27 days in Italy Itinerary

27 days in Italy Itinerary

Created using Inspirock Italy trip itinerary planner

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Route & dates

27 days in Italy Itinerary

Start: Montreal, Quebec
Fly:  13​h 15​min
1
Verona
— 3 nights
+3
Fly + Bus + Foot + Ferry:  5​h 15​min
2
Ischia, Isola d'Ischia
— 1 night
+2
Ferry + Foot + Ferry:  8​h 30​min
3
Isola di Favignana
— 1 night
Drive:  45​min
4
Trapani, Sicily
— 3 nights
Drive:  1​h 15​min
5
Palermo, Sicily
— 3 nights
Drive:  2​h 15​min
6
Piazza Armerina, Sicily
— 3 nights
Drive:  2​h
7
Syracuse, Sicily
— 3 nights
Drive:  1​h 15​min
8
Ragusa, Sicily
— 3 nights
+3
Bus + Foot + Fly + Train:  5​h
9
Cinque Terre
— 3 nights
+2
Train + Tram + Fly:  15​h 15​min
End: Montreal, Quebec

3
nights
Verona

Verona ©
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.
Palazzo Te and Il Vittoriale degli Italiani will appeal to museum buffs. Visit Castello Scaligero di Malcesine and Basilica di Sant’Antonio for their historical value. Explore the numerous day-trip ideas around Verona: Borghetto sul Mincio (in Valeggio Sul Mincio), Scrovegni Chapel (in Padua) and Trento (Piazza Duomo & MUSE - Museo delle Scienze di Trento). There's much more to do: pause for some serene contemplation at Basilica di San Zeno Maggiore, pick up a one of a kind souvenir at Libreria Antiquaria Perini, explore the world behind art at Museo di Castelvecchio, and stop by Fil Good.

To see maps, photos, where to stay, and tourist information, you can read our Verona road trip site .

Montreal, Canada to Verona is an approximately 13.5-hour combination of flight and train. You can also fly; or do a combination of train and flight. You'll lose 6 hours traveling from Montreal to Verona due to the time zone difference. When traveling from Montreal in October, plan for somewhat warmer days and about the same nights in Verona: temperatures range from 22°C by day to 11°C at night. Wrap up your sightseeing on the 9th (Tue) to allow time to travel to Ischia.

Things to do in Verona

Historic Sites Museums Childrens Museums

Side Trips

Trento, Padua, Scaliger Castle in Malcesine, Il Vittoriale degli Italiani, Borghetto sul Mincio
Highlights from your plan
Borghetto sul Mincio ©
Borghetto sul Mincio
Palazzo Te ©
Palazzo Te
Basilica di Santa Anastasia ©
Basilica di Santa Anastasia

1
night
Ischia, Isola d'Ischia

Ischia ©
Ischia is a volcanic island in the Tyrrhenian Sea. On the 10th (Wed), contemplate the long history of Sant'Angelo (Serrara Fontana), look for gifts at Ischia Salumi, then steep yourself in history at Castello Aragonese, and finally look for gifts at I Sapori dell’Isola d’Ischia. On the 11th (Thu), you'll have a packed day of sightseeing: take in the architecture and atmosphere at Chiesa di San Vito, pause for some serene contemplation at Chiesa del Soccorso, take in nature's colorful creations at Giardini La Mortella, look for gifts at Gelateria Ice da Luciano, then stop by Cioccolateria Atelier delle Dolcezze, and finally stop by Naturischia.

To find other places to visit, reviews, where to stay, and other tourist information, read our Ischia trip itinerary planning tool .

Do a combination of flight and ferry from Verona to Ischia in 5.5 hours. Alternatively, you can do a combination of train, flight, and ferry; or do a combination of bus, flight, and ferry. Traveling from Verona in October, things will get somewhat warmer in Ischia: highs are around 26°C and lows about 20°C. Finish your sightseeing early on the 11th (Thu) so you can ride a ferry to Isola di Favignana.

Things to do in Ischia

Historic Sites Shopping Nightlife

Side Trips

Forio, Sant'Angelo (Serrara Fontana), I Sapori dell’Isola d’Ischia
Highlights from your plan
Castello Aragonese d'Ischia ©
Castello Aragonese d'Ischia
Atelier delle Dolcezze ©
Atelier delle Dolcezze
Ischia Salumi ©
Ischia Salumi

1
night
Isola di Favignana

Isola di Favignana ©
Once famous for its white tuff shell quarries and tuna can factory--now turned into a museum--Isola di Favignana attracts divers and beachgoers with its jagged coastline rich in coves and caves.
Start off your visit on the 12th (Fri): contemplate the long history of Ex Stabilimento Florio delle Tonnare di Favignana e Formica, then examine the collection at Casa Museo Matteo Sercia, and then enjoy the sand and surf at Cala Rossa. Get ready for a full day of sightseeing on the next day: stop by mare, look for gifts at Monique Boutique, then stop by L'Arte del Creare, and finally stop by Medusa Souvenir.

