21 days in Italy Itinerary

21 days in Italy Itinerary

Created using Inspirock Italy tour itinerary planner

Make it your trip
Fly
1
Rome
— 4 nights
Drive
2
Pienza
— 2 nights
Drive
3
Florence
— 5 nights
Drive
4
Cinque Terre
— 1 night
Drive
5
Milan
— 2 nights
Drive
6
Ortisei
— 1 night
Drive
7
Venice
— 5 nights
Fly

S M T W T F S
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29
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31
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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, nightlife, and museums. Your plan includes some of its best attractions: contemplate the long history of Colosseum, explore the ancient world of Palatine Hill, admire the masterpieces at Galleria Borghese, and visit Trastevere.

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

Houston, USA to Rome is an approximately 15.5-hour flight. The time zone difference when traveling from Houston to Rome is 7 hours. Traveling from Houston in May, things will get little chillier in Rome: highs are around 75°F and lows about 58°F. Finish your sightseeing early on the 27th (Fri) to allow enough time to drive to Pienza.

Things to do in Rome

Historic Sites · Museums · Tours · Neighborhoods

Side Trip

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. On the 28th (Sat), learn about winemaking at Podere Il Cocco, then learn about winemaking at Ciacci Piccolomini d'Aragona, and then do a tasting at Castiglion del Bosco Winery. Get ready for a full day of sightseeing on the next day: look for all kinds of wild species at Crete Senesi, then learn about winemaking at Azienda Agricola Leuta, then view the masterpieces at Artemisia Gallery, and finally appreciate the views at Val d'Orcia.

For reviews, photos, and tourist information, go to the Pienza online road trip planner.

Drive from Rome to Pienza in 2.5 hours. Alternatively, you can do a combination of train and taxi; or take a bus. Traveling from Rome in May, expect little chillier with lows of 53°F in Pienza. Wrap up your sightseeing on the 29th (Sun) early enough to drive to Florence.

Things to do in Pienza

Wineries · Parks · Historic Sites · Nature

Side Trips

Florence

— 5 nights

Birthplace of the Italian Renaissance

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Explore Florence's surroundings by going to Pisa (Leaning Tower of Pisa & Food Tours), Castello San Donato in Perano (in Radda in Chianti) and Siena (Wine Tours & Tastings, Museo dell'Opera Metropolitana, &more). Next up on the itinerary: explore the world behind art at Florence Academy of Fine Arts, make a trip to Piazzale Michelangelo, take in the views from Ponte Vecchio, and steep yourself in history at Basilica of Santa Croce.

To find where to stay, ratings, more things to do, and tourist information, go to the Florence day trip planning website.

Drive from Pienza to Florence in 2 hours. Alternatively, you can take a bus; or do a combination of bus and train. In May, plan for daily highs up to 71°F, and evening lows to 52°F. Wrap up your sightseeing on the 3rd (Fri) early enough to drive to Cinque Terre.

Things to do in Florence

Historic Sites · Tours · Museums · Wineries

Side Trips

Cinque Terre

— 1 night

Italian Riviera

Made up of five picturesque towns on the Ligurian coast, Cinque Terre is Italy's answer to the French Riviera.
On the 4th (Sat), tour the pleasant surroundings at Cinque Terre footpaths, see some colorful creatures with Enjoy Cinqueterre Boat Tours, then stroll through Il Sentiero da Levanto a Monterosso, and finally trek along Footpath Monterosso - Vernazza.

For where to stay, ratings, reviews, and tourist information, use the Cinque Terre trip planning tool.

Getting from Florence to Cinque Terre by car takes about 2.5 hours. Other options: take a train. Traveling from Florence in June, you can expect nighttime temperatures to be slightly colder in Cinque Terre, with lows of 60°F. Wrap up your sightseeing on the 4th (Sat) to allow time to drive to Milan.

Things to do in Cinque Terre

Outdoors · Trails · Parks · Tours

Milan

— 2 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.
Kick off your visit on the 5th (Sun): admire the striking features of Galleria Vittorio Emanuele II, contemplate in the serene atmosphere at Duomo di Milano, then make a trip to Piazza del Duomo, then stroll the grounds of Monumental Cemetery, and finally admire the masterpieces at Pinacoteca Ambrosiana. On your second day here, take in the spiritual surroundings of Basilica di San Fedele, see a show at La Casa Maledetta, then pause for some serene contemplation at Basilica San Lorenzo Maggiore, and finally admire the masterpieces at Museo Poldi Pezzoli.

Plan my day in Milan using traveler tips and tourist information provided by Inspirock.

You can drive from Cinque Terre to Milan in 3 hours. Alternatively, you can drive; or take a train. In June, daytime highs in Milan are 83°F, while nighttime lows are 64°F. Finish your sightseeing early on the 6th (Mon) so you can drive to Ortisei.

Things to do in Milan

Historic Sites · Museums · Fun & Games · Nightlife

Side Trip

Ortisei

— 1 night
UrtijÃĢi is a town of 4,637 inhabitants in South Tyrol in northern Italy. Start off your visit on the 7th (Tue): pause for some serene contemplation at Chiesa di San Giacomo, then stroll through Val Gardena, then get outside with Seceda, and finally don't miss a visit to Ortisei: Zona Pedonale.

Use Inspirock's suggestions to plan your Ortisei trip and find the best activities and attractions for your vacation.

Traveling by car from Milan to Ortisei takes 3.5 hours. Alternatively, you can drive; or take a bus; or do a combination of train and bus. In June in Ortisei, expect temperatures between 84°F during the day and 60°F at night. Wrap up your sightseeing on the 7th (Tue) early enough to drive to Venice.

Things to do in Ortisei

Outdoors · Historic Sites · Parks · Winter Sports

Side Trip

Venice

— 5 nights

City of Romance

Virtually unchanged for the last six centuries, Venice is actually a group of islands made famous by a series of canals, bridges, monuments, piazzas, and narrow pedestrian lanes.
Get out of town with these interesting Venice side-trips: Verona (Museo di Castelvecchio, Basilica di San Zeno Maggiore, &more) and Padua (Basilica e Scoletta di S.Maria del Carmine, Scrovegni Chapel, &more). There's lots more to do: contemplate the waterfront views at Canal Grande, don't miss a visit to Basilica di San Marco, explore the world behind art at Gallerie dell'Accademia, and steep yourself in history at St Mark's Campanile.

For reviews, more things to do, traveler tips, and other tourist information, you can read our Venice vacation builder.

Getting from Ortisei to Venice by car takes about 3 hours. Other options: drive; or do a combination of bus and train; or take a bus. June in Venice sees daily highs of 81°F and lows of 63°F at night. On the 12th (Sun), wrap the sightseeing up by early afternoon so you can fly back home.

Things to do in Venice

Historic Sites · Museums · Tours · Outdoors

Side Trips

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.