The best historic Caribbean hotels for a classic tropical escape

If you’re hoping to tap into the classic spirit of the Caribbean for an upcoming vacation, a good bet may be one of these very special West Indian hotels that hang onto the past, stylishly celebrating simpler times. 

Whether it’s preserved colonial architecture or a historic location, each offers a time warp to a different era. Be warned that a 17th- or 18th-century vibe can also mean no telephones, TVs, or air-conditioning. If those amenities are important to you, check with the hotel before booking.

  • 1. Hermitage Plantation

    Hermitage Plantation

    Hermitage Nevis

    Built sometime between 1670 and 1740, the great house of Hermitage Plantation on Nevis is a rarity in the Caribbean—a surviving relic from Alexander Hamilton’s and Admiral Horatio Nelson’s days on the island. The wood-shuttered structure, which is made out of the famously tough lignum vitae wood, and 15 gingerbread cottages are well cared for today by the Lupinacci family. The great house on the foothill of Nevis Peak is filled with antiques that aren’t too fragile to endure an evening of rum punches and a pig roast.

  • 2. Montpelier Plantation & Beach

    Montpelier Plantation & Beach

    Montpelier Nevis

    Just down the road from Hermitage on Nevis is another survivor: Montpelier Plantation & Beach, one of the original 18th-century sugar plantations. It was here that Admiral Lord Nelson married Fanny Nisbet in 1787. The two-bedroom Little House villa, one of 19 modern accommodations, is within a century-old building. The 300-year-old sugar mill is open for dining. Montpelier shuttles guests down to its private beach.

  • 3. Admiral's Inn

    Admiral's Inn

    Admiral's Inn Antigua

    Admiral Lord Nelson made his rounds of the Caribbean, stationing himself for a spell in Antigua. Today the island claims the only surviving, and not modernized, Georgian dockyard in the world, Nelson’s Dockyard. Within the UNESCO World Heritage site is the 22-room Admiral’s Inn, housed in four 18th-century waterfront buildings, including a villa in a former gunpowder store. Bricks that make up the walls were formerly ballast.

  • 4. El Convento

    El Convento

    El Convento

    The Carmelites of Spain started construction of the wood-beamed El Convento in San Juan, Puerto Rico, almost 370 years ago. Much has changed since the 1640s: The convent is now a 58-room luxury hotel with three restaurants, a plunge pool, and a Jacuzzi—although a chapel remains.

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