• The Admiral's Inn (Antigua; http://admiralsantigua.com; tel. 268/460-1027): The most historically evocative corner of Antigua is Nelson's Dockyard, which was originally built in the 1700s to repair His Majesty's ships. The brick-and-stone inn that flourishes here today was once a warehouse for turpentine and pitch. In the late 1960s, it was transformed into a well-designed and very charming hotel. Note: If you're sensitive to noise, you might be bothered by the sometimes raucous bar and restaurant.
  • Avila Hotel (Curaçao; www.avilahotel.com; tel. 800/747-8162 or 599/9-461-4377): This hotel's historic core, built in 1780 as the "country house" of the island's governor, retains its dignity and elegance. Although it's been a hotel since the end of World War II, 150 bedrooms in outbuildings and upgraded sports and dining facilities were artfully added in recent years. Today the Avila provides a sandy beach and easy access to the shops and distractions of nearby Willemstad.
  • Spice Island Beach Resort (Grenada; www.spicebeachresort.com; tel. 473/444-4258): Each of this hotel's 64 units is a suite (with Jacuzzi) either beside the beach (one of Grenada's best) or near a swimming pool. Friday night features live music from the island's most popular bands.
  • Gallery Inn at Galería San Juan (Puerto Rico; www.thegalleryinn.com; tel. 866/572-ARTE [2783] or 787/722-1808): The most whimsically bohemian hotel in the Caribbean sits on a coastal bluff. Once the home of an aristocratic Spanish family, it is today filled with sculptures, silk screens, and original paintings by artist Jan D'esopo, who, along with husband Manuco Gandía, owns the inn. Many of the rooms have dramatic views of the coast, with two historic Spanish forts framing the view. Staying in one of the comfortable rooms here is like living in an art gallery.
  • Ottley's Plantation Inn (St. Kitts; www.ottleys.com; tel. 800/772-3039 in the U.S., or 869/465-7234): As you approach, the inn's dignified verandas appear majestically at the crest of 14 hectares (35 acres) of impeccably maintained lawns and gardens. It's one of the most charming plantation-house inns anywhere in the world, maintained with style and humor by its expatriate U.S. owners. The food is the best on the island, and the setting will soothe your tired nerves within a few hours of your arrival.
  • Montpelier Plantation Inn (Nevis; www.montpeliernevis.com; tel. 888/334-7609 or 869/469-3462): Style and grace are the hallmarks of this former 18th-century plantation, now converted to an inn and set on a 12-hectare (30-acre) estate. Guests have included the late Princess of Wales. Cottage rooms are spread across 4 hectares (10 acres) of ornamental gardens. Swimming, horseback riding, windsurfing, a private beach, and "eco-rambles" fill the agenda.
  • The Hermitage Plantation Inn (Nevis; www.hermitagenevis.com; tel. 800/682-4025 in the U.S., or 869/469-3477): Guests stay in clapboard-sided cottages separated by carefully maintained bougainvillea and grasslands. The beach is a short drive away, but this slice of 19th-century plantation life (complete with candlelit dinners amid the antiques and polished silver of the main house) is decidedly romantic.
  • The Frangipani (Bequia, the Grenadines; www.frangipanibequia.com; tel. 784/458-3255): This is the century-old homestead of the Mitchell family, whose most famous scion later became prime minister of St. Vincent. Today it's a small, very relaxed inn. It's fun to watch the yachts setting out to sea from the nearby marina.

Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.