53 days in Italy Itinerary

53 days in Italy Itinerary

Created using Inspirock Italy sightseeing planner

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Route & dates

53 days in Italy Itinerary

Start: Montreal
Fly:  12​h
1
Venice
— 3 nights
2
Bologna
— 4 nights
train:  2​h 45​min
3
Genoa
— 3 nights
train:  6​h 15​min
4
Assisi
— 5 nights
train:  2​h 45​min
5
Orvieto
— 5 nights
6
Naples
— 7 nights
Fly:  3​h 30​min
7
Alghero, Sardinia
— 6 nights
8
San Teodoro, Sardinia
— 5 nights
Fly + Drive:  4​h
9
San Vito lo Capo, Sicily
— 6 nights
Drive:  4​h 30​min
10
Taormina, Sicily
— 7 nights
Fly:  14​h 30​min
End: Montreal

3
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.
Deepen your sense of the past at sights like Cividale del Friuli - UNESCO World Heritage Centre and Borgo rurale di Clauiano. Discover out-of-the-way places like Battistero del Duomo and Chiesa di San Salvador. You'll find plenty of places to visit near Venice: Il Castello di Udine (in Udine) and Vicenza (Villa Valmarana ai Nani & Santuario della Madonna di Monte Berico). Next up on the itinerary: take in the spiritual surroundings of Santa Maria dei Miracoli, take in the architecture and atmosphere at Saint Mary of The Rosary, appreciate the extensive heritage of Campo San Maurizio, and explore the world behind art at Museo Querini Stampalia.

To find other places to visit, photos, reviews, and more tourist information, use the Venice trip itinerary website .

Montreal, Canada to Venice is an approximately 12-hour flight. You can also do a combination of train and flight. The time zone difference moving from Eastern Standard Time (EST) to Central European Time (CET) is 6 hours. When traveling from Montreal in July, plan for somewhat warmer days and about the same nights in Venice: temperatures range from 36°C by day to 22°C at night. Finish your sightseeing early on the 4th (Sat) to allow enough time to drive to Bologna.

Things to do in Venice

Historic Sites Museums Parks

Side Trips

Vicenza, Borgo rurale di Clauiano, Il Castello di Udine, Battistero del Duomo, Cividale del Friuli - UNESCO World Heritage Centre
Find places to stay Jun 30 — Jul 4:
Highlights from your plan

4
nights
Bologna

Bologna ©
A city famous for its cuisine, Bologna is the seat of the oldest university in the world, founded in 1088.
Get some historical perspective at Basilica di San Domenico and Portico del Pavaglione. Step out of the city life by going to Playa del Sol and Lido delle Sirene 101 - 102. Explore Bologna's surroundings by going to La Spiaggia Del Cuore 110 (in Riccione), Bagno 169 (in Cervia) and Oscar Spiaggia 298 (in Milano Marittima). There's still lots to do: appreciate the extensive heritage of Complesso Monumentale San Michele In Bosco, take in the architecture and design of Academya Lingue, explore the different monuments and memorials at Cimitero monumentale della Certosa, and take an in-depth tour of La Macchina del Tempo.

Ask Inspirock to suggest an itinerary and make planning a trip to Bologna fast, fun, and easy.

You can drive from Venice to Bologna in 2 hours. Other options are to take a train; or take a bus. In July, daily temperatures in Bologna can reach 37°C, while at night they dip to 22°C. Finish your sightseeing early on the 8th (Wed) so you can take a train to Genoa.

Things to do in Bologna

Parks Beaches Outdoors

Side Trips

Riccione, Cervia
Find places to stay Jul 4 — 8:
Highlights from your plan
Piazza Santo Stefano ©
Piazza Santo Stefano
Basilica di San Domenico ©
Basilica di San Domenico

3
nights
Genoa

Genoa ©
Once the most important harbor in the Mediterranean Sea, Genoa has a long history as a rich and powerful trade center in northern Italy.
Escape the urban bustle at Bagni Gallo and Bagni Liliana. Deepen your sense of the past at sights like Basilica DI Santa Maria Assunta and Chiesa di San Filippo Neri. Explore the numerous day-trip ideas around Genoa: River Beach (in Finale Ligure) and Pluto Beach (in Spotorno). And it doesn't end there: take in the spiritual surroundings of Abbazia di San Siro di Struppa, admire the landmark architecture of Antica Farmacia Erboristica Sant'Anna dei Frati Carmelitani Scalzi, see the interesting displays at Museo del Risorgimento Istituto Mazziniano, and take in the architecture and atmosphere at Basilica di Santa Maria Assunta di Carignano.

