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Just a few blocks from the bustle of Old Town and Duval Street, this Caribbean-style resort is a serene retreat with a swath of white-sand beach, a pool concierge, and a private pier for fishing or gazing out over clear turquoise waters. All of the contemporary rooms and suites are generously sized and have private balconies with views of the pool, courtyard, or ocean, but the real draw remains right outside your door. Guests can snorkel off the shore, face off on the giant chess board, or simply sway between two palms in one of the beachside hammocks. They also have privileges at sister resort Casa Marina, just up the beach, including at the oceanfront Spa al Mare. Have kids in tow? The hotel offers a full roster of activities, plus babysitting services for parents who want to hit the town.

No hotel in Jamaica blends better with its surroundings than the aptly named Rockhouse, a string of villas clinging to the top of a sea cliff at the western tip of the island. Local stone, timber, and thatch are the building materials, and a harmony of design and setting is the result. The feel is rustic, but not rough (the showers might be outdoors, but the rooms are air-conditioned), and the feeling carries over to the pool, which sits on a rock platform halfway down the cliff face, from where sunbathers can don snorkel and mask and clamber down into a usually calm Caribbean. Even the restaurant hangs over the water, adding emphasis to the promise of dishes being fresh from the sea.

As does practically every hotel in Jamaica, Rockhouse has its celebrity stories, going back to the early ‘70s when Bob Marley, Bob Dylan, and the Rolling Stones added their names to the guest register. But it wasn’t until 1994, when a group of Australian owners took over, that Rockhouse began to evolve its reputation as one of the most Jamaican of Jamaican hotels. It happened in part because Rockhouse has none of the formality that some of the island’s best-known hotels, with their British colonial roots, still possess. And in part because of its active role in funding local education projects, it’s a valued, and popular, part of the community. That, and the restaurant’s homemade jerk sausage is legendary.

Berlin: Off the Wall

Minsk, the austere capital of Belarus and a former Soviet satellite, harbors Beatles cover bands, bookish bohemians feasting on salo and vodka, and the curious legacy of Lee Harvey Oswald.

Have you ever had a drink while standing at the top of a 1,700-foot vertical drop, as the sun sets into the ocean? That’s what you get at Lovers’ Leap, less than a half-hour’s drive from Treasure Beach. Pay a small entrance fee and walk through the bar to reach the balcony with the jaw-dropping view. Of course, there’s a legend to go with the name of the cliff: Two enslaved lovers jumped together from this spot to their deaths to escape from their colonial master who wanted the girl for himself. A wood carving of the lovers stands just outside the entrance. The sunset panorama here is arguably the most stunning view in all of Jamaica.

Pier 1’s greatest appeal is its setting: The open-air restaurant and nightclub occupies a pier that extends out into the Caribbean in Montego Bay. By day and into the early evening, the restaurant draws visitors and locals interested in a good meal with a stellar water view. At night, regular parties start late and run into the wee hours of the morning. Skip the noisy chain restaurant-bars down the street and try something more Jamaican, instead.

With 800 miles of coastline, the Dominican Republic boasts more than 200 beaches, from remote stretches of sand with limestone cliffs and no crowds, to soft shores with calm waters. On this varied island, you’ll also find populated beaches lined with all-inclusive resorts and restaurants; coves that are difficult to reach but worth it for the privacy; and shores backed by coconut palm groves and towering sand dunes. Whether you want to swim in tranquil water, surf major waves, or simply relax and do nothing, you’ll find a place for that here, along with standout beauty.

This tiny hideaway overlooking the sea near Port Antonio originally served as a live-in recording studio for performers such as No Doubt, Alicia Keys, and Amy Winehouse. Although recording sessions still go on, Geejam is now a seven-room hotel, its guests often honeymooning couples acting out fantasies having nothing to do with rock and roll. Geejam’s cabins, especially, are very private, and guests sometimes spend days taking meals on their veranda and splashing in their outdoor Jacuzzi without being seen by anyone but the staff, who appear only when called. Of course, who wants to stay hidden forever when the Bushbar restaurant promises convivial chitchat, an occasional game of pool, and even live music? Not to mention that the hotel beach, in a cove across a road at the bottom of the property, promises four-poster sunbeds and, yes, Wi-Fi.

Jamaican food is not all jerk and meat patties! You can sample one of the island’s most popular snacks, pepper shrimp, along the south coast. In the town of Middle Quarters, roadside vendors cook the shrimp in big steaming pots on outdoor grills. The shrimp, caught in the Black River, are boiled in salty water and then spiced with chopped scotch bonnet peppers, sea salt, vinegar, and black pepper. Plastic bags of the fiery little shellfish are peddled to drivers passing on their way home from work and to lucky tourists for a messy and addictive snack.

The hike up the Mayfield River to the waterfall nicknamed the Washing Machine requires walking in the river itself at times, and at one point, swimming through a tunnel. Along the way, you’ll be surrounded by lush fern trees and bamboo. You’ll need water shoes, a swimsuit, and a sense of adventure to take part in this, one of the best ways to see Jamaica‘s verdant interior. The trailhed is an hour’s drive from from Negril, and you’ll find lockers and a small restaurant there. Guides are always on hand to show you the way—you won’t make it without them, they know all the right places to place your foot. (Be generous with your tips—they may be having a great time, but this is their job.) The reward at the end of your hike? Two waterfalls. Swim underneath and feel the refreshing force of nature.

A journey into the ethnic neighborhoods redefining the City of Light

On the still-bucolic site of a former coconut plantation just west of Montego Bay, Round Hill is another of the legendary hotels created in the early 1950s to accommodate wealthy Brits and Americans who were discovering the pleasures of a Jamaican winter. Since then, it has evolved into a thoroughly modern resort that manages to retain its original, exclusive, clublike spirit. In the beginning, Round Hill consisted of a group of shareholders (British playwright Noel Coward was one) who rented out their private villas when they were absent. That’s how it still works, although the celebrity shareholder most mentioned these days is designer Ralph Lauren, who rents neither of his two villas. Along with 27 other villas, which can be divided into 86 suites, there’s the Pineapple House, a seafront block of 36 rooms, all decorated, predominantly white on white, by Lauren. The ambience is quiet luxury, the service is relatively formal (the doorman wears white), and the children among the guests are treated as the heirs and future holiday decision makers that they are. Almost every villa has a story, whether it has to do with Coward, the Kennedys, or How Stella Got Her Groove Back. And Montego Bay, whose city lights can be seen only from the highest villa (#28), is still another world away.

Watching the sun set on Jamaica‘s west coast is a bona fide activity. The island’s red skies are a sight to behold. I have yet to experience a better Caribbean sunset than in Jamaica. From Montego Bay all the way to Negril--famous for having the best--to Whitehouse, get your camera and Red Stripe ready for the last hours of daylight. You won’t lack for choice of seafront bars or scenic spots--from the trendy Pier One in Montego Bay to the wooden shack watering holes along Negril’s West End cliffs. Wherever you end up, there’s a very good chance you’ll get hooked on this daily sunset viewing routine.

A visit to Dubrovnik can give you a glimpse of an older Europe, one with ancient Roman sites and medieval stone walls, with charming cobbled streets and sunny market squares and the blue Adriatic Sea glittering beyond. Savor your time here by walking the city walls, toasting the sunset from a terrace bar, shopping for local crafts and delicacies, and falling in love with the “Pearl of the Adriatic.”

Philadelphia, famous as a historic city, is more than a dusty archive of Americana. World-class museums, thriving markets, busy streets full of shops and terrific restaurants: Visitors may come to see the Liberty Bell, but they’ll fall for Philly.