29 days in Italy Itinerary
Created using Inspirock Italy vacation maker
Start: Chicago
Fly
1
Venice
— 3 nights
Drive
2
Trento
— 4 nights
Drive
3
Florence
— 2 nights
Drive
4
Assisi
— 4 nights
Drive to Piombino, Ferry to Portoferraio
5
Portoferraio, Elba Island
— 3 nights
Ferry to Porto Biglietterie Sud, Fly to San Vito lo Capo
6
San Vito lo Capo, Sicily
— 4 nights
Fly
7
Otranto
— 3 nights
Fly
8
Rome
— 5 nights
Fly
End: Chicago
Tue, Aug 23 - Tue, Sep 20
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View full calendar
Venice — 3 nights
©
City of Romance
Get some historical perspective at Piazza San Marco and Centro Storico di Venezia. Step off the beaten path and head to Basilica of St. Anthony and San Giorgio Maggiore. Change things up with a short trip to Scrovegni Chapel in Padua (about 54 minutes away). The adventure continues: contemplate in the serene atmosphere at Basilica di Santa Maria Gloriosa dei Frari, contemplate the waterfront views at Canal Grande, don't miss a visit to St Mark's Campanile, and take in the architecture and atmosphere at Basilica di Santa Maria della Salute.
To find reviews, ratings, more things to do, and more tourist information, read Venice day trip tool.
Chicago, USA to Venice is an approximately 12-hour flight. The time zone difference when traveling from Chicago to Venice is 7 hours. In August, plan for daily highs up to 85°F, and evening lows to 66°F. Finish your sightseeing early on the 26th (Fri) so you can drive to Trento.
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To find reviews, ratings, more things to do, and more tourist information, read Venice day trip tool.
Chicago, USA to Venice is an approximately 12-hour flight. The time zone difference when traveling from Chicago to Venice is 7 hours. In August, plan for daily highs up to 85°F, and evening lows to 66°F. Finish your sightseeing early on the 26th (Fri) so you can drive to Trento.
Side Trip
Find places to stay Aug 23 — 26:
Highlights from your trip
Trento — 4 nights
©
Painted City
Step off the beaten path and head to MUSE - Science Museum and Castello del Buonconsiglio Monumenti e Collezioni Provinciali. You'll visit kid-friendly attractions like Mountbaldo and Piazza Duomo. Venture out of the city with trips to Lago di Molveno (in Molveno), Castel Thun (in Ton) and Schlern-Rosengarten / Sciliar-Catinaccio Nature Park (in Tiers). There's still lots to do: contemplate in the serene atmosphere at Santuario di San Romedio.
For maps, more things to do, photos, and other tourist information, read Trento vacation maker.
Traveling by car from Venice to Trento takes 2.5 hours. Alternatively, you can take a train. In August, daily temperatures in Trento can reach 86°F, while at night they dip to 62°F. Finish your sightseeing early on the 30th (Tue) to allow enough time to drive to Florence.
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For maps, more things to do, photos, and other tourist information, read Trento vacation maker.
Traveling by car from Venice to Trento takes 2.5 hours. Alternatively, you can take a train. In August, daily temperatures in Trento can reach 86°F, while at night they dip to 62°F. Finish your sightseeing early on the 30th (Tue) to allow enough time to drive to Florence.
Side Trips
Mountbaldo, Lago di Molveno, Santuario di San Romedio, Castel Thun, Schlern-Rosengarten / Sciliar-Catinaccio Nature Park
Find places to stay Aug 26 — 30:
Highlights from your trip
Florence — 2 nights
©
Birthplace of the Italian Renaissance
Kick off your visit on the 31st (Wed): take in the views from Ponte Vecchio, get to know the fascinating history of Piazza del Duomo, take in the spiritual surroundings of Cathedral of Santa Maria del Fiore, then enjoy breathtaking views from Campanile di Giotto, and finally get to know the fascinating history of Piazza della Signoria. Get ready for a full day of sightseeing on the 1st (Thu): take in the architecture and atmosphere at Basilica of Santa Croce, admire the masterpieces at Florence Academy of Fine Arts, then don't miss a visit to Piazzale Michelangelo, and finally explore the world behind art at Pitti Palace.
