27 days in Italy Itinerary

27 days in Italy Itinerary

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Route & dates

27 days in Italy Itinerary

Start: Toronto
Fly:  12​h 30​min
1
Rome
— 4 nights
train:  1​h 15​min
2
Naples
— 2 nights
bus:  15​min
3
Pompeii
— 2 nights
Drive:  2​h 30​min
4
Capri, Island of Capri
— 2 nights
Drive:  3​h 15​min
5
Positano
— 3 nights
Drive:  5​h 15​min
6
Florence
— 3 nights
Drive:  2​h 30​min
7
Cinque Terre
— 2 nights
Drive:  4​h 15​min
8
Venice
— 4 nights
ferry:  30​min
9
Murano
— 2 nights
+2
ferry + foot + Fly:  13​h 15​min
End: Toronto


Learn more about your trip

4
nights
Rome

Rome ©
Aptly nicknamed the Eternal City, Rome is the birthplace of the Roman Empire, one of the world's greatest civilizations ever.
Rome is known for historic sites, nightlife, museums, classes, and shopping. Your plan includes some of its best attractions: contemplate the long history of Colosseum, explore the ancient world of Pantheon, admire the masterpieces at Vatican Museums, and pause for some serene contemplation at St. Peter's Basilica.

To see more things to do, other places to visit, photos, and more tourist information, use the Rome online vacation planner .

Toronto, Canada to Rome is an approximately 12.5-hour flight. You can also do a combination of bus and flight. The time zone changes from Eastern Standard Time (EST) to Central European Time (CET), which is usually a 6 hour difference. Plan for somewhat warmer temperatures traveling from Toronto in August, with highs in Rome at 38°C and lows at 24°C. Finish your sightseeing early on the 24th (Sat) to allow enough time to take a train to Naples.

Things to do in Rome

Historic Sites Museums Neighborhoods

Side Trip

Vatican City
Highlights from your plan
Colosseum ©
Colosseum
Pantheon ©
Pantheon
St. Peter's Basilica ©
St. Peter's Basilica

2
nights
Naples

Naples ©
Naples is the capital of the Italian region Campania and the third-largest municipality in Italy after Rome and Milan. Kick off your visit on the 25th (Sun): learn about all things military at Galleria Borbonica, see the interesting displays at Museo Archeologico Nazionale di Napoli, then steep yourself in history at Underground Naples, then browse the exhibits of Museo Cappella Sansevero, and finally look for gifts at Cardine. On the next day, take in nature's colorful creations at Reggia di Caserta, then delve into the distant past at The Neapolis Buried, then make a trip to Via San Gregorio Armeno, and finally appreciate the extensive heritage of Via Caracciolo e Lungomare di Napoli.

For photos, reviews, ratings, and more tourist information, refer to the Naples travel tool .

Traveling by train from Rome to Naples takes 1.5 hours. Alternatively, you can drive; or take a bus. In August, plan for daily highs up to 36°C, and evening lows to 25°C. Wrap up your sightseeing on the 26th (Mon) early enough to take a bus to Pompeii.

Things to do in Naples

Historic Sites Museums Parks

Side Trip

Reggia di Caserta
Highlights from your plan
Galleria Borbonica ©
Galleria Borbonica
Museo Archeologico Nazionale di Napoli ©
Museo Cappella Sansevero ©
Museo Cappella Sansevero

2
nights
Pompeii

Pompeii ©
Pompeii has been a tourist destination for more than 250 years.
On the 27th (Tue), explore the ancient world of Parco Acheologico di Ercolano, steep yourself in history at Villa dei Misteri, and then delve into the distant past at Pompeii Archaeological Park. On the next day, contemplate the geological forces at Vesuvius National Park.

To find more things to do, other places to visit, where to stay, and other tourist information, you can read our Pompeii online trip planner .

Pompeii is just a stone's throw from Naples. August in Pompeii sees daily highs of 36°C and lows of 25°C at night. On the 28th (Wed), wrap the sightseeing up by early afternoon so you can drive to Capri.

Things to do in Pompeii

Historic Sites Parks Nature

Side Trips

Vesuvio National Park, Parco Acheologico di Ercolano
Highlights from your plan
Pompeii Archaeological Park ©
Pompeii Archaeological Park
Villa dei Misteri ©
Villa dei Misteri
Parco Acheologico di Ercolano ©
Parco Acheologico di Ercolano

2
nights
Capri, Island of Capri

Capri
The island of Capri encompasses all the magical allure of the Mediterranean--dramatic blue waters, lush mountainous landscape, and picturesque island villages.
On the 29th (Thu), stroll through Marina Grande Public Beach, cruise along Via Krupp, explore the striking landscape at I Faraglioni, tour the pleasant surroundings at Giardini di Augusto, then make a trip to Piazza Umberto I, and finally make a trip to Chiesa di santo Stefano. Keep things going the next day: get great views at Belvedere Cannone, explore the ancient world of Villa Jovis, don't miss a visit to Villa Lysis, then pause for some photo ops at Natural Arch, then get engrossed in the history at Villa San Michele, and finally Head underground at Blue Grotto.

To see other places to visit, photos, maps, and tourist information, read Capri day trip site .

Traveling by car from Pompeii to Capri takes 2.5 hours. In August, plan for daily highs up to 36°C, and evening lows to 26°C. Wrap up your sightseeing on the 30th (Fri) early enough to drive to Positano.

