41 days in Italy Itinerary

41 days in Italy Itinerary

Created using Inspirock Europe trip itinerary planner

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Route & dates

Start: San Francisco
Fly:  16 h
1
Milan
— 1 night
Train:  2 h 30 min
2
Venice
— 3 nights
Drive:  4 h 15 min
3
Cinque Terre
— 3 nights
Drive:  2 h 30 min
4
Florence
— 3 nights
Bus:  1 h 15 min
5
Siena
— 7 nights
Drive:  2 h 30 min
6
Rome
— 5 nights
Drive:  3 h 15 min
7
Positano
— 2 nights
Ferry:  30 min
8
Sorrento
— 2 nights
Drive:  3 h
9
San Nicola Arcella
— 2 nights
Drive:  1 h 30 min
10
Civita
— 2 nights
Drive + Fly:  7 h 45 min
11
Palermo
— 2 nights
Drive:  1 h 45 min
12
San Vito lo Capo
— 2 nights
Drive:  3 h 15 min
13
Agrigento
— 2 nights
Drive:  2 h 45 min
14
Syracuse
— 2 nights
Bus + Fly:  18 h 45 min
End: San Francisco

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.
Kick off your visit on the 25th (Fri): admire the landmark architecture of Galleria Vittorio Emanuele II, then contemplate in the serene atmosphere at Duomo di Milano, then appreciate the extensive heritage of Piazza del Duomo, and finally explore the historical opulence of Castello Sforzesco. Get ready for a full day of sightseeing on the next day: explore the different monuments and memorials at Monumental Cemetery, take in the spiritual surroundings of Il Cenacolo, then explore the galleries of Basilica di Sant'Ambrogio, and finally explore the world behind art at Pinacoteca Ambrosiana.

For other places to visit, traveler tips, where to stay, and tourist information, go to the Milan vacation planner.

San Francisco, USA to Milan is an approximately 16- hour flight. You can also do a combination of flight and train; or do a combination of train and flight. Due to the time zone difference, you'll lose 9 hours traveling from San Francisco to Milan. In September, daily temperatures in Milan can reach 76°F, while at night they dip to 57°F. Cap off your sightseeing on the 26th (Sat) early enough to catch the train to Venice.

Things to do in Milan

Historic Sites Museums Shopping
Find places to stay Sep 25 — 26:
Highlights from your plan
Duomo di Milano ©
Duomo di Milano
Galleria Vittorio Emanuele II ©
Galleria Vittorio Emanuele II
Pinacoteca Ambrosiana ©
Pinacoteca Ambrosiana

3
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: Padua (Scrovegni Chapel & Chiesa degli Eremitani). Next up on the itinerary: contemplate the waterfront views at Canal Grande, explore the world behind art at Gallerie dell'Accademia, enjoy breathtaking views from St Mark's Campanile, and snap pictures at Ponte dei Sospiri.

To find ratings, more things to do, reviews, and other tourist information, refer to the Venice route planner.

Traveling by train from Milan to Venice takes 2.5 hours. Alternatively, you can drive; or do a combination of flight and train. In September, daytime highs in Venice are 77°F, while nighttime lows are 59°F. Cap off your sightseeing on the 29th (Tue) early enough to go by car to Cinque Terre.

Things to do in Venice

Historic Sites Museums Nature

Side Trip

Padua
Find places to stay Sep 26 — 29:
Highlights from your plan
Canal Grande ©
Canal Grande
Piazza San Marco ©
Piazza San Marco
Doge's Palace ©
Doge's Palace

3
nights
Cinque Terre

Cinque Terre ©
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 Genoa (Old Port, Cattedrale di San Lorenzo - Duomo di Genova, &more). And it doesn't end there: explore the wealth of natural beauty at Parco Nazionale Cinque Terre, look for gifts at Fannys Bazar, take a stroll around Vernazza, and step into the grandiose world of Castello Doria.

To see ratings, reviews, more things to do, and tourist information, read our Cinque Terre trip planning tool.

You can drive from Venice to Cinque Terre in 4.5 hours. Alternatively, you can take a train; or do a combination of bus and train. In September in Cinque Terre, expect temperatures between 78°F during the day and 59°F at night. Wrap up your sightseeing on the 2nd (Fri) early enough to drive to Florence.

