23 days in Italy Itinerary

23 days in Italy Itinerary

Created using Inspirock Italy journey maker

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Route & dates

Start: Cleveland
+2
Fly + Foot + Train:  16 h 15 min
1
Palermo
— 2 nights
Bus:  2 h
2
Agrigento
— 1 night
Drive:  2 h 45 min
3
Syracuse
— 1 night
Drive:  1 h 45 min
4
Castiglione di Sicilia
— 3 nights
Drive:  1 h
5
Taormina
— Few hours
Drive:  3 h
6
Tropea
— 1 day
Drive:  4 h 15 min
7
Matera
— 1 day
Drive:  1 h 15 min
8
Alberobello
— 1 night
Drive:  4 h 15 min
9
Sorrento
— 4 nights
Drive:  1 h 30 min
10
Caserta
— 4 nights
Drive:  2 h 15 min
11
Rome
— 3 nights
Fly:  14 h
End: Cleveland


Learn more about your trip

2
nights
Palermo

Palermo ©
The capital of Sicily, Palermo was founded by the Phoenicians under the name of Ziz.
On the 25th (Sun), take in the architecture and atmosphere at Chiesa Inferiore della Cappella Palatina, contemplate the long history of Norman Palace, admire the striking features of Palazzo Conte Federico, then explore the different monuments and memorials at Catacombe dei Cappuccini, then take in the architecture and atmosphere at Duomo di Monreale, and finally admire the natural beauty at Orto Botanico di Palermo. Keep things going the next day: steep yourself in history at Santa Maria dell'Ammiraglio, browse the collection at Biblioteca Comunale di Palermo, take in the architecture and atmosphere at Chiesa del Gesu, then contemplate in the serene atmosphere at Church of San Cataldo, then make a trip to Nobile e Monumentale Chiesa dell'Immacolata Concezione al Capo, and finally pause for some serene contemplation at Cattedrale di Palermo.

For ratings, reviews, photos, and tourist information, you can read our Palermo trip planner.

Cleveland, USA to Palermo is an approximately 16.5- hour combination of flight and train. You can also do a combination of flight and bus; or do a combination of bus, flight, and train. The time zone changes from Eastern Standard Time (EST) to Central European Standard Time (CET), which is usually a 6 hour difference. Finish your sightseeing early on the 27th (Tue) so you can take a bus to Agrigento.

Things to do in Palermo

Historic Sites Parks

Side Trip

Duomo di Monreale
Find places to stay Apr 25 — 27:
Highlights from your plan
Palazzo Conte Federico ©
Palazzo Conte Federico
Cattedrale di Palermo ©
Cattedrale di Palermo
Norman Palace ©
Norman Palace

1
night
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.
Start off your visit on the 27th (Tue): take in the spiritual surroundings of Valle dei Templi, then admire the natural beauty at Il Giardino della Kolymbethra, then get engrossed in the history at Museo Archeologico Regionale di Agrigento, and finally take in the spiritual surroundings of Chiesa San Nicola.

To find more things to do, photos, ratings, and tourist information, you can read our Agrigento visit planner.

Take a bus from Palermo to Agrigento in 2 hours. Alternatively, you can drive; or take a train. In April in Agrigento, expect temperatures between 68°F during the day and 56°F at night. Wrap up your sightseeing on the 28th (Wed) to allow time to drive to Syracuse.

Things to do in Agrigento

Historic Sites Museums Parks
Find places to stay Apr 27 — 28:
Highlights from your plan
Valle dei Templi ©
Valle dei Templi
Il Giardino della Kolymbethra ©
Il Giardino della Kolymbethra
Museo Archeologico Regionale di Agrigento ©
Museo Archeologico Regionale di Agrigento

1
night
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.
Start off your visit on the 28th (Wed): step off the mainland to explore Ortigia, then admire the striking features of Palazzo Vermexio, then take in the architecture and atmosphere at Duomo di Siracusa, and finally explore the ancient world of Teatro Greco.

To find photos and other tourist information, go to the Syracuse journey planner.

Traveling by car from Agrigento to Syracuse takes 3 hours. Alternatively, you can do a combination of bus and train; or take a bus. Finish your sightseeing early on the 29th (Thu) so you can drive to Castiglione di Sicilia.

