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There is a staggering amount of artwork on display here. It is said that if you stood at each piece for just one minute, it would take you four years to see everything. Created by Pope Julius II in the early 16th century, the museums have expanded over the past 500 years to their current size of more than 12 acres! Highlights include the Borgia Apartments, the Raphael Rooms, the Gallery of Maps, and of course, the sublime Sistine Chapel.

On first glance, it would be easy to dismiss the 101 Hotel as merely a functional option. Stepping inside the austere five-story concrete building on Hverfisgata, however, guests discover an ultra-modern boutique lodging with minimal black-and-white decor—the work of owner-designer Ingibjörg S. Pálmadóttir—that gives it the feel of a chic downtown gallery. Contemporary paintings, photography, and sculptures by local artists appear througout the property, complementing the oak floors and wood-heavy Nordic furniture in the 38 rooms. Queen and king-size beds (there are no twin rooms) come topped with fine Italian linens, entertainment systems are state of the art, and open-plan bathrooms make extensive use of glass and offer Aveda bath products; deluxe rooms and suites up the ante with with claw-foot tubs. The hotel also has a moody restaurant and bar, a gym and spa, and a comfortable lounge area where you can put your feet up by the fire.

The Court, an off-the-radar lounge bar with front row seats to the Colosseum, is the perfect place to wind down in Rome. The bar overlooks the archaeological ruins of the Ludus Magnus (the site where the gladiators trained) and offers a view of sunset over the Colosseum, the world’s most amazing arena. The cocktails are the creation of mastermind Matteo Zed, one of Rome’s top bartenders, whose tasty Rising Sun (a gin, yuzu, and matcha cocktail) may well keep you at the bar until dawn.

“Ristorante da Ivo is where George Clooney famously likes to dine, but it’s still completely charming. It’s a tiny trattoria and very expensive, but the food is stunning. The kitchen is still family-run and it feels very local, not at all pretentious. You can get dressed up or go in jeans and a jumper. Do try the baccala, which is salted dried cod that’s been soaked in milk and whipped up with olive oil. It’s creamy and delicious.”

Read about more of McAlpine’s Venice favorites.

Perched like an eagle’s nest in the lower Alps, just steps from Italy, this 1930s landmark restaurant faces a stunning rainbow of blues in the expansive view of ocean and sky just beyond its vertiginous glass walls. Taking inspiration from his own heritage and his international kitchen staff, Italo-Argentine chef Mauro Colagreco is making a name for himself for colorful cuisine that plays with contrasts of flavor and texture. Dishes often include an uncommon ingredient—the chamomile broth, for instance, or a combination of oysters, pears, and caviar; the bread served with a poem. The food is both pretty on the plate and a pleasure for the palate.

This family-run bakery has been making cantucci (what you might know as biscotti) for decades. The clan’s patriarch, Roberto, mixes and rolls everything by hand in the back, using a recipe that he knows by heart—ask, and he will happily show you the original recipe, now splattered with egg whites and cocoa. Roberto’s delicate cantucci are far from the tooth-cracking kind sold at many places. If you are really lucky, a fresh batch of the dark-chocolate-and-pistachio variety may have just been pulled out of the oven when you arrive.

Everyone seems to be talking about Chez Nous and, frankly, it’s easy to see why. A meal here feels like dining at your most fashionable friend’s place. The restaurant is tucked away from the main drag in a beautiful Charleston single house, with a handwritten menu that changes daily, with the chef taking inspiration from the daily market as well as the cuisines of Northern Italy, Northern Spain, and Southern France. If the weather’s nice, request a table on the porch or in the courtyard.

Isola has become Milan‘s hipster hangout, so you are going to want spend a lot of time here. Best way is sleeping over, and the Isola Apartments are key. Lots of light, minimal decor and all the trappings of home, the loft apartments are great for couples with kids or other kids of third wheels.

Start your day at Deus Ex Machina, a motorcycle store in an alley full of them, whose café is the perfect spot for a cappuccino and soft scrambled eggs while you ogle the Ducatis.

Camogli is a quick 30-minute train ride out of Genoa, making it easy for an evening out for cocktails and dinner. Leave from Brignole Station, and arrive in Camogli by 6:30pm so that you can get a seaside table at Bar Auriga for a perfect Aperol Spritz as the sun sets and the waves crash in.

If you come to Genoa in late winter, you will have to deal with many cool and rainy days. BUT, you will get the privilege of shopping the amazing (i.e. 40/50% off) sales. So it’s a toss-up! If you are looking for women’s clothing, Lo Spaventarasseri has beautiful, artisan options in a lovely calm environment - perfect for trying clothing on after the holidays of overeating!

Enjoy your Pasta Alla Norma (one of the most traditional Sicilian pastas with tomatoes and roasted/fried eggplant) like the Sicilians—straight from the eggplant itself! Find a gorgeous (and large!) eggplant in one of the many street markets in Cefalu, slice off the top, and roast it whole. When soft, scoop out the eggplant flesh, and fill it with the Pasta Alla Norma. A perfect one-dish-wonder.

Just be sure to get to the markets early for good produce.

Hop on the commuter train at Lido Station (next to the Piramide Metro stop) and make the 25-minute trip to Ostia Antica, Rome’s ancient port town and administrative center. The teeming city of up to 100,000 residents is relatively well preserved and allows visitors a peek into the daily life of ancient Romans. Walk the basalt streets, visit the Forum, descend into Mithraic sanctuaries, and peruse the market stalls, which were in use until around the 5th century C.E.

Once the bayside palazzo of a shipping magnate, the recently restored Romeo juxtaposes antique and modern art in a world-class collection. Fabrics, serving pieces, and porcelain by Hermès, Andrée Putman, and J.L. Coquet complement the Kenzo Tange–designed facade of undulate glass. Doubles from $240, 39/081-017-5001. Read Tom Downey’s “Tailor Made in Naples.”

Italy’s beloved region of Tuscany brings to mind bucolic vineyards, rolling hills, and roads lined with towering cypress trees. But there’s plenty else to delight and even surprise travelers. Consider the quaint town of Punta Ala: located along the southern Tuscan coast, it’s under the radar of most travelers, yet the go-to summer escape of generations of Romans and Florentines.

Punta Ala strikes a balance between relaxation and understated elegance that encourages lingering, and the same goes for its premier place to stay: Baglioni Hotel Cala del Porto. Set against the backdrop of the Mediterranean Sea and with two adjacent beach clubs (La Vela and Alleluja), the hotel’s 38 airy rooms offer views of the gardens and marina. In the heart of Maremma, Hotel Cala del Porto is perfectly located for day boating trips out to the island of Elba, wine tasting at notable Tuscan wineries, and some of the best golfing in Italy. The regional park Bandite di Scarlino beckons with hiking trails ideal for early morning risers.