36 days in Italy Itinerary

36 days in Italy Itinerary

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Route & dates

36 days in Italy Itinerary

Start: Portland
Fly:  23​h 30​min
1
Palermo, Sicily
— 2 nights
+2
Fly + train + subway:  3​h
2
Sorrento
— 3 nights
subway:  1​h
3
Pompeii
— 1 night
taxi + ferry:  1​h
4
Anacapri, Island of Capri
— 2 nights
ferry:  1​h
5
Naples
— 3 nights
6
Rome
— 4 nights
train:  2​h
7
Florence
— 2 nights
train:  1​h
8
Pisa
— 1 day
train:  2​h
9
Cinque Terre
— 3 nights
train:  3​h
10
Milan
— 3 nights
train:  1​h
11
Como
— 2 nights
12
Verona
— 4 nights
Drive:  1​h 30​min
13
Venice
— 4 nights
Fly:  17​h 45​min
End: Portland

2
nights
Palermo, Sicily

Palermo ©
The capital of Sicily, Palermo was founded by the Phoenicians under the name of Ziz.
Cattedrale di Palermo has been added to your itinerary. Start off your visit on the 30th (Thu): don't miss a visit to Cattedrale di Palermo, pause for some serene contemplation at Chiesa della Madonna di Monte Oliveto detta Badia Nuova, take in the architecture and atmosphere at Nobile e Monumentale Chiesa dell'Immacolata Concezione al Capo, then examine the collection at Museo Falcone - Borsellino, then take in the architecture and atmosphere at Norman Palace and Palatine Chapel, and finally take in the architecture and atmosphere at Chiesa del Gesu. On the 31st (Fri), you'll have a packed day of sightseeing: contemplate the long history of San Giuseppe dei Teatini and then learn about winemaking at Baglio di Pianetto.

To see where to stay, reviews, more things to do, and more tourist information, refer to the Palermo road trip planner.

Portland, USA to Palermo is an approximately 19.5-hour flight. You can also do a combination of flight and bus; or do a combination of train, flight, and bus. The time zone difference when traveling from Portland to Palermo is 9 hours. Finish your sightseeing early on the 31st (Fri) so you can travel to Sorrento.

Things to do in Palermo

Historic Sites Wineries Museums

Side Trip

Baglio di Pianetto
Find places to stay May 29 — 31:
Highlights from your plan
Cattedrale di Palermo ©
Cattedrale di Palermo
Church of Jesus ©
Church of Jesus
Norman Palace and Palatine Chapel ©
Norman Palace and Palatine Chapel

3
nights
Sorrento

Sorrento ©
A lovely town easily accessible from almost anywhere in the country, Sorrento overlooks the Bay of Naples and sits right on the Amalfi Drive.
Your day-by-day itinerary now includes Positano Car Service Private Day Tours as well as Sorrento Food Tours. Start off your visit on the 1st (Sat): admire the natural beauty at Villa Comunale, contemplate in the serene atmosphere at Basilica di Sant'Antonino, then pause for some serene contemplation at Cattedrale di Sorrento, and finally take in the spiritual surroundings of Duomo dei San Filippo e Giacomo. Get ready for a full day of sightseeing on the 2nd (Sun): do sightseeing your way with Positano Car Service Private Day Tours, then get a tailor-made plan with Sorrento Food Tours, and then stop by Fattoria Terranova Shop.

To find maps, traveler tips, and tourist information, go to the Sorrento visit site .

Traveling by combination of flight, train, and subway from Palermo to Sorrento takes 7 hours. Alternatively, you can do a combination of ferry and subway; or do a combination of train and subway. In May in Sorrento, expect temperatures between 74°F during the day and 60°F at night. Cap off your sightseeing on the 3rd (Mon) early enough to go by car to Pompeii.

Things to do in Sorrento

Tours Historic Sites Parks

Side Trip

Positano Car Service Private Day Tours
Find places to stay May 31 — Jun 3:
Highlights from your plan
Sorrento Food Tours ©
Sorrento Food Tours
Basilica di Sant'Antonino ©
Basilica di Sant'Antonino
Cattedrale di Sorrento ©
Cattedrale di Sorrento

1
night
Pompeii

Pompeii ©
Pompeii has been a tourist destination for more than 250 years.
Ruins of Herculaneum has been added to your itinerary. Kick off your visit on the 3rd (Mon): contemplate the long history of Ruins of Herculaneum.