To see ratings, traveler tips, and tourist information, you can read our Isola di Favignana trip itinerary builder site .

Traveling by ferry from Ischia to Isola di Favignana takes 8.5 hours. In October, daytime highs in Isola di Favignana are 29°C, while nighttime lows are 19°C. Finish your sightseeing early on the 13th (Sat) to allow enough time to ride a ferry to Trapani.

Things to do in Isola di Favignana

Museums Parks Beaches
Highlights from your plan

3
nights
Trapani, Sicily

Trapani ©
Historically known for its importance in salt production, Trapani has gained recognition as an enticing but affordable vacation locale in Sicily.
Get some historical perspective at Parco Archeologico di Selinunte and Tempio di Segesta. Step off the beaten path and head to La Pasticceria Maria Grammatico and Pensiero Contemporaneo. Take a break from Trapani with a short trip to Riserva Naturale Orientata dello Zingaro in Castellammare del Golfo, about 56 minutes away. There's more to do: look for gifts at Sicilia Bedda.

To see photos, where to stay, traveler tips, and tourist information, go to the Trapani travel site .

Traveling by ferry from Isola di Favignana to Trapani takes an hour. Expect a daytime high around 29°C in October, and nighttime lows around 19°C. Wrap up your sightseeing on the 16th (Tue) early enough to drive to Palermo.

Things to do in Trapani

Historic Sites Parks Wildlife

Side Trips

Erice, Marinella di Selinunte, Tempio di Segesta, Riserva Naturale Dello Zingaro
Highlights from your plan
Tempio di Segesta ©
Tempio di Segesta
Sicilia Bedda ©
Sicilia Bedda
La Pasticceria Maria Grammatico ©
La Pasticceria Maria Grammatico

3
nights
Palermo, Sicily

Palermo ©
The capital of Sicily, Palermo was founded by the Phoenicians under the name of Ziz.
For shopping fun, head to Mercato Ballaro or Upanaru - Best Sicily Food. Visit La Rocca and Duomo di Monreale for their historical value. Explore the numerous day-trip ideas around Palermo: Cefalu (Porta Pescara, Ceramiche Sireci, & more), eurako confetti di marcellino (in Termini Imerese) and Pasticceria Namio (in Marineo). There's lots more to do: steep yourself in history at Santa Maria dell'Ammiraglio, admire the natural beauty at Palazzo dei Normanni e Cappella Palatina, stop by Shahidi, and explore the different monuments and memorials at Catacombe dei Cappuccini.

For reviews, photos, and tourist information, use the Palermo travel route planner.

Traveling by car from Trapani to Palermo takes 1.5 hours. Alternatively, you can take a bus; or do a combination of train and bus. Cap off your sightseeing on the 19th (Fri) early enough to go by car to Piazza Armerina.

Things to do in Palermo

Shopping Historic Sites Parks

Side Trips

Cefalu, Monreale, Termini Imerese, Pasticceria Namio
Highlights from your plan
Pasticceria Namio ©
Pasticceria Namio
Porta Pescara ©
Porta Pescara
Upanaru - Best Sicily Food ©
Upanaru - Best Sicily Food

3
nights
Piazza Armerina, Sicily

Piazza Armerina
Piazza Armerina is an Italian comune in the province of Enna of the autonomous island region of Sicily.HistoryThe city of Piazza developed during the Norman domination in Sicily, when Lombards settled the central and eastern part of Sicily.But the area had been inhabited since prehistoric times. Do your shopping at Sicilia Outlet Village and Ceramiche Sun Light di Marletta Clara. Discover out-of-the-way places like Piazza Armerina and Villa Romana del Casale. Venture out of the city with trips to Santuario del SS. Crocifisso di Papardura (in Enna), Villaggio Bizantino di Vallone Canalotto (in Calascibetta) and Agira Canadian War Cemetery (in Agira). The adventure continues: stop by Ceramica a Modo Mio, take in the architecture and atmosphere at Collegio dei Gesuiti, and contemplate the long history of Castello di Mongialino.

Plan my trip to Piazza Armerina with suggested itineraries provided by Inspirock.

Traveling by car from Palermo to Piazza Armerina takes 2.5 hours. Alternatively, you can take a bus. Finish up your sightseeing early on the 22nd (Mon) so you can go by car to Syracuse.

