14 days in Italy Itinerary

Created using Inspirock Italy vacation planner
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Birthplace of the Italian Renaissance

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
For ratings, reviews, maps, and tourist information, you can read our Florence online trip maker.

Portland, USA to Florence is an approximately 16.5-hour flight. You'll lose 9 hours traveling from Portland to Florence due to the time zone difference. Traveling from Portland in June, things will get somewhat warmer in Florence: highs are around 83°F and lows about 65°F. You will leave for Pienza on the 19th (Mon).
Tours · Historic Sites · Shopping · Wineries
Find places to stay Jun 19 — 20:

Pienza — 3 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: Orvieto (Pozzo di San Patrizio, Duomo di Orvieto, &more). There's still lots to do: appreciate the views at Val d'Orcia, steep yourself in history at Historic Centre of the City of Pienza, view the masterpieces at Artemisia Gallery, and make a trip to The Checche Oak Tree.

To find more things to do, photos, maps, and more tourist information, use the Pienza trip planner.

Traveling by car from Florence to Pienza takes 2 hours. Alternatively, you can take a bus; or do a combination of train and bus. In June, daytime highs in Pienza are 84°F, while nighttime lows are 61°F. Finish your sightseeing early on the 22nd (Thu) to allow enough time to drive to Rome.
Historic Sites · Parks · Nature · Wildlife
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: explore the ancient world of Colosseum, don't miss a visit to Piazza Navona, steep yourself in history at St. Peter's Basilica, and admire the local landmark of Trevi Fountain.

For other places to visit, ratings, traveler tips, and other tourist information, read Rome trip planner.

Drive from Pienza to Rome in 2.5 hours. Alternatively, you can do a combination of taxi and train; or take a bus. In June in Rome, expect temperatures between 84°F during the day and 65°F at night. Wrap up your sightseeing on the 26th (Mon) to allow time to take a train to Sorrento.
Historic Sites · Museums · Neighborhoods
Side Trip
Find places to stay Jun 22 — 26:

Sorrento — 4 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.
Explore the numerous day-trip ideas around Sorrento: Ravello (Villa Rufolo & Duomo di Ravello), Positano (Fornillo, Absolute Positano, &more) and Pompeii Archaeological Park (in Pompeii). On the 27th (Tue), give your taste buds a day to remember with a local gastronomic tour. And it doesn't end there: see what you can catch with a fishing tour, don't miss a visit to Piazza Tasso, and take in the spiritual surroundings of St Francis Church and Convent.

To find where to stay, maps, photos, and more tourist information, go to the Sorrento road trip planning app.

You can take a train from Rome to Sorrento in 3 hours. Alternatively, you can drive; or take a bus. In June, plan for daily highs up to 82°F, and evening lows to 68°F. Wrap up your sightseeing on the 30th (Fri) early enough to fly back home.
Tours · Outdoors · Historic Sites · Wildlife
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.