Things to do in Capri

Parks Outdoors Beaches

Side Trip

Anacapri
Highlights from your plan
I Faraglioni
I Faraglioni
Belvedere Cannone ©
Belvedere Cannone
Giardini di Augusto ©
Giardini di Augusto

3
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.
Explore the numerous day-trip ideas around Positano: Ravello (Villa Cimbrone Gardens & Villa Rufolo) and Duomo di Sant'Andrea (in Amalfi). The adventure continues: enjoy the sand and surf at Fornillo, tour the pleasant surroundings at Spiaggia Grande, get interesting insight from Tours, and steep yourself in history at Church of Santa Maria Assunta.

To find photos, ratings, more things to do, and other tourist information, read our Positano driving holiday planner .

Getting from Capri to Positano by car takes about 3.5 hours. In August, daily temperatures in Positano can reach 36°C, while at night they dip to 26°C. Finish your sightseeing early on the 3rd (Tue) to allow enough time to drive to Florence.

Things to do in Positano

Outdoors Parks Beaches

Side Trips

Amalfi, Ravello
Highlights from your plan
Fornillo ©
Fornillo
Il Sentiero Degli Dei ©
Il Sentiero Degli Dei
Villa Cimbrone Gardens ©
Villa Cimbrone Gardens

3
nights
Florence

Florence ©
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Step out of Florence to go to Pisa and see Leaning Tower of Pisa, which is approximately 1h 10 min away. And it doesn't end there: admire the masterpieces at Gallerie Degli Uffizi, take in the spiritual surroundings of Cathedral of Santa Maria del Fiore, take in the views from Ponte Vecchio, and enjoy breathtaking views from Campanile di Giotto.

To find ratings, other places to visit, maps, and tourist information, refer to the Florence online trip builder .

Getting from Positano to Florence by car takes about 5.5 hours. Other options: do a combination of subway and train; or do a combination of subway, train, and flight. Traveling from Positano in September, you can expect nighttime temperatures to be slightly colder in Florence, with lows of 17°C. Finish your sightseeing early on the 6th (Fri) so you can drive to Cinque Terre.

Things to do in Florence

Museums Historic Sites Parks

Side Trip

Leaning Tower of Pisa
Highlights from your plan
Gallerie Degli Uffizi ©
Gallerie Degli Uffizi
Academy Of Florence Art Gallery ©
Academy Of Florence Art Gallery
Piazzale Michelangelo ©
Piazzale Michelangelo

2
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.
On the 7th (Sat), get into the urban bustle at Vernazza, stroll through Footpath Monterosso - Vernazza, then don't miss a visit to Oratorio della Confraternita dei Neri Mortis et Orationis, and finally don't miss a visit to Borgo Antico. Here are some ideas for day two: take in the architecture and atmosphere at Convento dei Cappuccini e Chiesa di San Francesco, make a trip to Chiesa di San Giovanni Battista, then get outside with Cinque Terre Trails, then take in the architecture and atmosphere at Santa Margherita di Antiochia Church, and finally explore the historical opulence of Castello Doria.

To find ratings, maps, photos, and more tourist information, refer to the Cinque Terre trip itinerary builder app .

Getting from Florence to Cinque Terre by car takes about 2.5 hours. Other options: take a train. In September in Cinque Terre, expect temperatures between 30°C during the day and 17°C at night. Wrap up your sightseeing on the 8th (Sun) early enough to drive to Venice.

Things to do in Cinque Terre

Parks Historic Sites Outdoors
Highlights from your plan
Footpath Monterosso - Vernazza ©
Footpath Monterosso - Vernazza
Cinque Terre Trails ©
Cinque Terre Trails
Vernazza ©
Vernazza

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.
Venture out of the city with trips to Padua (Basilica di Sant’Antonio & Scrovegni Chapel) and Verona (Piazza delle Erbe, Arena di Verona, & more). There's still lots to do: contemplate the waterfront views at Canal Grande, make a trip to St Mark's Campanile, hit the best photo ops around with an inspiring photography tour, and get to know the fascinating history of Piazza San Marco.

To see other places to visit, reviews, traveler tips, and tourist information, refer to the Venice trip planner .

Drive from Cinque Terre to Venice in 4.5 hours. Alternatively, you can take a train; or take a bus. In September in Venice, expect temperatures between 29°C during the day and 17°C at night. Finish up your sightseeing early on the 13th (Fri) so you can catch the ferry to Murano.

Things to do in Venice

Historic Sites Museums Parks

Side Trips

Verona, Padua
Highlights from your plan
Canal Grande ©
Canal Grande
Piazza San Marco ©
Piazza San Marco
Basilica di San Marco
Basilica di San Marco

2
nights
Murano

Murano ©
Murano is known for museums, shopping, and historic sites. Your plan includes some of its best attractions: make a trip to Isola di Murano, enjoy breathtaking views from Il Campanile Storto, stop by I Vetri di Lulu, and take in the architecture and atmosphere at Basilica di Santa Maria Assunta e Chiesa di Santa Fosca.

To see more things to do, traveler tips, maps, and tourist information, read our Murano journey planner.

Murano is very close to Venice. In September, daily temperatures in Murano can reach 29°C, while at night they dip to 17°C. On the 15th (Sun), wrap the sightseeing up by early afternoon so you can travel back home.

Things to do in Murano

Parks Historic Sites Outdoors

Side Trips

Burano, Blue Moon, Basilica di Santa Maria Assunta e Chiesa di Santa Fosca
Highlights from your plan
Blue Moon ©
Blue Moon
Museo del Merletto ©
Museo del Merletto
Church of Santa Maria e San Donato ©
Church of Santa Maria e San Donato

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