21 days in Italy Itinerary

21 days in Italy Itinerary

Created using Inspirock Italy trip itinerary planner

Make it your trip
Fly
1
Venice
— 2 nights
Drive
2
Florence
— 4 nights
Drive
3
San Gimignano
— 3 nights
Drive
4
Monteriggioni
— 3 nights
Drive
5
Rome
— 4 nights
Train
6
Sorrento
— 4 nights
Fly

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Venice

— 2 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.
Change things up with these side-trips from Venice: Padua (Basilica of St. Anthony, Scrovegni Chapel, &more). Next up on the itinerary: explore the activities along Canal Grande, get to know the fascinating history of Piazza San Marco, admire the masterpieces at Peggy Guggenheim Collection, and make a trip to St Mark's Campanile.

To see reviews, maps, more things to do, and other tourist information, read our Venice online trip builder.

Birmingham, UK to Venice is an approximately 5.5-hour flight. You can also take a train; or do a combination of car and train. Traveling from Birmingham to Venice, you'll lose 1 hour due to the time zone difference. Traveling from Birmingham in May, things will get somewhat warmer in Venice: highs are around 26°C and lows about 15°C. Finish your sightseeing early on the 4th (Wed) so you can drive to Florence.

Things to do in Venice

Historic Sites · Museums · Parks · Nature

Side Trip

Find places to stay May 2 — 4:
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Florence

— 4 nights

Birthplace of the Italian Renaissance

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
You'll find plenty of places to visit near Florence: San Michele in Foro (in Lucca) and Leaning Tower of Pisa (in Pisa). The adventure continues: admire the masterpieces at Florence Academy of Fine Arts, appreciate the history behind Campanile di Giotto, get to know the fascinating history of Piazza del Duomo, and admire the landmark architecture of The Baptistery of St. John.

To find other places to visit, where to stay, traveler tips, and other tourist information, go to the Florence trip itinerary builder app.

You can drive from Venice to Florence in 3 hours. Alternatively, you can take a train; or take a bus. In May, plan for daily highs up to 25°C, and evening lows to 13°C. Wrap up your sightseeing by early afternoon on the 8th (Sun) to allow enough time to drive to San Gimignano.

Things to do in Florence

Historic Sites · Museums · Parks

Side Trips

Find places to stay May 4 — 8:
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San Gimignano

— 3 nights

Town of Fine Towers

A historical gem in the heart of Tuscany, San Gimignano is known as the Town of Fine Towers for its jutting skyline of high city walls.
Get out of town with these interesting San Gimignano side-trips: Siena (Museo dell'Opera Metropolitana, Wine Tours & Tastings, &more). There's lots more to do: do a tasting at Guardastelle Vineyard, make a trip to Duomo di San Gimignano, and contemplate the long history of Historic Centre of San Gimignano.

To see where to stay, other places to visit, photos, and tourist information, refer to the San Gimignano day trip planning app.

You can drive from Florence to San Gimignano in 1.5 hours. Alternatively, you can take a train; or take a bus. Expect a daytime high around 25°C in May, and nighttime lows around 13°C. Finish your sightseeing early on the 11th (Wed) so you can drive to Monteriggioni.

Things to do in San Gimignano

Historic Sites · Wineries · Tours · Museums

Side Trip

Find places to stay May 8 — 11:
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Monteriggioni

— 3 nights
Change things up with these side-trips from Monteriggioni: Poggio Amorelli (in Castellina In Chianti), Radda in Chianti (Castello Monterinaldi & Fattoria di Montemaggio) and Montefioralle Winery (in Greve in Chianti).

To see more things to do, where to stay, maps, and more tourist information, go to the Monteriggioni trip builder.

You can drive from San Gimignano to Monteriggioni in an hour. Other options are to take a train; or take a bus. In May, daily temperatures in Monteriggioni can reach 27°C, while at night they dip to 13°C. On the 14th (Sat), wrap the sightseeing up by early afternoon so you can drive to Rome.

Things to do in Monteriggioni

Wineries · Tours

Side Trips

Find places to stay May 11 — 14:
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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 trip includes some of its best attractions: take in the architecture and atmosphere at St. Peter's Basilica, steep yourself in history at Palatine Hill, take in the spiritual surroundings of Vatican Museums, and don't miss a visit to Roman Forum.

For other places to visit, maps, reviews, and other tourist information, you can read our Rome attractions planner.

Traveling by car from Monteriggioni to Rome takes 3 hours. Alternatively, you can take a bus; or take a train. Expect a daytime high around 28°C in May, and nighttime lows around 17°C. Finish up your sightseeing early on the 18th (Wed) so you can catch the train to Sorrento.

Things to do in Rome

Side Trip

Find places to stay May 14 — 18:
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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.
Change things up with these side-trips from Sorrento: Amalfi (Antichi Sapori d'Amalfi, Duomo di Sant'Andrea, &more), Positano (Boat Tours & Water Sports, Il Sentiero Degli Dei, &more) and Pompeii (Odeon - Teatro Piccolo, Villa dei Misteri, &more). There's much more to do: steep yourself in history at Villa Rufolo, take in the spiritual surroundings of Duomo di Ravello, and don't miss a visit to Piazza Tasso.

For maps, where to stay, photos, and other tourist information, refer to the Sorrento visit planning app.

Traveling by train from Rome to Sorrento takes 3 hours. Alternatively, you can drive; or take a bus. Expect a daytime high around 27°C in May, and nighttime lows around 18°C. Wrap up your sightseeing on the 22nd (Sun) to allow time to fly back home.

Things to do in Sorrento

Historic Sites · Outdoors · Tours · Parks

Side Trips

Find places to stay May 18 — 22:
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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.