To find more things to do, reviews, and tourist information, you can read our Pompeii trip planning site .

You can drive from Sorrento to Pompeii in an hour. Other options are to take a subway; or take a bus. In June, daily temperatures in Pompeii can reach 82°F, while at night they dip to 66°F. Finish up your sightseeing early on the 4th (Tue) so you can travel to Anacapri.

Things to do in Pompeii

Historic Sites

Side Trip

Ruins of Herculaneum
Find places to stay Jun 3 — 4:
Highlights from your plan
Ruins of Herculaneum ©
Ruins of Herculaneum

2
nights
Anacapri, Island of Capri

Anacapri ©
Anacapri is a comune on the island of Capri, in the Metropolitan City of Naples, Italy. Your day-by-day itinerary now includes Gianni's Boat. Start off your visit on the 4th (Tue): contemplate the waterfront views at Marina Piccola, take in the spiritual surroundings of Santa Maria a Cetrella, then contemplate the long history of Villa San Michele, then stroll through Fortini Coastal Walk, and finally get to know the fascinating history of Scala Fenicia (Phoenician Steps). Keep things going the next day: get a new perspective on things with Gianni's Boat.

To see where to stay, more things to do, ratings, and tourist information, read Anacapri day trip planning app .

Getting from Pompeii to Anacapri by combination of taxi and ferry takes about an hour. Other options: do a combination of subway and ferry; or ride a ferry. June in Anacapri sees daily highs of 82°F and lows of 68°F at night. Finish your sightseeing early on the 6th (Thu) so you can ride a ferry to Naples.

Things to do in Anacapri

Outdoors Tours Parks

Side Trip

Capri
Find places to stay Jun 4 — 6:
Highlights from your plan
Villa San Michele ©
Villa San Michele
Gianni's Boat ©
Gianni's Boat
Scala Fenicia (Phoenician Steps) ©

3
nights
Naples

Naples ©
Naples is the capital of the Italian region Campania and the third-largest municipality in Italy after Rome and Milan. Your day-by-day itinerary now includes Castel dell'Ovo, Castel Nuovo - Maschio Angioino, Duomo di Napoli, and other attractions you added. You'll enjoy a bit of beach vacationing at Spiaggia Cala Nave and Spiaggia di Serapo. Appreciate the collections at Galleria Borbonica and National Archaeological Museum of Naples. Change things up with these side-trips from Naples: Villa Di Tiberio (in Sperlonga) and Evaso (in Ventotene). And it doesn't end there: steep yourself in history at Underground Naples, get to know the fascinating history of Via Caracciolo e Lungomare di Napoli, and delve into the distant past at Scavi Archeologici di Ercolano.

To find where to stay, more things to do, other places to visit, and other tourist information, go to the Naples tour itinerary planner.

Traveling by ferry from Anacapri to Naples takes an hour. Expect a daytime high around 82°F in June, and nighttime lows around 66°F. Wrap up your sightseeing on the 9th (Sun) to allow time to take a train to Rome.

Things to do in Naples

Historic Sites Beaches Outdoors

Side Trips

Ventotene, Villa Di Tiberio, Spiaggia di Serapo
Find places to stay Jun 6 — 9:
Highlights from your plan
Underground Naples ©
Underground Naples
Galleria Borbonica ©
Galleria Borbonica
Via Caracciolo e Lungomare di Napoli ©

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.
Your day-by-day itinerary now includes Spanish Steps. Deepen your sense of the past at sights like Civita di Bagnoregio and Palatine Hill. You'll discover tucked-away gems like Duomo di Orvieto and Centro Storico Associazione Centro Storico. Change things up with a short trip to Rocca Albornoziana in Orvieto (about 2 hours away). There's much more to do: get to know the fascinating history of Piazza Navona, explore the world behind art at Galleria Borghese, admire the landmark architecture of Pantheon, and take in the architecture and atmosphere at Santa Maria in Trastevere.

For maps, ratings, traveler tips, and other tourist information, read Rome journey builder tool .

Getting from Naples to Rome by train takes about 1.5 hours. Other options: drive; or take a bus. June in Rome sees daily highs of 84°F and lows of 65°F at night. Wrap up your sightseeing by early afternoon on the 13th (Thu) to allow enough time to take a train to Florence.