Things to do in Syracuse

Nature Parks Historic Sites
Find places to stay Apr 28 — 29:
Highlights from your plan
Ortigia ©
Ortigia
Duomo di Siracusa ©
Duomo di Siracusa
Teatro Greco ©
Teatro Greco

3
nights
Castiglione di Sicilia

Castiglione di Sicilia ©
You'll find plenty of places to visit near Castiglione di Sicilia: Etna Donkey Trekking (in Linguaglossa) and Borgo Medievale (in Montalbano Elicona).

To see maps, other places to visit, where to stay, and other tourist information, use the Castiglione di Sicilia trip planner.

Traveling by car from Syracuse to Castiglione di Sicilia takes 2 hours. Finish up your sightseeing early on the 2nd (Sun) so you can go by car to Taormina.

Things to do in Castiglione di Sicilia

Wineries Parks Historic Sites

Side Trips

Linguaglossa, Gole Alcantara Botanical and Geological Park, Borgo Medievale
Find places to stay Apr 29 — May 2:
Highlights from your plan
Etna Donkey Trekking ©
Etna Donkey Trekking
Gambino Vini ©
Gambino Vini
Fischetti ©
Fischetti

few
hours
Taormina

Taormina
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.
To see photos, where to stay, maps, and tourist information, you can read our Taormina holiday app.

You can drive from Castiglione di Sicilia to Taormina in an hour. In May, daily temperatures in Taormina can reach 75°F, while at night they dip to 61°F. On the 2nd (Sun), you'll travel to Tropea.

Things to do in Taormina

Outdoors Tours Historic Sites
Find places to stay May 2 — 3:

1
day
Tropea

Tropea ©
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 3rd (Mon): pause for some serene contemplation at Chiesa di San Michele Arcangelo, pause for some serene contemplation at Chiesa del Gesu, get great views at Affaccio Raf Vallone, take an in-depth tour of Artistic Creations The Lighthouse, then go for a stroll along the water at Porto Turistico di Tropea, and finally tour the pleasant surroundings at Tropea Beach.

To find other places to visit, traveler tips, more things to do, and more tourist information, refer to the Tropea trip maker app.

Drive from Taormina to Tropea in 3 hours. Traveling from Taormina in May, expect a bit cooler with lows of 56°F in Tropea. Wrap up your sightseeing on the 3rd (Mon) early enough to drive to Matera.

Things to do in Tropea

Parks Historic Sites Beaches
Find places to stay May 2 — 3:
Highlights from your plan
Tropea Beach ©
Tropea Beach
Artistic Creations The Lighthouse ©
Artistic Creations The Lighthouse
The Sanctuary of Santa Maria dell'Isola ©
The Sanctuary of Santa Maria dell'Isola

1
day
Matera

Matera ©
Famous for its resemblance to the ancient settlements of Jerusalem and Cappadocia, Matera remains one of the oldest inhabited cities in the world.
On the 4th (Tue), admire the striking features of Cattedrale di Matera, then get to know the fascinating history of Sassi di Matera, then explore the fascinating underground world of Casa Grotta di Vico Solitario, and finally make a trip to Palombaro Lungo.

To find ratings, reviews, traveler tips, and other tourist information, read our Matera trip itinerary builder tool.

You can drive from Tropea to Matera in 4.5 hours. Alternatively, you can do a combination of train and bus; or take a bus. May in Matera sees daily highs of 71°F and lows of 52°F at night. Finish up your sightseeing early on the 4th (Tue) so you can go by car to Alberobello.

Things to do in Matera

Historic Sites Museums Nature
Find places to stay May 3 — 4:
Highlights from your plan
Sassi di Matera ©
Sassi di Matera
Cattedrale di Matera ©
Cattedrale di Matera
Palombaro Lungo ©
Palombaro Lungo

1
night
Alberobello

Alberobello ©
Alberobello is a small town and comune of the Metropolitan City of Bari, Apulia, southern Italy. Kick off your visit on the 5th (Wed): admire the landmark architecture of Trullo Sovrano, cozy up to a beverage at Enoteca Tholos, and then admire the landmark architecture of I Trulli di Alberobello - World Heritage Site.

To find other places to visit, reviews, maps, and more tourist information, refer to the Alberobello online driving holiday planner.

