23 days in Italy Itinerary

23 days in Italy Itinerary

Created using Inspirock Italy travel route builder

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Route & dates

23 days in Italy Itinerary

Start: Toronto
Fly:  11​h 15​min
1
Milan
— 1 night
train:  2​h 30​min
2
Venice
— 4 nights
train:  2​h 15​min
3
Florence
— 4 nights
train:  1​h 45​min
4
Rome
— 4 nights
train:  1​h 15​min
5
Naples
— 4 nights
bus:  1​h 30​min
6
Positano
— 4 nights
train + Fly:  14​h 45​min
End: Toronto

1
night
Milan

Milan ©
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.
On the 5th (Sun), admire the landmark architecture of Galleria Vittorio Emanuele II, then contemplate in the serene atmosphere at Duomo di Milano, and then explore the different monuments and memorials at Monumental Cemetery. Get ready for a full day of sightseeing on the next day: examine the collection at Tempio Civico della Beata Vergine Incoronata, then step into the grandiose world of Castello Sforzesco, and then test your team's savvy at La Casa Maledetta.

To find other places to visit, ratings, reviews, and tourist information, use the Milan online tour itinerary planner .

Toronto, Canada to Milan is an approximately 11.5-hour flight. You can also do a combination of ferry and flight; or do a combination of flight and train. Traveling from Toronto to Milan, you'll lose 6 hours due to the time zone difference. Expect a bit warmer temperatures when traveling from Toronto in January; daily highs in Milan reach 9°C and lows reach 0°C. Cap off your sightseeing on the 6th (Mon) early enough to catch the train to Venice.

Things to do in Milan

Historic Sites Museums Fun & Games

Side Trip

Tempio Civico della Beata Vergine Incoronata
Find places to stay Jan 4 — 6:
Highlights from your plan
Duomo di Milano ©
Duomo di Milano
Galleria Vittorio Emanuele II ©
Galleria Vittorio Emanuele II
La Casa Maledetta ©
La Casa Maledetta

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.
You'll find plenty of places to visit near Venice: Verona (Torre dei Lamberti, Piazza delle Erbe, & more) and Scrovegni Chapel (in Padua). The adventure continues: explore the activities along Canal Grande, explore the world behind art at Gallerie dell'Accademia, enjoy breathtaking views from St Mark's Campanile, and get to know the fascinating history of Piazza San Marco.

Ask Inspirock to suggest an itinerary and make planning a trip to Venice fast, fun, and easy.

You can take a train from Milan to Venice in 2.5 hours. Other options are to drive; or do a combination of flight and train. January in Venice sees daily highs of 9°C and lows of 0°C at night. Finish your sightseeing early on the 10th (Fri) to allow enough time to take a train to Florence.

Things to do in Venice

Historic Sites Museums Nature

Side Trips

Verona, Scrovegni Chapel
Find places to stay Jan 6 — 10:
Highlights from your plan
Canal Grande ©
Canal Grande
Basilica di San Marco
Basilica di San Marco
Doge's Palace ©
Doge's Palace

4
nights
Florence

Florence ©
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 Piazza del Campo (in Siena) and Leaning Tower of Pisa (in Pisa). And it doesn't end there: explore the world behind art at Gallerie Degli Uffizi, get great views at Piazzale Michelangelo, see the interesting displays at Pitti Palace, and appreciate the extensive heritage of Piazza del Duomo.

To find other places to visit, more things to do, and tourist information, refer to the Florence trip planner .

Getting from Venice to Florence by train takes about 2.5 hours. Other options: drive; or take a bus. When traveling from Venice in January, plan for somewhat warmer days and about the same nights in Florence: temperatures range from 13°C by day to 3°C at night. Finish up your sightseeing early on the 14th (Tue) so you can catch the train to Rome.

