42 days in Italy Itinerary

42 days in Italy Itinerary

Created using Inspirock Italy itinerary planner

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Route & dates

42 days in Italy Itinerary

Start: Montreal
Fly:  12​h
1
Venice
— 6 nights
Drive:  3​h 45​min
2
Montepulciano
— 8 nights
Drive:  2​h 45​min
3
Massarosa
— 6 nights
+2
Drive + Fly + Drive:  5​h 15​min
4
Taranto
— 7 nights
+2
Drive + ferry + Drive:  8​h
5
Agrigento
— 3 nights
Drive:  2​h
6
Castellammare del Golfo
— 2 nights
Drive:  1​h 15​min
7
Palermo
— 3 nights
Fly + Drive:  5​h
8
Minori
— 5 nights
Drive + Fly:  18​h 30​min
End: Montreal

6
nights
Venice

Venice ©
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 in touch with nature at Bagni Alberoni and Pineta di Volano. Your cultural itinerary includes sights like Basilica di Santa Giustina and Esapolis - Museo Vivente degli insetti. Explore the numerous day-trip ideas around Venice: Pomposa Abbey (in Codigoro), Padua (Museo Veneto Del Giocattolo, Padova, Italia, Museo del Precinema, & more) and Castello Estense (in Ferrara). There's still lots to do: head outdoors with Venetian Lagoon, explore the world behind art at Castello del Catajo, browse the eclectic array of goods at Laguna di Venezia, and go for a stroll along the water at Malamocco.

To find ratings, reviews, more things to do, and more tourist information, refer to the Venice online route planner .

Montreal, Canada to Venice is an approximately 12-hour flight. You can also do a combination of train and flight. The time zone difference when traveling from Montreal to Venice is 6 hours. Expect a daytime high around 29°C in September, and nighttime lows around 17°C. Wrap up your sightseeing on the 13th (Sun) to allow time to drive to Montepulciano.

Things to do in Venice

Parks Museums Outdoors

Side Trips

Padua, Castello del Catajo, Pomposa Abbey, Laguna di Venezia, Castello Estense
Find places to stay Sep 7 — 13:
Highlights from your plan
Malamocco ©
Malamocco
Basilica di Santa Giustina ©
Basilica di Santa Giustina
Castello Estense ©
Castello Estense

8
nights
Montepulciano

Montepulciano ©
Perched on a limestone ridge in the heart of Tuscany, Montepulciano is known worldwide for its production of red wine, the Vino Noble.
Get some cultural insight at Ciacci Piccolomini d'Aragona and Chiesa di San Pietro. Get some historical perspective at Podere Il Cocco and Mate Winery. Explore the numerous day-trip ideas around Montepulciano: Pitigliano (Antico Ghetto e Sinagoga Pitigliano & Pitigliano Centro Storico), Civita di Bagnoregio (in Civita di Bagnoregio) and Cascate del Mulino (in Saturnia). The adventure continues: do a tasting at Poggio Rubino, steep yourself in history at Duomo di Orvieto, enjoy the sand and surf at Cala Violina, and take in nature's colorful creations at Giardino dei Tarocchi.

For reviews, other places to visit, traveler tips, and other tourist information, use the Montepulciano trip itinerary maker website .

Traveling by car from Venice to Montepulciano takes 4 hours. Alternatively, you can take a train; or do a combination of flight and train. September in Montepulciano sees daily highs of 32°C and lows of 19°C at night. Finish your sightseeing early on the 21st (Mon) to allow enough time to travel to Massarosa.

Things to do in Montepulciano

Historic Sites Parks Wineries

Side Trips

Montalcino, Pitigliano, Orvieto, Tarquinia, Giardino dei Tarocchi
Find places to stay Sep 13 — 21:
Highlights from your plan
Ciacci Piccolomini d'Aragona ©
Ciacci Piccolomini d'Aragona
Podere Il Cocco ©
Podere Il Cocco
Poggio Rubino ©
Poggio Rubino

6
nights
Massarosa

Massarosa ©
Botanical Garden Maria Ansaldi Pania di Corfino and Museo Delle Mummie Roccapelago will appeal to museum buffs. Visit Bergogno Borgo Medioevale and Pietra di Bismantova for their historical value. Get out of town with these interesting Massarosa side-trips: Rocca di Trassilico (in Trassilico), Grotta del Vento (in Fornovolasco) and Barga (Duomo di San Cristoforo & La Cantina del Vino). And it doesn't end there: take a peaceful walk through Sentiero n. 7b - Via delle Ginestre, take in the spiritual surroundings of Santuario dei Santi Pellegrino e Bianco, see the interesting displays at Museo Villa Puccini, and explore the stunning scenery at Orrido di Botri.

