11 days in Milan, Tuscany & Naples Itinerary

11 days in Milan, Tuscany & Naples Itinerary

Created using Inspirock Italy travel route planner
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— 4 nights
— 2 nights
— 3 nights


Milan — 4 nights

Fashion Capital of World

In many ways the most modern of Italian cities, Milan is a busy, elegant metropolis with an impressive list of grand palaces, fine churches, and important museums.
You'll find plenty of places to visit near Milan: Turin (Museo Nazionale del Cinema, Museo Egizio, &more) and Verona (Museo di Castelvecchio, Piazza delle Erbe, &more). There's still lots to do: buy something for everyone on your list at Galleria Vittorio Emanuele II and appreciate the extensive heritage of Piazza del Duomo.

To find where to stay, maps, ratings, and other tourist information, use the Milan trip itinerary maker.

Newark, USA to Milan is an approximately 12.5-hour flight. You'll lose 6 hours traveling from Newark to Milan due to the time zone difference. In December, daily temperatures in Milan can reach 46°F, while at night they dip to 34°F. Finish your sightseeing early on the 23rd (Fri) so you can drive to Pienza.
Museums · Historic Sites · Shopping · Neighborhoods
Side Trips
Find places to stay Dec 19 — 23:

Pienza — 2 nights

Pienza, a town and comune in the province of Siena, in the Val d'Orcia in Tuscany (central Italy), between the towns of Montepulciano and Montalcino, is the "touchstone of Renaissance urbanism."In 1996, UNESCO declared the town a World Heritage Site, and in 2004 the entire valley, the Val d'Orcia, was included on the list of UNESCO's World Cultural Landscapes.HistoryBefore the village was renamed to Pienza its name was Corsignano. Change things up with these side-trips from Pienza: Eremo Le Celle (in Cortona), Rapolano Terme (Spas & Pieve San Vittore) and Orvieto (Pozzo di San Patrizio, Duomo di Orvieto, &more). There's still lots to do: stop by RI Crea RE, don't miss a visit to Corso il Rossellino, take in the architecture and atmosphere at Church of San Francesco, and take in the spiritual surroundings of Tempio di San Biagio.

To find reviews, photos, and more tourist information, refer to the Pienza itinerary maker site.

You can drive from Milan to Pienza in 4.5 hours. Other options are to do a combination of train and bus; or do a combination of flight, train, and bus. Traveling from Milan in December, expect Pienza to be somewhat warmer, temps between 57°F and 40°F. Finish your sightseeing early on the 25th (Sun) to allow enough time to drive to Naples.
Historic Sites · Nature · Shopping · Parks
Side Trips
Find places to stay Dec 22 — 25:

Naples — 3 nights

Naples is the capital of the Italian region Campania and the third-largest municipality in Italy after Rome and Milan. On the 26th (Mon), appreciate the extensive heritage of Underground Naples, take in the spiritual surroundings of Museo Cappella Sansevero, stop by Cosmos-Artigianato Napoletano, then don't miss a visit to Via San Gregorio Armeno, and finally see the interesting displays at Museo Archeologico Nazionale di Napoli. On your second day here, take in the architecture and atmosphere at Duomo di Salerno, then make a trip to Centro Storico Salerno, then take in nature's colorful creations at Villa Comunale, and finally don't miss a visit to Promenade Trieste.

To find photos, other places to visit, maps, and more tourist information, read Naples tour planning app.

Traveling by car from Pienza to Naples takes 4 hours. Alternatively, you can do a combination of taxi and train; or do a combination of bus and train. In December in Naples, expect temperatures between 59°F during the day and 42°F at night. On the 28th (Wed), you'll have the morning to explore before heading back home.
Historic Sites · Museums · Parks · Shopping
Side Trip
Find places to stay Dec 25 — 28:

Tuscany travel guide

Landmarks · Art Museums · Sacred & Religious Sites
Birthplace of the Italian Renaissance
Known for its landscapes, traditions, and history, Tuscany possesses an unparalleled artistic legacy that continues to influence world culture. Regarded as the birthplace of the Italian Renaissance, the region boasts a lengthy list of attractions, including world-class museums, art galleries, and archeological sites. With a distinct culture and a very strong linguistic identity, this region is sometimes referred to as a nation within a nation. A land of picture-postcard areas, Tuscany contains plenty of places to visit on your holiday, with seven World Heritage Sites, including the historic town centers of Florence and Siena. With more than 120 protected nature preserves, Tuscany is not only a land of culture and historic monuments, but also a great place to discover and enjoy the Italian outdoors. Take it slowly here (as the locals do), and give yourself plenty of time to get to know the local culture and cuisine of Tuscany's medieval towns and ancient villages.