastel cottages, and pleasant locals in shorts hasn't changed much since Queen Elizabeth II first visited, in 1953. "It's a place that can erase your memories of the modern world," says one New Yorker who retreats to this British colony throughout the year.
How to Get There Bermuda is a short flight from Boston or Philadelphia (both two hours). With the arrival of JetBlue, which you can take from New York's JFK (two hours also), look for more affordable airfares.
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.
Why Extending along the Atlantic coast, Georgia's barrier islands are pristine and uncrowded—perfect for beach hopping. Our favorite locations include St. Simons, Jekyll, Sea, and Cumberland islands. (Note: Sea Island is private and is exclusive to hotel guests and members.)
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.