5 Best Hotels in Montserrat

Overflowing with character and characters, this rain-forest retreat is a photo album in the making, with memorable snapshots that include gardens framed by emerald hills and azure sea; colorful cocktail hours brimming with bonhomie and island gossip; and evening entertainment featuring hotly contested board games, comical calypso concerts, karaoke, ghost stories, or Montserratian dialect lessons. Warm and witty Lou and Shirley Spycalla treat guests like family, offering such complimentary extras as island tours, snack baskets, Wi-Fi access, Skype calls, beach transportation, and a cell phone loaner when hiking or beachcombing. Separate entrances guarantee privacy in the two snug, self-contained units (the poolside room is larger). If you'd rather not cook, you can feast family-style in the kitchen on enticing themed meals.

This secluded mountainside retreat offers remarkable value, individually decorated accommodations, splendid views, utter tranquility, and exquisite grounds—not to mention fascinating, self-sufficient owners who believe in respecting nature and supporting local culture. David and Clover Lea, who laughingly call themselves "well-done, but grown up hippies," built the villas themselves using recycled or indigenous materials wherever possible (even the soaps are homemade). Each one offers creative touches such as trompe l'oeil window frames, hand-painted tiles, and wraparound verandahs that afford extraordinary views. Mango Mini Cottage is nearest the 17-foot oval pool; the cozy Sweet & Simple efficiency has a microwave, CD player, TV, and fridge. Reasonably priced catering is available, using fixings from the permaculture garden and fresh eggs from the family's chickens. You can pluck your own breakfast from the extravagant fruit trees.

This aptly named inn is run by dynamo Theresa Silcott, who prides herself on being Montserrat's top hostess and who can take you to beaches and local shindigs, and even brew bracing bush teas using ingredients coaxed from her lovingly tended garden (replete with mini-nature trail). "When I'm not cooking for people," says Theresa, "I'm planting the food they eat." Locals justly laud her traditional cuisine: the intensely flavored goat water, stewed saltfish, and baked goods are cherished family recipes. A sports bar lures locals for darts, ping-pong, and events on the large-screen TV. Units are plain but clean and cheerful. Two budget rooms share a bath with a surcharge for TV and phone, while suites include a kitchenette and balcony. 

Rented to island hoteliers by Beatles producer Sir George Martin, this 1950s villa brims with history, including the owner's fabled AIR Studios (where Sting, Elton John, Eric Clapton, and Paul McCartney recorded) and guest rooms that are each named for a Beatles tune and adorned with a gold record, antiques, and sleigh or four-poster beds. Three guest rooms have access to the wraparound porch; the other three have air-conditioning. The 5 acres of lush grounds offer spectacular views of the steaming Soufrière. A Montserrat Who's Who gathers in the restaurant. Margaret, now the sole owner, greets arrivals with fresh-baked cookies, and her bountiful British breakfasts include fresh seasonal local juices and homemade preserves.

In late 2016, after a ten-year hiatus, Montserrat's oldest, classiest hostelry quite literally rose like a phoenix from the ashes; thanks to its gracious hosts, the Osborne family, its bar and restaurants again percolate with life in season, and its comfy, hexagonal rondavels are nestled amid grounds ablaze with red hibiscus, yellow allamanda, and pink oleander. Traditionally furnished rooms enlivened by local photos bear out the hotel's name with extraordinary volcano and/or water vistas: experience true tranquility sipping a rum punch on your terrace as the sun fireballs across the long, gray ribbon of Old Road Bay. Carol Osborne, American by birth, is as fiercely proud as any island native and a font of local lore and information.