36 days in Italy Itinerary

36 days in Italy Itinerary

Created using Inspirock Italy trip maker

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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.
Peggy Guggenheim Collection and San Giorgio Maggiore will appeal to history buffs. Museum-lovers will get to explore Doge's Palace and Punta della Dogana. Go for a jaunt from Venice to Sottomarina to see Bagni Sirena about 44 minutes away. Next up on the itinerary: contemplate the waterfront views at Canal Grande, contemplate in the serene atmosphere at Scuola Grande di San Rocco, explore the world behind art at Gallerie dell'Accademia, and admire the striking features of Basilica di San Marco.

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. Expect a bit warmer weather when traveling from Toronto in August: highs in Venice hover around 34°C, while lows dip to 22°C. Finish your sightseeing early on the 30th (Fri) so you can drive to Verona.

Things to do in Venice

Historic Sites Museums Parks

Side Trip

Bagni Sirena
Find places to stay Aug 26 — 30:
Highlights from your plan
San Giorgio Maggiore ©
San Giorgio Maggiore
St. Mark's Square ©
St. Mark's Square
Doge's Palace ©
Doge's Palace

5
nights
Florence

Florence ©
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Discover out-of-the-way places like Centro Storico di Siena and Basilica San Miniato al Monte. Your inner history buff will appreciate Historic Centre of San Gimignano and Piazza del Duomo. When in Florence, make a side trip to see Castello di Monteriggioni in Monteriggioni, approximately 1 hour away. The adventure continues: admire the masterpieces at Uffizi Galleries, examine the collection at Academy Of Florence Art Gallery, don't miss a visit to Piazzale Michelangelo, and take in the spiritual surroundings of The Baptistery of St. John.

For where to stay, other places to visit, traveler tips, and tourist information, you can read our Florence online trip planner .

Traveling by train from Venice to Florence takes 2.5 hours. Alternatively, you can drive; or take a bus. In August, daytime highs in Florence are 35°C, while nighttime lows are 20°C. Finish up your sightseeing early on the 4th (Wed) so you can catch the train to Rome.

Things to do in Florence

Historic Sites Museums

Side Trips

Centro Storico di Siena, Castello di Monteriggioni, Historic Centre of San Gimignano
Find places to stay Aug 30 — Sep 4:
Highlights from your plan
Cathedral of Santa Maria del Fiore ©
Uffizi Galleries ©
Uffizi Galleries
Historic Centre of San Gimignano ©

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 Cascata delle Marmore and Parco Archeologico di Ostia Antica. Let the collections at Galleria Borghese and Vatican Museums capture your imagination. Explore Rome's surroundings by going to Orvieto (Pozzo di San Patrizio & Duomo di Orvieto) and Villa d'Este (in Tivoli). The adventure continues: contemplate the long history of St. Peter's Basilica, explore the ancient world of Colosseum, make a trip to Roman Forum, and admire the striking features of Pantheon.

For photos, maps, more things to do, and other tourist information, use the Rome trip planner.

You can take a train from Florence to Rome in 2 hours. Alternatively, you can drive; or fly. In September, plan for daily highs up to 32°C, and evening lows to 18°C. Finish your sightseeing early on the 9th (Mon) so you can drive to Positano.

Things to do in Rome

Historic Sites Museums Parks

Side Trips

Orvieto, Vatican City, Cascata delle Marmore, Villa d'Este, Parco Archeologico di Ostia Antica
Find places to stay Sep 4 — 9:
Highlights from your plan
Colosseum ©
Colosseum
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.
Discover out-of-the-way places like Museo Archeologico Nazionale di Paestum and Parrocchia Ss. Annunziata. Your inner history buff will appreciate Duomo di Ravello and Villa Cimbrone Gardens. You'll find plenty of places to visit near Positano: Amalfi (Chiostro del Paradiso, Duomo di Sant'Andrea, & more), Ravello (Villa Rufolo & Ceramiche d'Arte Carmela) and Vietri sul Mare (Parrocchia San Giovanni & Le Vigne di Raito). There's much more to do: kick back and relax at Spiaggia di castiglione, tour the pleasant surroundings at Bagni d'Arienzo, cool off at Fornillo, and explore the ancient world of Temple of Athena.

For maps, traveler tips, and more tourist information, read Positano road trip app .

Traveling by car from Rome to Positano takes 3.5 hours. Alternatively, you can do a combination of train and subway; or take a bus. Plan for somewhat warmer nights when traveling from Rome in September since evenings lows in Positano dip to 23°C. Cap off your sightseeing on the 15th (Sun) early enough to travel to Taormina.

