61 days in Italy Itinerary

Created using Klarna Trips Italy trip planner
Make it your trip
Fly
1
Milan
— 3 nights
Train
2
Florence
— 5 nights
Drive
3
Monteriggioni
— 1 day
Drive
4
Siena
— 2 nights
Drive
5
Cortona
— 1 night
Drive
6
Montepulciano
— 2 nights
Drive
7
Pitigliano
— 2 nights
Drive
8
Saturnia
— 1 night
Drive
9
Rome
— 4 nights
Train
10
Naples
— 2 nights
Ferry
11
Ischia
— 2 nights
Ferry
12
Sorrento
— 5 nights
Fly
13
Palermo
— 1 night
Drive
14
Catania
— 4 nights
+2
Drive to Messina Marittima, Ferry to Villa San Giovanni, Drive to Tropea
15
Tropea
— 3 nights
Drive
16
Matera
— 3 nights
Drive
17
Alberobello
— 1 night
Drive
18
Torre dell'Orso
— 2 nights
Fly
19
Cagliari
— 4 nights
Fly
20
Cinque Terre
— 5 nights
Train
21
Pisa
— 1 night
Train
22
Verona
— 2 nights
Train
23
Venice
— 4 nights
Fly

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Milan — 3 nights

Fashion Capital of World

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 find plenty of places to visit near Milan: Castello di Vezio (in Vezio), I Giardini di Villa Melzi (in Bellagio) and Ponte Pedonale sul Naviglio Grande (in Robecco sul Naviglio). The adventure continues: contemplate in the serene atmosphere at Duomo di Milano, make a trip to Piazza del Duomo, steep yourself in history at Il Cenacolo, and contemplate the waterfront views at Lago di Como.

To see other places to visit, reviews, maps, and more tourist information, read Milan trip itinerary app.

Chur, Switzerland to Milan is an approximately 3-hour flight. You can also drive; or take a bus. In September in Milan, expect temperatures between 76°F during the day and 57°F at night. Finish up your sightseeing early on the 17th (Wed) so you can catch the train to Florence.
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Parks · Historic Sites · Nature
Side Trips
Find places to stay Sep 14 — 17:

Florence — 5 nights

Birthplace of the Italian Renaissance

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Step out of Florence to go to Vaglia and see Parco Mediceo di Pratolino (Villa Demidoff) - World Heritage Site, which is approximately 30 minutes away. There's still lots to do: take in the views from Ponte Vecchio, awaken your taste buds at Guido's Tours - Wine Tours in Tuscany, and admire the local landmark of Fontana del Porcellino.

To see reviews, ratings, photos, and other tourist information, use the Florence online trip itinerary planner.

Traveling by train from Milan to Florence takes 2.5 hours. Alternatively, you can drive; or take a bus. In September in Florence, expect temperatures between 78°F during the day and 59°F at night. Wrap up your sightseeing on the 22nd (Mon) early enough to drive to Monteriggioni.
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Tours · Wineries · Parks
Side Trip
Find places to stay Sep 17 — 22:

Monteriggioni — 1 day

Start off your visit on the 22nd (Mon): do a tasting at Sant'Agnese Farm, get to know the fascinating history of Centro storico di Monteriggioni, then contemplate in the serene atmosphere at Chiesa di Santa Maria Assunta, then explore the historical opulence of Castello di Monteriggioni, and finally learn about winemaking at Cantinetta di Monteriggioni.

To see ratings, where to stay, more things to do, and tourist information, go to the Monteriggioni trip site.

Traveling by car from Florence to Monteriggioni takes an hour. Alternatively, you can take a bus; or take a train. In September in Monteriggioni, expect temperatures between 81°F during the day and 61°F at night. Finish up your sightseeing early on the 22nd (Mon) so you can go by car to Siena.
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Wineries · Historic Sites · Shopping
Side Trip
Find places to stay Sep 22 — 23:

Siena — 2 nights

Cultural Heart of Tuscany

Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
To find maps, ratings, other places to visit, and more tourist information, use the Siena itinerary planner.