Things to do in Rome

Historic Sites Museums Neighborhoods

Side Trips

Vatican City, Orvieto, Civita di Bagnoregio
Find places to stay Jun 9 — 13:
Highlights from your plan
St. Peter's Basilica ©
St. Peter's Basilica
Colosseum ©
Colosseum
Civita di Bagnoregio ©
Civita di Bagnoregio

2
nights
Florence

Florence ©
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Kick off your visit on the 13th (Thu): steep yourself in history at Loggia dei Lanzi and then admire the masterpieces at Pitti Palace. Here are some ideas for day two: examine the collection at Academy Of Florence Art Gallery, admire the landmark architecture of Basilica San Miniato al Monte, don't miss a visit to Piazzale Michelangelo, then admire the masterpieces at Uffizi Galleries, then take in the spiritual surroundings of Cathedral of Santa Maria del Fiore, and finally appreciate the extensive heritage of Piazza del Duomo.

To find maps, other places to visit, ratings, and more tourist information, read our Florence sightseeing tool .

You can take a train from Rome to Florence in 2 hours. Other options are to drive; or fly. June in Florence sees daily highs of 83°F and lows of 65°F at night. Wrap up your sightseeing on the 15th (Sat) early enough to take a train to Pisa.

Things to do in Florence

Museums Historic Sites
Find places to stay Jun 13 — 15:
Highlights from your plan
Pitti Palace ©
Pitti Palace
Uffizi Galleries ©
Uffizi Galleries
Academy Of Florence Art Gallery ©
Academy Of Florence Art Gallery

1
day
Pisa

Pisa ©
Known worldwide for the Leaning Tower of Pisa, the city of Pisa historically served as a maritime power in the heart of Tuscany.
On the 15th (Sat), take in the spiritual surroundings of Chiesa di Santa Maria della Spina, then enjoy breathtaking views from Leaning Tower of Pisa, then contemplate the long history of Le mura di Lucca, and finally take in the spiritual surroundings of Basilica of San Frediano.

For other places to visit, ratings, maps, and tourist information, read our Pisa trip planner .

Traveling by train from Florence to Pisa takes an hour. Alternatively, you can drive; or take a bus. Traveling from Florence in June, Pisa is slightly colder at night with lows of 60°F. Finish your sightseeing early on the 15th (Sat) to allow enough time to take a train to Cinque Terre.

Things to do in Pisa

Historic Sites

Side Trip

Lucca
Find places to stay Jun 15 — 16:
Highlights from your plan
Basilica of San Frediano ©
Basilica of San Frediano
Chiesa di Santa Maria della Spina ©
Chiesa di Santa Maria della Spina
Leaning Tower of Pisa ©
Leaning Tower of Pisa

3
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.
Kick off your visit on the 16th (Sun): step into the grandiose world of Castello Doria, hike along Footpath Monterosso - Vernazza, then don't miss a visit to Borgo Antico, then pause for some serene contemplation at Convento dei Cappuccini e Chiesa di San Francesco, and finally contemplate in the serene atmosphere at Chiesa Di San Pietro. Here are some ideas for day two: pause for some serene contemplation at Santa Margherita di Antiochia Church.

For maps, traveler tips, more things to do, and other tourist information, read Cinque Terre road trip app .

Traveling by train from Pisa to Cinque Terre takes 2 hours. Alternatively, you can drive; or take a bus. June in Cinque Terre sees daily highs of 81°F and lows of 60°F at night. Wrap up your sightseeing by early afternoon on the 18th (Tue) to allow time for the train ride to Milan.

Things to do in Cinque Terre

Historic Sites Outdoors Parks
Find places to stay Jun 15 — 18:
Highlights from your plan
Castello Doria ©
Castello Doria
Footpath Monterosso - Vernazza ©
Footpath Monterosso - Vernazza
Vernazza ©
Vernazza

3
nights
Milan

Milan ©
In many ways the most modern of Italian cities, Milan is a busy, elegant metropolis with an impressive list of grand palaces, fine churches, and important museums.
Galleria Vittorio Emanuele II has been added to your itinerary. Explore hidden gems such as Goggiano Winery and Post dal Vin. Your cultural itinerary includes sights like Duomo di Milano and Piazza del Duomo. And it doesn't end there: step into the grandiose world of Castello Sforzesco, steep yourself in history at Il Cenacolo, and explore the world behind art at Pinacoteca di Brera.

