33 days in Italy Itinerary
Created using Inspirock Europe tour itinerary maker
Start: Toronto
Fly
1
Rome
— 1 night
Train
2
Cinque Terre
— 2 nights
Train to Asti, Bus to Barolo
3
Barolo
— 2 nights
Drive
4
Milan
— 1 night
Drive
5
Verona
— 2 nights
Train
6
Venice
— 3 nights
Train
7
Bologna
— 2 nights
Drive
8
Siena
— 7 nights
Drive
9
Florence
— 1 night
Train
10
Sorrento
— 1 night
Ferry
11
Capri
— 2 nights
Ferry
12
Naples
— 1 night
Train
13
Rome
— 6 nights
Fly
End: Toronto
Tue, Sep 12 - Sat, Oct 14
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View full calendar
Rome — 1 night
©
Eternal City
Start off your visit on the 13th (Wed): take in the local highlights with Walking tours.
To see ratings, where to stay, more things to do, and other tourist information, refer to the Rome trip itinerary maker tool.
Toronto, Canada to Rome is an approximately 13-hour flight. The time zone changes from Eastern Standard Time (EST) to Central European Standard Time (CET), which is usually a 6 hour difference. Traveling from Toronto in September, you will find days in Rome are a bit warmer (32°C), and nights are about the same (18°C). On the 14th (Thu), you'll have the morning to explore before heading off to Cinque Terre.
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To see ratings, where to stay, more things to do, and other tourist information, refer to the Rome trip itinerary maker tool.
Toronto, Canada to Rome is an approximately 13-hour flight. The time zone changes from Eastern Standard Time (EST) to Central European Standard Time (CET), which is usually a 6 hour difference. Traveling from Toronto in September, you will find days in Rome are a bit warmer (32°C), and nights are about the same (18°C). On the 14th (Thu), you'll have the morning to explore before heading off to Cinque Terre.
Find places to stay Sep 13 — 14:
Highlights from your trip
See timeline
Cinque Terre — 2 nights
©
Italian Riviera
Start off your visit on the 15th (Fri): don't miss a visit to Oratorio della Confraternita dei Neri Mortis et Orationis, appreciate the extensive heritage of Cinque Terre Trails, then explore the historical opulence of Castello Doria, then hike along Footpath Monterosso - Vernazza, and finally get into the urban bustle at Vernazza.
To see maps, photos, other places to visit, and more tourist information, use the Cinque Terre journey planning app.
You can fly from Rome to Cinque Terre in 3 hours. Other options are to take a train; or drive. September in Cinque Terre sees daily highs of 30°C and lows of 17°C at night. On the 16th (Sat), you'll have the morning to explore before heading off to Barolo.
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To see maps, photos, other places to visit, and more tourist information, use the Cinque Terre journey planning app.
You can fly from Rome to Cinque Terre in 3 hours. Other options are to take a train; or drive. September in Cinque Terre sees daily highs of 30°C and lows of 17°C at night. On the 16th (Sat), you'll have the morning to explore before heading off to Barolo.
Find places to stay Sep 14 — 16:
Highlights from your trip
Barolo — 2 nights
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Here are some ideas for day two: see the interesting displays at Corkscrew Museum, see the interesting displays at WiMu - Museo del Vino a Barolo, do a tasting at Marchesi di Barolo - Sede legale, magazzini e spedizioni, then step into the grandiose world of Castello di Grinzane Cavour, and finally let your taste buds guide you at a local gastronomic tour.
For traveler tips, more things to do, where to stay, and other tourist information, read our Barolo trip planner.
Traveling by car from Cinque Terre to Barolo takes 3.5 hours. Alternatively, you can do a combination of train and bus. Traveling from Cinque Terre in September, you can expect nighttime temperatures to be a bit cooler in Barolo, with lows of 14°C. Cap off your sightseeing on the 18th (Mon) early enough to go by car to Milan.
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For traveler tips, more things to do, where to stay, and other tourist information, read our Barolo trip planner.
Traveling by car from Cinque Terre to Barolo takes 3.5 hours. Alternatively, you can do a combination of train and bus. Traveling from Cinque Terre in September, you can expect nighttime temperatures to be a bit cooler in Barolo, with lows of 14°C. Cap off your sightseeing on the 18th (Mon) early enough to go by car to Milan.
Side Trips
Find places to stay Sep 16 — 18:
Highlights from your trip
Milan — 1 night
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Fashion Capital of World
To find traveler tips, reviews, ratings, and tourist information, read Milan trip itinerary planner.
You can drive from Barolo to Milan in 2 hours. Another option is to do a combination of bus and train. In September, daily temperatures in Milan can reach 28°C, while at night they dip to 16°C. Finish your sightseeing early on the 19th (Tue) so you can drive to Verona.
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You can drive from Barolo to Milan in 2 hours. Another option is to do a combination of bus and train. In September, daily temperatures in Milan can reach 28°C, while at night they dip to 16°C. Finish your sightseeing early on the 19th (Tue) so you can drive to Verona.