Things to do in Cinque Terre

Parks Nature Historic Sites

Side Trip

Genoa
Find places to stay Sep 29 — Oct 2:
Highlights from your plan
Footpath Monterosso - Vernazza ©
Footpath Monterosso - Vernazza
Aquarium of Genoa ©
Aquarium of Genoa
Parco Nazionale Cinque Terre ©
Parco Nazionale Cinque Terre

3
nights
Florence

Florence ©
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
On the 3rd (Sat), pause for some serene contemplation at Basilica of Santa Croce, admire the masterpieces at Florence Academy of Fine Arts, snap pictures at Ponte Vecchio, then don't miss a visit to Piazzale Michelangelo, and finally explore the world behind art at Pitti Palace. Keep things going the next day: appreciate the history behind Loggia dei Lanzi, contemplate the long history of L’importuno di Michelangelo, steep yourself in history at Palazzo Vecchio, appreciate the extensive heritage of Piazza del Duomo, then take in the spiritual surroundings of Cathedral of Santa Maria del Fiore, and finally take in panoramic vistas at Campanile di Giotto.

For maps, reviews, more things to do, and other tourist information, use the Florence trip planner.

You can drive from Cinque Terre to Florence in 2.5 hours. Alternatively, you can take a train. In October, plan for daily highs up to 71°F, and evening lows to 54°F. Finish your sightseeing early on the 5th (Mon) to allow enough time to take a bus to Siena.

Things to do in Florence

Historic Sites Museums
Find places to stay Oct 2 — 5:
Highlights from your plan
Cathedral of Santa Maria del Fiore ©
Cathedral of Santa Maria del Fiore
Florence Academy of Fine Arts ©
Florence Academy of Fine Arts
Piazzale Michelangelo ©
Piazzale Michelangelo

7
nights
Siena

Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
Explore the numerous day-trip ideas around Siena: San Gimignano (Podere La Marronaia- Sosta Alle Colonne, Historic Centre of San Gimignano, &more), Ciacci Piccolomini d'Aragona (in Castelnuovo dell'Abate) and Abbazia di San Galgano (in Chiusdino). There's lots more to do: awaken your taste buds at some of the top wineries in the area, contemplate in the serene atmosphere at Battistero di San Giovanni, pause for some serene contemplation at San Francesco, and deepen your understanding at Scuola di Cucina di Lella.

For traveler tips, photos, and other tourist information, use the Siena online vacation builder.

Take a bus from Florence to Siena in 1.5 hours. Alternatively, you can drive; or take a train. October in Siena sees daily highs of 73°F and lows of 56°F at night. Finish your sightseeing early on the 12th (Mon) so you can drive to Rome.

Things to do in Siena

Historic Sites Wineries Tours

Side Trips

San Gimignano, Spas, Cascate del Mulino, Castello di Monteriggioni, Ciacci Piccolomini d'Aragona
Find places to stay Oct 5 — 12:
Highlights from your plan
Wine Tours & Tastings
Guardastelle Vineyard ©
Guardastelle Vineyard
Duomo di Siena ©
Duomo di Siena

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.
Rome is known for historic sites, nightlife, and museums. Your plan includes some of its best attractions: explore the ancient world of Colosseum, admire the masterpieces at Galleria Borghese, don't miss a visit to Piazza Navona, and admire the landmark architecture of Pantheon.

To see photos, ratings, traveler tips, and other tourist information, use the Rome holiday builder app.

You can drive from Siena to Rome in 2.5 hours. Alternatively, you can take a bus; or take a train. In October in Rome, expect temperatures between 73°F during the day and 55°F at night. Finish your sightseeing early on the 17th (Sat) so you can drive to Positano.

Things to do in Rome

Historic Sites Museums Tours

Side Trip

Vatican City
Find places to stay Oct 12 — 17:
Highlights from your plan
Colosseum ©
Colosseum
Pantheon ©
Pantheon
St. Peter's Basilica ©
St. Peter's Basilica

2
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.
Kick off your visit on the 17th (Sat): take some stellar pictures from Il Sentiero Degli Dei, get a new perspective on things with Boat Tours & Water Sports, and then enjoy the sand and surf at Bagni d'Arienzo Beach Club, Positano. Get ready for a full day of sightseeing on the 18th (Sun): take in the pleasant sights at Positano, steep yourself in history at Duomo di Ravello, admire the landmark architecture of Villa Rufolo, take in nature's colorful creations at Villa Cimbrone Gardens, then ponder the design of Fontana sant'Andrea, and finally take in the architecture and atmosphere at Duomo di Sant'Andrea.

For reviews, more things to do, traveler tips, and tourist information, go to the Positano online trip planner.

Traveling by car from Rome to Positano takes 3.5 hours. Alternatively, you can do a combination of train, subway, and bus; or take a bus. Plan for somewhat warmer nights when traveling from Rome in October since evenings lows in Positano dip to 63°F. Finish up your sightseeing early on the 19th (Mon) so you can catch the ferry to Sorrento.