To find other places to visit, photos, where to stay, and other tourist information, read our Genoa trip itinerary maker site .

Take a train from Bologna to Genoa in 3 hours. Alternatively, you can drive; or take a bus. When traveling from Bologna in July, plan for little chillier days and about the same nights in Genoa: temperatures range from 32°C by day to 25°C at night. Wrap up your sightseeing on the 11th (Sat) early enough to drive to Assisi.

Things to do in Genoa

Parks Beaches Outdoors

Side Trips

Finale Ligure, Basilica DI Santa Maria Assunta, Pluto Beach
Find places to stay Jul 8 — 11:
Highlights from your plan
River Beach ©
River Beach
Basilica DI Santa Maria Assunta ©
Basilica DI Santa Maria Assunta
Abbazia di San Siro di Struppa ©
Abbazia di San Siro di Struppa

5
nights
Assisi

Assisi ©
Rich in culture and religious tradition, Assisi is known as the birthplace of St.
You'll discover tucked-away gems like Parrocchia Santa Maria Maggiore - Frati Cappuccini Assisi and Chiesa Nuova. Do some cultural sightseeing at Monastero di Sant'Andrea and Castello Pallotta. Change things up with these side-trips from Assisi: Loreto (Camminamenti di Ronda della Pontificia Basilica & Piazza della Madonna), Chiesa Santa Maria della Piazza (in Ancona) and Rocca Medievale Di Offagna (in Offagna). There's much more to do: appreciate the extensive heritage of Piazza Superiore di San Francesco, delve into the distant past at Museo Diocesano e Cripta di San Rufino, contemplate the long history of Arco del Seminario, and don't miss a visit to Piazza del Vescovado.

To see reviews, where to stay, and other tourist information, read Assisi trip itinerary planning app .

You can drive from Genoa to Assisi in 4.5 hours. Other options are to take a train; or do a combination of flight and train. When traveling from Genoa in July, plan for somewhat warmer days and little chillier nights in Assisi: temperatures range from 37°C by day to 20°C at night. Wrap up your sightseeing on the 16th (Thu) early enough to drive to Orvieto.

Things to do in Assisi

Historic Sites Museums Wineries

Side Trips

Montefalco, Loreto, Chiesa Santa Maria della Piazza, Castello Pallotta, Chiesa di San Silvestro
Find places to stay Jul 11 — 16:
Highlights from your plan
Castello Pallotta ©
Castello Pallotta
Monastero di Sant'Andrea ©
Monastero di Sant'Andrea

5
nights
Orvieto

Orvieto ©
The striking town of Orvieto, perched on a volcanic cliff overlooking the Umbrian countryside, is known as the Green Heart of Italy.
Your cultural itinerary includes sights like Winery Solaria Patrizia Cencioni and Palazzo dei Sette. Discover out-of-the-way places like Centro Storico Orvieto and Cappella del Corporale. Change things up with these side-trips from Orvieto: Montepulciano (Azienda Agricola Ercolani, Cantina Fattoria della Talosa, & more), Chiesa di Santa Maria Assunta (in San Quirico d'Orcia) and Archeological Museum and Tomb of Hell's Quadriga (in Sarteano). Next up on the itinerary: take in the spiritual surroundings of Santa Maria Maggiore, take in the architecture and atmosphere at Chiesa di Santa Maria e San Rocco, appreciate the extensive heritage of Rocca Albornoziana, and Head underground at Via Cava.

For other places to visit, maps, ratings, and tourist information, refer to the Orvieto trip planner.

Traveling by car from Assisi to Orvieto takes 1.5 hours. Alternatively, you can take a train; or take a bus. In July, daytime highs in Orvieto are 36°C, while nighttime lows are 21°C. Finish your sightseeing early on the 21st (Tue) so you can drive to Naples.

