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Colonial Seduction
Golden Rock Plantation Inn, Nevis
Don’t fret about the colonialist fantasies you’ll start entertaining during your stay at Golden Rock Plantation Inn, a converted 1811 sugar mill and estate tucked into the hilly interior of Nevis. Here you are, with your run of the bougainvillea-and-bromeliad gardens and cool, quiet interiors of a 96-acre manor overseen by the very accommodating Pam Barry, an American expat and descendant of the mill’s founder. You can’t be blamed for imagining that this lava-stone empire is your home, even if the fantasy is a tad un-PC. You’ll regain your senses when your prop plane takes off, leaving behind this 50-square-mile blip in the West Indies.
THE GOOD LIFE: From the fresh orange-passionfruit-banana juice served with breakfast on the shady patio to the seductive rum punch doled out at sundown from the bamboo bar in the lodge, Golden Rock provides visitors a peaceful, revitalizing escape. Wake to sea views from any of the seven guest cottages or the romantic sugar-mill suite. Amble over to breakfast, launch point for the day’s adventures, then return for dinner (islandy cuisine like tamarind-ginger chicken).
SPORTS ON-SITE: Hike a half-hour nature trail to spot the resident colony of black-faced vervet monkeys, as well as nutmeg trees and elephant ear plants.
BEYOND THE SAND: Horseback rides fuel aristocratic delusions, especially astride handsome equines like Barclay, a 16-year-old retired Thoroughbred racer. Outings from Nevis Equestrian Centre include cantering through the surf (90-minute rides, $55; 869-469-8118).
THE FINE PRINT: American Eagle (800-433-7300, ) flies to Nevis daily from San Juan, Puerto Rico (round-trip airfare from Denver costs about $980). From December 24 to April 14, doubles at Golden Rock (869-469-3346, ) cost $210–$275, including breakfast.—Janine Sieja

Linen Casual
Pink Beach Club, Bermuda
On Bermuda, the very proper British territory 640 miles off the coast of North Carolina—not technically in the Caribbean, though it feels like it—the hotel of the moment is the newly refurbished Pink Beach Club. The extensive renovation of this traditional Bermudian “cottage colony” made it through Hurricane Fabian in September 2003. The club centers on a manor-style main house, for dining and socializing, surrounded by 20 cottages with coral-colored stone walls and whitewashed roofs. It’s all steps from the, yes, pink beach.
THE GOOD LIFE: The Caribbean goes formal in the freshened-up guest rooms, with cherrywood beds, framed botanical prints on the walls, Italian ceramic-tile floors and, thankfully, still no televisions. The Hibiscus Lounge, with its colonial decor and fireplace, is the ideal perch for afternoon tea with scones, marmalade, and butter cookies.
SPORTS ON-SITE: Play tennis (of course) at the club, snorkel off the beach, or rent a bike for a mellow pedal.
BEYOND THE SAND: Paddle a glass-bottom sea kayak around St. George’s Bay with Vee McKey, of Kayak Bermuda, who’ll point out the soaring Bermuda longtails and the parrotfish and blue tangs darting around a reef’s fan coral, as well as the remains of a 17th-century British fort (two-and-a-half-hour tours, $65; 441-505-2925, ). Or go shipwreck diving—more than 400 boats have fallen prey to Bermuda’s treacherous reefs, including 16th-century Spanish treasure ships and modern-day freighters.
THE FINE PRINT: US Airways (800-428-4322, ) flies to Bermuda International Airport from New York, Boston, Philadelphia, and Washington, D.C., for about $700 round-trip. Doubles at the Pink Beach Club (800-355-6161, ) cost $385–$535 and include breakfast, dinner, and afternoon tea.—Jill Fergus

Cliffside Incognito
Steele Point, Tortola
Like a crude copy from the Sistine Chapel’s ceiling, Tortola’s westernmost finger is outstretched with the promise of divine rejuvenation. Reaching heaven may require a lifetime of purgatory, but at Steele Point—a gated eight-acre promontory splitting the Atlantic and the Caribbean—a loose grip on your checkbook will suffice. The estate’s two houses, one balanced like a spider crab in a 125-foot cliff and connected to the other by an orchid-garnished network of decks and catwalks, are popular among jetsetters with names like Rockefeller and Hearst.
THE GOOD LIFE: Steele Point mixes seclusion with the convenience and amenities of the largest British Virgin Island. The four-level, 4,200-square-foot main house, made of cypress, has four suites with marble floors and low-slung modern decor. The stucco Gestalt house also has four suites. Humble or extravagant, your tastes will be met by a personal chef, an on-call masseuse, and a staff that can provide anything from fresh wahoo to a 100-foot yacht.
SPORTS ON-SITE: From the Point’s docks you can access Anegada’s sand flats for legendary bonefishing or dive shipwrecks like the RMS Rhone.
BEYOND THE SAND: Tortola’s 21 square miles of undulating jungle provide ample room to pedal or gallop. After a ride, try a Pain Killer at Pusser’s Outpost, in Road Town; it’s made from the same rum the Royal Navy used as bottled courage for 300 years.
THE FINE PRINT: American Eagle (800-433-7300, ) flies from San Juan, Puerto Rico, to Tortola (round-trip from New York, about $500). A week in the four-bedroom main house at Steele Point (610-239-6445, ) costs $12,000 in high season—a not-so-astronomical $214 per person per night if you fill it to its eight-person capacity. The Gestalt house costs $6,500 per week. Prices cover lodging only.—Grayson Schaffer