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Italy

Waterfront Wanderings

Start your trip in super chic Milan; with a day or two of travel time in this cosmopolitan city, you’ll have some time to see the major sights and do a little shopping. I’ll help you uncover some retail secrets in this fashion capital.

Once in Cinque Terre, you’ll be equipped with all the information you need to successfully hike the famous Blue Trail that runs between the five towns. I’ll tell you where to try the local delicacies and the unique wines that make this region an incredible culinary destination. Seven days in this area also leaves you plenty of time for exciting day trips. I’ll guide you through authentic Genoa, a hidden gem that has successfully flown under the country’s tourism radar, and thus offers visitors the quintessential Italy experience. And for a taste of classic Tuscany, you can uncover the charms of nearby Lucca.

Stunning Lake Como has its fair share of hidden treasures. I’ll tell you about a lakeside hike that offers stunning views as it winds its way through tiny towns that are completely devoid of tourists. I’ll also show you exotic gardens, historic villas, and the best places to try Lombard food staples like risotto, gorgonzola, and polenta.

On both the Cinque Terre and Lake Como, I'll help you enjoy your watery surroundings with tips on boating rentals and swimming locations, should the water be warm enough.

Modern Milan

You’ll start your journey in Milan, the city that best showcases modern-day, Italian life; it will provide a great contrast to the historic areas that you’ll visit later on in your trip. With limited time on this travel day, spend the afternoon exploring the streets – especially its famous shopping districts.

Start with the big names in the Quadrilatero d’Oro, or the “rectangle of gold.” The buildings along vias Montenapoleone, Sant’Andrea, Manzoni, and della Spiga read like a catalogue of famous Italian designers; Armani, Cavalli, Prada, and Versace – you’ll find them all here. The high-end designers have also set up shop in the Gallerie Vittorio Emanuele II, a stunning, glass-domed arcade near the Duomo.

For designer duds at a fraction of the price, raid the racks at some of the city’s many outlets. These stores are packed with end-of-season shop and warehouse returns, stock from recently closed boutiques, and factory oversupply. There is a cluster of these outlets around the Vittorio Emanuele. A little further afield are Il Salvagente, which has three stories of well-organized merchandise, and Basement, which carries only women’s fashions and caters to upscale shoppers.

For dinner try Boccondivino, a festive spot near the Duomo that specializes in wine. Here, the sommelier takes his job very seriously, and you’ll reap the benefits with selections that perfectly compliment your food and your pallet.

Your Home Base

Lucky you! In addition to being the most beautiful of the five Cinque Terre towns, Manarola is also home to some of the best restaurants in the region.

At Trattoria dal Billy, you’ll enjoy family-style dining in the lush hills above town. The climb to the restaurant, which runs through a maze of charming alleyways, is almost as enchanting as its garden terraces, where you can sit and enjoy panoramic views of the vineyards and seascape. Though seafood is the main event here, there are plenty of pasta options that more than satisfy.

Cappun Magru is another spot offering atmospheric, al fresco dining. It’s a bit of a trek to the Casa di Marin, but your hotel can arrange transportation, and the restaurant’s hosts have been known to give their guests rides back to their hotels after dinner.

Marina Piccola is great for romance. Like most of the restaurants in the Cinque Terre, it has a beautiful view. But compared with the prolific mom-and-pop shops, it has a more upscale feel that is a lovely treat!

The Cinque Terre Trail

Today you’ll be tackling the breathtakingly beautiful terraced vineyards of Cinque Terre’s Sentiero No. 2, or blue trail. A trail pass is needed, and it can be bought at any one of the five towns’ train stations.

Take the local train to Riomaggiore, the southernmost of the five towns, and begin your hike north to your destination of Monterosso. Make sure to check the local train schedule before setting out so you don’t miss the last one of the day back to Manarola!

Along the way, you’ll enjoy incredible views, lush vineyards, and the crooked alleyways of the rainbow-colored towns; take mental notes, and save more in-depth exploration for another day, as you’ll want to finish the trail before sundown. Ristorante Belforte in the mid-point town of Vernazza is a great place for a lunch break. Reward yourself at the end of your hike with a Cinque Terre white wine and local food tasting at the Cantina du Sciacchetra in Monterosso.