Things to do in Orvieto

Historic Sites Parks Nature

Side Trips

Montepulciano, Sovana, Montefiascone, Santa Maria Maggiore, Chiesa di Santa Maria e San Rocco
Find places to stay Jul 16 — 21:
Highlights from your plan
Winery Solaria Patrizia Cencioni ©
Winery Solaria Patrizia Cencioni
Chiesa di Santa Maria e San Rocco ©
Chiesa di Santa Maria e San Rocco
Santa Maria Maggiore ©
Santa Maria Maggiore

7
nights
Naples

Naples ©
Naples is the capital of the Italian region Campania and the third-largest municipality in Italy after Rome and Milan. Get in touch with nature at Stabilimento Balneare Bagni Salvatore and Sentiero dei Limoni. Get a sense of the local culture at La Terrazza di M. Nonio Balbo and Casa di Nettuno e Anfitrite. Change things up with these side-trips from Naples: Basilica di Sant'Antonino (in Sorrento), Sorrentino Vini (in Boscotrecase) and Pompeii (Terme del Foro, Casa del Fauno, & more). The adventure continues: cool off at Bagno Elena, make a trip to Acquaquiglia del Pozzaro, see the interesting displays at Villa Floridiana, and pause for some serene contemplation at Parrocchia di S. Liborio alla Carita.

For traveler tips, reviews, ratings, and other tourist information, read Naples attractions planner.

Drive from Orvieto to Naples in 3.5 hours. Alternatively, you can take a train; or take a bus. Expect a daytime high around 36°C in July, and nighttime lows around 24°C. Finish your sightseeing early on the 28th (Tue) so you can travel to Alghero.

Things to do in Naples

Historic Sites Parks Outdoors

Side Trips

Pompeii, Sorrento, Amalfi, Ercolano, Ravello
Find places to stay Jul 21 — 28:
Highlights from your plan
San Domenico Maggiore ©
San Domenico Maggiore
Casa di Nettuno e Anfitrite ©
Casa di Nettuno e Anfitrite
Cumae (Cuma) ©
Cumae (Cuma)

6
nights
Alghero, Sardinia

Alghero ©
Built surrounding a 16th-century fortified port, Alghero remains one of Sardinia's most visited sites, rich in cultural and historical heritage.
Get some cultural insight at Cattedrale di Sant'Antonio Abate e Museum Ampuriense and Cattedrale di Santa Maria. You'll explore the less-touristy side of things at Maimoni Beach and Sa Mesa Longa. Change things up with these side-trips from Alghero: Sassari (Castrum Romano La Crucca, Cattedrale di San Nicola, & more), I Gatti di Su Pallosu (in San Vero Milis) and Porto Torres (Spiaggia di Balai, Basilica San Gavino, & more). There's lots more to do: kick back and relax at Cala Bramassa, take in the spiritual surroundings of Chiesa di San Giovanni in Sinis, explore the ancient world of La Necropoli di Anghelu Ruju, and tour the pleasant surroundings at Lido San Giovanni.

For ratings, reviews, maps, and tourist information, use the Alghero trip planner .

Fly from Naples to Alghero in 3.5 hours. Alternatively, you can do a combination of train and flight; or do a combination of train, ferry, and bus. Traveling from Naples in July, expect a bit cooler with lows of 21°C in Alghero. Finish your sightseeing early on the 3rd (Mon) so you can drive to San Teodoro.

Things to do in Alghero

Outdoors Parks Beaches

Side Trips

Sassari, San Vero Milis, Bosa, Porto Torres, Cattedrale di Sant'Antonio Abate e Museum Ampuriense
Find places to stay Jul 28 — Aug 3:
Highlights from your plan
Spiaggia di Balai ©
Spiaggia di Balai
Maimoni Beach ©
Maimoni Beach
Sa Mesa Longa ©
Sa Mesa Longa

5
nights
San Teodoro, Sardinia

San Teodoro ©
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 Murals of Orgosolo and Chiesa della Madonna del Monte Nero for their historical value. Sa Dommo e sos Corraine - Casa Museo di Orgosolo and Chiesa San Lorenzo are good opportunities to explore the local culture. Explore San Teodoro's surroundings by going to Parco Museo S'Abba Frisca (in Dorgali), Museo delle Maschere Mediterranee (in Mamoiada) and Osalla Beach (in Orosei). Next up on the itinerary: enjoy the sand and surf at Le Farfalle - Cala Suaraccia Beach, stroll through Cala Ginepro Beach, take in the dramatic scenery at La Punta Falls, and identify plant and animal life at L'Area Naturale Marina Protetta Tavolara - Punta Coda Cavallo.