Siena is just a short distance from Monteriggioni. Expect a daytime high around 81°F in September, and nighttime lows around 61°F. On the 24th (Wed), you'll have the morning to explore before heading off to Cortona.
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Find places to stay Sep 22 — 24:

Cortona — 1 night

City of Art

The hilltop town of Cortona gained international attention as the subject of the 2003 film "Under the Tuscan Sun." With the Chiana Valley and Lake Trasimeno as its backdrop, Cortona is one of Tuscany's hotspots for art and culture.
Kick off your visit on the 24th (Wed): take in the spiritual surroundings of Eremo Le Celle and then stop by DelBrenna Jewelry.

Plan a Cortona trip in moments using our itinerary builder.

You can drive from Siena to Cortona in 1.5 hours. Other options are to take a train; or do a combination of bus and train. Wrap up your sightseeing on the 25th (Thu) to allow time to drive to Montepulciano.
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Find places to stay Sep 24 — 25:

Montepulciano — 2 nights

Pearl of the 16th Century

Perched on a limestone ridge in the heart of Tuscany, Montepulciano is known worldwide for its production of red wine, the Vino Noble.
On the 26th (Fri), you'll have a packed day of sightseeing: contemplate in the serene atmosphere at Tempio di San Biagio, make a trip to Piazza Grande a Montepulciano, don't miss a visit to Terrazza Del Palazzo Comunale, then appreciate the extensive heritage of Via di Gracciano nel Corso, then learn about winemaking at Tenuta Valdipiatta, and finally do a tasting at Az. Agr. Poliziano.

To see more things to do, where to stay, reviews, and other tourist information, use the Montepulciano trip planner.

Traveling by car from Cortona to Montepulciano takes an hour. Alternatively, you can take a train; or take a bus. In September, daily temperatures in Montepulciano can reach 81°F, while at night they dip to 61°F. Wrap up your sightseeing on the 27th (Sat) to allow time to drive to Pitigliano.
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Wineries · Historic Sites
Find places to stay Sep 25 — 27:

Pitigliano — 2 nights

Pitigliano is a town in the province of Grosseto, located about 80km south-east of the city of Grosseto, in Italy. Start off your visit on the 27th (Sat): don't miss a visit to Via CAVA ETRUSCA SAN GIUSEPPE and then appreciate the extensive heritage of Pitigliano Centro Storico. Keep things going the next day: stroll around Parco Archeologico Citta del Tufo, admire the landmark architecture of Masso Leopoldino, and then appreciate the extensive heritage of Sorano Centro Storico.

For more things to do, where to stay, traveler tips, and other tourist information, read our Pitigliano day trip site.

Getting from Montepulciano to Pitigliano by car takes about 1.5 hours. Other options: take a bus. In September, daily temperatures in Pitigliano can reach 78°F, while at night they dip to 59°F. Wrap up your sightseeing on the 29th (Mon) to allow time to drive to Saturnia.
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Historic Sites · Parks
Side Trip
Find places to stay Sep 27 — 29:

Saturnia — 1 night

Start off your visit on the 29th (Mon): admire the sheer force of Cascate del Mulino and then take in the natural beauty of Terme di Saturnia - Parco Termale.

For reviews, other places to visit, more things to do, and other tourist information, refer to the Saturnia online travel planner.

Drive from Pitigliano to Saturnia in an hour. Alternatively, you can take a bus. In September, daily temperatures in Saturnia can reach 81°F, while at night they dip to 61°F. On the 30th (Tue), you'll have the morning to explore before heading off to Rome.
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Parks · Nature · Spas
Find places to stay Sep 29 — 30:

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.
Rome is known for historic sites, sightseeing, and nightlife. Your trip includes some of its best attractions: explore the ancient world of Pantheon, ponder the design of Trevi Fountain, get to know the fascinating history of Piazza Navona, and head off the coast to Isola Tiberina.

