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Work your way from Excelsior’s top floors (slinky Chloé dresses, Balmain leather jackets) to the main floor (watches, speakers, a sea of colorful iPad cases), then down to the subterranean floors for the impressive wine shop and restaurants.

My friend Andy says you can’t go to Milan without having an evening in Brera, the tiny artsy area adjacent to Milan’s fashion center. Bar Brera is the hangout of choice for expensive liquor and people watching.

Milan invented the art of bel cafè, the pedicured bar for a delicious morning coffee or afternoon aperitivo. Passerini has a delicious selection of pastries for mornings and afternoons, and is the ideal hideaway for an aperitivo in the city center.

Artist Dan Flavin’s last installation is the Church of Santa Maria Annuciata in Chiesa Rossa, fondly known as simply Chiesa Rossa. Flavin’s light installation is a technicolor dream of electric hues across the main nave and central apse.

Easy beach access and a laid back vibe.

Hotels often say they’re “steps from the sand,” but here, it’s actually true. Location is everything at Malibu Beach Inn; it’s right on the water, with all of the 47 guest rooms and suites overlooking the crashing surf from private balconies, and a few hundred meters from the historic pier. There are about eight steps from the hotel’s restaurant terrace to its private stretch of beach underneath, where guests can order a chicken club sandwich or a glass of wine from the extensive list to enjoy on loungers.

The hotel changed hands in 2015 and has since been re-imagined by L.A.-based interior designer Waldo Fernandez; rooms and communal spaces alike feature purpose built, hand-made white oak furniture and furnishings that make clever use of space. Our suite had custom built liquor shelves tucked into a tiny corner alcove. Across the hotel, artworks include prints by Donald Sultan and Jasper Johns.

The rooms are designed to evoke a private beach house. And as you drift off among Italian linens, gazing at the stars and lulled by the white noise of never-ending waves, it’s easy to dream.

The indoor dining room and lounge and outdoor patios surrounded by greenery at this chic waterfront restaurant in Brickell are elegant, and pretty much every table has an paralleled view of downtown Miami and the bay. The menu is Italian-influenced and consistently good, and the service is always on point. Lighter dishes made with quinoa and vegetables are on offer, along with favorites such as fried chicken and beef short ribs.

Even with Segway tours rolling through and street performers loudly competing for audiences, the 15th-century Piazza Navona somehow retains a shred of grace and elegance in modern Rome. Calm Renaissance palazzi face the piazza’s centerpiece, the famous and complicated Bernini work, Fontana dei Quattro Fiumi (“Are these colossal male depictions of the four great rivers of the world writhing on top of a boulder not fancy enough? Let’s top it with an obelisk for a little visual interest.”). The piazza itself was created when a 1st-century arena was paved over to create a market square—you can still sense the oval track of the arena in the shape of the opening. Come for a gelato and some excellent people-watching, especially in the evening.

Since few areas within the city of Venice afford high perspectives of the entire city, take the elevator (no stairs) to the top of San Marco’s Campanile in Piazza San Marco. You may have to put up with a few elbows to get a spot against the railing, but it is all worth it for the spectacular panoramic views of Venice and the lagoon. While here, contemplate the history of this spectacular bell tower and observe the view from the same spot where numerous doges have stood, as well as Galileo. It was here that he introduced his telescope to the doge!

“Buongiorno, Signor Farley,” said Umberto, the head waiter at Hotel Missoni’s Cucina restaurant. By the beginning of the third day of my stay, the staff knew my name. And what I drank with breakfast. An espresso doppio was delivered to my table a minute later. “Prego,” the server said.

You’d think I was in Italy. In fact, I was 2,500 miles southeast of the country’s heel, in the capital of diminutive, oil-rich Kuwait. Opened in spring 2011, Hotel Missoni, owned by the eponymous fashion and home furnishings house, is one of many designer-conceived hotels that have popped up around the globe.