To find out how to plan a trip to San Teodoro, use our trip itinerary maker.

You can drive from Alghero to San Teodoro in 2.5 hours. Other options are to take a train; or take a bus. In August, daily temperatures in San Teodoro can reach 36°C, while at night they dip to 22°C. Finish up your sightseeing early on the 8th (Sat) so you can travel to San Vito lo Capo.

Things to do in San Teodoro

Parks Beaches Outdoors

Side Trips

Olbia, Orgosolo, Budoni, Nuoro, Parco Museo S'Abba Frisca
Find places to stay Aug 3 — 8:
Highlights from your plan
Monte Ortobene ©
Monte Ortobene
Murals of Orgosolo ©
Murals of Orgosolo
Chiesa San Lorenzo ©
Chiesa San Lorenzo

6
nights
San Vito lo Capo, Sicily

San Vito lo Capo ©
A vacation in San Vito lo Capo offers a chance to enjoy a sheltered bay and a town with distinctive Arab-Norman architecture.
Your cultural itinerary includes sights like Chiesa di San Domenico and Parco Archeologico. Visit Lido Acqua Azzurra and Spiaggia dei Faraglioni for some beach relaxation. You'll find plenty of places to visit near San Vito lo Capo: Trapani (Corso Vittorio Emanuele di Trapani, Palazzo Manzo Gia' Pucci, & more), Giardini del Balio (in Erice) and Cala Mazzo di Sciacca (in Scopello). And it doesn't end there: kick back and relax at Spiaggia di Santa Margherita, get outside with YMCA San Vito Climbing House, step aboard Motonave Leonardo Davinci, and take in the spiritual surroundings of Santuario Di San Vito.

To plan San Vito lo Capo vacation without wasting time, ask Inspirock to design an itinerary.

Getting from San Teodoro to San Vito lo Capo by combination of flight and car takes about 4 hours. Other options: do a combination of train, flight, and taxi; or do a combination of flight and taxi. Traveling from San Teodoro in August, plan for somewhat warmer nights in San Vito lo Capo, with lows around 26°C. Wrap up your sightseeing on the 14th (Fri) to allow time to drive to Taormina.

Things to do in San Vito lo Capo

Historic Sites Outdoors Parks

Side Trips

Trapani, Castelvetrano, Alcamo, Castellammare del Golfo, Cattedrale San Salvatore
Find places to stay Aug 8 — 14:
Highlights from your plan
Museum Of Optical Illusions ©
Museum Of Optical Illusions
Chiesa di San Domenico ©
Chiesa di San Domenico

7
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 Duomo di Taormina and Palazzo Corvaja for their historical value. Step out of the city life by going to Etna Donkey Trekking and Spiaggia di Mazzeo. Venture out of the city with trips to Faro Sant'Anna (in Acireale), Castello Ruffo di Scilla (in Scilla) and Reggio Calabria (Basilica Cattedrale di Reggio Calabria Maria SS Asunta & Palazzo e Teatro Siracusa). There's lots more to do: kick back and relax at Lido Copacabana, steep yourself in history at Museo Naturalistico Regionale di Isolabella e Villa Caronia, explore the historical opulence of Castello Saraceno, and enjoy breathtaking views from Porta Catania di Taormina.

To find out how to plan a trip to Taormina, use our trip itinerary maker.

Traveling by car from San Vito lo Capo to Taormina takes 4.5 hours. Alternatively, you can do a combination of car and train; or do a combination of bus and train. August in Taormina sees daily highs of 37°C and lows of 28°C at night. Wrap up your sightseeing on the 21st (Fri) to allow time to travel back home.

Things to do in Taormina

Historic Sites Outdoors Parks

Side Trips

Reggio Calabria, Forza d'Agro, Randazzo, Castello Ruffo di Scilla, Etna Donkey Trekking
Find places to stay Aug 14 — 21:
Highlights from your plan
Castillo de Castelmola ©
Castillo de Castelmola
Etna Donkey Trekking ©
Etna Donkey Trekking
Scuba & Snorkeling

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