49 days in Italy Itinerary

49 days in Italy Itinerary

Created using Inspirock Italy vacation planner

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Route & dates

49 days in Italy Itinerary

Start: New York City
Fly:  12 h
1
Venice
— 5 nights
Bus:  2 h 30 min
2
Bologna
— 3 nights
Train:  1 h
3
Florence
— 5 nights
Train:  1 h 30 min
4
Siena
— 5 nights
Bus:  2 h
5
Assisi
— 4 nights
Train:  3 h
6
Orvieto
— 3 nights
Train:  1 h
7
Rome
— 6 nights
Train + Subway:  3 h
8
Ravello
— 5 nights
Bus:  2 h
9
Naples
— 6 nights
train:  4 h
10
Palermo, Sicily
— 5 nights
Fly:  14 h 30 min
End: New York City

5
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.
Museum-lovers will appreciate Doge's Palace and Ca' Pesaro Galleria Internazionale d'Arte Moderna. Visit Piazza San Marco and Basilica di San Marco for their historical value. Explore the numerous day-trip ideas around Venice: Castello di Gorizia (in Gorizia), Brescia (Tempio Capitolino e Piazza del Foro, Brescia Castle, &more) and Verona (Arche Scaligere, Basilica di Santa Anastasia, &more). There's still lots to do: contemplate in the serene atmosphere at Basilica di Santa Maria Gloriosa dei Frari, admire the landmark architecture of Scala Contarini del Bovolo, wander the streets of Dorsoduro, and learn more about the world around you at Natural History Museum.

To see where to stay, reviews, other places to visit, and other tourist information, you can read our Venice trip planning website .

New York City, USA to Venice is an approximately 11.5-hour combination of bus and flight. You can also fly; or do a combination of train and flight. The time zone changes from Eastern Standard Time to Central European Time, which is usually a 6 hour difference. Expect a daytime high around 56°F in November, and nighttime lows around 43°F. Wrap up your sightseeing on the 7th (Sat) to allow time to drive to Bologna.

Things to do in Venice

Historic Sites Museums Neighborhoods

Side Trips

Verona, Brescia, Basilica di Aquileia, Castello di Gorizia, Military Memorial Redipuglia
Find places to stay Nov 2 — 7:
Highlights from your plan
Piazza San Marco ©
Piazza San Marco
Doge's Palace ©
Doge's Palace
Military Memorial Redipuglia ©
Military Memorial Redipuglia

3
nights
Bologna

Bologna ©
A city famous for its cuisine, Bologna is the seat of the oldest university in the world, founded in 1088.
Visit Basilica - Santuario di Santo Stefano and Basilica di San Domenico for their historical value. You'll explore the less-touristy side of things at Chiesa di Santa Maria della Vita and Basilica di Santa Maria dei Servi Bologna. There's still lots to do: pause for some serene contemplation at Cattedrale di San Pietro, contemplate the long history of Piazza Maggiore, admire the masterpieces at Museo di Palazzo Poggi, and look for gifts at Salumeria Simoni.

Take the guesswork out of planning a Bologna vacation by using our trip itinerary maker.

Drive from Venice to Bologna in 2 hours. Alternatively, you can take a train; or take a bus. In November, daytime highs in Bologna are 55°F, while nighttime lows are 43°F. Finish your sightseeing early on the 10th (Tue) so you can take a train to Florence.

Things to do in Bologna

Historic Sites Museums Shopping
Find places to stay Nov 7 — 10:
Highlights from your plan
Basilica di San Petronio ©
Basilica di San Petronio
Basilica - Santuario di Santo Stefano ©
Chiesa di Santa Maria della Vita ©
Chiesa di Santa Maria della Vita

5
nights
Florence

Florence ©
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Give yourself a bit of retail therapy at Officina Profumo-Farmaceutica di Santa Maria Novella and Mercato Centrale. Your inner history buff will appreciate Cathedral of Santa Maria del Fiore and The Baptistery of St. John. Explore Florence's surroundings by going to Pisa (Camposanto, Duomo di Pisa, &more) and Lucca (San Michele in Foro, St Martin Cathedral, &more). There's still lots to do: admire the masterpieces at Academy Of Florence Art Gallery, examine the collection at Stibbert Museum, appreciate the extensive heritage of Piazza del Duomo, and take some stellar pictures from Basilica San Miniato al Monte.

