43 days in Italy Itinerary
Created using Inspirock Italy tour planner
Start: Toronto
Fly
1
Lampedusa
— 2 nights
Fly
2
Taormina, Sicily
— 2 nights
Fly
3
Villasimius, Sardinia
— 2 nights
Drive
4
Baunei, Sardinia
— 2 nights
Drive
5
San Teodoro, Sardinia
— 3 nights
Fly
6
Ravello
— 2 nights
Drive
7
Rome
— 5 nights
Drive
8
Assisi
— 4 nights
Drive
9
Siena
— 4 nights
Taxi to Piombino, Ferry to Portoferraio
10
Portoferraio, Elba Island
— 1 night
Ferry to Piombino, Drive to Florence
11
Florence
— 5 nights
Train
12
Verona
— 5 nights
Drive
13
Venice
— 5 nights
Fly
End: Toronto
Wed, Sep 20 - Wed, Nov 1
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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 21st (Thu): tour the pleasant surroundings at La Tabaccara. On the 22nd (Fri), you'll have a packed day of sightseeing: 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 tour the pleasant surroundings at Cala Croce Beach.
Start your trip to Lampedusa by creating a personalized itinerary on Inspirock.
Toronto, Canada to Lampedusa is an approximately 14.5-hour flight. The time zone changes from Eastern Standard Time to Central European Standard Time, which is usually a 6 hour difference. In September, Lampedusa is somewhat warmer than Toronto - with highs of 32°C and lows of 28°C. Cap off your sightseeing on the 22nd (Fri) early enough to catch the flight to Taormina.
Highlights from your trip
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 23rd (Sat), step off the mainland to explore Isola Bella, go for a walk through Piazza IX Aprile, don't miss a visit to Corso Umberto, then take in the spiritual surroundings of Chiesa del Varo, then stroll around Villa Comunale, and finally take in the architecture and atmosphere at Duomo di Taormina. On the next day, explore the ancient world of Ancient Theatre of Taormina, then do a tasting at Gambino Vini, and then see some colorful creatures with a scuba or snorkeling tour.
For traveler tips, photos, reviews, and more tourist information, refer to the Taormina trip planner.
You can fly from Lampedusa to Taormina in 3 hours. Alternatively, you can do a combination of ferry and car; or do a combination of ferry and bus. Traveling from Lampedusa in September, plan for slightly colder nights in Taormina, with lows around 24°C. Finish your sightseeing early on the 24th (Sun) so you can fly to Villasimius.
Side Trips
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Villasimius, Sardinia — 2 nights

Start off your visit on the 25th (Mon): kick back and relax at Cala Pira, tour the pleasant surroundings at Spiaggia di Mari Pintau, and then enjoy the sand and surf at Timi Ama Beach. Get ready for a full day of sightseeing on the 26th (Tue): do a tasting at Colline del Vento, then enjoy the sand and surf at Spiaggia di Punta Molentis, then tour the pleasant surroundings at Simius Beach, and finally tour the pleasant surroundings at Porto Giunco.
To see ratings, reviews, where to stay, and more tourist information, read Villasimius travel route builder site.
Getting from Taormina to Villasimius by flight takes about 3 hours. Other options: do a combination of bus and ferry; or do a combination of train, ferry, and bus. Expect a bit cooler evenings in Villasimius when traveling from Taormina in September, with lows around 20°C. Finish up your sightseeing early on the 26th (Tue) so you can go by car to Baunei.
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To see ratings, reviews, where to stay, and more tourist information, read Villasimius travel route builder site.
Getting from Taormina to Villasimius by flight takes about 3 hours. Other options: do a combination of bus and ferry; or do a combination of train, ferry, and bus. Expect a bit cooler evenings in Villasimius when traveling from Taormina in September, with lows around 20°C. Finish up your sightseeing early on the 26th (Tue) so you can go by car to Baunei.
Side Trips
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Baunei, Sardinia — 2 nights