Start your trip to Massarosa by creating a personalized itinerary on Inspirock.

You can drive from Montepulciano to Massarosa in 2.5 hours. In September, daytime highs in Massarosa are 30°C, while nighttime lows are 17°C. Cap off your sightseeing on the 27th (Sun) early enough to travel to Taranto.

Things to do in Massarosa

Parks Nature Historic Sites

Side Trips

Castelnuovo di Garfagnana, Barga, Grotta del Vento, Fortezza delle Verrucole - Archeopark, Rocca di Trassilico
Find places to stay Sep 21 — 27:
Highlights from your plan
Grotta del Vento ©
Grotta del Vento
Museo Delle Mummie Roccapelago ©
Museo Delle Mummie Roccapelago
Santuario dei Santi Pellegrino e Bianco ©

7
nights
Taranto

Taranto ©
Taranto is a coastal city in Apulia, Southern Italy. Visit Sassi di Matera and Masseria Brancati for their historical value. Do some cultural sightseeing at Castello Aragonese and Centro Storico. Change things up with these side-trips from Taranto: Castello (in Avetrana), Area Marina Protetta Torre Guaceto (in Carovigno) and Porto Cesareo (Togo Bay Beach & Palude del Conte e Duna Costiera). There's lots more to do: look for all kinds of wild species at Jonian Dolphin Conservation, take in the architecture and atmosphere at Chiesetta di San Francesco da Paola al Borgo, contemplate in the serene atmosphere at Chiesa del Carmine, and examine the collection at Museo Archeologico Nazionale di Metaponto.

To find ratings, traveler tips, where to stay, and more tourist information, go to the Taranto trip builder website .

The Route module can help you plan travel from Massarosa to Taranto. Traveling from Massarosa in September, you can expect nighttime temperatures to be a bit warmer in Taranto, with lows of 22°C. Finish your sightseeing early on the 4th (Sun) to allow enough time to travel to Agrigento.

Things to do in Taranto

Parks Historic Sites Beaches

Side Trips

Porto Cesareo, Ostuni, Castello, Area Marina Protetta Torre Guaceto, Museo Archeologico Nazionale di Metaponto
Find places to stay Sep 27 — Oct 4:
Highlights from your plan
Jonian Dolphin Conservation ©
Jonian Dolphin Conservation
Sassi di Matera ©
Sassi di Matera
Masseria Brancati ©
Masseria Brancati

3
nights
Agrigento

Agrigento ©
Historically one of ancient Greece's leading cities, Sicily's Agrigento is home to the seven monumental temples that make up the well-preserved Valley of the Temples.
You'll explore and learn at Valley of the Temples (Valle dei Templi) and Scala dei Turchi. Museo del Giocattolo Sciacca and Museo Etnoantropologico are good opportunities to explore the local culture. Explore the numerous day-trip ideas around Agrigento: Riserva Naturale Orientata Foce del Fiume Platani (in Cattolica Eraclea) and Museo Degli Archi Di Pasqua (in San Biagio Platani). There's still lots to do: look for all kinds of wild species at Riserva Naturale Orientata Torre Salsa, browse the exhibits of Casa Natale di Luigi Pirandello, explore the historical opulence of Castello Chiaramonte, and get engrossed in the history at Museo Archeologico Regionale di Agrigento.

To find ratings, other places to visit, traveler tips, and tourist information, refer to the Agrigento online vacation planner .

Getting from Taranto to Agrigento by combination of car and ferry takes about 8 hours. Other options: do a combination of train and flight; or take a bus. Traveling from Taranto in October, you can expect nighttime temperatures to be a bit warmer in Agrigento, with lows of 22°C. Wrap up your sightseeing on the 7th (Wed) early enough to drive to Castellammare del Golfo.

