41 days in Italy Itinerary

41 days in Italy Itinerary

Created using Inspirock Europe trip itinerary planner

Make it your trip
Fly
1
Milan
— 1 night
Drive
2
Venice
— 3 nights
Drive
3
Cinque Terre
— 3 nights
Drive
4
Florence
— 3 nights
Drive
5
Siena
— 7 nights
Drive
6
Rome
— 5 nights
Drive
7
Positano
— 2 nights
Drive
8
Sorrento
— 2 nights
Drive
9
San Nicola Arcella
— 2 nights
Drive
10
Civita
— 2 nights
Drive to Lamezia Terme Airport, Fly to Palermo
11
Palermo
— 2 nights
Drive
12
San Vito lo Capo
— 2 nights
Drive
13
Agrigento
— 2 nights
Drive
14
Syracuse
— 2 nights
Fly

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Milan

— 1 night

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.
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 pause for some serene contemplation at Basilica di Sant'Ambrogio, and finally explore the world behind art at Pinacoteca Ambrosiana.

To see reviews, where to stay, other places to visit, and tourist information, go to the Milan vacation planner.

San Francisco, USA to Milan is an approximately 15.5-hour 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 go by car to Venice.

Things to do in Milan

Historic Sites · Museums · Shopping

Venice

— 3 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.
You'll find plenty of places to visit near Venice: Padua (Scrovegni Chapel & Chiesa degli Eremitani). There's still lots to do: contemplate the waterfront views at Canal Grande, steep yourself in history at Ponte dei Sospiri, admire the masterpieces at Peggy Guggenheim Collection, and get to know the fascinating history of Piazza San Marco.

Use Inspirock's suggestions to plan your Venice trip and find the best activities and attractions for your vacation.

Traveling by car from Milan to Venice takes 3 hours. Alternatively, you can take a train; or take a bus. September in Venice sees daily highs of 77°F and lows of 59°F at night. Finish up your sightseeing early on the 29th (Tue) so you can go by car to Cinque Terre.

Things to do in Venice

Historic Sites · Museums · Nature · Parks

Side Trip

Cinque Terre

— 3 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 Genoa (Old Port, Cattedrale di San Lorenzo - Duomo di Genova, &more). There's lots more to do: explore the striking landscape of Parco Nazionale Cinque Terre, stop by Fannys Bazar, step into the grandiose world of Castello Doria, and trek along Cinque Terre Trails.

To see ratings, reviews, more things to do, and more tourist information, you can read our Cinque Terre road trip planner.

Getting from Venice to Cinque Terre by car takes about 4.5 hours. Other options: fly; or take a train. September in Cinque Terre sees daily highs of 78°F and lows of 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 · Outdoors · Historic Sites

Side Trip

Florence

— 3 nights

Birthplace of the Italian Renaissance

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 reviews, traveler tips, 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 drive to Siena.

Things to do in Florence

Historic Sites · Museums

Siena

— 7 nights

Cultural Heart of Tuscany

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: Ciacci Piccolomini d'Aragona (in Castelnuovo dell'Abate), San Gimignano (Podere La Marronaia- Sosta Alle Colonne, Historic Centre of San Gimignano, &more) 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 San Francesco, take in the dramatic scenery at Cascate del Mulino, and make a trip to Piazza del Campo.

To see other places to visit and other tourist information, use the Siena online vacation builder.

Drive from Florence to Siena in 1.5 hours. Alternatively, you can take a bus; 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 · Museums

Side Trips

Rome

— 5 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, nightlife, and museums. Your plan includes some of its best attractions: steep yourself in history at St. Peter's Basilica, admire the masterpieces at Galleria Borghese, explore the galleries of Vatican Museums, and explore the ancient world of Colosseum.

To see traveler tips, reviews, where to stay, and other tourist information, use the Rome trip itinerary builder website.

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 up your sightseeing early on the 17th (Sat) so you can go by car to Positano.

Things to do in Rome

Historic Sites · Museums · Tours · Wineries

Side Trip

Positano

— 2 nights
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.

To see traveler tips, maps, more things to do, 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 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 go by car to Sorrento.

Things to do in Positano

Historic Sites · Outdoors · Parks · Beaches

Side Trips

Sorrento

— 2 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.
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 your second day here, take a leisurely stroll along Marina Grande - Antico Borgo Marinaro and then kick back and relax at Villa di Pollio Felice - Bagni della Regina Giovanna.

