26 days in Italy Itinerary

26 days in Italy Itinerary

Created using Inspirock Italy travel route planner

Make it your trip
Fly
1
Palermo
— 2 nights
Drive
2
Agrigento
— 1 night
Drive
3
Syracuse
— 2 nights
Drive
4
Taormina
— 2 nights
+2
Drive to Messina Marittima, Ferry to Villa San Giovanni, Drive to Tropea
5
Tropea
— 1 night
Drive
6
Matera
— 1 night
Drive
7
Alberobello
— 1 night
Drive
8
Sorrento
— 4 nights
Drive
9
Caserta
— 2 nights
Drive
10
Riardo
— 1 night
Drive
11
Cassino
— 1 night
Drive
12
Magione
— 3 nights
Drive
13
Rome
— 3 nights
Fly

S M T W T F S
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Palermo

— 2 nights
The capital of Sicily, Palermo was founded by the Phoenicians under the name of Ziz.
Change things up with these side-trips from Palermo: Duomo di Monreale (in Monreale) and Riserva Naturale Dello Zingaro (in Castellammare del Golfo). And it doesn't end there: don't miss a visit to Cattedrale di Palermo, savor the flavors at Food & Drink, pause for some serene contemplation at Church of San Cataldo, and contemplate the long history of Norman Palace.

To see ratings, other places to visit, more things to do, and tourist information, read our Palermo trip itinerary builder website.

Cleveland, USA to Palermo is an approximately 15.5-hour flight. The time zone difference moving from Eastern Standard Time to Central European Standard Time is 6 hours. Finish up your sightseeing early on the 3rd (Tue) so you can go by car to Agrigento.

Things to do in Palermo

Historic Sites · Parks · Wildlife · Tours

Side Trips

Agrigento

— 1 night

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.
On the 4th (Wed), explore the ancient world of Valle dei Templi and then take an in-depth tour of Museo Archeologico Regionale di Agrigento.

To see where to stay, reviews, more things to do, and tourist information, you can read our Agrigento trip planner.

Traveling by car from Palermo to Agrigento takes 2.5 hours. Alternatively, you can drive; or take a bus; or take a train. In May in Agrigento, expect temperatures between 72°F during the day and 61°F at night. Wrap up your sightseeing on the 4th (Wed) to allow time to drive to Syracuse.

Things to do in Agrigento

Historic Sites · Museums

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.
On the 5th (Thu), get engrossed in the history at Museo Archeologico Regionale Paolo Orsi, delve into the distant past at Parco Archeologico della Neapolis, explore the ancient world of Teatro Greco, delve into the distant past at Temple of Apollo (Tempio di Apollo), then take in the architecture and atmosphere at Duomo di Siracusa, and finally admire the striking features of Palazzo Vermexio.

To find where to stay, traveler tips, reviews, and more tourist information, read Syracuse trip itinerary builder app.

Getting from Agrigento to Syracuse by car takes about 3 hours. Other options: drive; or take a bus; or take a bus. Wrap up your sightseeing on the 6th (Fri) to allow time to drive to Taormina.

Things to do in Syracuse

Historic Sites · Museums

Taormina

— 2 nights
With its warm island weather and cliffside location overlooking the Ionion Sea, Taormina has been one of Sicily's most popular getaway destinations since the early 19th century.
Start off your visit on the 6th (Fri): take in the architecture and atmosphere at Duomo di Taormina, make a trip to Ancient Theatre of Taormina, stroll around Villa Comunale, then see the interesting displays at Pavone Francesco, then don't miss a visit to Corso Umberto, and finally go for a walk through Piazza IX Aprile. Get ready for a full day of sightseeing on the 7th (Sat): take in breathtaking views at Gole Alcantara Botanical and Geological Park, do a tasting at Il vino della Rosa, learn about winemaking at Gambino Vini, then kick back and relax at Isola Bella, and finally take in the spiritual surroundings of Chiesa del Varo.

To find other places to visit, maps, ratings, and more tourist information, read Taormina trip itinerary planning site.