To find photos, ratings, other places to visit, and tourist information, use the Rome trip maker.

Traveling by car from Saturnia to Rome takes 2.5 hours. Alternatively, you can do a combination of taxi and train. In September, daytime highs in Rome are 81°F, while nighttime lows are 60°F. Wrap up your sightseeing on the 4th (Sat) early enough to take a train to Naples.
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Side Trip
Find places to stay Sep 30 — Oct 4:

Naples — 2 nights

Naples is the capital of the Italian region Campania and the third-largest municipality in Italy after Rome and Milan. On the 4th (Sat), take an in-depth tour of Galleria Borbonica. On the 5th (Sun), you'll have a packed day of sightseeing: stroll the grounds of Cimitero delle Fontanelle.

To see where to stay, reviews, and other tourist information, read our Naples trip maker site.

Getting from Rome to Naples by train takes about 2 hours. Other options: drive; or fly. In October in Naples, expect temperatures between 74°F during the day and 58°F at night. On the 6th (Mon), wrap the sightseeing up by early afternoon so you can ride a ferry to Ischia.
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Find places to stay Oct 4 — 6:

Ischia — 2 nights

Ischia is a volcanic island in the Tyrrhenian Sea. On the 6th (Mon), explore the historical opulence of Castello Aragonese d'Ischia. Keep things going the next day: contemplate the waterfront views at Baia di San Montano and then admire the ancient design of Negombo.

To find maps, photos, other places to visit, and tourist information, go to the Ischia online road trip planner.

Ride a ferry from Naples to Ischia in 2 hours. Expect a daytime high around 72°F in October, and nighttime lows around 63°F. You'll have a few hours on the 8th (Wed) to wrap things up before traveling to Sorrento.
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Parks · Baths · Historic Sites · Spas
Side Trip
Find places to stay Oct 6 — 8:

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.
Venture out of the city with trips to Positano (Fornillo, Spiaggia Grande, &more), Pompeii (Pompeii Archaeological Park, Villa dei Misteri, &more) and Vesuvio National Park (in Ottaviano). There's much more to do: stop by Fattoria Terranova Shop, take in nature's colorful creations at I Giardini di Cataldo, get to know the fascinating history of Corso Italia, and tour the pleasant surroundings at Il Vallone dei Mulini.

To find traveler tips, other places to visit, and tourist information, go to the Sorrento route builder.

Ride a ferry from Ischia to Sorrento in 2 hours. In October, daytime highs in Sorrento are 72°F, while nighttime lows are 63°F. You will leave for Palermo on the 13th (Mon).
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Side Trips
Find places to stay Oct 8 — 13:

Palermo — 1 night

The capital of Sicily, Palermo was founded by the Phoenicians under the name of Ziz.
Kick off your visit on the 13th (Mon): don't miss a visit to Cattedrale di Palermo, then don't miss a visit to Quattro Canti, and then indulge in some culinary diversions at a local gastronomic tour.

To find reviews, ratings, traveler tips, and other tourist information, read our Palermo day trip planner.

You can fly from Sorrento to Palermo in 2.5 hours. Other options are to take a train; or ride a ferry. Wrap up your sightseeing on the 14th (Tue) to allow time to drive to Catania.
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Find places to stay Oct 13 — 14:

Catania — 4 nights

Black Pearl of Ionian Sea

The landscape surrounding Catania, a medieval city on Sicily's eastern coast, is dominated by Mount Etna, the tallest active volcano in Europe.
Get out of town with these interesting Catania side-trips: Taormina (Corso Umberto, Ancient Theatre of Taormina, &more). And it doesn't end there: get impressive views of Mt Etna, see Off-Road Tours, and don't miss a visit to Piazza del Duomo.

To see other places to visit, photos, reviews, and tourist information, use the Catania vacation builder tool.