Planning Florence trip won't be overwhelming when you use Inspirock's itinerary maker.
Getting from Trento to Florence by car takes about 3 hours. Other options: take a train; or take a bus. In August, daytime highs in Florence are 86°F, while nighttime lows are 64°F. Wrap up your sightseeing on the 1st (Thu) to allow time to drive to Assisi.
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Planning Florence trip won't be overwhelming when you use Inspirock's itinerary maker.
Getting from Trento to Florence by car takes about 3 hours. Other options: take a train; or take a bus. In August, daytime highs in Florence are 86°F, while nighttime lows are 64°F. Wrap up your sightseeing on the 1st (Thu) to allow time to drive to Assisi.
Find places to stay Aug 30 — Sep 1:
Assisi — 4 nights
©
City of Peace
Step off the beaten path and head to Cascata delle Marmore and Duomo di Orvieto. Family-friendly places like Basilica di Santa Chiara and Eremo delle Carceri will thrill your kids. Explore Assisi's surroundings by going to Cattedrale di Santa Maria Assunta Spoleto (in Spoleto) and Pozzo di San Patrizio (in Orvieto). There's still lots to do: contemplate in the serene atmosphere at Basilica di Santa Maria degli Angeli, explore the historical opulence of Rocca Paolina, take in the architecture and atmosphere at Basilica Papale e Sacro Convento di San Francesco d'Assisi, and delve into the distant past at Roman Forum and Archaeological Museum.
To find other places to visit, where to stay, ratings, and more tourist information, you can read our Assisi online tour planner.
You can drive from Florence to Assisi in 2.5 hours. Another option is to take a train. In September, plan for daily highs up to 78°F, and evening lows to 57°F. Finish up your sightseeing early on the 5th (Mon) so you can travel to Portoferraio.
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To find other places to visit, where to stay, ratings, and more tourist information, you can read our Assisi online tour planner.
You can drive from Florence to Assisi in 2.5 hours. Another option is to take a train. In September, plan for daily highs up to 78°F, and evening lows to 57°F. Finish up your sightseeing early on the 5th (Mon) so you can travel to Portoferraio.
Side Trips
Find places to stay Sep 1 — 5:
Highlights from your trip
Portoferraio, Elba Island — 3 nights
©
Discover out-of-the-way places like Spiaggia Di Sansone and Spiaggia Della Biodola. Get outdoors at Spiaggia di Cavoli and Dolphin & Whale Watching.
To see where to stay, traveler tips, and tourist information, you can read our Portoferraio tour itinerary tool.
Traveling by combination of car and ferry from Assisi to Portoferraio takes 5 hours. Alternatively, you can do a combination of train and ferry; or do a combination of bus, train, and ferry. In September, plan for daily highs up to 75°F, and evening lows to 62°F. Wrap up your sightseeing on the 8th (Thu) early enough to travel to San Vito lo Capo.
more
To see where to stay, traveler tips, and tourist information, you can read our Portoferraio tour itinerary tool.
Traveling by combination of car and ferry from Assisi to Portoferraio takes 5 hours. Alternatively, you can do a combination of train and ferry; or do a combination of bus, train, and ferry. In September, plan for daily highs up to 75°F, and evening lows to 62°F. Wrap up your sightseeing on the 8th (Thu) early enough to travel to San Vito lo Capo.