Find places to stay Sep 18 — 19:
Verona — 2 nights
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City of Romeo and Juliet
On the 20th (Wed), pause for some serene contemplation at Chiesa di San Zeno in Oratorio, step into the grandiose world of Museo di Castelvecchio, take in the architecture and atmosphere at Basilica di San Zeno Maggiore, then examine the collection at Casa di Giulietta, then take a stroll through Piazza delle Erbe, and finally enjoy breathtaking views from Torre dei Lamberti.
To see maps and tourist information, you can read our Verona trip planner.
You can drive from Milan to Verona in 2 hours. Alternatively, you can take a train. September in Verona sees daily highs of 30°C and lows of 17°C at night. On the 21st (Thu), wrap the sightseeing up by early afternoon so you can drive to Venice.
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To see maps and tourist information, you can read our Verona trip planner.
You can drive from Milan to Verona in 2 hours. Alternatively, you can take a train. September in Verona sees daily highs of 30°C and lows of 17°C at night. On the 21st (Thu), wrap the sightseeing up by early afternoon so you can drive to Venice.
Find places to stay Sep 19 — 21:
Highlights from your trip
Venice — 3 nights
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City of Romance
Venture out of the city with trips to Padua (Chiesa degli Eremitani - World Heritage Site, Scrovegni Chapel, &more). There's lots more to do: explore the activities along Canal Grande, take in the architecture and atmosphere at Basilica di San Marco, explore the world behind art at Peggy Guggenheim Collection, and examine the collection at Doge's Palace.
For photos, maps, and other tourist information, read Venice trip itinerary maker site.
Getting from Verona to Venice by car takes about 1.5 hours. Other options: take a shuttle; or take a train. September in Venice sees daily highs of 29°C and lows of 17°C at night. On the 24th (Sun), wrap the sightseeing up by early afternoon so you can drive to Bologna.
more
For photos, maps, and other tourist information, read Venice trip itinerary maker site.
Getting from Verona to Venice by car takes about 1.5 hours. Other options: take a shuttle; or take a train. September in Venice sees daily highs of 29°C and lows of 17°C at night. On the 24th (Sun), wrap the sightseeing up by early afternoon so you can drive to Bologna.
Side Trip
Find places to stay Sep 21 — 24:
Highlights from your trip
Bologna — 2 nights
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Heart of Italian Cuisine
Start off your visit on the 24th (Sun): admire the striking features of Fontana del Nettuno and then pause for some serene contemplation at Chiesa di San Giacomo Maggiore.
To find more things to do, where to stay, photos, and more tourist information, go to the Bologna attractions planner.
You can drive from Venice to Bologna in 2 hours. Alternatively, you can take a train. Expect a daytime high around 30°C in September, and nighttime lows around 17°C. Cap off your sightseeing on the 26th (Tue) early enough to go by car to Siena.
more
To find more things to do, where to stay, photos, and more tourist information, go to the Bologna attractions planner.
You can drive from Venice to Bologna in 2 hours. Alternatively, you can take a train. Expect a daytime high around 30°C in September, and nighttime lows around 17°C. Cap off your sightseeing on the 26th (Tue) early enough to go by car to Siena.
Find places to stay Sep 24 — 26:
Highlights from your trip
Siena — 7 nights
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Cultural Heart of Tuscany
Get out of town with these interesting Siena side-trips: Assisi (Rocca Maggiore, Basilica Papale e Sacro Convento di San Francesco d'Assisi, &more), Cascate del Mulino (in Saturnia) and Giardino dei Tarocchi (in Pescia Fiorentina). And it doesn't end there: do a tasting at Guardastelle Vineyard, let your taste buds guide you at a local gastronomic tour, indulge your senses at some of the top wineries in the area, and explore the historical opulence of Palazzo Pubblico and Museo Civico.
For photos, traveler tips, and other tourist information, refer to the Siena journey planning site.
Getting from Bologna to Siena by car takes about 2 hours. Other options: take a train; or do a combination of train and bus. In September, daily temperatures in Siena can reach 32°C, while at night they dip to 19°C. Wrap up your sightseeing by early afternoon on the 3rd (Tue) to allow enough time to drive to Florence.
more
For photos, traveler tips, and other tourist information, refer to the Siena journey planning site.
Getting from Bologna to Siena by car takes about 2 hours. Other options: take a train; or do a combination of train and bus. In September, daily temperatures in Siena can reach 32°C, while at night they dip to 19°C. Wrap up your sightseeing by early afternoon on the 3rd (Tue) to allow enough time to drive to Florence.
Side Trips
Find places to stay Sep 26 — Oct 3:
Highlights from your trip
Florence — 1 night
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Birthplace of the Italian Renaissance
On the 3rd (Tue), take in the spiritual surroundings of Cathedral of Santa Maria del Fiore, don't miss a visit to Piazzale Michelangelo, and then explore the world behind art at Florence Academy of Fine Arts.
For maps, ratings, where to stay, and tourist information, refer to the Florence trip planner.