You can drive from Matera to Alberobello in 1.5 hours. Another option is to take a bus. May in Alberobello sees daily highs of 71°F and lows of 52°F at night. Wrap up your sightseeing by early afternoon on the 5th (Wed) to allow enough time to drive to Sorrento.

Things to do in Alberobello

Nightlife Historic Sites Museums
Find places to stay May 4 — 5:
Highlights from your plan
Enoteca Tholos ©
Enoteca Tholos
I Trulli di Alberobello - World Heritage Site ©
Trullo Sovrano ©
Trullo Sovrano

4
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.
Change things up with these side-trips from Sorrento: Il Sentiero Degli Dei (in Positano) and Duomo di Sant'Andrea (in Amalfi). Dedicate the 9th (Sun) to wine at some of the top wineries in the area. There's lots more to do: stop by Art & Craft Gallery, contemplate the long history of Church of Santa Maria Assunta, admire the natural beauty at I Giardini di Cataldo, and take in the spiritual surroundings of St Francis Church and Convent.

To see maps, reviews, traveler tips, and other tourist information, refer to the Sorrento online trip itinerary builder.

Traveling by car from Alberobello to Sorrento takes 4.5 hours. Alternatively, you can do a combination of bus and subway; or do a combination of bus, flight, and subway. Traveling from Alberobello in May, expect somewhat warmer with lows of 60°F in Sorrento. Wrap up your sightseeing on the 9th (Sun) to allow time to drive to Caserta.

Things to do in Sorrento

Tours Outdoors Wildlife

Side Trips

Positano, Duomo di Sant'Andrea
Find places to stay May 5 — 9:
Highlights from your plan
Food Tours
Il Sentiero Degli Dei ©
Il Sentiero Degli Dei
Duomo di Sant'Andrea ©
Duomo di Sant'Andrea

4
nights
Caserta

Caserta ©
Caserta is the capital of the province of Caserta in the Campania region of Italy. Venture out of the city with trips to Pompeii Archaeological Park (in Pompeii), Parco Acheologico di Ercolano (in Ercolano) and Ponte sul Martorano (in Sant'Agata de' Goti). There's lots more to do: appreciate the extensive heritage of Prata Sannita, look for all kinds of wild species at La Ghiandaia - Oasi WWF Bosco di San Silvestro, explore the different monuments and memorials at Caserta War Cemetery, and take in nature's colorful creations at Reggia di Caserta.

For photos, other places to visit, maps, and tourist information, go to the Caserta tour itinerary planner.

Traveling by car from Sorrento to Caserta takes 1.5 hours. Alternatively, you can take a train; or do a combination of train and bus. Traveling from Sorrento in May, Caserta is slightly colder at night with lows of 52°F. On the 13th (Thu), wrap the sightseeing up by early afternoon so you can take a train to Rome.

Things to do in Caserta

Historic Sites Parks Wildlife

Side Trips

Pompeii Archaeological Park, Parco Acheologico di Ercolano, Centro Carni di Esposito Pasquale, Ponte sul Martorano
Find places to stay May 9 — 13:
Highlights from your plan
Reggia di Caserta ©
Reggia di Caserta
Pompeii Archaeological Park ©
Pompeii Archaeological Park
Parco Acheologico di Ercolano ©
Parco Acheologico di Ercolano

3
nights
Rome

Rome ©
Aptly nicknamed the Eternal City, Rome is the birthplace of the Roman Empire, one of the world's greatest civilizations ever.
On the 13th (Thu), explore the ancient world of Colosseum. Keep things going the next day: explore the world behind art at Vatican Museums, contemplate the long history of St. Peter's Basilica, then delve into the distant past at Pantheon, and finally admire the local landmark of Trevi Fountain.

For reviews, ratings, where to stay, and tourist information, you can read our Rome trip itinerary planner.

You can take a train from Caserta to Rome in 1.5 hours. Alternatively, you can drive; or take a bus. Traveling from Caserta in May, you can expect nighttime temperatures to be somewhat warmer in Rome, with lows of 58°F. Finish up your sightseeing early on the 16th (Sun) so you can travel back home.

Things to do in Rome

Historic Sites Museums

Side Trip

Vatican City
Find places to stay May 13 — 16:
Highlights from your plan
Colosseum ©
Colosseum
St. Peter's Basilica ©
St. Peter's Basilica
Pantheon ©
Pantheon

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