29 days in Italy Itinerary
Created using Inspirock Italy travel route planner
Start: Chicago
Fly
1
Alghero, Sardinia
— 2 nights
Fly to Pisa, Ferry to Portoferraio
2
Portoferraio, Elba Island
— 3 nights
Ferry to Piombino, Fly to Palinuro
3
Palinuro
— 3 nights
Drive
4
Otranto
— 4 nights
Fly
5
Lampedusa
— 2 nights
Fly
6
Noto, Sicily
— 4 nights
Fly
7
Trento
— 5 nights
Drive
8
Assisi
— 5 nights
Train to Rome, Fly to Chicago
End: Chicago
Fri, Aug 26 - Fri, Sep 23
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View full calendar
Alghero, Sardinia — 2 nights
©
Little Barcelona
Kick off your visit on the 27th (Sat): explore the fascinating underground world of Capo Caccia and then stroll through Spiaggia Mugoni. On the next day, stroll through Spiaggia di Maria Pia and then discover the deep blue sea with a scuba or snorkeling tour.
Plan a trip to Alghero easily and quickly by telling Inspirock to suggest an itinerary.
Chicago, USA to Alghero is an approximately 14-hour flight. The time zone difference moving from Central Standard Time to Central European Standard Time is 7 hours. When traveling from Chicago in August, plan for somewhat warmer days and about the same nights in Alghero: temperatures range from 89°F by day to 64°F at night. Finish your sightseeing early on the 28th (Sun) so you can travel to Portoferraio.
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Plan a trip to Alghero easily and quickly by telling Inspirock to suggest an itinerary.
Chicago, USA to Alghero is an approximately 14-hour flight. The time zone difference moving from Central Standard Time to Central European Standard Time is 7 hours. When traveling from Chicago in August, plan for somewhat warmer days and about the same nights in Alghero: temperatures range from 89°F by day to 64°F at night. Finish your sightseeing early on the 28th (Sun) so you can travel to Portoferraio.
Find places to stay Aug 26 — 28:
Highlights from your trip
Portoferraio, Elba Island — 3 nights
©
Bring the kids along to Spiaggia Di Sansone and Spiaggia delle Ghiaie. Get outdoors at Spiaggia di Cavoli and Spiaggia Della Biodola.
To find traveler tips, photos, other places to visit, and more tourist information, go to the Portoferraio trip itinerary website.
You can do a combination of flight and ferry from Alghero to Portoferraio in 4.5 hours. Other options are to do a combination of bus and ferry; or do a combination of bus, ferry, and train. When traveling from Alghero in August, plan for slightly colder days and about the same nights in Portoferraio: temperatures range from 83°F by day to 68°F at night. Wrap up your sightseeing on the 31st (Wed) to allow time to travel to Palinuro.
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To find traveler tips, photos, other places to visit, and more tourist information, go to the Portoferraio trip itinerary website.
You can do a combination of flight and ferry from Alghero to Portoferraio in 4.5 hours. Other options are to do a combination of bus and ferry; or do a combination of bus, ferry, and train. When traveling from Alghero in August, plan for slightly colder days and about the same nights in Portoferraio: temperatures range from 83°F by day to 68°F at night. Wrap up your sightseeing on the 31st (Wed) to allow time to travel to Palinuro.
Side Trips
Find places to stay Aug 28 — 31:
Highlights from your trip
Palinuro — 3 nights
©
You'll discover tucked-away gems like Cooperativa Rosa dei Venti and Baia del Buon Dormire. Family-friendly places like Grotte Marine di Capo Palinuro and Spiaggia della Marinella will thrill your kids. Take a break from Palinuro with a short trip to Statua del Cristo Redentore di Maratea in Maratea, about 1h 20 min away.
Inspirock's itinerary builder makes planning a Palinuro trip simple and quick.
You can do a combination of ferry and flight from Portoferraio to Palinuro in 5 hours. Other options are to do a combination of ferry and car; or do a combination of ferry, train, and bus. Finish up your sightseeing early on the 3rd (Sat) so you can go by car to Otranto.
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Inspirock's itinerary builder makes planning a Palinuro trip simple and quick.
You can do a combination of ferry and flight from Portoferraio to Palinuro in 5 hours. Other options are to do a combination of ferry and car; or do a combination of ferry, train, and bus. Finish up your sightseeing early on the 3rd (Sat) so you can go by car to Otranto.
Side Trips
Find places to stay Aug 31 — Sep 3:
Highlights from your trip
Otranto — 4 nights
©
You'll get in some beach time at Channel Ciolo and Spiaggia Alimini. Escape the urban bustle at Circolo Ippico Malepezza and Grotta della Poesia. Step out of Otranto with an excursion to Scuba & Snorkeling in Santa Maria di Leuca--about 56 minutes away.
For ratings, maps, where to stay, and more tourist information, refer to the Otranto travel itinerary planner.
Traveling by car from Palinuro to Otranto takes 5.5 hours. Alternatively, you can do a combination of bus and train; or take a bus. In September in Otranto, expect temperatures between 81°F during the day and 62°F at night. Cap off your sightseeing on the 7th (Wed) early enough to catch the flight to Lampedusa.
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For ratings, maps, where to stay, and more tourist information, refer to the Otranto travel itinerary planner.
Traveling by car from Palinuro to Otranto takes 5.5 hours. Alternatively, you can do a combination of bus and train; or take a bus. In September in Otranto, expect temperatures between 81°F during the day and 62°F at night. Cap off your sightseeing on the 7th (Wed) early enough to catch the flight to Lampedusa.
