29 days in Italy Itinerary

29 days in Italy Itinerary

Created using Inspirock Italy trip builder
Make it your trip
Fly
1
Venice
— 3 nights
Fly
2
Lampedusa
— 2 nights
Fly
3
Palermo, Sicily
— 2 nights
Fly
4
Ravello
— 2 nights
Fly
5
San Teodoro, Sardinia
— 2 nights
Fly to Pisa, Ferry to Portoferraio
6
Portoferraio, Elba Island
— 2 nights
Ferry to Piombino, Drive to Florence
7
Florence
— 5 nights
Drive
8
Assisi
— 4 nights
Drive
9
Rome
— 6 nights
Fly

S M T W T F S
18
19
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25
26
27
28
29
30
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Venice — 3 nights

City of Romance

Virtually unchanged for the last six centuries, Venice is actually a group of islands made famous by a series of canals, bridges, monuments, piazzas, and narrow pedestrian lanes.
Eschew the tourist crowds and head to Basilica of St. Anthony and Basilica di Santa Maria Gloriosa dei Frari. Deepen your sense of the past at sights like Piazza San Marco and Scrovegni Chapel. When in Venice, make a side trip to see Padua Botanical Garden - World Heritage Site in Padua, approximately Padua away. There's still lots to do: examine the collection at Doge's Palace, visit Cannaregio, explore the world behind art at Peggy Guggenheim Collection, and contemplate the long history of Ponte dei Sospiri.

To see ratings, photos, where to stay, and other tourist information, refer to the Venice itinerary builder tool.

Cartagena, Colombia to Venice is an approximately 15.5-hour flight. The time zone difference when traveling from Cartagena to Venice is 6 hours. Prepare for little chillier weather when traveling from Cartagena in September: high temperatures in Venice hover around 29°C and lows are around 17°C. Wrap up your sightseeing on the 23rd (Fri) early enough to fly to Lampedusa.
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Historic Sites · Museums · Parks · Nature
Side Trip
Find places to stay Sep 20 — 23:

Lampedusa — 2 nights

Italy's southernmost territory, Lampedusa, is known for its turquoise waters, white-sand beaches, and island charm.
On the 24th (Sat), take a tour by water with Boat Tours & Water Sports. Get ready for a full day of sightseeing on the next day: kick back and relax at Cala Pulcino, then enjoy the sand and surf at Spiaggia dei Conigli, and then kick back and relax at Cala Croce Beach.

To see other places to visit, maps, more things to do, and more tourist information, go to the Lampedusa road trip planner.

Traveling by flight from Venice to Lampedusa takes 3.5 hours. Alternatively, you can do a combination of train, ferry, and bus; or do a combination of bus and ferry. Traveling from Venice in September, expect a bit warmer with lows of 28°C in Lampedusa. Finish your sightseeing early on the 25th (Sun) to allow enough time to fly to Palermo.
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Outdoors · Beaches · Parks · Tours
Find places to stay Sep 23 — 25:

Palermo, Sicily — 2 nights

The capital of Sicily, Palermo was founded by the Phoenicians under the name of Ziz.
On the 26th (Mon), admire the striking features of Norman Palace, then pause for some serene contemplation at Duomo di Monreale, then contemplate the long history of Catacombe dei Cappuccini, and finally don't miss a visit to Cattedrale di Palermo. On your second day here, pause for some serene contemplation at Santa Maria dell'Ammiraglio, make a trip to Quattro Canti, then pause for some serene contemplation at Chiesa Del Gesu, then admire the striking features of Palazzo Conte Federico, and finally pause for some serene contemplation at Chiesa Inferiore.

To see ratings, maps, traveler tips, and tourist information, go to the Palermo attractions site.

You can fly from Lampedusa to Palermo in 2.5 hours. Alternatively, you can do a combination of ferry and car; or do a combination of ferry and bus. Finish up your sightseeing early on the 27th (Tue) so you can catch the flight to Ravello.
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Historic Sites
Side Trip
Find places to stay Sep 25 — 27:

Ravello — 2 nights

Best known for its celebrated terraced gardens, Ravello is a hidden gem of Italy's Amalfi Coast.
Kick off your visit on the 28th (Wed): take in the exciting artwork at Ceramiche Cosmolena di Margherita di Palma, admire the natural beauty at Villa Cimbrone Gardens, then take in the architecture and atmosphere at Convento Frati Minori Conventuali S.Francesco, then contemplate the long history of Duomo di Ravello, and finally admire the striking features of Villa Rufolo. On the next day, see the interesting displays at Museo della Carta, take in the spiritual surroundings of Duomo di Sant'Andrea, then pause for some serene contemplation at Cloister del Paradiso, and finally stroll through Fornillo.

To find more things to do, photos, reviews, and more tourist information, read Ravello trip planner.

Traveling by flight from Palermo to Ravello takes 2.5 hours. Alternatively, you can do a combination of train and taxi; or ride a ferry. In September in Ravello, expect temperatures between 30°C during the day and 24°C at night. Finish your sightseeing early on the 29th (Thu) to allow enough time to fly to San Teodoro.
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Historic Sites · Parks · Beaches · Outdoors
Side Trips
Find places to stay Sep 27 — 29:

San Teodoro, Sardinia — 2 nights

A chance to sip cocktails at swanky beach bars by day and experience the vibrant club scene by night makes San Tedoro vacations extremely popular.
Kick off your visit on the 30th (Fri): kick back and relax at Cala Brandinchi, enjoy the sand and surf at Lu Impostu Beach, and then tour the pleasant surroundings at Spiaggia La Cinta. Get ready for a full day of sightseeing on the 1st (Sat): enjoy the sand and surf at Spiaggia Capo Coda Cavallo, kick back and relax at Porto Taverna Beach, and then kick back and relax at Porto Istana Beach.