You can drive from Syracuse to Taormina in 1.5 hours. Other options are to take a train; or take a bus. May in Taormina sees daily highs of 75°F and lows of 61°F at night. Wrap up your sightseeing on the 8th (Sun) early enough to travel to Tropea.

Things to do in Taormina

Parks · Nature · Historic Sites · Wineries

Side Trips

Tropea

— 1 night
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. Kick off your visit on the 8th (Sun): look for gifts at Gourmetit, contemplate in the serene atmosphere at The Sanctuary of Santa Maria dell'Isola, kick back and relax at Tropea Beach, have fun and explore at Artistic Creations The Lighthouse, then tour the pleasant surroundings at Capo Vaticano, and finally enjoy the sand and surf at Grotticelle beach.

To see photos, traveler tips, reviews, and other tourist information, read our Tropea road trip app.

You can do a combination of car and ferry from Taormina to Tropea in 3 hours. Alternatively, you can do a combination of bus and train; or take a train. Plan for slightly colder nights when traveling from Taormina in May since evenings lows in Tropea dip to 56°F. Finish up your sightseeing early on the 9th (Mon) so you can go by car to Matera.

Things to do in Tropea

Outdoors · Parks · Beaches · Museums

Side Trip

Matera

— 1 night

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.
Kick off your visit on the 9th (Mon): don't miss a visit to Palombaro Lungo, explore the ancient world of Materasum Ipogeo, don't miss a visit to Chiesa rupestre di Santa Lucia alle Malve, stroll through Casa Grotta di Vico Solitario, then make a trip to Casa Noha, and finally appreciate the extensive heritage of Sassi di Matera.

To find other places to visit, where to stay, more things to do, and more tourist information, use the Matera road trip site.

Traveling by car from Tropea to Matera takes 4 hours. Alternatively, you can do a combination of train and bus. In May, daily temperatures in Matera can reach 71°F, while at night they dip to 52°F. Wrap up your sightseeing on the 10th (Tue) early enough to drive to Alberobello.

Things to do in Matera

Historic Sites · Museums · Parks · Nature

Alberobello

— 1 night
Alberobello is a small town and comune of the Metropolitan City of Bari, Apulia, southern Italy. On the 10th (Tue), experience the excitement of Zoosafari, don't miss a visit to Parrocchia Sant'Antonio di Padova, then admire the striking features of I Trulli di Alberobello - World Heritage Site, and finally admire the landmark architecture of Trullo Sovrano.

To find photos, maps, and more tourist information, use the Alberobello road trip planning site.

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. May in Alberobello sees daily highs of 71°F and lows of 52°F at night. Cap off your sightseeing on the 11th (Wed) early enough to go by car to Sorrento.

Things to do in Alberobello

Zoos & Aquariums · Parks · Nightlife · Fun & Games

Side Trip

Sorrento

— 4 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.
Sorrento is known for nightlife, historic sites, and beaches. Your plan includes some of its best attractions: indulge in some culinary diversions at a local gastronomic tour, admire the natural beauty at Vivaio Ruoppo, contemplate in the serene atmosphere at St Francis Church and Convent, and take in the waterfront at Marina Grande - Antico Borgo Marinaro.

To see other places to visit, maps, and tourist information, read our Sorrento trip itinerary maker website.

Drive from Alberobello to Sorrento in 4.5 hours. Alternatively, you can drive; or take a bus; or do a combination of bus and train. Traveling from Alberobello in May, expect somewhat warmer with lows of 60°F in Sorrento. Finish up your sightseeing early on the 15th (Sun) so you can go by car to Caserta.

Things to do in Sorrento

Tours · Historic Sites · Outdoors · Wildlife

Caserta

— 2 nights
Caserta is the capital of the province of Caserta in the Campania region of Italy. Step out of Caserta with an excursion to Duomo di San Paolo in Aversa--about 34 minutes away. And it doesn't end there: take in nature's colorful creations at Reggia di Caserta, do a tasting at Terre del Principe, make a trip to Chiesa di San Ferdinando Re, and take a stroll through Casertavecchia.

To see more things to do, traveler tips, photos, and other tourist information, you can read our Caserta online trip planner.