Terre Hopping

Spend some time riding the rails between the Cinque Terre towns to get a more in-depth look at the ones that you found most enticing on your hike. Once on the move, you’ll uncover plenty of surprises: Peek into charming churches, climb ancient lookout towers, take chilly dips in some of the trail-side swimming holes, relax with wine and pasta on restaurant terraces, and consider a sunset boat cruise with Angelo, leaving from Monterosso. Your best dining bets in the area are Enoteca Dau Cila in Riomaggiore and Gastronomia San Martino in Monterosso.

A Secret Beach

For a guaranteed tourist-free experience, spend an afternoon relaxing on a secret beach near the town of Corniglia. Guvano is a clothing-optional slice of coast that is as fun to find as it is to relax on.

Take the train to Corniglia; above and to the right of the rail platform, you’ll find a narrow flight of stairs. Go down them, walk along a brick coastal wall, turn right, and continue until you come to an industrial tunnel with a metal gate. Ring the bell to the left to get buzzed in, and then take the path for 10 minutes until you reach a private vineyard overlooking two beaches. A paltry 5 euros will grant you entrance to this hidden, heavenly spot.

Authentic Italy

For an exciting day trip, explore the port city of Genoa, a hidden gem that has successfully flown under the country’s tourism radar, and thus offers visitors the quintessential Italy experience.

The charm of the city is in its vicoli, or historical center, which is said to be the largest in Europe. Here you can wander the twisting caruggi, or alleyways, for hours and happen upon a plethora of unexpected pleasures. Majestic palaces, secret passages, grand fountains, and imposing monuments reveal the city’s former standing as the most important harbor town of the Mediterranean.

Spend a good chunk of your time exploring the harbor and the old town, making sure not to miss peeking inside your favorite Palazzi dei Rolli along Via Garibaldi. The Basilica of Santa Maria di Castello makes for an interesting stop. You can also take a hike up to the Spianata Castelletto for views over the city and ocean.

Genoa is the birthplace of pesto, and the best place to try it is Sa Pesta. For a snack, try focaccia from one the city’s many Focacceria or gelato from Cremeria delle Erbe, which is tucked away into the Piazza Delle Erbe.

A Taste of Tuscany

If you want a change of scenery, head inland to Lucca, a Tuscan classic. Get acquainted with the city by walking the 4 km loop around the top of the old town walls – the trail serves as a park promenade and provides spectacular views of Lucca and Tuscany’s rolling hills.

Speaking of views, climb the Guinigi Tower for the best one of the city, and then explore the surrounding piazzas, duck into the San Frediano and San Michele in Foro churches, visit the duomo, and walk the beautiful gardens of Palazzo Pfanner.

Refuel at the cozy Buca di San Antonio or the more upscale Ristorante Giglio, both serving traditional Lucchesi fare. For a snack, stop by Taddeucci for some buccellato, a raisin- and anise-flavored sweet bread found only in Lucca.

If you have the interest and the time, swing by Pisa to see its famous leaning tower on your way to or from Lucca.

The Pleasures of Parma

With its five-hour, round-trip train ride, Parma makes for a more ambitious day trip than either Genoa or Tuscany. But foodies might find this lengthy journey worth the effort. Parma is one of Italy’s culinary capitals, and it serves up delicious dishes with an elegant backdrop – though primarily known for its food, the city also boasts gorgeous squares, basilicas, and theaters, which you can explore in between meals.

Sightseeing highlights of the city include the incredible Teatro Farnese, a stately theater constructed completely of wood, the frescoed ceilings of the Camera di San Paolo convent, and Cathedral Square.

The walk to Ristorante Cocchi, which is located in an unassuming hotel on the outskirts of town, is a small price to pay for the culinary delights you’ll find here. Arguably Parma’s best restaurant, this is the place to try the Parma trilogy of prosciutto, parmesan cheese, and pasta.

