36 days in Italy Itinerary

36 days in Italy Itinerary

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Route & dates

36 days in Italy Itinerary

Start: Toronto
Fly:  11​h 15​min
1
Venice
— 4 nights
Train:  2​h 15​min
2
Florence
— 5 nights
Train:  1​h 45​min
3
Rome
— 5 nights
Drive:  3​h 15​min
4
Positano
— 6 nights
Drive:  4​h 15​min
5
Polignano a Mare
— 5 nights
+3
Fly + Bus + Foot + Train:  5​h 30​min
6
Taormina, Sicily
— 5 nights
+2
Drive + Fly + Drive:  6​h
7
Carloforte, Sardinia
— 4 nights
Drive + Fly:  16​h
End: Toronto

4
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.
Explore hidden gems such as San Giorgio Maggiore and Ponte dei Sospiri. Get some cultural insight at Piazza San Marco and Peggy Guggenheim Collection. Next up on the itinerary: contemplate the waterfront views at Canal Grande, take in the architecture and atmosphere at Basilica di Santa Maria della Salute, explore the world behind art at Gallerie dell'Accademia, and take in the spiritual surroundings of Scuola Grande di San Rocco.

For maps and other tourist information, use the Venice online tour builder .

Toronto, Canada to Venice is an approximately 11.5-hour flight. You can also do a combination of flight and train. Traveling from Toronto to Venice, you'll lose 6 hours due to the time zone difference. May in Venice sees daily highs of 26°C and lows of 15°C at night. Wrap up your sightseeing on the 26th (Tue) early enough to take a train to Florence.

Things to do in Venice

Historic Sites Museums Nature
Highlights from your plan
Piazza San Marco ©
Piazza San Marco
Doge's Palace ©
Doge's Palace
Basilica di San Marco
Basilica di San Marco

5
nights
Florence

Florence ©
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Museum-lovers will get to explore Gallerie Degli Uffizi and Basilica di Santa Croce. Piazzale Michelangelo and Academy Of Florence Art Gallery are good opportunities to explore the local culture. Explore Florence's surroundings by going to Monteriggioni (Castello di Monteriggioni & Walls of Monteriggioni) and Centro Storico di Siena (in Siena). There's still lots to do: see the interesting displays at Pitti Palace, take in the architecture and atmosphere at Cathedral of Santa Maria del Fiore, admire the landmark architecture of Loggia dei Lanzi, and make a trip to Palazzo Vecchio.

To see where to stay, maps, and more tourist information, refer to the Florence trip planner.

Traveling by train from Venice to Florence takes 2.5 hours. Alternatively, you can drive; or take a bus. In May, plan for daily highs up to 25°C, and evening lows to 13°C. Wrap up your sightseeing on the 31st (Sun) early enough to take a train to Rome.

Things to do in Florence

Historic Sites Museums

Side Trips

Monteriggioni, Centro Storico di Siena
Highlights from your plan
The Baptistery of St. John ©
The Baptistery of St. John
Gallerie Degli Uffizi ©
Gallerie Degli Uffizi
Academy Of Florence Art Gallery ©
Academy Of Florence Art Gallery

5
nights
Rome

Rome ©
Aptly nicknamed the Eternal City, Rome is the birthplace of the Roman Empire, one of the world's greatest civilizations ever.
You'll explore the less-touristy side of things at Villa d'Este and Cascata delle Marmore. Let the collections at Vatican Museums and Galleria Borghese capture your imagination. Explore Rome's surroundings by going to Centro Storico di Massa Martana (in Massa Martana), Parco Archeologico di Ostia Antica (in Ostia Antica) and Orvieto (Duomo di Orvieto & Pozzo di San Patrizio). The adventure continues: delve into the distant past at Pantheon, contemplate the long history of Basilica Papale San Paolo fuori le Mura, make a trip to Trevi Fountain, and take in the spiritual surroundings of Chiesa di Santa Maria del Popolo.

To find photos, other places to visit, maps, and other tourist information, read Rome trip website .

Traveling by train from Florence to Rome takes 2 hours. Alternatively, you can drive; or fly. Expect a bit warmer evenings in Rome when traveling from Florence in May, with lows around 17°C. Finish up your sightseeing early on the 5th (Fri) so you can go by car to Positano.

Things to do in Rome

Historic Sites Museums Parks

Side Trips

Orvieto, Vatican City, Villa d'Este, Centro Storico di Massa Martana, Cascata delle Marmore
Highlights from your plan
Pantheon ©
Pantheon
Vatican Museums
Vatican Museums
St. Peter's Basilica ©
St. Peter's Basilica

6
nights
Positano

Positano ©
Often referred to as the gem of the Amalfi Coast, Positano remains one of southern Italy's most sought-after vacation locales, thanks to its hillside location and picturesque, pastel buildings.
Duomo di Sant'Andrea and Ceramiche d'Arte Carmela are good opportunities to explore the local culture. Escape the urban bustle at Fornillo and Bagni d'Arienzo Beach Club, Positano. Change things up with these side-trips from Positano: Ravello (Villa Cimbrone Gardens, Duomo di Ravello, & more), Amalfi (Museo della Carta & Valle delle Ferriere) and Castiglione (Spiaggia di castiglione & Lido di Ravello). And it doesn't end there: get great views at Il Sentiero Degli Dei, enjoy the sand and surf at Spiaggia Grande, stroll through Lido Capo di Conca, and look for gifts at Nana' Positano.

To see more things to do, where to stay, maps, and other tourist information, read our Positano road trip planning app .