Baunei is a comune (municipality) in the Province of Nuoro in the Italian island of Sardinia.GeographyThe municipality of Baunei is located about 100km northeast of Cagliari and about 11km north of Tortolì. Start off your visit on the 27th (Wed): enjoy the sand and surf at Cala Goloritzè, then kick back and relax at Cala dei Gabbiani, then see some colorful creatures with Diving Cala Mariolu, and finally tour the pleasant surroundings at Cala Mariolu. On the 28th (Thu), you'll have a packed day of sightseeing: Head underground at Grotta del Bue Marino, then enjoy the sand and surf at Spiaggia di Cala Luna, and then enjoy the sand and surf at Lido di Orri.
For maps, reviews, other places to visit, and tourist information, read our Baunei trip maker tool.
Traveling by car from Villasimius to Baunei takes 2 hours. Alternatively, you can take a bus. In September, plan for daily highs up to 32°C, and evening lows to 22°C. Finish your sightseeing early on the 28th (Thu) to allow enough time to drive to San Teodoro.
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For maps, reviews, other places to visit, and tourist information, read our Baunei trip maker tool.
Traveling by car from Villasimius to Baunei takes 2 hours. Alternatively, you can take a bus. In September, plan for daily highs up to 32°C, and evening lows to 22°C. Finish your sightseeing early on the 28th (Thu) to allow enough time to drive to San Teodoro.
Side Trips
Highlights from your trip
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.Visit Spiaggia La Cinta and Cala Brandinchi for some beach relaxation. Explore hidden gems such as Lu Impostu Beach and Porto Istana Beach. Explore San Teodoro's surroundings by going to Oasi Biderosa (in Orosei), Golfo Aranci (Dolphin & Whale Watching & Spiaggia Bianca) and Spiaggia di Capo Comino (in Siniscola). There's still lots to do: enjoy the sand and surf at Spiaggia Capo Coda Cavallo and tour the pleasant surroundings at Porto Taverna Beach.
To see maps, photos, traveler tips, and more tourist information, read our San Teodoro visit planner.
You can drive from Baunei to San Teodoro in 2 hours. Alternatively, you can take a bus. Traveling from Baunei in September, expect a bit cooler with lows of 19°C in San Teodoro. Finish your sightseeing early on the 1st (Sun) so you can fly to Ravello.
Side Trips
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Ravello — 2 nights

Best known for its celebrated terraced gardens, Ravello is a hidden gem of Italy's Amalfi Coast.Start off your visit on the 2nd (Mon): head outdoors with Outdoor Activities, tour the pleasant surroundings at Fornillo, then contemplate in the serene atmosphere at Cloister del Paradiso, then contemplate in the serene atmosphere at Duomo di Sant'Andrea, and finally take in the exciting artwork at Ceramiche Cosmolena di Margherita di Palma. Keep things going the next day: take in the spiritual surroundings of Duomo di Ravello, admire the landmark architecture of Villa Rufolo, tour the pleasant surroundings at Villa Cimbrone Gardens, then pause for some serene contemplation at Convento Frati Minori Conventuali S.Francesco, then see the interesting displays at Museo della Carta, and finally head outdoors with Amalfi Coast.
To find maps, ratings, more things to do, and other tourist information, read Ravello road trip site.
Traveling by flight from San Teodoro to Ravello takes 3 hours. Alternatively, you can do a combination of bus, ferry, train, and taxi; or do a combination of bus, ferry, and train. Traveling from San Teodoro in October, Ravello is somewhat warmer at night with lows of 20°C. Cap off your sightseeing on the 3rd (Tue) early enough to go by car to Rome.
Side Trips
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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.You'll discover tucked-away gems like Villa d'Este and Arcibasilica di San Giovanni in Laterano. Visit Colosseum and Pantheon for their historical value. Change things up with a short trip to Villa Adriana in Tivoli (about 36 minutes away). And it doesn't end there: admire the striking features of Villa Borghese, browse the exhibits of Vatican Museums, take in the architecture and atmosphere at Basilica di San Pietro in Vincoli, and steep yourself in history at Roman Forum.
To find other places to visit, photos, where to stay, and more tourist information, read our Rome online trip maker.
You can drive from Ravello to Rome in 3.5 hours. Alternatively, you can do a combination of taxi and train; or take a bus. Expect little chillier evenings in Rome when traveling from Ravello in October, with lows around 15°C. Finish your sightseeing early on the 8th (Sun) so you can drive to Assisi.
Side Trips
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Assisi — 4 nights

City of Peace
Rich in culture and religious tradition, Assisi is known as the birthplace of St.Satisfy your inner culture vulture at Duomo di Orvieto and Pozzo di San Patrizio. Get some historical perspective at Civita di Bagnoregio and Cattedrale di Santa Maria Assunta Spoleto. And it doesn't end there: take in the architecture and atmosphere at San Damiano, take in the spiritual surroundings of Eremo delle Carceri, admire the striking features of Basilica di Santa Chiara, and do a tasting at Azienda Agraria Saio.
To find other places to visit, more things to do, where to stay, and more tourist information, use the Assisi tour itinerary planning website.
Traveling by car from Rome to Assisi takes 2.5 hours. Alternatively, you can take a train; or take a bus. Expect a daytime high around 24°C in October, and nighttime lows around 12°C. Cap off your sightseeing on the 12th (Thu) early enough to go by car to Siena.
Side Trips
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Siena — 4 nights