On your way out of town, stop by the Salumeria Garibaldi delicatessen and grab some Parma ham, parmigiano reggiano cheese, and Lambrusco wine to-go; chances are this delicious feast won’t survive your return trip!

Lakeside Luxury

Travel to Como town where you’ll trade in wheels for paddles; the preferred method of transportation in the luxe Italian Lake District is ferryboat!

Spend your afternoon exploring bustling Como Town, your home base for the next three nights. Here you can visit the Duomo and the Basilica of San Fedele, one of the oldest churches in the region. Or, take a funicular ride to Brunate, a charming town that offers incredible views over the lake.

Como is also the best town on the lake for shopping! The region supplies about 75% of Europe’s silk products, so you’ll be getting high-quality goods like ties, scarves, and shirts straight from the source.

For dinner, take the 15-minute taxi ride from the ferry terminal to Trattoria alla Costa. This family-style restaurant is homey, full of Italians, and a great place to try Lombard food staples like risotto, gorgonzola, and polenta.

The Greenway del Lago di Como

Take the area’s path less traveled on a long, lakeside walk. The Greenway del Lago di Como spans 10 km from Colonno to Cadenabbia; take the ferry from Como to the well-connected Tremezzo, and start walking southwest from there.

Along your journey, tour the Villa Carlotta and its extensive, multi-level botanical gardens, have anincredible pizza lunch at Il Cris Ristorante in the hills above Lenno, and take a detour to the famous Villa Balbianello, which you may recognize fromt he movie Casino Royale.

When you reach Colonno, you’ll have to travel by bus back to Lenno where you’ll find the nearest ferry dock hub. Or, if you’re up for it, walk there, and you’ll be afforded an entirely new set of views. Before catching your boat, grab a bottle of Vanini Osvaldo, arguably one of the world’s best olive oils, straight from the producer in Lenno.

Lake Como’s Most Charming Towns

Spend the first half of your day in the real Bellagio, a gorgeous town that inspired Vegas’s most prestigious hotel. Take your time exploring the ornate treasures hidden down every cobblestone passage and around each crooked corner. Lunch at Enoteca Cava Turacciolo is a must: In this wine cave hidden below a tucked away side street, you can sample varietals from all over Italy and purchase bottles of your favorite selections. Pair your tasting with a delicious cheese and charcuterie board.

After lunch, enjoy the scenic boat ride to Varenna, a town offering pastel-splattered charm without being over-commercialized. Consider a stop at the Villa Monastero and a hike to the Castle of Vezio, which is perched high above town and offers gorgeous views over the lake. Try dinner and dessert (tiramisu in a jar anyone?) at Osteria Quatro Pass in the village center.

Old-World Milan

While bustling Milan shows a greater resemblance to new-world cities than to the country’s classics further south, you can still find touches of old-world Italian art and charm… if you know where to look.

You likely already got a glimpse of the stately Duomo during your shopping spree; though a work of art in itself, Milan’s most famous masterpiece is a bit more difficult to catch a glimpse of. The city is home to Leonardo da Vinci’s famous Last Supper painting, and you can only see it if you book a ticket in advance. However, if you sign up for one of the city tours or guided visits that have set aside pre-arranged tickets, like Last Supper Tickets, you may be able to see this famous piece during your trip.

If you can’t score tickets to the Last Supper, two other great options for viewing Renaissance paintings are the Pinacoteca Ambrosiana and the Pinacoteca di Brera. A more offbeat gallery is found in the Cimitero Monumentale, a graveyard that doubles as an open-air museum of Italian sculpture.

Takeaways

For a traditional Milanese meal, try Ribot. This meat only – no fish – spot is a town institution and dishes up one of the best risottos in the city.

Don’t order cappuccino… after 11 am… unless you don’t mind getting quizzical looks from the locals.

In Italian markets… it’s considered rude to handle the produce. You can look, but don’t touch!

Always bring a corkscrew… to Italy (and, if you can, portable cups). You never know when the mood might strike you to buy a cheap-but-guaranteed-to-be-delicious bottle of wine.

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