31 days in Italy Itinerary

31 days in Italy Itinerary

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Route & dates

31 days in Italy Itinerary

Start: Toronto
Fly:  11​h 15​min
1
Venice
— 4 nights
Fly:  3​h 15​min
2
Rome
— 5 nights
Train:  1​h 15​min
3
Naples
— 5 nights
Subway + Taxi:  1​h 30​min
4
Amalfi
— 4 nights
Drive:  4​h 30​min
5
Assisi
— 4 nights
Drive:  2​h 15​min
6
Florence
— 4 nights
Train:  1​h 45​min
7
Milan
— 3 nights
Fly:  11​h 15​min
End: Toronto

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.
Your inner history buff will appreciate Passeggiata lungo la restera and Chiesa di Santo Stefano. Step off the beaten path and head to Poli Museo della Grappa and Santa Maria dei Miracoli. Explore the numerous day-trip ideas around Venice: Villa Contarini (in Piazzola sul Brenta), Piazza Castello (in Marostica) and Centro Storico di Treviso (in Treviso). There's lots more to do: learn more about the world around you at Natural History Museum, admire the masterpieces at Museo Querini Stampalia, browse the exhibits of Palazzo Mocenigo, and appreciate the extensive heritage of Via Garibaldi.

To see traveler tips and other tourist information, read Venice travel route site .

Toronto, Canada to Venice is an approximately 11.5-hour flight. You can also do a combination of flight and train. You'll lose 6 hours traveling from Toronto to Venice due to the time zone difference. In December, Venice is somewhat warmer than Toronto - with highs of 11°C and lows of 1°C. Finish your sightseeing early on the 5th (Thu) so you can travel to Rome.

Things to do in Venice

Historic Sites Museums Parks

Side Trips

Treviso, Piazza Castello, Chiesa di San Martino Vescovo, Villa Contarini, Poli Museo della Grappa
Find places to stay Nov 30 — Dec 5:
Highlights from your plan
Chiesa di San Rocco ©
Chiesa di San Rocco
Passeggiata lungo la restera ©
Passeggiata lungo la restera
Poli Museo della Grappa ©
Poli Museo della Grappa

5
nights
Rome

Rome ©
Aptly nicknamed the Eternal City, Rome is the birthplace of the Roman Empire, one of the world's greatest civilizations ever.
Museum-lovers will get to explore Mercati di Traiano - Museo dei Fori Imperiali and Museo Archeologico Nazionale di Palestrina. Get some historical perspective at Chiesa di Santa Maria del Popolo and Basilica di Santa Prassede. Change things up with these side-trips from Rome: Santa Maria Maggiore (in Tuscania), Cappella di San Lanno (in Vasanello) and Quartiere San Pellegrino (in Viterbo). And it doesn't end there: appreciate the extensive heritage of Colle Aventino, admire the masterpieces at National Gallery of Ancient Art in Barberini Palace, take in the spiritual surroundings of Abbazia di San Martino al Cimino, and get a sense of history and politics at Quirinale Palace (Palazzo del Quirinale).

For where to stay, ratings, more things to do, and other tourist information, read Rome holiday builder tool .

You can fly from Venice to Rome in 3.5 hours. Other options are to take a train; or drive. Traveling from Venice in December, expect nights in Rome to be about the same, around 4°C, while days are a bit warmer, around 16°C. Wrap up your sightseeing on the 10th (Tue) to allow time to take a train to Naples.

Things to do in Rome

Historic Sites Museums Neighborhoods

Side Trips

Viterbo, Museo Archeologico Nazionale di Palestrina, Cappella di San Lanno, Santa Maria Maggiore, Museo Storico dell'Aeronautica Militare
Find places to stay Dec 5 — 10:
Highlights from your plan
Chiesa di Santa Maria del Popolo ©
Chiesa di Santa Maria del Popolo
Colle Aventino ©
Colle Aventino
Basilica di Santa Prassede ©
Basilica di Santa Prassede

5
nights
Naples

Naples ©
Naples is the capital of the Italian region Campania and the third-largest municipality in Italy after Rome and Milan. Get a sense of the local culture at Cattedrale di Pozzuoli and La Terrazza di M. Nonio Balbo. Discover out-of-the-way places like Casa Natale di Padre Pio and Rione Terra. Explore the numerous day-trip ideas around Naples: Basilica della Madonna delle Grazie (in Benevento), Convent of Friars Minor Capuchin of Pietrelcina (in Pietrelcina) and Pompeii (Lupanar, House of Menander (Casa del Menandro), & more). Next up on the itinerary: explore the ancient world of Casa di Nettuno e Anfitrite, take an in-depth tour of Museo delle Torture, steep yourself in history at Acquaquiglia del Pozzaro, and wander the streets of Vomero.

To find photos, other places to visit, more things to do, and tourist information, use the Naples itinerary planner.

Traveling by train from Rome to Naples takes 1.5 hours. Alternatively, you can drive; or take a bus. In December, plan for daily highs up to 17°C, and evening lows to 6°C. Finish up your sightseeing early on the 15th (Sun) so you can travel to Amalfi.