Cultural Heart of Tuscany
Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.Get a sense of the local culture at Historic Centre of San Gimignano and Abbazia di San Galgano. Get some historical perspective at Centro Storico di Siena and Walls of Monteriggioni. Venture out of the city with trips to San Gimignano (Duomo di San Gimignano, Piazza della Cisterna, &more) and Fattoria Casa Sola (in Barberino Val d'Elsa). There's lots more to do: take in panoramic vistas at Torre del Mangia, explore the historical opulence of Castello di Monteriggioni, make a trip to Piazza del Campo, and deepen your understanding at Scuola di Cucina di Lella.
For reviews, traveler tips, photos, and more tourist information, go to the Siena trip planner.
Traveling by car from Assisi to Siena takes 2 hours. Alternatively, you can take a bus; or take a train. October in Siena sees daily highs of 26°C and lows of 15°C at night. Cap off your sightseeing on the 16th (Mon) early enough to travel to Portoferraio.
Side Trips
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Portoferraio, Elba Island — 1 night

Portoferraio is a town and comune in the province of Livorno, on the edge of the eponymous harbour of the island of Elba. Start off your visit on the 17th (Tue): enjoy the sand and surf at La Crocetta, tour the pleasant surroundings at Spiaggia di Cavoli, then kick back and relax at Spiaggia Di Sansone, and finally tour the pleasant surroundings at Spiaggia di Capo Bianco.
To find photos, traveler tips, more things to do, and tourist information, use the Portoferraio trip tool.
Getting from Siena to Portoferraio by combination of taxi and ferry takes about 3.5 hours. Other options: do a combination of train and ferry; or do a combination of bus, train, and ferry. Traveling from Siena in October, you will find days in Portoferraio are little chillier (22°C), and nights are about the same (17°C). Wrap up your sightseeing on the 17th (Tue) early enough to travel to Florence.
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To find photos, traveler tips, more things to do, and tourist information, use the Portoferraio trip tool.
Getting from Siena to Portoferraio by combination of taxi and ferry takes about 3.5 hours. Other options: do a combination of train and ferry; or do a combination of bus, train, and ferry. Traveling from Siena in October, you will find days in Portoferraio are little chillier (22°C), and nights are about the same (17°C). Wrap up your sightseeing on the 17th (Tue) early enough to travel to Florence.
Side Trips
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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.Visit Cathedral of Santa Maria del Fiore and Basilica San Miniato al Monte for their historical value. Your cultural itinerary includes sights like Piazzale Michelangelo and Duomo di Pisa. Change things up with these side-trips from Florence: St Martin Cathedral (in Lucca), Pisa (Knights’ Square, Battistero di San Giovanni, &more) and Montecatini Alto (in Montecatini Alto). There's still lots to do: steep yourself in history at The Baptistery of St. John, pause for some serene contemplation at Basilica of Santa Croce, ponder the world of politics at Museo Nazionale del Bargello, and wander the streets of Portovenere.
For photos, other places to visit, maps, and other tourist information, go to the Florence trip builder app.
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. Wrap up your sightseeing on the 22nd (Sun) to allow time to take a train to Verona.
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Verona — 5 nights

City of Romeo and Juliet
The famous setting for Shakespeare's star-crossed lovers, Romeo and Juliet, Verona is one of northern Italy's main tourist destinations, largely owing to its incredibly rich artistic heritage.Get some cultural insight at Castello Scaligero and Borghetto sul Mincio. Deepen your sense of the past at sights like Palazzo Te and Scaliger Castle in Malcesine. Explore the numerous day-trip ideas around Verona: Mountbaldo (in Malcesine), Santuario Basilica Madonna della Corona (in Ferrara di Monte Baldo) and Sirmione (Grotte di Catullo & Spa Termale Aquaria). And it doesn't end there: contemplate in the serene atmosphere at Basilica di San Zeno Maggiore, make a trip to Torre dei Lamberti, explore the historical opulence of Museo di Castelvecchio, and take in the architecture and atmosphere at Basilica di Santa Anastasia.
To find ratings, traveler tips, other places to visit, and other tourist information, refer to the Verona trip planner.
Take a train from Florence to Verona in 2.5 hours. Alternatively, you can drive. Traveling from Florence in October, you will find days in Verona are little chillier (22°C), and nights are about the same (11°C). Wrap up your sightseeing on the 27th (Fri) to allow time to drive to Venice.
Side Trips
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Venice — 5 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.Get some cultural insight at Piazza San Marco and Scrovegni Chapel. Discover out-of-the-way places like San Giorgio Maggiore and Padua Botanical Garden - World Heritage Site. Get out of town with these interesting Venice side-trips: PDC Cartizze (in Valdobbiadene) and Chiesa degli Eremitani - World Heritage Site (in Padua). The adventure continues: take in the architecture and atmosphere at Basilica di San Marco, contemplate in the serene atmosphere at Scuola Grande di San Rocco, make a trip to Peggy Guggenheim Collection, and examine the collection at Doge's Palace.
To see reviews, where to stay, more things to do, and other tourist information, read Venice driving holiday planning app.
You can drive from Verona to Venice in 1.5 hours. Alternatively, you can take a shuttle; or take a train. In October, daytime highs in Venice are 22°C, while nighttime lows are 12°C. Wrap up your sightseeing on the 1st (Wed) early enough to fly back home.
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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.