Things to do in Positano

Historic Sites Outdoors Parks

Side Trips

Ravello, Amalfi
Find places to stay Oct 17 — 19:
Highlights from your plan
Villa Cimbrone Gardens ©
Villa Cimbrone Gardens
Boat Tours & Water Sports
Duomo di Ravello ©
Duomo di Ravello

2
nights
Sorrento

A lovely town easily accessible from almost anywhere in the country, Sorrento overlooks the Bay of Naples and sits right on the Amalfi Drive.
Kick off your visit on the 19th (Mon): do sightseeing your way with Private Tours, get a new perspective on things with Boat Tours & Water Sports, stroll through Il Vallone dei Mulini, then take in the spiritual surroundings of St Francis Church and Convent, and finally make a trip to Piazza Tasso. On the 20th (Tue), you'll have a packed day of sightseeing: awaken your taste buds at some of the top wineries in the area, then take in the waterfront at Marina Grande - Antico Borgo Marinaro, and then enjoy the sand and surf at Villa di Pollio Felice - Bagni della Regina Giovanna.

For maps, reviews, ratings, and other tourist information, use the Sorrento tour itinerary builder website.

Sorrento is just a stone's throw from Positano. Expect a daytime high around 72°F in October, and nighttime lows around 63°F. Cap off your sightseeing on the 21st (Wed) early enough to travel to San Nicola Arcella.

Things to do in Sorrento

Tours Outdoors Parks
Find places to stay Oct 19 — 21:
Highlights from your plan
Wine Tours & Tastings
Food Tours
Boat Tours & Water Sports

2
nights
San Nicola Arcella

San Nicola Arcella is a town and comune in the province of Cosenza in the Calabria region of southern Italy. When in San Nicola Arcella, make a side trip to see River Rafting & Tubing in Laino Borgo, approximately Laino Borgo away. There's lots more to do: head off the coast to Island Dino, get outside with Spiaggia di San Nicola Arcella, explore the fascinating underground world of Grotta Azzurra, and make a trip to Arco Magno.

To find traveler tips, maps, ratings, and more tourist information, you can read our San Nicola Arcella trip planner.

Getting from Sorrento to San Nicola Arcella by car takes about 3 hours. Wrap up your sightseeing by early afternoon on the 23rd (Fri) to allow time for the car ride to Civita.

Things to do in San Nicola Arcella

Outdoors Parks Tours

Side Trips

Praia A Mare, Diamante, River Rafting & Tubing
Find places to stay Oct 21 — 23:
Highlights from your plan
River Rafting & Tubing
Island Dino ©
Island Dino
Arco Magno ©
Arco Magno

2
nights
Civita

Civita ©
Civita is a hilltown and comune in the province of Cosenza in the Calabria region of southern Italy. On the 23rd (Fri), explore the historical opulence of Castello di Rocca Imperiale. Here are some ideas for day two: make a trip to Sanctuary of St Maria of Weapons, then take in the natural beauty of Grotta delle Ninfe, then look for all kinds of wild species at Setteventi del Pollino, and finally snap pictures at Il ponte del diavolo.

For traveler tips, maps, other places to visit, and tourist information, use the Civita trip itinerary planning app.

Getting from San Nicola Arcella to Civita by car takes about 1.5 hours. Finish your sightseeing early on the 25th (Sun) to allow enough time to travel to Palermo.

Things to do in Civita

Parks Historic Sites Wildlife

Side Trips

Cerchiara di Calabria, Castello di Morano Calabro, Castello di Rocca Imperiale
Find places to stay Oct 23 — 25:
Highlights from your plan
Chiesa di S. Maria Assunta ©
Chiesa di S. Maria Assunta
Sanctuary of St Maria of Weapons ©
Sanctuary of St Maria of Weapons
Castello di Morano Calabro ©
Castello di Morano Calabro

2
nights
Palermo

The capital of Sicily, Palermo was founded by the Phoenicians under the name of Ziz.
Kick off your visit on the 26th (Mon): indulge in some culinary diversions at a local gastronomic tour, steep yourself in history at Norman Palace, explore the different monuments and memorials at Catacombe dei Cappuccini, then take in the architecture and atmosphere at Cattedrale di Palermo, and finally make a trip to Quattro Canti.

To find where to stay, photos, traveler tips, and more tourist information, read Palermo trip planner.

Use the Route module to find suitable travel options from Civita to Palermo. Wrap up your sightseeing on the 27th (Tue) early enough to drive to San Vito lo Capo.