Drive from Sorrento to Caserta in 1.5 hours. Alternatively, you can take a train; or take a bus. Expect a bit cooler evenings in Caserta when traveling from Sorrento in May, with lows around 52°F. Cap off your sightseeing on the 17th (Tue) early enough to travel to Riardo.

Things to do in Caserta

Historic Sites · Parks · Wineries · Neighborhoods

Side Trips

Riardo

— 1 night
Riardo is a comune (municipality) in the Province of Caserta in the Italian region Campania, located about 50km north of Naples and about 25km northwest of Caserta.Riardo borders the following municipalities: Pietramelara, Pietravairano, Rocchetta e Croce, Teano, Vairano Patenora. To see other places to visit, photos, ratings, and more tourist information, you can read our Riardo trip itinerary maker website.

Drive from Caserta to Riardo in an hour. In May, daily temperatures in Riardo can reach 75°F, while at night they dip to 52°F. On the 18th (Wed), you're off to Cassino.

Things to do in Riardo

Historic Sites · Parks · Shopping · Nightlife

Cassino

— 1 night
Cassino is a comune in the province of Frosinone, Italy, at the southern end of the region of Lazio.Cassino is located at the foot of Monte Cairo near the confluence of the Gari and Liri rivers. Kick off your visit on the 18th (Wed): see the interesting displays at Monte Cassino, explore the different monuments and memorials at Monte Cassino Polish War Cemetery, then examine the collection at Historiale di Cassino, and finally stroll the grounds of Cassino Memorial.

To see where to stay, other places to visit, and tourist information, go to the Cassino vacation site.

You can drive from Riardo to Cassino in an hour. Expect a daytime high around 74°F in May, and nighttime lows around 53°F. Wrap up your sightseeing on the 19th (Thu) early enough to travel to Magione.

Things to do in Cassino

Historic Sites · Museums

Magione

— 3 nights
Magione is a comune (municipality) in the Province of Perugia in the Italian region Umbria, located about 15 km west of Perugia. Explore Magione's surroundings by going to Podere Il Cocco (in Montalcino), Castelnuovo dell'Abate (Abbazia di Sant'Antimo & Ciacci Piccolomini d'Aragona) and Crete Senesi (in Asciano). There's lots more to do: tour the pleasant surroundings at Val d'Orcia, don't miss a visit to Piazza Signorelli, take in the spiritual surroundings of Eremo Le Celle, and test the waters at Piscine Termali Theia.

For traveler tips, more things to do, other places to visit, and tourist information, use the Magione trip planner.

You can drive from Cassino to Magione in 3.5 hours. Expect a daytime high around 71°F in May, and nighttime lows around 51°F. Wrap up your sightseeing on the 22nd (Sun) early enough to travel to Rome.

Things to do in Magione

Historic Sites · Wineries · Parks · Museums

Side Trips

Rome

— 3 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: contemplate the long history of Colosseum, admire the masterpieces at Galleria Borghese, appreciate the extensive heritage of Piazza Navona, and pause for some serene contemplation at Santa Maria in Trastevere.

For traveler tips, other places to visit, ratings, and more tourist information, go to the Rome online trip itinerary builder.

Getting from Magione to Rome by car takes about 2.5 hours. Traveling from Magione in May, you can expect nighttime temperatures to be a bit warmer in Rome, with lows of 58°F. Finish your sightseeing early on the 25th (Wed) to allow enough time to fly back home.

Things to do in Rome

Historic Sites · Museums

Side Trip

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.

Umbria travel guide

4.4
Churches · Landmarks · Architectural Buildings
Characterized by a landscape of green hills, attractive towns, and World Heritage-listed monuments, Umbria is the only region in the country with neither a coastline nor an international border. Umbria is home to the town of Assisi, a World Heritage Site and a major religious center that houses a number of attractions. Its Franciscan church has one of the world's finest medieval collections of frescos, a must-see on any itinerary here. Umbria is one of Italy's smaller regions, yet what it lacks in size, it more than makes up in the natural beauty of its agricultural lands and quaint villages.