29 days in Italy Itinerary

Created using Klarna Trips Italy planner
Make it your trip
Fly
1
Rome
— 5 nights
Fly
2
Lampedusa
— 2 nights
Fly
3
Taormina, Sicily
— 2 nights
Fly to Naples, Ferry to Capri
4
Capri, Island of Capri
— 1 night
Ferry
5
Ravello
— 2 nights
Fly
6
San Teodoro, Sardinia
— 3 nights
Drive
7
Alghero, Sardinia
— 2 nights
Fly to Pisa, Ferry to Portoferraio
8
Portoferraio, Elba Island
— 2 nights
Ferry to Piombino, Drive to Florence
9
Florence
— 5 nights
Drive
10
Venice
— 4 nights
Fly

S M T W T F S
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25
26
27
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30
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Rome — 5 nights

Eternal City

Aptly nicknamed the Eternal City, Rome is the birthplace of the Roman Empire, one of the world's greatest civilizations ever.
Visiting Cascata delle Marmore and Catacombs of Saint Callixtus will get you outdoors. Discover out-of-the-way places like Arcibasilica di San Giovanni in Laterano and Parco Archeologico di Ostia Antica. Take a break from Rome with a short trip to Duomo di Orvieto in Orvieto, about 1h 40 min away. And it doesn't end there: appreciate the extensive heritage of Piazza Navona, explore the ancient world of Colosseum, admire the landmark architecture of Pantheon, and pause for some serene contemplation at Basilica di San Pietro in Vincoli.

For where to stay, ratings, reviews, and more tourist information, use the Rome online journey planner.

Toronto, Canada to Rome is an approximately 13-hour flight. The time zone difference when traveling from Toronto to Rome is 6 hours. Traveling from Toronto in September, expect nights in Rome to be about the same, around 18°C, while days are somewhat warmer, around 32°C. Finish up your sightseeing early on the 23rd (Sat) so you can catch the flight to Lampedusa.
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Side Trips
Find places to stay Sep 18 — 23:

Lampedusa — 2 nights

Italy's southernmost territory, Lampedusa, is known for its turquoise waters, white-sand beaches, and island charm.
Start off your visit on the 24th (Sun): take a tour by water with Boat Tours & Water Sports. Here are some ideas for day two: look for all kinds of wild species at Capo Ponente, kick back and relax at Cala Pulcino, then enjoy the sand and surf at Spiaggia dei Conigli, and finally kick back and relax at Cala Croce Beach.

To see more things to do, other places to visit, ratings, and tourist information, go to the Lampedusa vacation tool.

You can fly from Rome to Lampedusa in 3 hours. Alternatively, you can do a combination of bus and ferry; or do a combination of train, bus, and ferry. Traveling from Rome in September, plan for somewhat warmer nights in Lampedusa, with lows around 28°C. Wrap up your sightseeing on the 25th (Mon) early enough to fly to Taormina.
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Find places to stay Sep 23 — 25:

Taormina, Sicily — 2 nights

With its warm island weather and cliffside location overlooking the Ionion Sea, Taormina has been one of Sicily's most popular getaway destinations since the early 19th century.
On the 26th (Tue), identify plant and animal life at Wildlife Areas, go for a walk through Piazza IX Aprile, then make a trip to Corso Umberto, and finally walk around Villa Comunale. Keep things going the next day: pause for some serene contemplation at Duomo di Taormina, then delve into the distant past at Ancient Theatre of Taormina, then learn about winemaking at Gambino Vini, and finally step off the mainland to explore Isola Bella.

To see other places to visit, ratings, more things to do, and tourist information, use the Taormina online attractions planner.

You can fly from Lampedusa to Taormina in 3 hours. Other options are to do a combination of ferry and car; or do a combination of ferry and bus. Traveling from Lampedusa in September, expect little chillier with lows of 24°C in Taormina. Wrap up your sightseeing on the 27th (Wed) early enough to travel to Capri.
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Find places to stay Sep 25 — 27:

Capri, Island of Capri — 1 night

The island of Capri encompasses all the magical allure of the Mediterranean--dramatic blue waters, lush mountainous landscape, and picturesque island villages.
Start off your visit on the 28th (Thu): tour the pleasant surroundings at Fortini Coastal Walk, get great views at Monte Solaro, take an in-depth tour of Villa San Michele, get great views at Belvedere Cannone, then stroll through I Faraglioni, and finally admire the natural beauty at Giardini di Augusto.

To find traveler tips, photos, reviews, and more tourist information, read our Capri attractions planning website.

Traveling by combination of flight and ferry from Taormina to Capri takes 4.5 hours. Alternatively, you can do a combination of train and ferry; or do a combination of bus and ferry. September in Capri sees daily highs of 31°C and lows of 23°C at night. Cap off your sightseeing on the 28th (Thu) early enough to catch the ferry to Ravello.
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Find places to stay Sep 27 — 28:

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 29th (Fri): see the interesting displays at Museo della Carta, contemplate in the serene atmosphere at Duomo di Sant'Andrea, get outside with Amalfi Coast, then take in nature's colorful creations at Villa Cimbrone Gardens, then contemplate the long history of Villa Rufolo, and finally take in the spiritual surroundings of Duomo di Ravello. Here are some ideas for day two: enjoy the sand and surf at Lido Capo di Conca, get a new perspective on things with Boat Tours & Water Sports, then kick back and relax at Fornillo, and finally shop like a local with Art & Craft Gallery.