Drive from Palermo to Catania in 2.5 hours. Alternatively, you can take a bus; or take a train. October in Catania sees daily highs of 76°F and lows of 58°F at night. Finish up your sightseeing early on the 18th (Sat) so you can travel to Tropea.
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Parks · Nature · Tours · Outdoors
Side Trip
Find places to stay Oct 14 — 18:

Tropea — 3 nights

Tropea is a municipality located within the province of Vibo Valentia, in Calabria (southern Italy).The town is a famous bathing place, situated on a reef, in the gulf of St. Tropea is known for beaches, historic sites, and adventure. Your trip includes some of its best attractions: enjoy the sand and surf at Tropea Beach, get outside with Blanca Beach Club Tropea, and don't miss a visit to Capo Vaticano.

To find reviews, where to stay, other places to visit, and tourist information, refer to the Tropea travel itinerary planner.

Traveling by combination of car and ferry from Catania to Tropea takes 3.5 hours. Alternatively, you can do a combination of bus and train; or take a train. In October, daytime highs in Tropea are 75°F, while nighttime lows are 57°F. On the 21st (Tue), you'll have the morning to explore before heading off to Matera.
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Outdoors · Parks · Beaches
Side Trip
Find places to stay Oct 18 — 21:

Matera — 3 nights

Subterranean City

Famous for its resemblance to the ancient settlements of Jerusalem and Cappadocia, Matera remains one of the oldest inhabited cities in the world.
Step out of Matera to go to Castellana Grotte and see Grotte di Castellana, which is approximately 1h 15 min away. There's more to do: make a trip to Sassi di Matera and explore the ancient world of Materasum Ipogeo.

To see more things to do, photos, maps, and more tourist information, refer to the Matera tour planner.

You can drive from Tropea to Matera in 4 hours. Another option is to do a combination of train and bus. Traveling from Tropea in October, expect nights in Matera to be about the same, around 53°F, while days are a bit cooler, around 68°F. Wrap up your sightseeing by early afternoon on the 24th (Fri) to allow time for the car ride to Alberobello.
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Historic Sites · Parks · Nature
Side Trip
Find places to stay Oct 21 — 24:

Alberobello — 1 night

Alberobello is a small town and comune of the Metropolitan City of Bari, Apulia, southern Italy. Kick off your visit on the 24th (Fri): don't miss a visit to Statua di Domenico Modugno and then don't miss a visit to Centro Storico di Polignano a Mare.

To see reviews, ratings, maps, and tourist information, refer to the Alberobello attractions planner.

You can drive from Matera to Alberobello in 1.5 hours. Other options are to take a bus; or do a combination of train and bus. In October, plan for daily highs up to 68°F, and evening lows to 53°F. On the 25th (Sat), you'll have the morning to explore before heading off to Torre dell'Orso.
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Find places to stay Oct 24 — 25:

Torre dell'Orso — 2 nights

To find more things to do, traveler tips, maps, and other tourist information, go to the Torre dell'Orso tour planner.

You can drive from Alberobello to Torre dell'Orso in 2 hours. Alternatively, you can do a combination of train and bus; or take a bus. In October, plan for daily highs up to 73°F, and evening lows to 55°F. You will have some time to spend on the 27th (Mon) before leaving for Cagliari.
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Parks · Nature
Side Trip
Find places to stay Oct 25 — 27:

Cagliari — 4 nights

City of Sun

The capital of Sardinia, Cagliari is spread out over seven hills and still bears the marks of its past conquerors, including the Phoenicians, Carthaginians, and Romans.
Explore the numerous day-trip ideas around Cagliari: Porto Flavia (in Iglesias), Area Archeologica di Nora (in Pula) and Cala Domestica (in Buggerru). It doesn't end there: enjoy the sand and surf at Poetto.

For reviews, other places to visit, photos, and more tourist information, refer to the Cagliari travel route website.