Side Trips
Find places to stay Sep 5 — 8:
Highlights from your trip
San Vito lo Capo, Sicily — 4 nights
©
Step off the beaten path and head to SEI - Saline Ettore E Infersa and Spiaggia di Macari. Get outdoors at Spiaggia di San Vito lo Capo and Spiaggia Isuledda. Step out of San Vito lo Capo with an excursion to Riserva Naturale Saline Di Trapani E Paceco in Trapani--about 48 minutes away. There's more to do: get a new perspective on things with Boat Tours & Water Sports and kick back and relax at Calette Santa Margherita.
For ratings, where to stay, more things to do, and more tourist information, go to the San Vito lo Capo journey builder.
You can do a combination of ferry and flight from Portoferraio to San Vito lo Capo in 5 hours. Other options are to do a combination of ferry, train, and bus; or do a combination of ferry, train, and taxi. Traveling from Portoferraio in September, expect somewhat warmer with lows of 70°F in San Vito lo Capo. Finish up your sightseeing early on the 12th (Mon) so you can catch the flight to Otranto.
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For ratings, where to stay, more things to do, and more tourist information, go to the San Vito lo Capo journey builder.
You can do a combination of ferry and flight from Portoferraio to San Vito lo Capo in 5 hours. Other options are to do a combination of ferry, train, and bus; or do a combination of ferry, train, and taxi. Traveling from Portoferraio in September, expect somewhat warmer with lows of 70°F in San Vito lo Capo. Finish up your sightseeing early on the 12th (Mon) so you can catch the flight to Otranto.
Side Trips
Find places to stay Sep 8 — 12:
Highlights from your trip
Otranto — 3 nights
©
You'll discover tucked-away gems like Centro Storico Otranto and Channel Ciolo. Take a break from the city and head to Grotta della Poesia and Circolo Ippico Malepezza. Change things up with a short trip to Scuba & Snorkeling in Santa Maria di Leuca (about 56 minutes away).
To see ratings, photos, maps, and tourist information, refer to the Otranto tour itinerary planning app.
You can fly from San Vito lo Capo to Otranto in 3 hours. Other options are to do a combination of car and ferry; or take a bus. Traveling from San Vito lo Capo in September, expect a bit cooler with lows of 62°F in Otranto. Wrap up your sightseeing on the 15th (Thu) early enough to fly to Rome.
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To see ratings, photos, maps, and tourist information, refer to the Otranto tour itinerary planning app.
You can fly from San Vito lo Capo to Otranto in 3 hours. Other options are to do a combination of car and ferry; or take a bus. Traveling from San Vito lo Capo in September, expect a bit cooler with lows of 62°F in Otranto. Wrap up your sightseeing on the 15th (Thu) early enough to fly to Rome.
Side Trips
Find places to stay Sep 12 — 15:
Highlights from your trip
Rome — 5 nights
©
Eternal City
Eschew the tourist crowds and head to Villa Borghese and Catacombs of Saint Callixtus. You'll visit kid-friendly attractions like Colosseum and Church of St. Louis of the French. Take a break from Rome with a short trip to Villa Adriana in Tivoli, about 38 minutes away. The adventure continues: get to know the fascinating history of Piazza Navona, steep yourself in history at Palatine Hill, pause for some serene contemplation at St. Peter's Basilica, and admire the masterpieces at Vatican Museums.
For where to stay, traveler tips, and other tourist information, read our Rome holiday planner.
You can fly from Otranto to Rome in 3 hours. Alternatively, you can drive; or do a combination of bus and train. In September, daily temperatures in Rome can reach 81°F, while at night they dip to 60°F. Finish up your sightseeing early on the 20th (Tue) so you can catch the flight back home.
more
For where to stay, traveler tips, and other tourist information, read our Rome holiday planner.
You can fly from Otranto to Rome in 3 hours. Alternatively, you can drive; or do a combination of bus and train. In September, daily temperatures in Rome can reach 81°F, while at night they dip to 60°F. Finish up your sightseeing early on the 20th (Tue) so you can catch the flight back home.
Side Trips
Find places to stay Sep 15 — 20:
Highlights from your trip
Italy travel guide
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.