To find ratings, more things to do, photos, and more tourist information, read our Ravello driving holiday planner.

Traveling by ferry from Capri to Ravello takes 1.5 hours. Alternatively, you can do a combination of ferry and taxi; or do a combination of ferry and bus. Expect a daytime high around 30°C in September, and nighttime lows around 24°C. Finish up your sightseeing early on the 30th (Sat) so you can catch the flight to San Teodoro.
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Find places to stay Sep 28 — 30:

San Teodoro, Sardinia — 3 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.
Get in touch with nature at Spiaggia La Cinta and Spiaggia Capo Coda Cavallo. You'll explore the less-touristy side of things at Cala Brandinchi and Porto Istana Beach. Venture out of the city with trips to Cala Gonone (Grotta del Bue Marino & Cala Fuili Beach), Grotta di Ispinigoli (in Dorgali) and Golfo Aranci (Dolphin & Whale Watching & Spiaggia Bianca). Next up on the itinerary: kick back and relax at Lu Impostu Beach and stroll through Porto Taverna Beach.

To see maps, traveler tips, reviews, and other tourist information, use the San Teodoro planning site.

Traveling by flight from Ravello to San Teodoro takes 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, expect a bit cooler with lows of 19°C in San Teodoro. Wrap up your sightseeing on the 3rd (Tue) early enough to drive to Alghero.
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Find places to stay Sep 30 — Oct 3:

Alghero, Sardinia — 2 nights

Little Barcelona

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 4th (Wed): get to know the fascinating history of Centro Storico, then explore the striking landscape at Capo Caccia, and then kick back and relax at Spiaggia Mugoni. Keep things going the next day: get a new perspective on things with Boat Tours & Water Sports, then kick back and relax at Spiaggia di Maria Pia, and then learn about winemaking at Azienda Agricola Leda' d'Ittiri.

For where to stay, photos, ratings, and tourist information, use the Alghero holiday planner.

You can drive from San Teodoro to Alghero in 2.5 hours. Alternatively, you can do a combination of bus and train; or take a bus. In October, daily temperatures in Alghero can reach 28°C, while at night they dip to 15°C. Finish your sightseeing early on the 5th (Thu) so you can travel to Portoferraio.
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Find places to stay Oct 3 — 5:

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 6th (Fri), kick back and relax at Spiaggia delle Ghiaie, stroll through Spiaggia di Capo Bianco, then tour the pleasant surroundings at Spiaggia Di Sansone, and finally tour the pleasant surroundings at Spiaggia La Sorgente. On the 7th (Sat), you'll have a packed day of sightseeing: kick back and relax at Spiaggia di Cavoli, then kick back and relax at Spiaggia delle Tombe, then take your sightseeing to a higher altitude at Monte Capanne, and finally stroll through Spiaggia di Spartaia.

To see ratings, other places to visit, reviews, and more tourist information, use the Portoferraio trip site.

Traveling by combination of flight and ferry from Alghero to Portoferraio takes 4.5 hours. Alternatively, you can do a combination of bus and ferry; or do a combination of bus, ferry, and train. When traveling from Alghero in October, plan for little chillier days in Portoferraio, with highs around 22°C, while nights are about the same with lows around 17°C. Finish your sightseeing early on the 7th (Sat) so you can travel to Florence.
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Find places to stay Oct 5 — 7:

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.
Satisfy your inner culture vulture at Piazzale Michelangelo and Florence Academy of Fine Arts. Cathedral of Santa Maria del Fiore and Historic Centre of San Gimignano will appeal to history buffs. Explore Florence's surroundings by going to Castello del Trebbio (in Santa Brigida), San Gimignano (Guardastelle Vineyard & Duomo di San Gimignano) and Siena (Battistero di San Giovanni, Torre del Mangia, &more). There's much more to do: steep yourself in history at The Baptistery of St. John, admire the natural beauty at The Boboli Gardens, enjoy breathtaking views from Campanile di Giotto, and appreciate the history behind Loggia dei Lanzi.

To find more things to do, ratings, and more tourist information, read Florence holiday planner.

You can do a combination of ferry and car from Portoferraio to Florence in 4 hours. Another option is to do a combination of ferry and train. In October, plan for daily highs up to 25°C, and evening lows to 14°C. Wrap up your sightseeing on the 12th (Thu) to allow time to drive to Venice.
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Find places to stay Oct 7 — 12:

Venice — 4 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.
Satisfy your inner culture vulture at Piazza San Marco and Basilica of St. Anthony. You'll discover tucked-away gems like Scrovegni Chapel and Cannaregio. When in Venice, make a side trip to see Castello Estense in Ferrara, approximately Ferrara away. Next up on the itinerary: pause for some serene contemplation at San Giorgio Maggiore, make a trip to Basilica di Santa Maria Gloriosa dei Frari, admire the striking features of Basilica di San Marco, and explore the world behind art at Peggy Guggenheim Collection.

To find maps, traveler tips, and other tourist information, go to the Venice vacation planning tool.

You can drive from Florence to Venice in 3 hours. Other options are to take a train; or take a bus. Traveling from Florence in October, expect nights in Venice to be about the same, around 12°C, while days are little chillier, around 22°C. Cap off your sightseeing on the 16th (Mon) early enough to catch the flight back home.
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Find places to stay Oct 12 — 16:

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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