To find traveler tips, where to stay, reviews, and tourist information, read our Florence road trip planning site .

You can take a train from Bologna to Florence in an hour. Alternatively, you can take a bus; or drive. While traveling from Bologna, expect somewhat warmer days and about the same nights in Florence, ranging from highs of 61°F to lows of 46°F. Wrap up your sightseeing on the 15th (Sun) to allow time to take a bus to Siena.

Things to do in Florence

Historic Sites Museums Shopping

Side Trips

Pisa, Lucca, Mercato Centrale
Find places to stay Nov 10 — 15:
Highlights from your plan
Cathedral of Santa Maria del Fiore ©
Cathedral of Santa Maria del Fiore
Centro Storico ©
Centro Storico
Academy Of Florence Art Gallery ©
Academy Of Florence Art Gallery

5
nights
Siena

Siena ©
Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
Appreciate the collections at Palazzo Pubblico and Museo Civico and Casa Bicocchi e Mostra Permanente Guerrieri ed Artigiani. You'll discover tucked-away gems like Duomo di San Gimignano and Val d'Orcia. Explore the numerous day-trip ideas around Siena: San Gimignano (La Bottega del Sale di Duccio Nacci photographer & Piazza del Duomo), Volterra (Piazza dei Priori & Palazzo Viti) and Pienza (La Taverna del Pecorino, Palazzo Piccolomini, &more). Next up on the itinerary: steep yourself in history at Battistero di San Giovanni, enjoy breathtaking views from Torre del Mangia, view the masterpieces at Art Studio di Adelina Quadri, and take in the spiritual surroundings of Sinagoga di Siena.

To see reviews, ratings, photos, and other tourist information, use the Siena vacation site .

Getting from Florence to Siena by bus takes about 1.5 hours. Other options: drive; or take a train. In November, daily temperatures in Siena can reach 63°F, while at night they dip to 48°F. Finish up your sightseeing early on the 20th (Fri) so you can go by car to Assisi.

Things to do in Siena

Historic Sites Museums Shopping

Side Trips

Pienza, San Gimignano, Volterra, Cappella della Madonna di Vitaleta, Val d'Orcia
Find places to stay Nov 15 — 20:
Highlights from your plan
Val d'Orcia ©
Val d'Orcia
Duomo di San Gimignano ©
Duomo di San Gimignano
Palazzo Pubblico and Museo Civico ©
Palazzo Pubblico and Museo Civico

4
nights
Assisi

Assisi ©
Rich in culture and religious tradition, Assisi is known as the birthplace of St.
You'll explore the less-touristy side of things at Basilica di Santa Maria degli Angeli - Porziuncola and Eremo delle Carceri. Popular historic sites such as San Damiano and Rocca Maggiore are in your itinerary. Go for a jaunt from Assisi to Foligno to see Centro Storico Rasiglia about 46 minutes away. The adventure continues: see the interesting displays at Museo della Porziuncola, contemplate in the serene atmosphere at Cripta di San Francesco, take in the architecture and atmosphere at Basilica Papale e Sacro Convento di San Francesco d'Assisi, and admire the masterpieces at Museo-Laboratorio di Vetrate Artistiche Moretti Caselli.

For ratings, maps, other places to visit, and other tourist information, use the Assisi online trip itinerary maker .

Getting from Siena to Assisi by car takes about 2 hours. Other options: take a bus; or take a train. Traveling from Siena in November, expect nights in Assisi to be about the same, around 44°F, while days are a bit cooler, around 58°F. Wrap up your sightseeing on the 24th (Tue) to allow time to drive to Orvieto.