Things to do in Positano

Outdoors Parks Beaches

Side Trips

Ravello, Amalfi, Paestum, Vietri sul Mare, Castello Aragonese
Find places to stay Sep 9 — 15:
Highlights from your plan
Fornillo ©
Fornillo
Museo Archeologico Nazionale di Paestum ©
Sentiero degli dei (Path of the Gods) ©

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 Grotte di Castellana and Basilica Cattedrale Maria Santissima della Madia. Visiting Costa Dei Trulli and Indiana Park will get you outdoors. Explore the numerous day-trip ideas around Polignano a Mare: Parrocchia Santuario Basilica S.S. Cosma E Damiano (in Alberobello), Taranto (Taranto Catherdral - Duomo of San Cataldo & Castello Aragonese) and Basilica di San Martino (in Martina Franca). Next up on the itinerary: take in the architecture and atmosphere at Cattedrale di Conversano, look for all kinds of wild species at Valle d’itria e Dintorni, contemplate the long history of Castello Marchione, and explore the historical opulence of Castello di Carlo V.

To find maps, other places to visit, ratings, and other tourist information, read Polignano a Mare road trip website .

You can drive from Positano to Polignano a Mare in 4.5 hours. Other options are to take a train; or do a combination of bus and subway. Traveling from Positano in September, you can expect nighttime temperatures to be slightly colder in Polignano a Mare, with lows of 17°C. Finish your sightseeing early on the 20th (Fri) to allow enough time to travel to Taormina.

Things to do in Polignano a Mare

Parks Historic Sites Outdoors

Side Trips

Monopoli, Ostuni, Castellana Grotte, Taranto, Conversano
Find places to stay Sep 15 — 20:
Highlights from your plan
Castello Aragonese ©
Castello Aragonese
Grotte di Castellana ©
Grotte di Castellana
Masseria Brancati ©
Masseria Brancati

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 Chiesa Madonna della Rocca and Quattro Fontane di Taormina for their historical value. You'll discover tucked-away gems like Spiaggia Capo Calava and Spiaggia San Gregorio. Explore Taormina's surroundings by going to Diocesi Di Acireale (in Acireale), Randazzo (Casa della Musica e della Liuteria Medievale & Basilica di Santa Maria) and EtnaExcursion.it (in Trecastagni). Next up on the itinerary: stroll through Grotte Beach Mongiove, take in the spiritual surroundings of Chiesa del Varo, take a tour by water with Boat Tours & Water Sports, and head off the coast to Isola Bella.

Use Inspirock's suggestions to plan your Taormina trip and find the best activities and attractions for your vacation.

Traveling by combination of flight and train from Polignano a Mare to Taormina takes 5.5 hours. Alternatively, you can do a combination of car and ferry; or take a bus. Traveling from Polignano a Mare in September, expect somewhat warmer with lows of 24°C in Taormina. On the 26th (Thu), wrap the sightseeing up by early afternoon so you can travel to Carloforte.

Things to do in Taormina

Outdoors Parks Beaches

Side Trips

Randazzo, Spiaggia San Gregorio, Riserva Naturale Orientata Laghetti di Marinello, Spiaggia Capo Calava, Grotte Beach Mongiove
Find places to stay Sep 20 — 26:
Highlights from your plan
Isola Bella ©
Isola Bella
Scuba & Snorkeling
Spiaggia Capo Calava ©
Spiaggia Capo Calava

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. Satisfy your inner culture vulture at Cattedrale di Santa Maria di Monserrato and Chiesa San Carlo Borromeo. Relax by the water at Spiaggia di Cala Fico and Spiaggia di Punta Nera. Change things up with these side-trips from Carloforte: Museo del Bisso di Chiara Vigo (in Sant'Antioco), Spiaggia Is Arenas Bianca (in Teulada) and Centro Ippico Meurreddus a Cuaddu (in San Giovanni Suergiu). The adventure continues: tour the pleasant surroundings at Punta Delle Colonne, kick back and relax at Cape Sandalo, and pause for some serene contemplation at Chiesa della Madonna dello Schiavo.

To find other places to visit, maps, and more tourist information, go to the Carloforte trip itinerary builder website .

The Route module can help you plan travel from Taormina to Carloforte. Traveling from Taormina in September, expect slightly colder with lows of 20°C in Carloforte. On the 30th (Mon), wrap the sightseeing up by early afternoon so you can travel back home.

Things to do in Carloforte

Parks Outdoors Beaches

Side Trips

Museo del Bisso di Chiara Vigo, Cattedrale di Santa Maria di Monserrato, Spiaggia Is Arenas Bianca, Centro Ippico Meurreddus a Cuaddu
Find places to stay Sep 26 — 30:
Highlights from your plan
Centro Ippico Meurreddus a Cuaddu ©
Centro Ippico Meurreddus a Cuaddu
Spiaggia di Cala Fico ©
Spiaggia di Cala Fico
Spiaggia di Punta Nera ©
Spiaggia di Punta Nera

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