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We were offered the chance to visit Pompeii or Herculaneum when we docked at Sorrento. People rave about Pompeii because it’s absolutely huge and gives you a great sense of just how sophisticated Roman civilisation was. Herculaneum, by contrast, was a Roman seaside town, a sort of holiday resort, and doesn’t offer the same kind of scale. Still. I remembered my Latin lessons, and how we’d learned that while Pompeii’s buildings were smashed and burned by the falling volcanic ash, Herculaneum was actually preserved in the thick mud that engulfed it. And it’s true: wandering around the archaeological remains of the town, you feel like you’re in a place that’s only recently been abandoned. The wine shop (above) still has its amphorae stacked to the side, the houses have beautifully preserved frescoes and mosaics. What it lacks in size it more than makes up for in detail.

The Old Town’s main street, Stradun, also known as Placa, can’t be missed—it’s the biggest and widest of all the thoroughfares, and you will probably walk it several times during your stay here. It’s especially nice in the late afternoon, when the angle of the sun makes the pavement shine and the swallows soar overhead. Continue down to the old port and along the waterfront to the far end. Porporela Pier, built courtesy of the Austrian administration’s rule in Dubrovnik during the 19th century, is today somewhat of a lovers’ rendezvous. After your stroll, the benches along the pier provide a simple relaxing moment to take in the views of Lokrum island and Cavtat in the distance.

Not every celebrity who visits Harbour Island stays at the Pink Sands Hotel. Bill Gates, for instance, has his own home on the island. But Keith Richards has checked in here, as have Martha Stewart and Kate Moss. Since its opening in the 1950s, the 25-room hotel, like the island itself, has been a low-key enclave of the rich and famous, drawn not just by the like-attracts-like vibe (one of the previous owners was Island Records founder and Bob Marley “discoverer” Chris Blackwell), but by its location on Pink Sands Beach, widely considered one of the world’s prettiest. Accommodations are in plush one- and two-room cottages that have king beds and ocean or garden views; some have outdoor showers. Reserve a table at the British-colonial–inspired Malcolm 51 for island-style bouillabaisse and charred octopus salad, but don’t get too carried away with the sundowners. All manner of aquatic activities (snorkeling the nearby coral reef, bonefishing in the shallows, or merely swimming in the heated freshwater pool) await in the morning.

Ontario has another wine destination, Prince Edward County, affectionately named “The County.” This cluster of towns, about 2.5 hours east of Toronto, is home to some of Ontario’s best wineries. But never was there a great place to stay until summer 2015 when Jeff Stober, the hotelier behind Toronto’s stylish Drake Hotel, opened a rural clone, the Drake Devonshire. It’s the ideal retreat for travelers wanting their Drake by Lake Ontario. Once a 19^th-century foundry, the building is now a contemporary farmhouse-cottage, decked out with 11 individually-designed hotel rooms and two suites in the quaint town of Wellington. The property offers coziness all year round in the communal living room and out back over a lakeside fire pit and s’mores. Guests can hang in the barnlike Pavilion for musical performances, sommelier seminars, seasonal events, or just to gawk at the floor-to-ceiling mural by Brooklyn artist FAILE. It doesn’t hurt that Sandbanks Provincial Park—known for its 60-foot sand dunes—is practically the backyard of the Drake Dev.

With its lanes of thatched-roof, old-Irish bungalows fronted by flowering gardens, lovely little Adare is beloved by a certain subset of Irish grannies as the prettiest village in Ireland. It’s easy to see why: An hour south of Shannon Airport on the river Maigue, the town has charm to spare (although it’s quite touristy these days). Adare’s crown jewel is east of the town center, where the 19th-century Adare Manor lies with its pergola-covered stone walls, turrets, and gables on 840 acres of manicured gardens and wild woodlands.

Designed in grand Gothic Revival style and completed in 1862, the manor took 30 years to build—and provided valuable industry for villagers during the potato famine years. Inside, it’s a castle with some quirks: 365 stained-glass windows and 52 chimneys, for instance, for each day and week of the year. Rooms have four-poster or carved-mahogany beds, sitting areas, and semi-chintzy drapes.