Things to do in Florence

Historic Sites Museums

Side Trips

Leaning Tower of Pisa, Piazza del Campo
Find places to stay Jan 10 — 14:
Highlights from your plan
Cathedral of Santa Maria del Fiore ©
Gallerie Degli Uffizi ©
Gallerie Degli Uffizi
Academy Of Florence Art Gallery ©
Academy Of Florence Art Gallery

4
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: explore the ancient world of Colosseum, wander the streets of Trastevere, make a trip to Trevi Fountain, and get to know the fascinating history of Piazza Navona.

You can plan Rome trip in no time by asking Inspirock to help create your itinerary.

Traveling by train from Florence to Rome takes 2 hours. Alternatively, you can drive; or fly. In January, daytime highs in Rome are 15°C, while nighttime lows are 4°C. Finish your sightseeing early on the 18th (Sat) to allow enough time to take a train to Naples.

Things to do in Rome

Historic Sites Museums Neighborhoods

Side Trip

Vatican City
Find places to stay Jan 14 — 18:
Highlights from your plan
Colosseum ©
Colosseum
Pantheon ©
Pantheon
Trevi Fountain ©
Trevi Fountain

4
nights
Naples

Naples ©
Naples is the capital of the Italian region Campania and the third-largest municipality in Italy after Rome and Milan. Explore Naples' surroundings by going to Arciconfraternita della Santissima Annunziata e del Santissimo Rosario (in Vietri sul Mare), Salerno (Chiesa San Pietro a Corte, Palazzo Fruscione, & more) and Chiesa San Pietro Apostolo (in Cetara). Next up on the itinerary: delve into the distant past at Pompeii Archaeological Park, don't miss a visit to Miglio Sacro, admire the masterpieces at Museo Cappella Sansevero, and brush up on your military savvy at Galleria Borbonica.

To see ratings, more things to do, maps, and tourist information, read Naples online tour itinerary planner .

Take a train from Rome to Naples in 1.5 hours. Alternatively, you can drive; or take a bus. Expect a daytime high around 15°C in January, and nighttime lows around 6°C. Finish your sightseeing early on the 22nd (Wed) to allow enough time to take a bus to Positano.

Things to do in Naples

Historic Sites Museums Parks

Side Trips

Salerno, Chiesa San Pietro Apostolo, Pompeii Archaeological Park, Arciconfraternita della Santissima Annunziata e del Santissimo Rosario
Find places to stay Jan 18 — 22:
Highlights from your plan
Miglio Sacro ©
Miglio Sacro
Chiesa San Pietro a Corte ©
Chiesa San Pietro a Corte
Centro Storico Salerno ©
Centro Storico Salerno

4
nights
Positano

Positano ©
Often referred to as the gem of the Amalfi Coast, Positano remains one of southern Italy's most sought-after vacation locales, thanks to its hillside location and picturesque, pastel buildings.
You'll find plenty of places to visit near Positano: Torre dello Ziro (in Amalfi), Atrani (S.Maria Maddalena & Vicoli, scale e archi) and Ravello (Belvedere Principessa di Piemonte & Cappella Sant'Angelo all'Ospedale). There's lots more to do: explore the fascinating underground world of Grotte di Suppraiano, sample the fine beverages at Liquorificio Mansi Carlo, pause for some serene contemplation at Chiesa di San Francesco, and don't miss a visit to Parocchia di San Luca Evangelista.

To see more things to do, photos, maps, and more tourist information, you can read our Positano travel route planner.

You can take a bus from Naples to Positano in 1.5 hours. Alternatively, you can drive; or do a combination of subway and bus. Plan for a bit warmer nights when traveling from Naples in January since evenings lows in Positano dip to 10°C. On the 26th (Sun), wrap the sightseeing up by early afternoon so you can travel back home.

Things to do in Positano

Historic Sites Parks Spas

Side Trips

Amalfi, Praiano, Maiori, Ravello, Atrani
Find places to stay Jan 22 — 26:
Highlights from your plan
Chiesa di San Francesco ©
Chiesa di San Francesco
Grotte di Suppraiano ©
Grotte di Suppraiano
Tennis Al Settimo Piano ©
Tennis Al Settimo Piano

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