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Perched high above the Bay of Positano, Il San Pietro is the epitome of Italian seaside glamour—the hotel has attracted a coterie of international VIPs since its opening in 1970, including Gregory Peck, George Clooney, and Julia Roberts—but retains the charm of a family-run inn. Michelin-starred Zass restaurant culls ingredients from the property’s organic gardens, which spill down to the sea across 10 terraces teeming with local produce, and rooms feature custom ceramic tiles made in local factories using traditional techniques. If the 400 steps down to Positano’s only private beach sound daunting, an elevator cuts through the rock to water level, where tangerine loungers on the stone sundeck give way to a cove with sandy shores. Here, breezy Carlino restaurant serves up lemon spaghetti beneath a cheerful thatched roof. Prefer more active endeavors? Hugging the cliff face above, seaside tennis courts serve up sets with a dazzling view.

A departure from the pastel villas that dominate the Amalfi Coast, Parco dei Principi is a modernist edifice enveloped in tropical gardens and set on the outskirts of Sorrento. The work of famed Italian architect and designer Gio Ponti, the boxy white structure bears his signature at every turn, from the furniture and fixtures down to the blue-and-white floor tiles (each of the 96 guest rooms features a different pattern). Beyond the eye-catching geometry, accommodations are minimalist in style, featuring midcentury chairs and crisp white beds. Even the saltwater pool looks like an art piece, its angularity punctuated by a diving board that sits swanlike above the water. Tunnels cut through the cliffside lead to a private beach, where an alfresco restaurant on the waterside deck serves up fresh-caught seafood in the summer. For a bird’s-eye view of the scene, opt instead for the panoramic vistas from the terrace of the hotel’s Gio Ponti restaurant.

Right in the center of town, Capri Tiberio Palace mixes la dolce vita glamour with a globe-trotting sensibility that’s equal parts quirky and elegant. Wanderlust-inducing knickknacks such as globes, vintage trunks, and an eclectic collection of art stud the public spaces, and bookshelves are stocked with coffee-table tomes from the publisher Taschen. A white baby grand provides the soundtrack for aperitivo hour at the Jacky Bar, where wicker poufs, striped blue-and-white banquettes, and Panama hats repurposed as wall decor signal vacation vibes; things are slightly more reserved at the terrace restaurant, a formal space whose brightly colored dishes (think seared scallops with almond sauce and beef tartare with chestnut cream as well as kosher fare) are rivaled only by the panoramic views of the island’s craggy peaks coast and azure sea. And the indoor-outdoor swimming pool, though small, is a savior in the summer heat.

Copenhagen (and Denmark) are famous for being incredibly environmentally friendly. Windmills play a huge role in making that possible. One of the best places to see the large windmills installed just off Copenhagen’s coast is from the beach at Amager Beach Park. I find that the fact that they are marine windmills makes them even cooler and more fascinating than those installed on land.

The Roscioli family, famous for their nearby bakery Antico Forno Roscioli, opened this restaurant/wine bar/gourmet shop in 2005. Book several days in advance for lunch or dinner and be sure to request a ground floor table near the back of the dining room, the best of the available dining areas. Start with a selection of cured meats and a plate of burrata, then move on to spaghetti alla carbonara, one of the best in town, therefore the world. The wine list is outstanding and has surprisingly affordable labels from every Italian region. If you can’t snag a table, pop in for an apertif before dinner service.

Tucked in an alley near the historic downtown you’ll find this small restaurant serving traditional, regional dishes (at a great price especially for the area). With open-air courtyard seating surrounded by vines, it makes for a relaxing lunch. For the best and freshest thing on the menu, take advantage of the friendly staff and ask for a recommendation– they’ll point you in the right direction. If you’re like me and spend the entire day walking until you’re ravenous, this is a great place close to the Duomo. Try the stuffed zucchini flowers (one of my favorites in any Italian restaurant)!

Let the wind blow through your hair as you take a 30-minute vaporetto ride to Burano, an island in the lagoons of Venice. Known for its brightly-colored fishermen’s homes, the island is largely free of the tourist crush of the rest of Venice. Spend the afternoon shopping for exquisite handmade lace and sampling gelato, then do as the locals do - gather in the town square at sunset to enjoy drinks and people-watching in one of the many cafes.

We settled in at Trattoria Da Primo, where the bartender recommended a typical Venetian drink, the “Spritz” (Prosecco, Aperol or Campari liqueur, and soda). Then get ready to feast at Trattoria da Romano, regular host to locals, tourists, and visiting artists. The restaurant is famous for Venetian specialities such as creamy Goh fish risotto and fresh seafood. Burano is definitely the place to go for a quiet, small-town feeling night out in Italy.

A Naples legend well before Julia Roberts (in Eat, Pray, Love) gave it celebrity sheen, Da Michele was opened by the Condurro family in 1930. The only pizzas are marinara and margherita, and they are pure classics. 39/081-553-9204.