To see where to stay, other places to visit, traveler tips, and other tourist information, read Milan travel route planner .

Getting from Cinque Terre to Milan by train takes about 3 hours. Other options: drive. In June in Milan, expect temperatures between 83°F during the day and 64°F at night. Finish your sightseeing early on the 21st (Fri) so you can take a train to Como.

Things to do in Milan

Historic Sites Museums Wineries

Side Trips

Goggiano Winery, Post dal Vin
Find places to stay Jun 18 — 21:
Highlights from your plan
Duomo di Milano ©
Duomo di Milano
Pinacoteca di Brera ©
Pinacoteca di Brera
Castello Sforzesco ©
Castello Sforzesco

2
nights
Como

Como ©
Known for its idyllic location on the shores of Lake Como and at the foot of the Alps, Como is one of northern Italy's most popular tourist destinations.
Get ready for a full day of sightseeing on the 23rd (Sun): admire the landmark architecture of Villa del Balbianello.

For maps, traveler tips, reviews, and other tourist information, you can read our Como trip itinerary app .

Traveling by train from Milan to Como takes an hour. Alternatively, you can drive. In June in Como, expect temperatures between 81°F during the day and 61°F at night. Wrap up your sightseeing by early afternoon on the 23rd (Sun) to allow time for the car ride to Verona.
Find places to stay Jun 21 — 23:
Highlights from your plan
Villa del Balbianello ©
Villa del Balbianello

4
nights
Verona

Verona ©
The famous setting for Shakespeare's star-crossed lovers, Romeo and Juliet, Verona is one of northern Italy's main tourist destinations, largely owing to its incredibly rich artistic heritage.
Your day-by-day itinerary now includes Verona's Cathedral (Duomo). Get some historical perspective at Arena di Verona and Museo di Castelvecchio. Your cultural itinerary includes sights like Basilica di San Zeno Maggiore and Palazzo Ducale Mantova. Explore Verona's surroundings by going to Rocca Scaligera di Sirmione (in Sirmione) and Basilica di Sant'Andrea di Mantova (in Mantua). There's still lots to do: pause for some serene contemplation at Chiesa di Sant'Anastasia, explore the historical opulence of Piazzale Castel San Pietro, wander the streets of Piazza delle Erbe, and steep yourself in history at I Portoni della Bra.

To see photos, maps, ratings, and other tourist information, use the Verona trip planner.

Traveling by car from Como to Verona takes 2 hours. Alternatively, you can take a train; or take a bus. In June, daily temperatures in Verona can reach 84°F, while at night they dip to 63°F. Wrap up your sightseeing on the 27th (Thu) to allow time to drive to Venice.

Things to do in Verona

Historic Sites Neighborhoods Shopping

Side Trips

Mantua, Rocca Scaligera di Sirmione
Find places to stay Jun 23 — 27:
Highlights from your plan
Chiesa di Sant'Anastasia ©
Chiesa di Sant'Anastasia
Piazzale Castel San Pietro ©
Piazzale Castel San Pietro
Rocca Scaligera di Sirmione ©
Rocca Scaligera di Sirmione

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.
Do some cultural sightseeing at Peggy Guggenheim Collection and St. Mark's Square. You'll get in some beach time at Riviera 6 - Bagno 6 and Laguna di Bibione. And it doesn't end there: explore the activities along Canal Grande, admire the landmark architecture of Basilica di San Marco, take in the architecture and atmosphere at San Giorgio Maggiore, and take a stroll through Cannaregio.

To find traveler tips, ratings, and more tourist information, go to the Venice sightseeing planning site .

You can drive from Verona to Venice in 1.5 hours. Other options are to take a bus; or take a shuttle. In June, plan for daily highs up to 81°F, and evening lows to 63°F. Cap off your sightseeing on the 1st (Mon) early enough to travel back home.

Things to do in Venice

Historic Sites Museums Parks

Side Trips

Riviera 6 - Bagno 6, Laguna di Bibione
Find places to stay Jun 27 — Jul 1:
Highlights from your plan
Cannaregio ©
Cannaregio
St. Mark's Square ©
St. Mark's Square
Doge's Palace ©
Doge's Palace

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