I have to confess: I have a complicated relationship with fashion. Maybe it’s related to my childhood. (Isn’t everything?) In the seventh grade, I wore a T-shirt to school that read, “My Son Is in the Navy.” My trend-conscious peers, who clearly had no sense of irony, laughed at me until the final bell rang. When I wore bowling shoes to high school, I was similarly mocked. How would I do in a hotel designed by a couturier?

I was picked up at the airport in Kuwait City in a Maserati (a complimentary perk for all Missoni guests). Not a bad start.

The property (like its sister hotel in Edinburgh, which opened in June 2009) is the brainchild of the Missoni family matriarch, Rosita. The hotel’s 169 rooms were designed to feel like her home. Compact Hans Wegner wishbone chairs and tuliplike Eero Saarinen–designed tables rest on hardwood floors, and everything—espresso cups, towels, even the swimming pool—displays the colorful striped patterns Missoni is known for. Generous helpings of turquoise, gold, and beige are splashed throughout the hotel to evoke the bayfront landscape outside, and every room looks out on the ever-expanding Kuwait City skyline. Like many things Italian, the hotel is simple and comfortable.

The Missoni team, which is fine-tuning its approach before opening hotels in larger markets, learns fast. There are no design hotel clichés here: no faucets with the function designed out of them, no overly formal staff. “Are those Camper shoes?” a waiter asked me one day at breakfast. I nodded. “Like bowling shoes,” he said. “Very cool.” Here, it seemed, fashion and I got along great.

965/2577-0000, from $414. This appeared in the September, 2012 issue.

Bicycle shop Rossignoli has been keeping Milan on two wheels for more than a century. Rossignoli is known for its fashionable cycles, which can be refurbished and reused. Likewise, they keep creativity in motion with new products and avant-garde installations during Salone del Mobile.

Family-run Ruggero is a bit of a hike from the centre of town, but in my mind, it is the best traditional trattoria in Florence, so worth the effort. You can expect textbook versions of Florentine classics from ribollita (a hearty bean-and-bread-based vegetable soup) to arista al forno (rosemary and garlic-spiked roast loin of pork), and an authentic, friendly atmosphere.

The modern minimalism of Le Méridien Chambers boutique hotel is accented by all things art. Graffiti-covered stairwells and hallways lead to rooms, each with their own original piece of art by the likes of Brits Damien Hirst and Gary Hume. Located in the vibrant Theatre District, entertainment from live music to stand-up comedy is just outside the door. As a guest, you’ll be granted free admission to the popular Walker Art Museum one mile away. Aside from the art, there are thoughtful amenities like the rain shower and heated floors, and fresh Italian cuisine at the hotel’s Marin Restaurant & Bar.

Immediately adjacent to Loews Regency, the Sant Ambroeus Coffee Bar is one of the latest outposts of this popular group of New York, by way of Milan, restaurants. The original Milan restaurant opened in 1936, and there are now three others in Manhattan, as well as one in Southampton. The Park Avenue coffee bar has an Italian art deco decor, bringing a little bit of Milan’s style to the neighborhood, and several outdoor tables. Choose from a panini or one of Sant Ambroeus’s famous pastries.

Walking through the narrow streets of Boston‘s North End might have you thinking about a delicious Italian meal. Take the time, however to explore the area on Hanover Street where the surrounding brick buildings suddenly give way to a park where Paul Revere stands guard. Commemorating his ride to warn the colonists of the impending British Invasion, the statue stands in front of a small park leading to the famous Old North Church. The setting is a perfect spot to relive the beginning of the American Revolution, and after exploring, leaves you in a location filled to the brim with restaurants and cafes to recharge before moving on.

There are few better places from which to enjoy river views and sunsets than the Ponte Vecchio, built in 1345. Spanning the Arno’s narrowest point, this is the only bridge to have survived the German bombing of the city in 1944. There have always been shops on the bridge; the original butchers and grocers were replaced by sweeter-smelling gold and silversmiths in 1593. Sitting right in the middle is a bust of Benvenuto Cellini (1500-1571), the most famous goldsmith of them all.