23 days in Italy Itinerary

23 days in Italy Itinerary

Created using Inspirock Italy tour planner

Make it your trip
Fly
1
Venice
— 3 nights
Drive
2
Cinque Terre
— 3 nights
Drive
3
Florence
— 7 nights
Train
4
Sorrento
— 5 nights
Train
5
Rome
— 4 nights
Fly

S M T W T F S
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Venice

— 3 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.
Your inner history buff will appreciate Piazza San Marco and Peggy Guggenheim Collection. Doge's Palace and Ponte dei Sospiri are good opportunities to explore the local culture. Explore the numerous day-trip ideas around Venice: PDC Cartizze (in Valdobbiadene) and Padua (Basilica of St. Anthony & Scrovegni Chapel). Next up on the itinerary: admire the striking features of Basilica di San Marco, take in the architecture and atmosphere at Santa Maria dei Miracoli, snap pictures at Ponte di Rialto, and explore the activities along Canal Grande.

Quickly create a custom-made itinerary for Venice using our trip planner.

Toronto, Canada to Venice is an approximately 11.5-hour flight. Due to the time zone difference, you'll lose 6 hours traveling from Toronto to Venice. In September in Venice, expect temperatures between 29°C during the day and 17°C at night. Finish up your sightseeing early on the 19th (Mon) so you can go by car to Cinque Terre.

Things to do in Venice

Historic Sites · Museums · Wineries · Nature

Side Trips

Find places to stay Sep 16 — 19:
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Cinque Terre

— 3 nights

Italian Riviera

Made up of five picturesque towns on the Ligurian coast, Cinque Terre is Italy's answer to the French Riviera.
On the 20th (Tue), step into the grandiose world of Castello Doria, then trek along Footpath Monterosso - Vernazza, and then get into the urban bustle at Vernazza. Get ready for a full day of sightseeing on the next day: hike along Cinque Terre Trails, then take in the waterfront at Passeggiata Lungomare, and then enjoy the sand and surf at Spiaggia di Fegina.

To see where to stay, other places to visit, maps, and tourist information, read our Cinque Terre itinerary site.

You can drive from Venice to Cinque Terre in 4.5 hours. Alternatively, you can fly; or take a train. Expect a daytime high around 30°C in September, and nighttime lows around 17°C. Finish your sightseeing early on the 22nd (Thu) so you can drive to Florence.

Things to do in Cinque Terre

Outdoors · Parks · Trails · Historic Sites
Find places to stay Sep 19 — 22:
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Florence

— 7 nights

Birthplace of the Italian Renaissance

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Your inner history buff will appreciate Cathedral of Santa Maria del Fiore and The Baptistery of St. John. Do some cultural sightseeing at Piazzale Michelangelo and Ponte Vecchio. Venture out of the city with trips to Siena (Palazzo Pubblico and Museo Civico, Duomo di Siena, &more), Fattoria Casa Sola (in Barberino Val d'Elsa) and Castello di Verrazzano (in Greve in Chianti). There's lots more to do: admire the masterpieces at Pitti Palace, enjoy breathtaking views from Campanile di Giotto, learn about winemaking at Castello del Trebbio, and get to know the fascinating history of Piazza del Duomo.

To find reviews and more tourist information, read our Florence online sightseeing planner.

You can drive from Cinque Terre to Florence in 2.5 hours. Another option is to take a train. In September, daily temperatures in Florence can reach 30°C, while at night they dip to 17°C. Finish your sightseeing early on the 29th (Thu) so you can take a train to Sorrento.

Things to do in Florence

Historic Sites · Wineries · Museums · Tours

Side Trips

Find places to stay Sep 22 — 29:
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Sorrento

— 5 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.
Deepen your sense of the past at sights like Pompeii Archaeological Park and Duomo di Sant'Andrea. Your itinerary includes some good beach time at Fornillo and Marina di Puolo. Explore Sorrento's surroundings by going to Ravello (Villa Rufolo, Duomo di Ravello, &more), Il Sentiero Degli Dei (in Positano) and Amalfi (Museo della Carta, Antichi Sapori d'Amalfi, &more). The adventure continues: take in the spiritual surroundings of Pontificio Santuario della Beata Maria Vergine del Santo Rosario di Pompei, take a tour by water with Boat Tours & Water Sports, steep yourself in history at Lupanar, and take in the waterfront at Marina Grande - Antico Borgo Marinaro.

For traveler tips, reviews, and more tourist information, go to the Sorrento trip planning app.

Traveling by train from Florence to Sorrento takes 4.5 hours. Alternatively, you can do a combination of train and flight; or drive. Plan for a bit warmer nights when traveling from Florence in September since evenings lows in Sorrento dip to 23°C. Wrap up your sightseeing on the 4th (Tue) early enough to take a train to Rome.

Things to do in Sorrento

Historic Sites · Outdoors · Tours · Parks

Side Trips

Find places to stay Sep 28 — Oct 4:
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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.
Deepen your sense of the past at sights like Colosseum and Piazza Navona. Let the collections at Vatican Museums and Galleria Borghese capture your imagination. And it doesn't end there: delve into the distant past at Pantheon, contemplate the long history of Roman Forum, take in the architecture and atmosphere at St. Peter's Basilica, and ponder the design of Trevi Fountain.

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

Take a train from Sorrento to Rome in 3 hours. Alternatively, you can drive; or take a bus. Expect slightly colder evenings in Rome when traveling from Sorrento in October, with lows around 15°C. Wrap up your sightseeing on the 8th (Sat) early enough to fly back home.

Things to do in Rome

Side Trip

Find places to stay Oct 4 — 8:
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Italy travel guide

4.6
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.