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Leeward Islands
By Matthew Joyce, Tom Morrisey

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The islands of the Lesser Antilles' northern chain may share a location sheltered from prevailing northeasterlies, but that's about all they have in common. Name your sport, then pick your island.

Anguilla
The scrub-covered, flat, dry interior of this 35-square-mile island is no place to spend your hard-earned time off, but if you keep to the perimeter you're in beachgoers' heaven. Of Anguilla's 33 stellar beaches, hailed as the best in the Caribbean, first prize goes to Rendezvous Bay, a two-mile-long sandy crescent on the island's southwest side, where you can search for driftwood and seashells among the dunes. First runner-up is palm-shaded Savannah Bay, on the relatively undeveloped east end, which serves up respectable bodysurfing waves and a steady onshore breeze. Also in the east end is Shoal Bay Beach, a favorite among the locals because of its beachfront cafés and snorkeling on a close-to-shore reef.

When the ocean is calm, Dive Anguilla (two-tank dive, $70; 809-497-2020), in Sandy Ground on the northwest side, can take you to Prickly Pear Reef, an underwater canyon eight miles off the north coast, where you can swim among huge staghorn corals, sergeant majors, and striped squirrelfish. Closer in is Sandy Deep, a mini-wall rising 15 to 60 vertical feet. After dark, fill up on lobster and beer at Johnno's in Sandy Ground, where locals gather for barbecues and live reggae.

For beachfront digs, you could splurge at Cap Juluca Resort (doubles, $595-$1050 per night, including breakfast and all water-sports; 800-323-0139), a Moorish extravaganza of white-domed villas on Maunday's Bay in the west end, but your money goes twice as far at La Sirena Hotel (doubles, $230-$295; villas, $295-$495; 800-331-9358). Near Mead's Bay Beach, also on the west end, it has 20 rooms and five villas spread around two pools and a landscaped garden. For bargain rates, stay in one of three beachside studio apartments at La Palma Guesthouse in Sandy Ground (doubles $75; 809-497-3260).

Nevis
During the seventeenth century, provincial Nevis became the social hub of the Caribbean when it attracted European aristocrats to its renowned Bath Hotel and Spa just outside Charlestown, the capital. The spa spent a long time in ruins, but a recent renovation has opened it to twentieth-century travelers (a 15-minute soak costs just $2).

You can get to Nevis from its sister island, St. Kitts, via the daily plane (one way, $25), but it's better to approach this laid-back, 36-square-mile island on the old green ferry (one way, $4) that links Basseterre, the Kittitian capital, to Charlestown. During the 11-mile, 45-minute ride, the island comes into focus: cloud-capped Nevis Peak, long-abandoned sugarcane fields, and the remnants of the old sugar mills that once were the island's economic mainstay.

The best way to see the island is on foot. Because of a welcome dearth of tourist-oriented businesses, arrangements for hikes, walks, and horseback rides are best made through individual resorts. Golden Rock Estate (doubles, $245, breakfast and dinner included; 809-469-3346), in the hills above the east coast, is a 16-room former sugar estate with bougainvillea-covered stone buildings, hiking trails, and 96 acres thick with orange, mango, and grapefruit trees.

The oceanfront Nisbet Plantation Beach Club (doubles, $355-$455, including breakfast and dinner; 809-469-9325), on the north shore, recalls its previous incarnation as an eighteenth-century coconut plantation with a reconstructed great house and 38 ceiling-fan-cooled rooms. Horseback riding along the beach and through old plantation pastureland ($45 for two hours) as well as guided hikes ($30 per person) can be arranged through the hotel. The most challenging is a five-hour vine-and-root-grabbing ascent of 3,232-foot Nevis Peak, but given the clouds that often obscure the mountain, you may see more scenery 50 feet under at Monkey Shoals reef, where you'll spot nurse sharks and octopuses hiding among sea fans and fluorescent sponges. Scuba Safaris in Oualie Beach (two tank dive, $80; 809-469-9518) handles everything from resort courses to full certification.

Montserrat
With lush rain forests, waterfalls, black-sand beaches, and sawtooth mountains, Montserrat inexplicably ranks among the least-developed and least-visited islands in the Eastern Caribbean. and the volcano spewing ash at press time certainly won't help. Nevertheless, the 39-square-mile island is well-known among road cyclists and mountain bikers, who appreciate its tortuous terrain. Montserrat's perimeter road measures less than 28 miles, but it climbs from sea level to 800 or more feet seven times, making it a challenging ride for even the fittest cyclists. Mountain bikers come for the annual Montserrat Mountain Bike Challenge (this year, November 8-15; see calendar, page 24), a weeklong festival sponsored by Island Bikes (rentals, $25 a day, $140 a week; 800-675-1945) in Plymouth, the island's only real town.