Things to do in Agrigento

Parks Museums Wildlife

Side Trips

Siculiana, Museo Degli Archi Di Pasqua, Museo Etnoantropologico, Riserva Naturale Orientata Foce del Fiume Platani, Museo del Giocattolo Sciacca
Find places to stay Oct 4 — 7:
Highlights from your plan
Museo del Giocattolo Sciacca ©
Museo del Giocattolo Sciacca
Museo Etnoantropologico ©
Museo Etnoantropologico

2
nights
Castellammare del Golfo

Castellammare del Golfo ©
Castellammare del Golfo is a town and comune in the Trapani Province of Sicily. Kick off your visit on the 8th (Thu): make a trip to Baglio Di Scopello, then enjoy the sand and surf at Spiaggia Guidaloca, and then stroll through Spiaggia di Castellamare del Golfo. Here are some ideas for day two: look for gifts at La Pasticceria Maria Grammatico, pause for some serene contemplation at Chiesa di Sant'Agostino, then see the interesting displays at Museo del sale, and finally admire the landmark architecture of Tonnara di Scopello.

For where to stay, traveler tips, other places to visit, and tourist information, read Castellammare del Golfo online vacation planner .

You can drive from Agrigento to Castellammare del Golfo in 2 hours. Alternatively, you can take a bus; or do a combination of train and bus. In October in Castellammare del Golfo, expect temperatures between 28°C during the day and 20°C at night. Wrap up your sightseeing on the 9th (Fri) early enough to drive to Palermo.

Things to do in Castellammare del Golfo

Beaches Parks Outdoors

Side Trips

Trapani, La Pasticceria Maria Grammatico
Find places to stay Oct 7 — 9:
Highlights from your plan
Museo del sale ©
Museo del sale
La Pasticceria Maria Grammatico ©
La Pasticceria Maria Grammatico
Tonnara di Scopello ©
Tonnara di Scopello

3
nights
Palermo

Palermo ©
The capital of Sicily, Palermo was founded by the Phoenicians under the name of Ziz.
Start off your visit on the 10th (Sat): contemplate in the serene atmosphere at Church of San Cataldo, admire the striking features of Palazzo Conte Federico, explore the different monuments and memorials at Catacombe dei Cappuccini, admire the striking features of Norman Palace and Palatine Chapel, then take in the architecture and atmosphere at Chiesa Inferiore della Cappella Palatina, and finally pause for some serene contemplation at Cattedrale di Palermo. Get ready for a full day of sightseeing on the next day: steep yourself in history at La Rocca, steep yourself in history at Duomo di Cefalu, then pause for some serene contemplation at Duomo di Monreale, and finally steep yourself in history at Santa Maria dell'Ammiraglio.

For where to stay, maps, and more tourist information, read our Palermo trip planner .

Traveling by car from Castellammare del Golfo to Palermo takes 1.5 hours. Alternatively, you can take a bus; or take a train. Wrap up your sightseeing by early afternoon on the 12th (Mon) to allow time for travel to Minori.

Things to do in Palermo

Historic Sites Museums

Side Trips

Cefalu, Museo dell'Acciuga, Duomo di Monreale
Find places to stay Oct 9 — 12:
Highlights from your plan
Museo dell'Acciuga ©
Museo dell'Acciuga
Cattedrale di Palermo ©
Cattedrale di Palermo
Duomo di Monreale ©
Duomo di Monreale

5
nights
Minori

Minori ©
Minori is a town and a comune in the province of Salerno in the Campania region of southwestern Italy, situated on the Amalfi Coast. Take a break from the city and head to Sentiero degli dei (Path of the Gods) and Chalet de Mar. Deepen your sense of the past at sights like Duomo di Ravello and Duomo di Sant'Andrea. Change things up with a short trip to Le Vigne di Raito in Vietri sul Mare (about 38 minutes away). There's still lots to do: contemplate the long history of Villa Cimbrone Gardens, examine the collection at Museo della Carta, enjoy the sand and surf at Spiaggia Di Minori, and admire the landmark architecture of Villa Rufolo.

For where to stay, more things to do, reviews, and tourist information, read Minori trip planner .

The Route module can help you plan travel from Palermo to Minori. In October, daytime highs in Minori are 26°C, while nighttime lows are 20°C. Wrap up your sightseeing on the 17th (Sat) early enough to travel back home.

Things to do in Minori

Outdoors Parks Historic Sites

Side Trips

Ravello, Amalfi, Vietri sul Mare, Sentiero degli dei (Path of the Gods)
Find places to stay Oct 12 — 17:
Highlights from your plan
Duomo di Ravello ©
Duomo di Ravello
Villa Cimbrone Gardens ©
Villa Cimbrone Gardens
Villa Rufolo ©
Villa Rufolo

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