23 days in Italy Itinerary

23 days in Italy Itinerary

Created using Inspirock Italy tour itinerary planner

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Route & dates

23 days in Italy Itinerary

Start: Toronto
Fly:  12​h 30​min
1
Rome
— 3 nights
Train + Subway:  3​h
2
Ravello
— 4 nights
Drive:  4​h 30​min
3
Assisi
— 3 nights
Drive:  1​h 45​min
4
Siena
— 3 nights
Bus:  1​h 15​min
5
Florence
— 4 nights
Train:  2​h 15​min
6
Venice
— 4 nights
Fly:  11​h 15​min
End: Toronto

3
nights
Rome

Rome ©
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, museums, classes, and shopping. Your plan includes some of its best attractions: delve into the distant past at Colosseum, steep yourself in history at Palatine Hill, admire the masterpieces at Vatican Museums, and admire the local landmark of Trevi Fountain.

Plan trip to Rome with our itinerary maker to find out where to go and what to do.

Toronto, Canada to Rome is an approximately 12.5-hour flight. You can also do a combination of bus and flight. Traveling from Toronto to Rome, you'll lose 6 hours due to the time zone difference. Traveling from Toronto in August, expect Rome to be somewhat warmer, temps between 38°C and 24°C. Finish your sightseeing early on the 19th (Wed) to allow enough time to travel to Ravello.

Things to do in Rome

Historic Sites Museums Neighborhoods

Side Trip

Vatican City
Find places to stay Aug 15 — 19:
Highlights from your plan
Colosseum ©
Colosseum
Pantheon ©
Pantheon
St. Peter's Basilica ©
St. Peter's Basilica

4
nights
Ravello

Ravello ©
You'll find plenty of places to visit near Ravello: Positano (Il Sentiero Degli Dei, Kayaking & Canoeing, & more).

Plan a trip to Ravello easily and quickly by telling Inspirock to suggest an itinerary.

Getting from Rome to Ravello by combination of train and subway takes about 3 hours. Other options: drive; or do a combination of train and bus. Expect slightly colder weather when traveling from Rome in August: highs in Ravello hover around 34°C, while lows dip to 28°C. Finish your sightseeing early on the 23rd (Sun) to allow enough time to drive to Assisi.

Things to do in Ravello

Parks Outdoors Beaches

Side Trips

Positano, Amalfi, Lido Capo di Conca
Find places to stay Aug 19 — 23:
Highlights from your plan
Fornillo ©
Fornillo
Spiaggia di castiglione ©
Spiaggia di castiglione

3
nights
Assisi

Assisi ©
Rich in culture and religious tradition, Assisi is known as the birthplace of St.
Venture out of the city with trips to Montioni Frantoio e Cantina (in Montefalco) and Decugnano dei Barbi (in Orvieto). Next up on the itinerary: take in the architecture and atmosphere at Basilica Papale e Sacro Convento di San Francesco d'Assisi, contemplate in the serene atmosphere at San Damiano, walk around Mount Subasio, and learn about winemaking at Bibenda Assisi.

To see ratings, more things to do, other places to visit, and more tourist information, use the Assisi road trip tool .

Drive from Ravello to Assisi in 4.5 hours. Alternatively, you can take a train; or do a combination of bus and train. Traveling from Ravello in August, plan for little chillier nights in Assisi, with lows around 20°C. Wrap up your sightseeing on the 26th (Wed) to allow time to drive to Siena.

Things to do in Assisi

Wineries Historic Sites Parks

Side Trips

Decugnano dei Barbi, Montioni Frantoio e Cantina
Find places to stay Aug 23 — 26:
Highlights from your plan
Tili Vini Societa Agricola ©
Tili Vini Societa Agricola
Eremo delle Carceri ©
Eremo delle Carceri

3
nights
Siena

Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
When in Siena, make a side trip to see Guardastelle Vineyard in San Gimignano, approximately 52 minutes away. There's lots more to do: make a trip to Piazza del Campo, browse the collection at Biblioteca Piccolomini, deepen your understanding at Scuola di Cucina di Lella, and pause for some serene contemplation at Duomo di Siena.

For photos, more things to do, and more tourist information, refer to the Siena visit website .

You can drive from Assisi to Siena in 2 hours. Alternatively, you can take a bus; or take a train. In August, daytime highs in Siena are 37°C, while nighttime lows are 22°C. Finish up your sightseeing early on the 29th (Sat) so you can catcht the bus to Florence.

Things to do in Siena

Tours Historic Sites Wineries

Side Trip

Guardastelle Vineyard
Find places to stay Aug 26 — 29:
Highlights from your plan
Wine Tours & Tastings
Piazza del Campo ©
Piazza del Campo
Duomo di Siena ©
Duomo di Siena

4
nights
Florence

Florence ©
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Step out of Florence to go to Pisa and see Leaning Tower of Pisa, which is approximately 1h 20 min away. There's much more to do: see the interesting displays at Academy Of Florence Art Gallery, take an in-depth tour of Basilica di Santa Croce, get great views at Piazzale Michelangelo, and enjoy breathtaking views from Campanile di Giotto.

To find photos, reviews, where to stay, and more tourist information, refer to the Florence trip planner.

Take a bus from Siena to Florence in 1.5 hours. Alternatively, you can drive; or take a train. In August, plan for daily highs up to 35°C, and evening lows to 20°C. Wrap up your sightseeing on the 2nd (Wed) to allow time to take a train to Venice.

Things to do in Florence

Historic Sites Museums Tours

Side Trip

Leaning Tower of Pisa
Find places to stay Aug 29 — Sep 2:
Highlights from your plan
Cathedral of Santa Maria del Fiore ©
Academy Of Florence Art Gallery ©
Academy Of Florence Art Gallery
Piazzale Michelangelo ©
Piazzale Michelangelo

4
nights
Venice

Venice ©
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.
Explore the numerous day-trip ideas around Venice: Arena di Verona (in Verona) and Scrovegni Chapel (in Padua). And it doesn't end there: explore the activities along Canal Grande, capture your vacation like a pro with an inspiring photography tour, browse the exhibits of Doge's Palace, and make a trip to Piazza San Marco.

To see maps, more things to do, traveler tips, and other tourist information, refer to the Venice journey maker app .

Traveling by train from Florence to Venice takes 2.5 hours. Alternatively, you can drive; or take a bus. In September, plan for daily highs up to 29°C, and evening lows to 17°C. Wrap up your sightseeing on the 6th (Sun) early enough to travel back home.

Things to do in Venice

Historic Sites Museums Tours

Side Trips

Scrovegni Chapel, Arena di Verona
Find places to stay Sep 2 — 6:
Highlights from your plan
Canal Grande ©
Canal Grande
Basilica di San Marco
Basilica di San Marco
Doge's Palace ©
Doge's Palace

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