After strolling through the Prague Castle complex and seeing the Cathedral and square, the traveler is further rewarded with a beautiful view of the city from a high point. Parts of Lesser Town can be seen among the sea of red-orange rooftops and greenery.

If you’re hoping to see all of Laguna in a short amount of time, hop on the free trolley, which runs in five neighborhoods during the week and along the Coast Highway on weekends. Hours vary by day and season, but are long enough to make the trolley a fun, convenient way to get around town. For special occasions from September through mid-June, you can even charter a trolley for a tour or a memorable ride to your event.

Bontemps Pâtisserie may have a name inspired by the fictional Louisiana town from the vampire series True Blood, but this retro-chic bakery is French through and through. The pâtisserie offers a refreshing twist on the signature French sable, a classic shortbread cookie, by using seasonal fillings (wild strawberry, passion fruit, blood orange). Don’t miss the larger tartes, from pecan to apple, which use the same light and crumbly shortbread crust. Take a box of minis to the Square du Temple across the street for an al fresco goûter.

Barba offers a fresh take on fast food, serving tasty items like octopus and shrimp burgers, anchovy sandwiches, and fried calamari, all made with today’s catch. Located on a small side street off Stradun, the shop is tiny and friendly—the perfect pit stop during a day of Dubrovnik sightseeing. Snag the prime table by the front window and watch the rivers of people entering town through the Buža Gate as you eat. Then, be sure to contribute to the restaurant’s growing collection of wooden forks, on which customers from all over the world write messages commemorating their travels.

After strolling Storm King Art Center or DIA Beacon, Tarry Lodge is the perfect stop on your way back to New York City. Mario Batali opened it up as a neighborhood restaurant for the Port Chester crowd and a go-to for out-of-town Manhattanites who love his Italian comfort food. Don’t miss the clam, chili, and oregano or pistachio and goat cheese pizzas. Waits can be long so if you’re trying to beat traffic just get take out from their curbside service.

Everybody loves the highs and lows of Bergamo. The charming city is actually two towns--Bergamo Alta (high) and Bergamo Bassa (low). Bergamo Alta is a beautiful walled city whose architecture dates back to medieval times. Its Piazza Vecchia, slightly overhauled in the Renaissance, is considered the most beautiful square in Italy. Bergamo Bassa is the more modern city, with architecture from the 19th and 20th century, though it still has some signs of early Renaissance. Bergamo is the gateway to the Swiss Alps.

With a massive apertivo buffet, stop by Storico for the cheapest dinner/drinks combo in town (and delicious, to boot!). For 7 euros, get a cocktail or a glass of wine, and fill your plate as many times as you like from the buffet of warm snacks—focaccia, pizza, pasta dishes, cold salads, and chips are always found on the “menu”! Make sure you sit outside, though, to get the best view of the people milling about in the beautiful Piazza de Ferrari.

Cocktails are not a huge part of the Italian culture, especially not those involving tequila. But at Bar Les Rouges, the three brothers who own the bar mix up one amazing margarita (They even come to your table asking you to sample which salt you want on the rim. Go for the smoked one, it’s perfection!). Housed in a dimly lit and slightly crumbling 16th-century palace, this is one of the most romantic spots in town—a perfect date night out.

The secluded entrance from busy Grensen Street leads you into an almost Parisian courtyard where jazz cafe Bare Jazz is located. Friendly atmosphere that welcomes all kinds of people, with a record shop on the ground floor and a coffee shop on the first floor. The best carrot cake in town, delicious coffee, and some of the best tunes around. Gigs are held frequently, showcasing local talent, but bigger stars on the Norwegian jazz sky also play there. Have a listen and enjoy a glass of red.

A favorite live music venue among locals and tourists in Negril, MXIII attracts a variety of big and smaller names onto its outdoor stage throughout the year. It also hosts the well-known annual Bob Marley Birthday Bash festival in February. Located on the cliffside of Negril, the venue is run by active, longtime resident entrepreneurs who are passionate about keeping the West End’s authenticity and entertainment vibe alive. Look for posters around town or billboards outside the venue for upcoming performances.