14 days in Italy Itinerary

Created using Inspirock Italy vacation planner
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Drive to Perugia San Francesco d'Assisi – Umbria International Airport, Fly to Portland



Birthplace of the Italian Renaissance

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
To find reviews, more things to do, other places to visit, and more tourist information, read Florence trip planner.

Portland, USA to Florence is an approximately 16.5-hour flight. The time zone difference moving from Pacific Standard Time to Central European Standard Time is 9 hours. Expect a bit warmer temperatures when traveling from Portland in June; daily highs in Florence reach 83°F and lows reach 65°F. On the 19th (Mon), you'll travel to Sorrento.
Tours · Historic Sites · Shopping · Wineries
Find places to stay Jun 19 — 20:

Sorrento — 3 nights

Land of the Sirens

A lovely town easily accessible from almost anywhere in the country, Sorrento overlooks the Bay of Naples and sits right on the Amalfi Drive.
Change things up with these side-trips from Sorrento: Ravello (Duomo di Ravello & Villa Rufolo), Ruderi della Basilica di Sant'Eustachio (in Scala) and Duomo di Sant'Andrea (in Amalfi). On the 20th (Tue), give your taste buds a day to remember with a local gastronomic tour. There's much more to do: tour the pleasant surroundings at Fornillo, get outside with Outdoor Activities, get a taste of the local shopping with Miniaci Art Gallery, and enjoy the sand and surf at Spiaggia Grande.

Make your Sorrento itinerary with Inspirock to find out what to see and where to go.

Traveling by train from Florence to Sorrento takes 4.5 hours. Alternatively, you can do a combination of train and flight; or drive. In June in Sorrento, expect temperatures between 82°F during the day and 68°F at night. Finish your sightseeing early on the 22nd (Thu) to allow enough time to take a train to Rome.
Tours · Historic Sites · Outdoors · Beaches
Side Trips
Find places to stay Jun 19 — 22:

Rome — 4 nights

Eternal City

Aptly nicknamed the Eternal City, Rome is the birthplace of the Roman Empire, one of the world's greatest civilizations ever.
Rome is known for historic sites, sightseeing, and nightlife. Your trip includes some of its best attractions: make a trip to St. Peter's Basilica, admire the landmark architecture of Pantheon, steep yourself in history at Roman Forum, and explore the ancient world of Palatine Hill.

To find maps, where to stay, traveler tips, and more tourist information, read Rome journey app.

You can take a train from Sorrento to Rome in 3 hours. Other options are to drive; or take a bus. In June, daily temperatures in Rome can reach 84°F, while at night they dip to 65°F. Finish your sightseeing early on the 26th (Mon) to allow enough time to drive to Pienza.
Historic Sites · Museums
Side Trip
Find places to stay Jun 22 — 26:

Pienza — 4 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. You'll find plenty of places to visit near Pienza: Castelnuovo dell'Abate (Abbazia di Sant'Antimo & Ciacci Piccolomini d'Aragona), Orvieto (Orvieto Underground, Madonna del Latte, &more) and Montalcino (Poggio Rubino, Mate Winery, &more). There's still lots to do: admire the verdant scenery at Val d'Orcia, take in the exciting artwork at Artemisia Gallery, take a stroll through Monticchiello, and learn about winemaking at Icario Winery.

To find reviews, maps, ratings, and tourist information, go to the Pienza journey maker website.

Traveling by car from Rome to Pienza takes 2.5 hours. Alternatively, you can do a combination of train and taxi; or take a bus. In June, daily temperatures in Pienza can reach 84°F, while at night they dip to 61°F. Cap off your sightseeing on the 30th (Fri) early enough to travel back home.
Wineries · Historic Sites · Nature · Shopping
Side Trips
Find places to stay Jun 26 — 30:

Italy travel guide

Landmarks · Ruins · Beaches
Italy is a land of high fashion, fine art, exquisite architecture, luxury sports cars, outstanding cuisine--and an insatiable taste for "la dolce vita." It's also home to the greatest number of World Heritage Sites in the world, making it an ideal place for your next holiday. The country boasts a varied landscape of mountain ranges, alpine lakes, and coastal towns, so it's no wonder travelers often refer to it as the bel paese (beautiful country). With so many places to visit, visitors often have a difficult time planning their itinerary. The smaller villages each feature a distinct character and a blend of architecture, art, and cuisine. In the country, you'll find countless archeological sites dating back to Roman times and beyond. The country's cities and seaside resorts are cosmopolitan powerhouses with museums, galleries, restaurants, shops, open-air markets, and pedestrian-friendly historic areas.