Historical Resort on Jamaica’s Northwest Coast with Snorkeling, Kayaking, and Glass-Bottom-Boat Trips

Black-and-white photographs line a wood-paneled bar at Round Hill Hotel and Villas in Jamaica’s Montego Bay. These photos provide a window into the early 1950s, when the resort’s guests and principal owners put on tuxedos and ball gowns to socialize on Jamaica’s sunny northwestern coastline. You might notice some familiar faces: Cole Porter, Grace Kelley, and Jackie Kennedy all preferred Round Hill for their Caribbean getaways. The warm hospitality that drew celebrities here still permeates throughout Round Hill, as Fodor’s says “most guests return again and again because of the personal service and excellent management.” The service, combined with a double-edge infinity pool, award-winning restaurant, and complimentary snorkeling and glass-bottom-boat trips helped the resort earn a spot on Travel + Leisure's T + L 500 World’s Best Hotels list in 2011.

The resort’s accommodations are divided between oceanfront rooms in the Ralph Lauren–designed Pineapple House and deluxe villa suites, which share a semiprivate pool surrounded by the island’s lush greenery. Rooms and villas strike a balance between opulence and understatement, seen in its minimalist four-poster beds, high ceilings, and twice-daily housekeeping. That balanced aesthetic spreads to the full-service spa and in the Kids Club, where staff plan full-day itineraries for visiting kids.

Executive Chef Martin Maginley and the team at Round Hill Restaurant craft contemporary Caribbean cuisine using fresh veggies and herbs from the resort’s own organic garden. Drink in ocean views along with a tropical cocktail at the new Grill at Round Hill, where chefs prepare your meal in Jamaica’s only indoor wood-fired grill. Each night of the week offers a different form of entertainment, from calypso tunes on Tuesdays to reggae and Jamaican folklore on Thursdays.

Click here for a full list of the resort’s amenities.

Montego Bay, Jamaica: Coastal City with Tropical Jungles and Vibrant Markets

Situated on Jamaica's northwest coast, Montego Bay draws vacationers year-round with its temperate climate, clear waters, and postcard-perfect beaches. Just a short ways inland, freshwater rivers cut through expanses of jungle and forested mountains, making for adventurous whitewater rafting on the Martha Brae River.

Years ago, Montego Bay was a thriving banana and sugar exporter. Remnants of the city's past line cobblestone streets at Sam Sharpe Square, where you’ll find grand Georgian architecture and a cast-iron fountain donated by a former banana baron. The city’s dynamic "Hip Strip" buzzes with duty-free boutiques and lively flea markets with brightly colored textiles, carved wooden sculptures, and natural healing oils that double as cassette-tape lubricant.

Read the Fine Print for important info on travel dates and other restrictions.