Traveling by car from Siena to Florence takes 1.5 hours. Alternatively, you can drive; or take a bus; or take a train. In October in Florence, expect temperatures between 25°C during the day and 14°C at night. Finish your sightseeing early on the 4th (Wed) to allow enough time to take a train to Sorrento.
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For maps, ratings, where to stay, and tourist information, refer to the Florence trip planner.
Traveling by car from Siena to Florence takes 1.5 hours. Alternatively, you can drive; or take a bus; or take a train. In October in Florence, expect temperatures between 25°C during the day and 14°C at night. Finish your sightseeing early on the 4th (Wed) to allow enough time to take a train to Sorrento.
Find places to stay Oct 3 — 4:
Highlights from your trip
Sorrento — 1 night
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Land of the Sirens
On the 4th (Wed), let your taste buds guide you at a local gastronomic tour.
To see maps, more things to do, and more tourist information, go to the Sorrento online driving holiday planner.
Take a train from Florence to Sorrento in 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 October since evenings lows in Sorrento dip to 20°C. You will have some time to spend on the 5th (Thu) before leaving for Capri.
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To see maps, more things to do, and more tourist information, go to the Sorrento online driving holiday planner.
Take a train from Florence to Sorrento in 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 October since evenings lows in Sorrento dip to 20°C. You will have some time to spend on the 5th (Thu) before leaving for Capri.
Find places to stay Oct 4 — 5:
Highlights from your trip
Capri — 2 nights
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Kick off your visit on the 5th (Thu): Head underground at Blue Grotto, contemplate the long history of Villa San Michele, take your sightseeing to a higher altitude at Monte Solaro, then take a memorable drive along Via Krupp, then stroll through I Faraglioni, and finally make a trip to Giardini di Augusto. Here are some ideas for day two: get great views at Belvedere Cannone, contemplate the waterfront views at Marina Piccola, head outdoors with Outdoor Activities, then take in panoramic vistas at Belvedere di Tragara, then make a trip to Piazza Umberto I, and finally stop by Eco Capri.
To find more things to do, maps, and more tourist information, refer to the Capri trip itinerary builder app.
Traveling by ferry from Sorrento to Capri takes an hour. In October, daytime highs in Capri are 26°C, while nighttime lows are 20°C. On the 7th (Sat), you're off to Naples.
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To find more things to do, maps, and more tourist information, refer to the Capri trip itinerary builder app.
Traveling by ferry from Sorrento to Capri takes an hour. In October, daytime highs in Capri are 26°C, while nighttime lows are 20°C. On the 7th (Sat), you're off to Naples.
Side Trip
Find places to stay Oct 5 — 7:
Highlights from your trip
Naples — 1 night
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Start off your visit on the 7th (Sat): delve into the distant past at Parco Acheologico di Ercolano, make a trip to Via San Gregorio Armeno, and then see the interesting displays at Museo Archeologico Nazionale di Napoli.
For more things to do, reviews, and other tourist information, refer to the Naples trip maker tool.
Traveling by ferry from Capri to Naples takes 1.5 hours. Traveling from Capri in October, Naples is slightly colder at night with lows of 17°C. You will leave for Rome on the 8th (Sun).
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For more things to do, reviews, and other tourist information, refer to the Naples trip maker tool.
Traveling by ferry from Capri to Naples takes 1.5 hours. Traveling from Capri in October, Naples is slightly colder at night with lows of 17°C. You will leave for Rome on the 8th (Sun).
Side Trip
Find places to stay Oct 7 — 8:
Highlights from your trip
Rome — 6 nights
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Eternal City
Explore the numerous day-trip ideas around Rome: Tivoli (Villa d'Este & Villa Adriana). See some other sides of Rome: contemplate the long history of Colosseum, admire the local landmark of Trevi Fountain, let your taste buds guide you at a local gastronomic tour, and don't miss a visit to Piazza Navona.
To find ratings, reviews, other places to visit, and more tourist information, read our Rome trip itinerary planner.
You can take a train from Naples to Rome in 2 hours. Alternatively, you can drive; or fly. You'll have a few hours on the 14th (Sat) to wrap things up before traveling home.
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To find ratings, reviews, other places to visit, and more tourist information, read our Rome trip itinerary planner.
You can take a train from Naples to Rome in 2 hours. Alternatively, you can drive; or fly. You'll have a few hours on the 14th (Sat) to wrap things up before traveling home.
Side Trips
Find places to stay Oct 8 — 14:
Highlights from your trip
Italy travel guide
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.
Province of Florence travel guide
Island of Capri travel guide
Capri, just 5 km (3 mi) from the mainland of Italy, has been a celebrated vacation spot and a coastal resort since the Roman Republic. Known in Greek mythology as an island favored by the sirens, Capri was a popular leisure destination for numerous Roman emperors. One of the more notorious emperors, Tiberius, built an extravagant villa on the island and allegedly flung visitors who displeased him from the high cliffs of his estate. Escape the swarms of visitors by sightseeing inland. The coastal areas may be known for attractions like beaches and caves carved out of cliffs, but deeper inland are other places to visit, including secluded natural trails and several abandoned forts.