Side Trips
Find places to stay Sep 3 — 7:
Highlights from your trip
Lampedusa — 2 nights
©
On the 8th (Thu), get a new perspective on things with Boat Tours & Water Sports and then tour the pleasant surroundings at Cala Croce Beach. Here are some ideas for day two: kick back and relax at Cala Pulcino and then stroll through Spiaggia dei Conigli.
To find photos, traveler tips, ratings, and more tourist information, use the Lampedusa visit app.
Getting from Otranto to Lampedusa by flight takes about 6 hours. Other options: do a combination of bus and ferry; or do a combination of bus and ferry. Traveling from Otranto in September, expect somewhat warmer with lows of 75°F in Lampedusa. Finish your sightseeing early on the 9th (Fri) to allow enough time to fly to Noto.
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To find photos, traveler tips, ratings, and more tourist information, use the Lampedusa visit app.
Getting from Otranto to Lampedusa by flight takes about 6 hours. Other options: do a combination of bus and ferry; or do a combination of bus and ferry. Traveling from Otranto in September, expect somewhat warmer with lows of 75°F in Lampedusa. Finish your sightseeing early on the 9th (Fri) to allow enough time to fly to Noto.
Find places to stay Sep 7 — 9:
Highlights from your trip
Noto, Sicily — 4 nights
©
Kids will appreciate attractions like St. Nicholas Cathedral and Cavagrande del Cassibile. Satisfy your inner culture vulture at Cathedral of St. George and Duomo di Siracusa. Explore the numerous day-trip ideas around Noto: Ear of Dionysius (Orecchio di Dionisio) (in Syracuse) and Centro storico di Scicli - World Heritage Site (in Scicli).
For photos, ratings, traveler tips, and more tourist information, refer to the Noto trip site.
Traveling by flight from Lampedusa to Noto takes 3.5 hours. Alternatively, you can do a combination of ferry and car; or do a combination of ferry and bus. Wrap up your sightseeing on the 13th (Tue) to allow time to fly to Trento.
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For photos, ratings, traveler tips, and more tourist information, refer to the Noto trip site.
Traveling by flight from Lampedusa to Noto takes 3.5 hours. Alternatively, you can do a combination of ferry and car; or do a combination of ferry and bus. Wrap up your sightseeing on the 13th (Tue) to allow time to fly to Trento.
Side Trips
Syracuse, Cavagrande del Cassibile, Centro storico di Scicli - World Heritage Site, Cathedral of St. George
Find places to stay Sep 9 — 13:
Highlights from your trip
Trento — 5 nights
©
Painted City
Take a break from the city and head to Road of 52 Tunnels and Lago di Molveno. Castel Thun and Piazza Duomo will appeal to history buffs. Venture out of the city with trips to South Tyrol Museum of Archaeology (in Bolzano), Santuario di San Romedio (in Coredo) and Borghetto sul Mincio (in Valeggio Sul Mincio). There's still lots to do: admire the masterpieces at Castello del Buonconsiglio Monumenti e Collezioni Provinciali, get curious at MUSE - Science Museum, and get to know the fascinating history of Merano Centro Storico.
To find maps, where to stay, and other tourist information, read our Trento travel planner.
Getting from Noto to Trento by flight takes about 3.5 hours. Other options: do a combination of flight and train; or do a combination of car and ferry. In September, plan for daily highs up to 77°F, and evening lows to 55°F. Cap off your sightseeing on the 18th (Sun) early enough to go by car to Assisi.
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To find maps, where to stay, and other tourist information, read our Trento travel planner.
Getting from Noto to Trento by flight takes about 3.5 hours. Other options: do a combination of flight and train; or do a combination of car and ferry. In September, plan for daily highs up to 77°F, and evening lows to 55°F. Cap off your sightseeing on the 18th (Sun) early enough to go by car to Assisi.
Side Trips
Lago di Molveno, South Tyrol Museum of Archaeology, Merano Centro Storico, Santuario di San Romedio, Borghetto sul Mincio
Find places to stay Sep 13 — 18:
Highlights from your trip
Assisi — 5 nights
©
City of Peace
Galleria Nazionale dell'Umbria and Museo della Porziuncola will appeal to museum buffs. Popular historic sites such as San Damiano and Cattedrale di Santa Maria Assunta Spoleto are in your itinerary. Venture out of the city with trips to Grotte di Frasassi (in Genga) and Pozzo di San Patrizio (in Orvieto). And it doesn't end there: take in the architecture and atmosphere at Cattedrale di San Rufino, contemplate in the serene atmosphere at Basilica di Santa Maria degli Angeli, admire the landmark architecture of Basilica di Santa Chiara, and steep yourself in history at Eremo delle Carceri.
To see reviews, maps, more things to do, and tourist information, you can read our Assisi trip itinerary planner.
You can drive from Trento to Assisi in 5 hours. Other options are to take a train; or do a combination of flight and train. September in Assisi sees daily highs of 78°F and lows of 57°F at night. On the 23rd (Fri), wrap the sightseeing up by early afternoon so you can travel back home.
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To see reviews, maps, more things to do, and tourist information, you can read our Assisi trip itinerary planner.
You can drive from Trento to Assisi in 5 hours. Other options are to take a train; or do a combination of flight and train. September in Assisi sees daily highs of 78°F and lows of 57°F at night. On the 23rd (Fri), wrap the sightseeing up by early afternoon so you can travel back home.
Side Trips
Find places to stay Sep 18 — 23:
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.