You can fly from Torre dell'Orso to Cagliari in 3 hours. Alternatively, you can do a combination of bus, train, and ferry; or do a combination of bus and ferry. In October in Cagliari, expect temperatures between 77°F during the day and 59°F at night. On the 31st (Fri), you'll have the morning to explore before heading off to Cinque Terre.
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Parks · Beaches · Outdoors · Historic Sites
Side Trips
Find places to stay Oct 27 — 31:

Cinque Terre — 5 nights

Italian Riviera

Made up of five picturesque towns on the Ligurian coast, Cinque Terre is Italy's answer to the French Riviera.
Explore Cinque Terre's surroundings by going to Porto Venere (Castello Doria, Palazzata a Mare, &more). Next up on the itinerary: trek along Cinque Terre footpaths, appreciate the extensive heritage of Borgo Storico di Corniglia, tour the pleasant surroundings at Footpath Monterosso - Vernazza, and take a stroll around Vernazza.

To find ratings, where to stay, reviews, and other tourist information, use the Cinque Terre online trip builder.

You can fly from Cagliari to Cinque Terre in 3 hours. Other options are to do a combination of bus, ferry, and train; or do a combination of train, bus, and ferry. Traveling from Cagliari in October, things will get a bit cooler in Cinque Terre: highs are around 71°F and lows about 54°F. On the 5th (Wed), you'll have the morning to explore before heading off to Pisa.
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Historic Sites · Parks · Outdoors · Trails
Side Trip
Find places to stay Oct 31 — Nov 5:

Pisa — 1 night

Known worldwide for the Leaning Tower of Pisa, the city of Pisa historically served as a maritime power in the heart of Tuscany.
Kick off your visit on the 5th (Wed): don't miss a visit to Piazza dei Miracoli, stroll the grounds of Camposanto, take in panoramic vistas at Leaning Tower of Pisa, admire the landmark architecture of Duomo di Pisa, then get to know the fascinating history of Knights’ Square, and finally take in the views from Ponte di Mezzo.

To find where to stay and other tourist information, read our Pisa trip itinerary maker website.

You can take a train from Cinque Terre to Pisa in 2 hours. Another option is to drive. In November, daily temperatures in Pisa can reach 61°F, while at night they dip to 46°F. Wrap up your sightseeing on the 6th (Thu) early enough to take a train to Verona.
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Find places to stay Nov 5 — 6:

Verona — 2 nights

City of Romeo and Juliet

The famous setting for Shakespeare's star-crossed lovers, Romeo and Juliet, Verona is one of northern Italy's main tourist destinations, largely owing to its incredibly rich artistic heritage.
Start off your visit on the 6th (Thu): look for gifts at Cioccolateria Via Conventino and then wander the streets of Quinzano. Keep things going the next day: wander the streets of Piazza delle Erbe, admire the landmark architecture of Domus Mercatorum, examine the collection at Casa di Giulietta, then enjoy breathtaking views from Torre dei Lamberti, then explore the historical opulence of Piazzale Castel San Pietro, and finally listen to music at Teatro romano di Verona.

For ratings, where to stay, more things to do, and tourist information, you can read our Verona trip website.

You can take a train from Pisa to Verona in 3 hours. Alternatively, you can drive; or take a bus. Traveling from Pisa in November, things will get slightly colder in Verona: highs are around 54°F and lows about 41°F. You will have some time to spend on the 8th (Sat) before leaving for Venice.
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Historic Sites · Neighborhoods · Shopping · Nightlife
Find places to stay Nov 6 — 8:

Venice — 4 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.
Venice is known for sightseeing, historic sites, and museums. Your trip includes some of its best attractions: explore the activities along Canal Grande, enjoy breathtaking views from Torre dell'Orologio, take a stroll through Campo del Ghetto, and stop by Cannaregio.

To see other places to visit, ratings, more things to do, and more tourist information, read Venice tour itinerary planner.

Drive from Verona to Venice in 1.5 hours. Alternatively, you can take a shuttle; or take a train. In November in Venice, expect temperatures between 56°F during the day and 43°F at night. Finish up your sightseeing early on the 12th (Wed) so you can catch the flight back home.
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Find places to stay Nov 8 — 12:

Italy travel guide

4.6
Landmarks · Ruins · Beaches
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.
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