The most spectacular route for hiking or biking is a day-long trip through the South Soufrière Hills. It starts with a climb to the top of 1,700-foot Galway's Soufrière, then races downhill through head-high ferns and dense bamboo thickets before crossing elfin woodland, steep gullies, and banana fields and ending with a rollercoaster ride over the Centre Hills back into town.

Settle in at the Providence Estate House (doubles, $77- $92; 809-491-6476), a secluded two-room bed-and-breakfast plantation home that has hosted Paul McCartney and Stevie Wonder. But the island's best digs are at the Vue Pointe Hotel (doubles, $140; cottages, $195; 800-235-0709) with 12 rooms and 28 hexagonal cottages perched above the gray sands of Olde Road Bay on the northwest coast. Snorkeling, diving, and fishing trips with local boat captains can be booked through Aquatic Discoveries at the hotel (two-tank dive, $65; charters, $200-$350), which also rents sea kayaks (half-day, $45; full day, $75).

Guadeloupe
Your high-school French comes in handy on this tropical-island outpost of France, where English speakers are as common as Wonder bread in a boulangerie. Located near the southern end of the Leeward chain, the 530-square-mile island has a butterfly shape and a split personality. Grande-Terre, its eastern wing, is as flat as a crepe and fringed with beaches, while its wild, mountainous western half, Basse-Terre, gets fewer visitors than downtown Detroit.

Hikers should head for the 74,000-acre Parc National on Basse-Terre, where Organisation des Guides de Montagne de la Caraïbe (011-590-80-0579) leads daylong treks amid the rainforest-covered peaks ($122 per person), as well as half-day sorties ($75 per person) up the sulfur-spewing, 4,813-foot La Soufrière volcano. Mountain bikers can work off their French-Creole suppers with a thigh-burning climb up 16-mile Route de la Traversée over a 2,350-foot pass. Bikes cost $16 a day or $96 a week at Locatesse (590-88-9143) in Sainte Anne, a fishing village turned resort town on Grande-Terre's south coast.

Pigeon Island, off the west coast of Basse-Terre, ranks among Jacques Costeau's ten best dive sites for its sponge-encrusted walls and teeming schools of tropicals. Les Heures Saines (590-98-8663) offers single-tank dives ($38) and weeklong dive/villa packages ($662 per person, including lodging, breakfast, and ten dives) at Le Paradis Creole, a ten-room hotel with patios overlooking Pigeon Island.

Boardsailors hang out at Centre UCPA ($500 per person per week, including lodging, meals, equipment, and lessons; 590-88-6480), a no-frills, 60-room complex on the southeast coast. You can also stay in Sainte Anne at Hôtel La Toubana (doubles, $187-$318, breakfast included; 590-88-2578), with 32 air-conditioned, red-roofed bungalows on a bluff above Caravelle Beach.

Saba
There's unmistakable charm in an island where conch shells serve as alarm clocks, cottages are chalk-white with red roofs, the only “highway” is called simply The Road, and the capital, situated at the foot of the mountain, is officially called The Bottom.

It is Saba's other bottom that attracts most of the 28,000 annual visitors to this five-square-mile island. The Saba Marine Park (011-599-4-63295), which protects Saban waters down to 200 feet, contains some of the most pristine reefs and walls in the Caribbean. It maintains moorings on 26 designated sites ($2-per-dive use fee), ranging from the 45-foot-deep Hot Springs, where the geothermal-spring-bathed sand is warm to the touch, to Third Encounter, a seamount at 90 to 100 feet.

Winter water temperatures here are in the high seventies, perfect for attracting pelagics. If the currents are right, you can swim due west from Third Encounter and, after a minute or two, a skyscraperlike form begins to resolve from the underwater mist. This is Eye of the Needle (90 feet), a slender volcanic pinnacle festooned with sponges and frequented by barracuda and blacktip sharks. For a shallower dive, you can circumnavigate Man of War Shoal (70 feet), which offers encounters with virtually every species of Caribbean reef fauna.

A small-party specialist charter is Saba Deep Dive Center (two-tank dives, $80, equipment included; 599-4-63347) in Fort Bay Harbor. Somewhat larger boats are operated by Sea Saba Advanced Dive Center (two-tank dive, $89; 599-4-62246) and Wilson's Dive Shop (two-tank dive, $80; 599-4-62541), but Saba really has no cattle-boat operations.

On Saba, most divers stay in the town of Windwardside. One of the largest properties is the Captain's Quarters (doubles, $135, breakfast included; 599-4-62201), with 12 rooms. The newly opened Cottage Club (one-bedroom units, $105; 599-4-62386) has ten cottages on the edge of a ravine. Willard's of Saba (doubles, $180-$300; 599- 4-62498), secluded high on the mountain, is Saba's luxury hotel, with seven rooms, a pool, and tennis courts.

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