29 days in Italy Itinerary

29 days in Italy Itinerary

Created using Inspirock Italy travel route planner
Make it your trip
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

S M T W T F S
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27
28
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30
31
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Alghero, Sardinia — 2 nights

Built surrounding a 16th-century fortified port, Alghero remains one of Sardinia's most visited sites, rich in cultural and historical heritage.
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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Outdoors · Parks · Beaches · Wildlife
Find places to stay Aug 26 — 28:

Portoferraio, Elba Island — 3 nights

Portoferraio is a town and comune in the province of Livorno, on the edge of the eponymous harbour of the island of Elba. Bring the kids along to Spiaggia Di Sansone and Spiaggia di Cavoli. You'll explore the less-touristy side of things at Spiaggia Della Biodola and Dolphin & Whale Watching. There's more to do: kick back and relax at Spiaggia di Capo Bianco and tour the pleasant surroundings at Spiaggia delle Ghiaie.

To find maps, photos, ratings, and other tourist information, read our Portoferraio trip maker 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. Expect little chillier weather when traveling from Alghero in August: highs in Portoferraio hover around 83°F, while lows dip to 68°F. Cap off your sightseeing on the 31st (Wed) early enough to travel to Palinuro.
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Side Trips
Find places to stay Aug 28 — 31:

Palinuro — 3 nights

Palinuro is an Italian small town, the most populated civil parish of Centola, Province of Salerno, in the Campania region. You'll discover tucked-away gems like Grotte Marine di Capo Palinuro and Baia del Buon Dormire. Family-friendly places like Cooperativa Rosa dei Venti 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 30 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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Find places to stay Aug 31 — Sep 3:

Otranto — 4 nights

Otranto is a town and comune in the province of Lecce (Apulia, Italy), in a fertile region once famous for its breed of horses.It is located on the east coast of the Salento peninsula. Relax by the water at Channel Ciolo and I Due Mori. Your inner history buff will appreciate Cattedrale Di Otranto and Centro Storico Otranto. Venture out of the city with trips to Scuba & Snorkeling (in Santa Maria di Leuca) and Grotta della Poesia (in Roca Vecchia). The adventure continues: head outdoors with Circolo Ippico Malepezza and enjoy the sand and surf at Spiaggia Alimini.

To find where to stay, ratings, photos, and other tourist information, refer to the Otranto trip itinerary planning app.

You can drive from Palinuro to Otranto in 5.5 hours. Other options are to 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. Finish up your sightseeing early on the 7th (Wed) so you can catch the flight to Lampedusa.
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Find places to stay Sep 3 — 7:

Lampedusa — 2 nights

Italy's southernmost territory, Lampedusa, is known for its turquoise waters, white-sand beaches, and island charm.
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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Find places to stay Sep 7 — 9:

Noto, Sicily — 4 nights

Noto is a city and comune in the Province of Syracuse, Sicily, Italy. Kids will appreciate attractions like Riserva Naturale Orientata Oasi faunistica di Vendicari and Centro storico di Scicli - World Heritage Site. You'll explore the less-touristy side of things at Cathedral of St. George and Cavagrande del Cassibile. Explore Noto's surroundings by going to Syracuse (Ear of Dionysius (Orecchio di Dionisio) & Duomo di Siracusa). There's more to do: pause for some serene contemplation at St. Nicholas Cathedral and make a trip to Centro Storico.

To find ratings, maps, reviews, and more tourist information, refer to the Noto trip itinerary maker app.

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. Cap off your sightseeing on the 13th (Tue) early enough to catch the flight to Trento.
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Find places to stay Sep 9 — 13:

Trento — 5 nights

Tyrol's capital and one of the nation's wealthiest cities, Trento serves as the commercial and cultural center of the region.
Take a break from the city and head to Road of 52 Tunnels and Lago di Molveno. Castel Thun and Merano Centro Storico will appeal to history buffs. Venture out of the city with trips to Borghetto sul Mincio (in Valeggio Sul Mincio), Santuario di San Romedio (in Coredo) and South Tyrol Museum of Archaeology (in Bolzano). There's still lots to do: explore the world behind art at Castello del Buonconsiglio Monumenti e Collezioni Provinciali, get curious at MUSE - Science Museum, and appreciate the extensive heritage of Piazza Duomo.

For other places to visit, more things to do, maps, and more tourist information, use the Trento online trip itinerary builder.

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. Wrap up your sightseeing on the 18th (Sun) to allow time to drive to Assisi.
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Find places to stay Sep 13 — 18:

Assisi — 5 nights

Rich in culture and religious tradition, Assisi is known as the birthplace of St.
Museo della Porziuncola and Galleria Nazionale dell'Umbria will appeal to museum buffs. Popular historic sites such as Cattedrale di Santa Maria Assunta Spoleto and Rocca Paolina are in your itinerary. Venture out of the city with trips to Pozzo di San Patrizio (in Orvieto) and Grotte di Frasassi (in Genga). There's lots more to do: take in the architecture and atmosphere at San Damiano, contemplate in the serene atmosphere at Basilica di Santa Maria degli Angeli - Porziuncola, admire the landmark architecture of Basilica di Santa Chiara, and steep yourself in history at Eremo delle Carceri.

To see reviews, other places to visit, traveler tips, and tourist information, you can read our Assisi trip maker website.

Getting from Trento to Assisi by car takes about 5 hours. Other options: take a train; or do a combination of flight and train. In September, plan for daily highs up to 78°F, and evening lows to 57°F. Wrap up your sightseeing by early afternoon on the 23rd (Fri) to allow enough time to travel back home.
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Side Trips
Find places to stay Sep 18 — 23:

Italy travel guide

4.6
Landmarks · Ruins · Sacred & Religious Sites
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.
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