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It’s obviously difficult to see the top sights of Italy—and to see them properly—in just 2 weeks. But in this itinerary, we show you some of the best of them. We’ll go beyond the well-trodden (and spectacular) Rome–Florence–Venice trail to include the southern region of Campania, specifically Pompeii, which has Italy’s most complete Roman ruins. Additional stops in the center and north are Pisa (for the Leaning Tower and more) and Verona (the city of lovers since “Romeo and Juliet”).

 

Days 1, 2 & 3: Rome ★★★

Follow the itinerary suggested in “Italy in One Week." Because an extra week allows you to add a trip to Pompeii, you can probably skip Ostia Antica: Choose your third day from between the catacombs of the Via Appia Antica and Rome’s less visited museums.

Day 4: Naples ★★

Leave Rome as early as you can so that you can take in the major attractions of Naples, the “capital” of southern Italy. There is an unparalleled collection of ancient artifacts at the Museo Archeologico Nazionale, plus Titians and Caravaggios at the Museo e Gallerie Nazionale di Capodimonte. After dark, wander Spaccanapoli—the old center's main east–west thoroughfare—then make a date with a pizzeria: Neapolitans stake a reasonable claim that pizza was invented here. After dinner, wander the Mergellina boardwalk to enjoy the breezes and views of the Bay of Naples. Stay overnight in Naples, the first of 3 nights based here.

Day 5: Pompeii ★★

On day 5, take the Circumvesuviana train 24km (15 miles) south of Naples to spend a day wandering Europe’s Best-Preserved Roman Ruins at Pompeii. Be sure to pack water and lunch, because onsite services aren’t great. The city was buried for almost 2,000 years, having suffered devastation when nearby Vesuvius erupted in a.d. 79. Some of the great treasures of Italy—including the remarkable patrician villa Casa dei Vettii and the frescoed Villa dei Misteri—are found here. Return to Naples for overnighting.

Day 6: the Amalfi Coast ★★

On the morning of day 6, rent a car and drive 49km (30 miles) south of Naples along A3 until you see the turnoff for Sorrento. At Sorrento, head east along the curvy Amalfi Drive, of which Andre Gide said “[There is] nothing more beautiful on this earth.” The drive winds around the twisting, steep coastline, to the southern resorts of Positano and Amalfi, either of which would make an idyllic stopover to extend your stay. Allow at least 3 hours for this drive because it is slow moving. Alternatively, do the death-defying Amalfi Coast drive as part of an organized tour from Naples.

Days 7 & 8: Florence ★★★

Jump on the early high-speed train from Naples to Florence, then follow the Florence itinerary suggested in “Italy in One Week."

Day 9: Gothic Siena ★★★

It’s just over an hour to Siena on the rapida bus from Florence's bus station. Leave early and set out immediately on arrival for Piazza del Campo, the shell-shaped main square, including its art-filled Museo Civico (inside the Palazzo Pubblico). This is a flying visit, but you still have time to squeeze in a look at the Duomo and Museo dell’Opera Metropolitana, where you’ll find Sienese master Duccio’s giant “Maestà.” Stop on the Campo for an early evening drink and then head to a restaurant in Siena’s atmospheric back streets. Reserve an early table: The last bus back to Florence departs at 8:45pm.

Day 10: Pisa & its Leaning Tower ★★

The set-piece piazza here is one of the most photographed slices of real estate on the planet. Pisa’s Campo dei Miracoli (“Field of Miracles”) is home to the Leaning Tower, of course. You can visit the Duomo, with its Arab-influenced Pisan-Romanesque facade, the Battistero with its carved pulpit and crazy acoustics, and the rest of the piazza’s monuments and museums on the same combination ticket. You should book a slot ahead of time if you want to climb the Leaning Tower, however. For dining alla pisana, head away from the touristy piazza. The “real Pisa” lies in the warren of streets around the market square, Piazza delle Vettovaglie. Finish your visit with a stroll along the handsome promenade beside the River Arno. The last train back to Florence usually leaves at 10:30pm.

Days 11 & 12: Venice ★★★

Follow the Venice itinerary suggested in “Italy in One Week."

Day 13: Verona: city of lovers & gladiators ★★★

Although he likely never set foot in the place, Shakespeare placed the world’s most famous love story, “Romeo and Juliet,” here. Wander Piazza dei Signori and take in another square, Piazza delle Erbe, before descending on the Arena di Verona: Evoking Rome’s Colosseum, it’s the world’s best-preserved gladiatorial arena, still used for monumental opera performances in summer months. Head back to Venice for the night. It is well worth booking your tickets for the high-speed Frecciabianca train ahead of time. The journey is just 1 hour, 10 minutes, compared with over 2 hours for local service.

Day 14: Milan ★★

 

The most bustling city in Italy isn’t only about industry and commerce. Milan possesses one of Europe's great Gothic cathedrals, the Duomo. Its Biblioteca-Pinacoteca Ambrosiana, with cartoons by Raphael, is one of the great galleries of Italy. The city of St. Ambrose also hosts the Pinacoteca di Brera, a treasure-trove of art, laden with masterpieces from the likes of Mantegna and Piero della Francesca. Book ahead, too, to view Leonardo’s fading but still magnificent “Last Supper”. Stay overnight here if you are flying home or onward: It is one of the major transportation hubs of Europe.

Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.