44 days in Italy Itinerary

Created using Inspirock Italy trip itinerary builder
Make it your trip
Fly
1
Florence
— 11 nights
Drive
2
Pienza
— 9 nights
Drive
3
Rome
— 10 nights
Train
4
Sorrento
— 12 nights
Fly

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1

Florence — 11 nights

Birthplace of the Italian Renaissance

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Venture out of the city with trips to San Gimignano (Historic Centre of San Gimignano, Fattoria Il Piano, &more), Siena (Complesso Museale Santa Maria della Scala, Centro Storico di Siena, &more) and Pisa (Piazza dei Miracoli, Leaning Tower of Pisa, &more). Next up on the itinerary: explore the world behind art at Florence Academy of Fine Arts, contemplate in the serene atmosphere at Cathedral of Santa Maria del Fiore, enjoy breathtaking views from Campanile di Giotto, and make a trip to Piazzale Michelangelo.

For reviews, maps, and tourist information, read Florence holiday planner.

Seattle, USA to Florence is an approximately 16-hour flight. The time zone difference moving from Pacific Standard Time to Central European Standard Time is 9 hours. In May, plan for daily highs up to 71°F, and evening lows to 52°F. On the 31st (Wed), you'll have the morning to explore before heading off to Pienza.
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Historic Sites · Museums · Shopping · Tours
Side Trips
Find places to stay May 19 — 31:

Pienza — 9 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. Venture out of the city with trips to Castiglion Fiorentino (Cantina Gabriele Mazzeschi, winery Agriturismo Santo Stefano, &more), Montalcino (Terralsole, Azienda Agricola Capanna di Cencioni, &more) and Ciacci Piccolomini d'Aragona (in Castelnuovo dell'Abate). There's lots more to do: tour the pleasant surroundings at Val d'Orcia, do a tasting at Decugnano dei Barbi, don't miss a visit to Corso il Rossellino, and shop like a local with Artemisia Gallery.

To find ratings, maps, traveler tips, and more tourist information, read our Pienza trip itinerary planning site.

Traveling by car from Florence to Pienza takes 2 hours. Alternatively, you can take a bus; or do a combination of train and bus. May in Pienza sees daily highs of 74°F and lows of 53°F at night. On the 9th (Fri), wrap the sightseeing up by early afternoon so you can drive to Rome.
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Wineries · Historic Sites · Shopping · Parks
Side Trips
Find places to stay May 31 — Jun 9:

Rome — 10 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, let your taste buds guide you at a local gastronomic tour, steep yourself in history at Palatine Hill, and visit Trastevere.

To find traveler tips, other places to visit, more things to do, and tourist information, refer to the Rome trip maker tool.

Traveling by car from Pienza to Rome takes 2.5 hours. Alternatively, you can do a combination of taxi and train; or take a bus. In June, plan for daily highs up to 84°F, and evening lows to 65°F. Wrap up your sightseeing on the 19th (Mon) to allow time to take a train to Sorrento.
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Historic Sites · Museums · Neighborhoods · Tours
Side Trip
Find places to stay Jun 9 — 19:

Sorrento — 12 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: Collegiate Santa Maria Maddalena (in Atrani), Positano (Il Sentiero Degli Dei, Chiesa di Santa Caterina, &more) and Praiano (IL Presepe nella Roccia, Parrocchia Di San Gennaro, &more). Next up on the itinerary: don't miss a visit to Pompeii Archaeological Park, explore the ancient world of Odeon - Teatro Piccolo, take a memorable drive along Amalfi Coast, and admire the landmark architecture of Villa dei Misteri.

To find ratings, reviews, other places to visit, and tourist information, refer to the Sorrento trip planning app.

Traveling by train from Rome to Sorrento takes 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. Finish up your sightseeing early on the 1st (Sat) so you can catch the flight back home.
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Historic Sites · Parks · Tours · Outdoors
Side Trips
Find places to stay Jun 19 — Jul 1:

Italy travel guide

4.6
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.
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