48 Hours in Montego Bay, Jamaica

Day 1: Afternoon

10:30 a.m.: Once your flight lands at Montego Bay International Airport, head to your weekend retreat: Round Hill Hotel & Villas. A long-standing resort for the jet-set, beachfront Round Hill is a secluded collection of hotel rooms and private serviced villas. Ralph Lauren, who owns two of the villas, designed all the rooms and common areas, lending a chic, luxurious vibe to the property.

1 p.m.: Once you've settled in, kick off your easy-going Caribbean weekend with a trip to the spa. Round Hill's spa is situated along the bay, set in an old plantation home on 10 acres. Here, you can have a seaside massage or enjoy an outdoor Vichy shower surrounded by tropical foliage. The spa area offers its own secluded beachfront as well.

Day 1: Evening

6 p.m.: For dinner, head to the HouseBoat, which is almost exactly as it sounds. It takes a quick ferry ride to get to this Montego Bay establishment, which initially opened in the '70s—Steve McQueen's rumored to have stayed aboard while filming "Papillon." Today, HouseBoat is a buzzy hotspot (reservations are a must), serving a menu of light, locally-sourced fare. Dine upstairs, where the romantic setting proves to be ideal for watching the sunset. If you're visiting during lobster season, you'd be remiss not to have the HouseBoat's rendition of the tasty crustacean, served with a spicy scotch bonnet pepper beurre blanc.

9 p.m.: If you're ready to experience Jamaican nightlife, head to the Hip Strip. The colloquial name for Gloucester Avenue, this drag is loaded with bars, restaurants, shops, and other forms of entertainment. It's worth exploring during the day, but at night, you'll find live local bands, DJs spinning everything from rock to reggae, and plenty of flowing rum. Make your first stop Pier1, a small and affordable bar that plays great music, serves excellent seafood, and keeps cheap drinks flowing all night.

Day 2: Morning

9 a.m.: This morning, get out on the water—but we don't mean the Caribbean Sea. Climb aboard a 30-foot bamboo raft on the Martha Brae River, which your captain will navigate down three miles of the river, passing through the scenic jungles and forests of relawny. You'll start your voyage with a fruity welcome drink and a visit to Mrs. Martha's Herb Garden, home to countless medicinal plants and herbs used in traditional Jamaican medicine. The relaxing experience is a great way to jumpstart your day.

Day 2: Afternoon

12 p.m.: By now you're likely feeling a bit peckish. For some great jerk food without hordes of tourists, head to the Pork Pit on Gloucester Avenue. With its ramshackle exterior—think fading paint and rickety wooden stairs—you just might miss it, but once you smell the meat on the grill, you'll know you're in the right place. While jerk chicken fans rave about the barbecue at nearby Scotchies, The Pork Pit is a worthy (and much less crowded) contender. Jerk chicken and pork are cooked over open fires of pimento wood and rubbed with herbs and spices.

2 p.m.: Take a 10-minute walk down the Hip Strip to the Montego Bay Cultural Centre, home to a gallery and museum dedicated to paintings, sculptures, and other forms of art centered around Jamaica's vibrant culture. Permanent exhibits highlight arts and crafts from the area, but rotating temporary exhibits highlight other facets of the island's history, like Rastafari heritage.

Afterward, walk through the craft market to look for handmade souvenirs. You'll find straw baskets, beaded jewelry, wooden platters, instruments, and more.

Day 2: Evening

6 p.m.: For a truly unique dinner just a stone's throw from Round Hill, head to Lobster Trapp. Visible from Round Hill's beach, this low-key, family-run restaurant specializes in spiny lobster. Call the morning of or the day before you want to dine and they'll catch your lobster from one of their many traps, floating just off the coast. The lobster is then basted in a secret sauce and cooked over pimento wood—it's a truly unique experience, especially if you go at sunset. Make reservations and bring cash.

Day 3: Morning

9 a.m.: Sneak in some last-minute beach time at Round Hill's secluded beach. You can also take a Hobie Cat out for a sail, or grab some snorkeling gear—the reef near to the hotel is rife with marine life and the waters are calm and clear.

11 a.m.: Before you head to the airport, there's one Round Hill must-do: a property tour with Kingsley Blake, the resort's long-running concierge who's positively iconic in his blue jacket. On his daily tours, Blake regals guests with tales of celebrities and Hollywood's most glamorous age. He started his career at Round Hill as a teenager and can share interesting tidbits about everything from the furniture to the clientele.