The tram gives Portland visitors stunning views of the city, river, and mountains beyond. Grab the streetcar from downtown out to the waterfront. You’re delivered to the lower terminal for the three-minute ride carrying you 3,300 feet at 20 MPH to the upper terminal at OHSU. Linger for photo ops then head back down to explore. If it’s nice, skip the streetcar and walk back along the river. Daily workout, check. Roundtrip cost: $4. At the lower terminal, the Daily Cafe is an easy find in the atrium of the OHSU Clinical building as you disembark the pill-shaped car, built with precision by the Swiss. Head for the river and stroll along the shore in any weather. Double back along SW Bond Ave and consider lunch at Bambuza Vietnamese Bistro. Check out the pricey high-rise condos on the market in the real estate office windows, then relax in one of the pocket parks to people watch. It snows in Portland. A couple of times a winter, even downtown gets dusted and it’s a huge mess. I’ve dreamed about getting my ski gear on, grabbing my boards and heading for the PDX Tram at the South Waterfront. I’d casually climb aboard with the patients and medical folks heading up to “Pill Hill” and blow their minds.

An hour’s cross-island drive takes you to Kalinago Territory, officially established in 1903 as the Caribbean’s only autonomous enclave for indigenous people. The settlement covers six square miles, and many of its 3,000 inhabitants live in traditional wooden huts. Guests are welcome at a model village, where they can watch dance performances and shop for reed baskets and other crafts.

Cesare al Casaletto is far off the well-beaten tourist track, but it is easy to get to: just take the 8 tram from Piazza Venezia or Largo Argentina and get off at the very last stop. Fifty yards from the tram tracks sits Rome‘s best trattoria, where spectacular fried appetizers (get them all, or at least the gnocchi fritti and polpette di bollito) give way to classic pasta dishes like carbonara and gricia. The second courses are excellent and fall-off-the-tailbone braised oxtail is a favorite. Pair it all with fairly priced natural wines from all over Italy and be sure to leave room for dessert, preferably the panna cotta.

One of Florence’s grand cafés since its founding in 1733, Caffè Gilli is easily recognized by the Swiss clock hanging outside above its entrance and by the glass display case of multicolored confections inside. Enjoy your morning cappuccino or evening prosecco while standing at the marble-topped bar, or experience the café’s formal service by sitting at a polished wooden table under elegant chandeliers in the tearoom. For more-casual warm-weather meals, there is a large shaded patio with comfortable seating and a fantastic view of the carousel in Piazza della Repubblica.

While the enormous Royal Palace in Stockholm’s Old Town is the king’s official residence, the family lives outside the center at Drottningholm. And this being Sweden, everyone is allowed to stop by. You can visit the interior, excluding the royal family’s private wing, and then roam around the extensive grounds. The estate is also famed for its theater, which still uses the original stage equipment from the 18th century. UNESCO lists Drottningholm as a World Heritage Site: “With its palace, perfectly preserved theatre (built in 1766), Chinese pavilion and gardens, it is the finest example of an 18th-century northern European royal residence inspired by the Palace of Versailles.”

In a pastel villa that presides over pine-covered slopes and the deep blue waters of the Ligurian Sea, Belmond Hotel Splendido was a 16th-century monastery before it became a cliff-side luxury hotel at the turn of the 20th century. Today, it is one of Portofino’s most iconic resorts, with 70 sunlit rooms (think herringbone hardwood floors, marble baths, and wrought iron terraces) that have hosted the Duke of Windsor, Ava Gardner, and Catherine Deneuve. You’ll get the VIP treatment while sipping champagne on a sunset cruise aboard the hotel’s Chris-Craft Corsair 36, dining on seabream ceviche at La Terrazza, or indulging in a chamomile footbath at the spa. A shuttle can run you down to intimate sister property Splendido Mare, which overlooks the central Piazzetta and is a dressed-up version of a fishing village pied-à-terre, with 16 whitewashed rooms and its own buzzy restaurant.

Tucked away on the less-trafficked slopes of Mount Portofino, above the picturesque waterfront town of Camogli and scenic Riviera di Levante, Villa Rosmarino is that Italian friend’s vacation house you’ve been dreaming of. Owners Mario Pietraccetta and Fulvio Zendrini left Milanese corporate life to transform this dilapidated turn-of-the-century palazzo into a midcentury-style oasis with touches of Italian modernism, then moved in permanently, inviting others to experience their personal brand of la dolce vita. The library is outfitted with stylish armchairs, warm wood ceiling beams, and a collection of art and travel books that spans the walls, and the living room’s well-stocked honesty bar is the backdrop for friendly nightcaps. Rooms aren’t numbered, and the sprawling gardens are easy to get lost in. Mario and Fulvio are likely to chat guests up while lounging by the pool or sipping espresso on the balcony, offering their insider knowledge about the area and arranging one-of-a-kind excursions, from visits to secluded beach clubs to rides in their wooden motorboat.