Getting from Rome to Positano by car takes about 3.5 hours. Other options: do a combination of train and subway; or take a bus. Expect a daytime high around 32°C in June, and nighttime lows around 23°C. Wrap up your sightseeing on the 11th (Thu) to allow time to drive to Polignano a Mare.

Things to do in Positano

Parks Outdoors Beaches

Side Trips

Ravello, Amalfi, Lido Capo di Conca, Parrocchia San Giovanni, Castello di San Nicola de Thoro-Plano
Highlights from your plan
Villa Cimbrone Gardens ©
Villa Cimbrone Gardens
Spiaggia di castiglione ©
Spiaggia di castiglione
Duomo di Ravello ©
Duomo di Ravello

5
nights
Polignano a Mare

Polignano a Mare ©
Polignano a Mare is a town and comune in the Metropolitan City of Bari, Apulia, southern Italy, located on the Adriatic Sea. You'll explore the less-touristy side of things at Centro Storico di Polignano a Mare and Costa Dei Trulli. Visiting Lido Zanzibar and Lama Monachile will get you outdoors. Explore the numerous day-trip ideas around Polignano a Mare: Valle d’itria e Dintorni (in Cisternino), Masseria Brancati (in Ostuni) and Martina Franca (Centro Storico, Basilica di San Martino, & more). There's much more to do: kick back and relax at Spiaggia Torre Canne, steep yourself in history at Piazza Dell'orologio, take in the architecture and atmosphere at Chiesa di Santa Maria del Suffragio detta del Purgatorio, and take in the views from Ponte Borbonico di Lama Monachile.

For traveler tips, maps, ratings, and tourist information, you can read our Polignano a Mare trip itinerary maker site .

Getting from Positano to Polignano a Mare by car takes about 4.5 hours. Other options: take a train; or do a combination of bus and subway. Traveling from Positano in June, Polignano a Mare is slightly colder at night with lows of 19°C. Finish your sightseeing early on the 16th (Tue) so you can travel to Taormina.

Things to do in Polignano a Mare

Outdoors Parks Beaches

Side Trips

Martina Franca, Monopoli, Lido Zanzibar, Masseria Brancati, Cattedrale di Conversano
Highlights from your plan
Masseria Brancati ©
Masseria Brancati
I Pastini ©
I Pastini
L'Acropoli di Puglia ©
L'Acropoli di Puglia

5
nights
Taormina, Sicily

Taormina ©
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.
Visit The Odeon and Palazzo Corvaja for their historical value. You'll discover tucked-away gems like Isola Bella and Grotte Beach Mongiove. Explore Taormina's surroundings by going to Linguaglossa (Etna Donkey Trekking & Il vino della Rosa), Randazzo (Casa della Musica e della Liuteria Medievale & Basilica di Santa Maria) and Spiaggia Capo Calava (in Gioiosa Marea). The adventure continues: don't miss a visit to Corso Umberto, tour on your own time with EtnaExcursion.it, take in the architecture and atmosphere at Duomo di Taormina, and take in the spiritual surroundings of Chiesa del Varo.

To find photos, ratings, where to stay, and more tourist information, refer to the Taormina trip planning app .

Do a combination of flight and train from Polignano a Mare to Taormina in 5.5 hours. Alternatively, you can do a combination of car and ferry; or take a bus. Traveling from Polignano a Mare in June, Taormina is a bit warmer at night with lows of 24°C. Wrap up your sightseeing by early afternoon on the 22nd (Mon) to allow time for travel to Carloforte.

Things to do in Taormina

Outdoors Parks Historic Sites

Side Trips

Randazzo, Linguaglossa, Grotte Beach Mongiove, EtnaExcursion.it, Castello Ruffo di Scilla
Highlights from your plan
Etna Donkey Trekking ©
Etna Donkey Trekking
Isola Bella ©
Isola Bella
Duomo di Taormina ©
Duomo di Taormina

4
nights
Carloforte, Sardinia

Carloforte ©
Carloforte is a fishing and resort town of located on Isola di San Pietro, approximately 7km off the southwestern coast of Sardinia, in southern Sardinia, Italy.HistoryAccording to a legend, a local church was founded in the early 14th century in honour of hundreds of participants to the so-called Children's Crusade of 1212 who perished in a shipwreck just off the island on their way to North Africa during a gale. You'll discover tucked-away gems like Spiaggia Is Arenas Bianca and Spiaggia di Punta Nera. Get some cultural insight at Cattedrale di Santa Maria di Monserrato and Museo del Bisso di Chiara Vigo. Go for a jaunt from Carloforte to Sant'Antioco to see Museo Etnografico Su Magasinu De Su Binu about 1h 05 min away. There's much more to do: kick back and relax at spiaggia dello Spalmatore, tour the pleasant surroundings at Spiaggia di Guidi, and look for all kinds of wild species at Spiaggia di Cala Fico.

To find photos, other places to visit, where to stay, and tourist information, refer to the Carloforte trip maker app .

Explore your travel options from Taormina to Carloforte with the Route module. Traveling from Taormina in June, expect little chillier with lows of 19°C in Carloforte. Wrap up your sightseeing by early afternoon on the 26th (Fri) to allow time for travel back home.

Things to do in Carloforte

Outdoors Beaches Parks

Side Trips

Sant'Antioco, Spiaggia Is Arenas Bianca, Cattedrale di Santa Maria di Monserrato
Highlights from your plan
Cape Sandalo ©
Cape Sandalo
Spiaggia di Guidi ©
Spiaggia di Guidi
Spiaggia di Punta Nera ©
Spiaggia di Punta Nera

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