Things to do in Piazza Armerina

Historic Sites Shopping Classes

Side Trips

Agira, Caltagirone, Ceramiche Sun Light di Marletta Clara, Villaggio Bizantino di Vallone Canalotto, Ceramica a Modo Mio
Highlights from your plan
Villa Romana del Casale
Villa Romana del Casale
Piazza Armerina ©
Piazza Armerina
Sicilia Outlet Village ©
Sicilia Outlet Village

3
nights
Syracuse, Sicily

Syracuse ©
Philosopher Cicero once described Syracuse as "the greatest Greek city and the most beautiful of them all." A powerful city-state of ancient Greece, Syracuse now is the capital of the eponymous Italian province on the eastern coast of Sicily.
Explore hidden gems such as Cathedral of Syracuse and Chiesa Santa Chiara. Shop till you drop at Souvenir Avola and Tabare. When in Syracuse, make a side trip to see Centro Storico di Noto in Noto, approximately 36 minutes away. And it doesn't end there: stop by Aretusa Souvenir, take in the architecture and atmosphere at Duomo di Siracusa, hunt for treasures at Il Mercato di Ortigia, and explore the ancient world of Greek Theater.

To see photos, ratings, where to stay, and tourist information, read Syracuse trip site .

You can drive from Piazza Armerina to Syracuse in 2 hours. Alternatively, you can do a combination of bus and train; or take a bus. Wrap up your sightseeing on the 25th (Thu) early enough to drive to Ragusa.

Things to do in Syracuse

Shopping Historic Sites

Side Trips

Noto, Ibla Souvenir Avola
Highlights from your plan
Ibla Souvenir Avola ©
Ibla Souvenir Avola
Chiesa Santa Chiara ©
Chiesa Santa Chiara
Caseificio Borderi ©
Caseificio Borderi

3
nights
Ragusa, Sicily

Ragusa ©
Once a flourishing ancient city, Ragusa was rebuilt after a devastating earthquake in 1693.
For shopping fun, head to Civico 14 wine chocolate design or Ara' espressione di idee. Your inner history buff will appreciate Scicli and Via del Mare. You'll find plenty of places to visit near Ragusa: Scicli (Piazza Busacca & Suore Adoratrici Del Ss. Sacramento) and Faro di Punta Secca (in Punta Secca). There's still lots to do: take in the architecture and atmosphere at Chiesa di San Giorgio, take in the spiritual surroundings of Duomo San Giorgio, get to know the fascinating history of Ragusa Ibla, and stop by Antica Dolceria Bonajuto.

For photos, traveler tips, where to stay, and tourist information, read Ragusa trip maker tool .

Traveling by car from Syracuse to Ragusa takes 1.5 hours. Alternatively, you can take a train. In October, daily temperatures in Ragusa can reach 29°C, while at night they dip to 17°C. Wrap up your sightseeing on the 28th (Sun) to allow time to travel to Cinque Terre.

Things to do in Ragusa

Historic Sites Shopping Museums

Side Trips

Modica, Scicli, Faro di Punta Secca, Castello di Donnafugata
Highlights from your plan
Cathedral of St. George ©
Cathedral of St. George
Duomo San Giorgio ©
Duomo San Giorgio
Castello di Donnafugata ©
Castello di Donnafugata

3
nights
Cinque Terre

Cinque Terre ©
Made up of five picturesque towns on the Ligurian coast, Cinque Terre is Italy's answer to the French Riviera.
Start off your visit on the 29th (Mon): look for gifts at Il Laboratorio del Pesto, then look for gifts at Cinque Terre Trekking Gear Shop, then get outside with Cinque Terre Trails, and finally get into the urban bustle at Vernazza. Get ready for a full day of sightseeing on the 30th (Tue): take in the spiritual surroundings of Cattedrale di San Lorenzo - Duomo di Genova, see the interesting displays at Galata Museo del Mare, then look for gifts at DiVino Emporio, and finally look for gifts at L'Ancoretta.

To find where to stay, ratings, and tourist information, go to the Cinque Terre trip maker .

Traveling by combination of taxi, flight, and train from Ragusa to Cinque Terre takes 5 hours. Alternatively, you can do a combination of bus, flight, and train; or do a combination of bus and train. Prepare for slightly colder weather when traveling from Ragusa in October: high temperatures in Cinque Terre hover around 25°C and lows are around 14°C. Wrap up your sightseeing by early afternoon on the 31st (Wed) to allow enough time to travel back home.

Things to do in Cinque Terre

Shopping Historic Sites Trails

Side Trips

Genoa, Chiavari, Il Laboratorio del Pesto, Azienda Agraria La Valle
Highlights from your plan
Vernazza ©
Vernazza
Azienda Agraria La Valle ©
Azienda Agraria La Valle
DiVino Emporio ©
DiVino Emporio

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