To see photos, traveler tips, other places to visit, and more tourist information, refer to the San Teodoro road trip app.

You can fly from Ravello to San Teodoro in 3 hours. Alternatively, you can do a combination of taxi, train, ferry, and bus; or do a combination of bus, train, and ferry. Traveling from Ravello in September, plan for little chillier nights in San Teodoro, with lows around 19°C. Finish up your sightseeing early on the 1st (Sat) so you can travel to Portoferraio.
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Beaches · Parks · Outdoors
Side Trips
Find places to stay Sep 29 — Oct 1:

Portoferraio, Elba Island — 2 nights

Portoferraio is a town and comune in the province of Livorno, on the edge of the eponymous harbour of the island of Elba. On the 2nd (Sun), kick back and relax at Spiaggia Della Biodola, kick back and relax at Spiaggia di Cavoli, and then kick back and relax at Spiaggia di Chiessi. On your second day here, tour the pleasant surroundings at Spiaggia Di Sansone, tour the pleasant surroundings at Spiaggia di Capo Bianco, and then enjoy the sand and surf at Spiaggia delle Ghiaie.

To find other places to visit, maps, ratings, and tourist information, you can read our Portoferraio trip itinerary site.

You can do a combination of flight and ferry from San Teodoro to Portoferraio in 4.5 hours. Other options are to do a combination of bus and ferry; or do a combination of bus, train, and ferry. While traveling from San Teodoro, expect a bit cooler days and about the same nights in Portoferraio, ranging from highs of 22°C to lows of 17°C. Finish your sightseeing early on the 3rd (Mon) to allow enough time to travel to Florence.
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Beaches · Parks · Outdoors
Side Trips
Find places to stay Oct 1 — 3:

Florence — 5 nights

Birthplace of the Italian Renaissance

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Your cultural itinerary includes sights like Cathedral of Santa Maria del Fiore and Duomo di Pisa. Popular historic sites such as Historic Centre of San Gimignano and Battistero di San Giovanni are in your itinerary. Explore the numerous day-trip ideas around Florence: Abbazia di San Galgano (in Chiusdino), Camposanto (in Pisa) and Duomo di Siena (in Siena). Next up on the itinerary: explore the world behind art at Florence Academy of Fine Arts, see the interesting displays at Pitti Palace, take in the spiritual surroundings of Campanile di Giotto, and snap pictures at Ponte Vecchio.

To find reviews, where to stay, and tourist information, read Florence journey maker.

Traveling by combination of ferry and car from Portoferraio to Florence takes 4 hours. Alternatively, you can do a combination of ferry and train. Expect a daytime high around 25°C in October, and nighttime lows around 14°C. Cap off your sightseeing on the 8th (Sat) early enough to go by car to Assisi.
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Historic Sites · Museums · Parks
Side Trips
Find places to stay Oct 3 — 8:

Assisi — 4 nights

City of Peace

Rich in culture and religious tradition, Assisi is known as the birthplace of St.
Museum-lovers will appreciate Museo della Porziuncola and Roman Forum and Archaeological Museum. Visit Duomo di Orvieto and Cattedrale di Santa Maria Assunta Spoleto for their historical value. Get out of town with these interesting Assisi side-trips: Orvieto (Decugnano dei Barbi & Pozzo di San Patrizio). And it doesn't end there: pause for some serene contemplation at San Damiano, take in the spiritual surroundings of Basilica di Santa Maria degli Angeli - Porziuncola, learn about winemaking at Tili Vini Societa Agricola, and steep yourself in history at Eremo delle Carceri.

To see maps, where to stay, reviews, and more tourist information, go to the Assisi driving holiday tool.

You can drive from Florence to Assisi in 2.5 hours. Alternatively, you can take a train. Expect a daytime high around 24°C in October, and nighttime lows around 12°C. Finish up your sightseeing early on the 12th (Wed) so you can go by car to Rome.
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Historic Sites · Wineries · Museums
Side Trips
Find places to stay Oct 8 — 12:

Rome — 6 nights

Eternal City

Aptly nicknamed the Eternal City, Rome is the birthplace of the Roman Empire, one of the world's greatest civilizations ever.
Discover out-of-the-way places like Arcibasilica di San Giovanni in Laterano and Stanze di Raffaello. Satisfy your inner culture vulture at Colosseum and Pantheon. Step out of Rome with an excursion to Parco Archeologico di Ostia Antica in Ostia Antica--about 42 minutes away. There's lots more to do: steep yourself in history at St. Peter's Basilica, admire the local landmark of Fontana dei Quattro Fiumi, get to know the fascinating history of Piazza Navona, and don't miss a visit to Trevi Fountain.

For traveler tips, other places to visit, maps, and tourist information, read Rome travel route builder tool.

Drive from Assisi to Rome in 2.5 hours. Alternatively, you can take a train; or take a bus. In October, daily temperatures in Rome can reach 26°C, while at night they dip to 15°C. Wrap up your sightseeing by early afternoon on the 18th (Tue) to allow enough time to fly back home.
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Historic Sites · Museums
Side Trips
Find places to stay Oct 12 — 18:

Italy travel guide

4.6
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.
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