Things to do in Naples

Historic Sites Museums Neighborhoods

Side Trips

Pompeii, Pozzuoli, Ercolano, Pietrelcina, Basilica della Madonna delle Grazie
Find places to stay Dec 10 — 15:
Highlights from your plan
Lupanar ©
Lupanar
Casa di Nettuno e Anfitrite ©
Casa di Nettuno e Anfitrite

4
nights
Amalfi

Known for its impressive hillside cascade of colorful stone buildings down to the Mediterranean shore, Amalfi is the cultural and commercial heart of southern Italy's Amalfi Coast.
Museum-lovers will appreciate Ceramiche Cosmolena di Margherita di Palma and Museo della Carta. Do some cultural sightseeing at Badia della Santissima Trinita' and Luna Convento. Step out of Amalfi to go to Positano and see Bagni d'Arienzo Beach Club, Positano, which is approximately 42 minutes away. And it doesn't end there: get to know the fascinating history of Centro Storico, contemplate in the serene atmosphere at Basilica of Saint Trofimena, admire the local landmark of Fontana sant'Andrea, and appreciate the views at Valle dei Mulini.

To find where to stay, maps, more things to do, and tourist information, go to the Amalfi trip planner.

Traveling by combination of subway and taxi from Naples to Amalfi takes 1.5 hours. Alternatively, you can drive; or take a bus. Expect somewhat warmer evenings in Amalfi when traveling from Naples in December, with lows around 11°C. Finish your sightseeing early on the 19th (Thu) to allow enough time to drive to Assisi.

Things to do in Amalfi

Outdoors Parks Historic Sites

Side Trips

Ravello, Bagni d'Arienzo Beach Club, Positano, Basilica of Saint Trofimena, Badia della Santissima Trinita'
Find places to stay Dec 15 — 19:
Highlights from your plan
Speed Boats Tours
Badia della Santissima Trinita' ©
Badia della Santissima Trinita'

4
nights
Assisi

Assisi ©
Rich in culture and religious tradition, Assisi is known as the birthplace of St.
Your cultural itinerary includes sights like Azienda Agricola Leuta and Monastero di Sant'Andrea. You'll discover tucked-away gems like Parrocchia Santa Maria Maggiore - Frati Cappuccini Assisi and Oratorio dei Pellegrini. Change things up with these side-trips from Assisi: Museo Diocesano (in Cortona), Palazzo della Corgna - Palazzo Ducale (in Castiglione del Lago) and Centro Storico (in Montefalco). And it doesn't end there: pause for some serene contemplation at Monastero di San Giuseppe, browse the collection at Palazzo Giacobetti, don't miss a visit to Oratorio S. Francesco Piccolino, and appreciate the extensive heritage of Piazza Superiore di San Francesco.

For where to stay, traveler tips, reviews, and other tourist information, you can read our Assisi day trip planning tool .

You can drive from Amalfi to Assisi in 4.5 hours. Alternatively, you can take a train; or do a combination of bus and train. Plan for slightly colder temperatures traveling from Amalfi in December, with highs in Assisi at 11°C and lows at 2°C. Wrap up your sightseeing on the 23rd (Mon) to allow time to drive to Florence.

Things to do in Assisi

Historic Sites Wineries Museums

Side Trips

Cortona, Chiesa di San Silvestro, Centro Storico, Palazzo della Corgna - Palazzo Ducale
Find places to stay Dec 19 — 23:
Highlights from your plan

4
nights
Florence

Florence ©
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Explore hidden gems such as Palazzo Strozzi and Corridoio Vasariano. Your cultural itinerary includes sights like Duomo di San Gimignano and Church and Museum of Orsanmichele. Get out of town with these interesting Florence side-trips: San Gimignano (Piazza del Duomo, Torre e Casa Campatelli, & more) and Accademia del Buon Gusto (in Panzano in Chianti). There's still lots to do: appreciate the history behind Loggia dei Lanzi, contemplate in the serene atmosphere at Church of Santa Felicita, admire the masterpieces at Accademia di Belle Arti, and make a trip to Torre di Arnolfo.

To see where to stay, ratings, and other tourist information, read our Florence itinerary planning tool .

Traveling by car from Assisi to Florence takes 2.5 hours. Alternatively, you can take a train. In December, daytime highs in Florence are 15°C, while nighttime lows are 4°C. Wrap up your sightseeing on the 27th (Fri) to allow time to take a train to Milan.

Things to do in Florence

Museums Historic Sites Nature

Side Trips

San Gimignano, Accademia del Buon Gusto
Find places to stay Dec 23 — 27:
Highlights from your plan
Accademia del Buon Gusto ©
Accademia del Buon Gusto
Duomo di San Gimignano ©
Duomo di San Gimignano
Palazzo Strozzi ©
Palazzo Strozzi

3
nights
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.
You'll explore the less-touristy side of things at Museo Fratelli Cozzi Alfa Romeo and Piazza Motta. Get some cultural insight at Chiesa di San Vittore and Palazzo Clerici. Next up on the itinerary: take in the spiritual surroundings of Chiesa di San Babila, get engrossed in the history at Memoriale Della Shoah Di Milano, see La Casa Maledetta, and get a sense of history and politics at Palazzo Marino.

To see where to stay, more things to do, other places to visit, and other tourist information, read Milan trip builder site .

You can take a train from Florence to Milan in 2 hours. Alternatively, you can drive; or fly. Prepare for slightly colder weather when traveling from Florence in December: high temperatures in Milan hover around 9°C and lows are around 1°C. Finish your sightseeing early on the 30th (Mon) to allow enough time to travel back home.

Things to do in Milan

Historic Sites Museums Nightlife

Side Trips

Museo Fratelli Cozzi Alfa Romeo, Chiesa di San Vittore, Piazza Motta
Find places to stay Dec 27 — 30:
Highlights from your plan
Museo Fratelli Cozzi Alfa Romeo ©
Museo Fratelli Cozzi Alfa Romeo
Chiesa di San Vittore ©
Chiesa di San Vittore
Chiesa di San Babila ©
Chiesa di San Babila

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