To see where to stay, other places to visit, more things to do, and other tourist information, use the Sorrento tour planning app.

Traveling by car from Positano to Sorrento takes an hour. Alternatively, you can ride a ferry; or take a bus. In October, daytime highs in Sorrento are 72°F, while nighttime lows are 63°F. Wrap up your sightseeing on the 21st (Wed) to allow time to travel to San Nicola Arcella.

Things to do in Sorrento

Tours · Outdoors · Parks · Beaches

San Nicola Arcella

— 2 nights
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: appreciate the extensive heritage of Murales, get outside with Spiaggia di San Nicola Arcella, make a trip to Isola Di Cirella, and step off the mainland to explore Island Dino.

To see other places to visit, reviews, maps, 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 · Nature

Side Trips

Civita

— 2 nights
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. On the 24th (Sat), you'll have a packed day of sightseeing: take in the spiritual surroundings of Sanctuary of St Maria of Weapons, witness a stunning natural landmark at Grotta delle Ninfe, then identify plant and animal life at Setteventi del Pollino, and finally snap pictures at Il ponte del diavolo.

To see traveler tips, maps, other places to visit, and other tourist information, go to the Civita trip builder tool.

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

Things to do in Civita

Historic Sites · Parks · Wildlife · Nature

Side Trips

Palermo

— 2 nights
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 photos, where to stay, more things to do, 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

San Vito lo Capo

— 2 nights
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: get a dose of culture at 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 maps, other places to visit, traveler tips, 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 taxi; 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 · Beaches · Parks · Tours

Agrigento

— 2 nights

Valley of the Temples

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 admire the landmark architecture of Casa Natale di Luigi Pirandello, and finally make a trip to Statua di Icaro caduto.

To find reviews, other places to visit, more things to do, 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 taxi 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

Syracuse

— 2 nights

Pearl of the Mediterranean

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.
Explore the numerous day-trip ideas around Syracuse: Chiesa di Santa Maria di Betlem (in Modica), Noto (Chiesa Santa Chiara & Centro Storico) and Ragusa Ibla (in Ragusa). There's much more to do: step off the mainland to explore Ortigia, admire the striking features of Palazzo Vermexio, explore the ancient world of Teatro Greco, and take an in-depth tour of Museo Archeologico Regionale Paolo Orsi.

To find reviews, ratings, where to stay, and tourist information, read our Syracuse road trip app.

You can drive from Agrigento to Syracuse in 2.5 hours. Alternatively, you can take a bus; or take a bus. On the 2nd (Mon), wrap the sightseeing up by early afternoon so you can fly back home.

Things to do in Syracuse

Historic Sites · Nature · Parks · Museums

Side Trips

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.

Province of Cosenza travel guide

4.2
River Rafting & Tubing · Landmarks · Beaches
Cosenza is a city in the Calabria region of Southern Italy. The city proper has a population of 71,000; the urban area counts over 268,000 inhabitants. It is the capital of the Province of Cosenza, which has a population of around 735,000.The ancient town is the seat of the Cosentian Academy, the second academy of philosophical and literary studies to be founded in the Kingdom of Naples (1511) and one of the oldest in Europe. To this day, the city remains a major cultural hub in Southern Italy, with several museums, theatres, libraries and the University of Calabria.Geography and ClimateLocated at the confluence of two historical rivers, the Busento and the Crati, Cosenza stands 238 m above sea level in a valley between the Sila plateau and the coastal range of mountains. The old town, overshadowed by its Norman castle, descends to the river Crati. The modern city lies to the north, beyond the Busento, on level ground.Almost completely surrounded by mountains, Cosenza is subject to a microclimate scarcely influenced by the Mediterranean Sea, with cold winters and hot summers.

Source

Sicily travel guide

4.5
Beaches · Ruins · Churches
The largest island in the Mediterranean Sea, Sicily is a ruggedly attractive land. The island has a long history of foreign domination and has been controlled by the Greeks, Romans, Arabs, and Normans. The result is a distinct culture blending elements from all of those areas and featuring an intriguing dialect. This is a huge island with plenty of small villages to tour, each with its own treasures. Beyond the popular coastal areas, Sicily's inland attractions include an unspoiled landscape of mountains, hills, and villages that sometimes seem frozen in time. While the natural environment is its biggest draw, Sicily's greatest asset may be its people. They are proud of their traditions and incredibly hospitable to visitors.