5 days in Italy Itinerary

Created using Inspirock Italy vacation planner
Make it your trip
— 2 nights
Palermo, Sicily
— 2 nights


Assisi — 2 nights

City of Peace

Rich in culture and religious tradition, Assisi is known as the birthplace of St.
Kick off your visit on the 20th (Mon): admire the landmark architecture of San Pietro, learn about winemaking at Cantina Lungarotti - Torgiano, then see the interesting displays at MUVIT Museo del Vino Torgiano Museum, then contemplate in the serene atmosphere at Abbazia di Sassovivo, and finally appreciate the extensive heritage of Centro Storico. On the 21st (Tue), you'll have a packed day of sightseeing: contemplate in the serene atmosphere at Cripta di San Francesco, take in the exciting artwork at Chiesa di Santa Maria delle Rose. Mostra Maria, then take in the architecture and atmosphere at Chiesa Santo Stefano, then get to know the fascinating history of Centro Storico, and finally learn about winemaking at Antonelli San Marco.

To find reviews, more things to do, where to stay, and tourist information, refer to the Assisi trip itinerary maker site.

Rome to Assisi is an approximately 2.5-hour car ride. You can also take a train; or take a bus. Traveling from Rome in May, Assisi is slightly colder at night with lows of 13°C. Finish up your sightseeing early on the 22nd (Wed) so you can catch the flight to Palermo.
Historic Sites · Wineries · Museums · Shopping
Side Trips
Find places to stay May 20 — 22:

Palermo, Sicily — 2 nights

The capital of Sicily, Palermo was founded by the Phoenicians under the name of Ziz.
Your cultural itinerary includes sights like Castello Ventimiglia and Museo dell'Acciuga. Step off the beaten path and head to Chiesa di Santa Maria dello Spasimo and Scuba & Snorkeling. You'll find plenty of places to visit near Palermo: La Bottega nella Roccia (in Caccamo), CIDMA: Mafia and Anti-Mafia Center Guided Visits (in Corleone) and Santuario Gibilmanna (in Cefalu). It doesn't end there: see the interesting displays at Museo Diocesano di Palermo and take in the spiritual surroundings of Chiesa di S. Domenico e Chiostro.

For other places to visit, more things to do, ratings, and other tourist information, use the Palermo sightseeing tool.

Getting from Assisi to Palermo by flight takes about 3 hours. Other options: take a train; or do a combination of train and bus. Finish up your sightseeing early on the 24th (Fri) so you can catch the flight back home.
Historic Sites · Tours · Outdoors · Wildlife
Side Trips
Find places to stay May 22 — 24:

Italy travel guide

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.