Things to do in Palermo

Tours Historic Sites
Find places to stay Oct 25 — 27:
Highlights from your plan
Food Tours
Cattedrale di Palermo ©
Cattedrale di Palermo
Norman Palace ©
Norman Palace

2
nights
San Vito lo Capo

San Vito lo Capo ©
A vacation in San Vito lo Capo offers a chance to enjoy a sheltered bay and a town with distinctive Arab-Norman architecture.
On the 27th (Tue), kick back and relax at Spiaggia di San Vito lo Capo and then enjoy the sand and surf at Spiaggia di Macari. On the 28th (Wed), you'll have a packed day of sightseeing: visit Cous Cous Fest, contemplate in the serene atmosphere at Santuario Di San Vito, then don't miss a visit to Cappella di Santa Crescenzia, then take a tour by water with Boat Tours & Water Sports, and finally look for gifts at Enoteca Dioniso.

To find photos, ratings, maps, and other tourist information, refer to the San Vito lo Capo online vacation planner.

Traveling by car from Palermo to San Vito lo Capo takes 2 hours. Alternatively, you can do a combination of train and car; or take a bus. October in San Vito lo Capo sees daily highs of 75°F and lows of 64°F at night. Wrap up your sightseeing on the 29th (Thu) to allow time to drive to Agrigento.

Things to do in San Vito lo Capo

Outdoors Parks Beaches
Find places to stay Oct 27 — 29:
Highlights from your plan
Spiaggia di San Vito lo Capo ©
Spiaggia di San Vito lo Capo
Boat Tours & Water Sports
Cous Cous Fest ©
Cous Cous Fest

2
nights
Agrigento

Agrigento ©
Historically one of ancient Greece's leading cities, Sicily's Agrigento is home to the seven monumental temples that make up the well-preserved Valley of the Temples.
Kick off your visit on the 29th (Thu): delve into the distant past at Valle dei Templi, then take in nature's colorful creations at Il Giardino della Kolymbethra, then get engrossed in the history at Museo Archeologico Regionale di Agrigento, and finally pause for some serene contemplation at Chiesa San Nicola. Keep things going the next day: contemplate in the serene atmosphere at Santuario di San Calogero, then explore the ancient world of Eraclea Minoa, then examine the collection at Casa Natale di Luigi Pirandello, and finally make a trip to Statua di Icaro caduto.

To see other places to visit, more things to do, where to stay, and tourist information, refer to the Agrigento travel itinerary planner.

Drive from San Vito lo Capo to Agrigento in 3.5 hours. Alternatively, you can do a combination of car and train; or take a bus. October in Agrigento sees daily highs of 76°F and lows of 67°F at night. Finish up your sightseeing early on the 31st (Sat) so you can go by car to Syracuse.

Things to do in Agrigento

Historic Sites Museums Parks
Find places to stay Oct 29 — 31:
Highlights from your plan
Valle dei Templi ©
Valle dei Templi
Museo Archeologico Regionale di Agrigento ©
Museo Archeologico Regionale di Agrigento
Santuario di San Calogero ©
Santuario di San Calogero

2
nights
Syracuse

Syracuse ©
Philosopher Cicero once described Syracuse as "the greatest Greek city and the most beautiful of them all." A powerful city-state of ancient Greece, Syracuse now is the capital of the eponymous Italian province on the eastern coast of Sicily.
You'll find plenty of places to visit near Syracuse: Chiesa di Santa Maria di Betlem (in Modica), Ragusa Ibla (in Ragusa) and Noto (Chiesa Santa Chiara & Centro Storico). And it doesn't end there: step off the mainland to explore Ortigia, take in the architecture and atmosphere at Duomo di Siracusa, admire the striking features of Palazzo Vermexio, and get engrossed in the history at Museo Archeologico Regionale Paolo Orsi.

To find other places to visit, traveler tips, where to stay, and more tourist information, you can read our Syracuse driving holiday planning site.

Getting from Agrigento to Syracuse by car takes about 3 hours. Other options: do a combination of bus and train; or take a bus. Wrap up your sightseeing by early afternoon on the 2nd (Mon) to allow enough time to travel back home.

Things to do in Syracuse

Historic Sites Nature Parks

Side Trips

Noto, Chiesa di Santa Maria di Betlem, Ragusa Ibla
Find places to stay Oct 31 — Nov 2:
Highlights from your plan
Duomo di Siracusa ©
Duomo di Siracusa
Ortigia ©
Ortigia
Museo Archeologico Regionale Paolo Orsi ©
Museo Archeologico Regionale Paolo Orsi

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