Things to do in Assisi

Historic Sites Wineries Museums

Side Trips

Centro Storico, Centro Storico Rasiglia, Museo-Laboratorio di Vetrate Artistiche Moretti Caselli
Find places to stay Nov 20 — 24:
Highlights from your plan
San Damiano ©
San Damiano
Museo della Porziuncola ©
Museo della Porziuncola

3
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 inner history buff will appreciate Duomo di Orvieto and Pozzo di San Patrizio. Eschew the tourist crowds and head to Cappella del Corporale and Abbey of Saints Severus and Martyrius. Change things up with a short trip to Chiesa di San Flaviano in Montefiascone (about 36 minutes away). There's much more to do: appreciate the extensive heritage of Centro Storico Orvieto, learn about winemaking at Decugnano dei Barbi, look for gifts at Il Negozietto, and take in the architecture and atmosphere at Sant'Andrea, Orvieto.

Plan my day in Orvieto using traveler tips and tourist information provided by Inspirock.

You can drive from Assisi to Orvieto in 1.5 hours. Other options are to take a train; or take a bus. Expect a daytime high around 59°F in November, and nighttime lows around 45°F. Finish up your sightseeing early on the 27th (Fri) so you can catch the train to Rome.

Things to do in Orvieto

Historic Sites Wineries Museums

Side Trip

Chiesa di San Flaviano
Find places to stay Nov 24 — 27:
Highlights from your plan
Duomo di Orvieto ©
Duomo di Orvieto
Pozzo di San Patrizio ©
Pozzo di San Patrizio
Chiesa di San Flaviano ©
Chiesa di San Flaviano

6
nights
Rome

Rome ©
Aptly nicknamed the Eternal City, Rome is the birthplace of the Roman Empire, one of the world's greatest civilizations ever.
Colosseum and Palatine Hill will appeal to history buffs. Museum-lovers will appreciate Le Domus Romane di Palazzo Valentini and Trevimage. You'll find plenty of places to visit near Rome: Il Borgo Di Vejano (in Vejano) and Castello Orsini-Odescalchi (in Bracciano). There's still lots to do: get to know the fascinating history of Centro Storico Associazione Centro Storico, see the interesting displays at Stanze di Raffaello, contemplate the long history of St. Peter's Basilica, and contemplate in the serene atmosphere at Basilica Papale San Paolo fuori le Mura.

To see maps, more things to do, traveler tips, and more tourist information, use the Rome day trip planning website .

You can take a train from Orvieto to Rome in an hour. Alternatively, you can take a bus; or drive. In November, plan for daily highs up to 63°F, and evening lows to 47°F. Finish your sightseeing early on the 3rd (Thu) to allow enough time to travel to Ravello.

Things to do in Rome

Historic Sites Shopping Museums

Side Trips

Vatican City, Castello Orsini-Odescalchi, Il Borgo Di Vejano
Find places to stay Nov 27 — Dec 3:
Highlights from your plan
Abbey of St. Paul Outside the Walls ©
Abbey of St. Paul Outside the Walls
St. Peter's Basilica ©
St. Peter's Basilica
Colosseum ©
Colosseum

5
nights
Ravello

Ravello ©
Popular historic sites such as Duomo di Ravello and Centro Storico Ravello are in your itinerary. You'll discover tucked-away gems like Villa Cimbrone Gardens and Duomo di Sant'Andrea. Venture out of the city with trips to Chiesa San Pietro Apostolo (in Cetara) and Badia della Santissima Trinita' (in Cava De' Tirreni).

To find maps, ratings, more things to do, and more tourist information, go to the Ravello online road trip planner .

You can do a combination of train and subway from Rome to Ravello in 3 hours. Alternatively, you can drive; or do a combination of train and bus. Expect a bit warmer evenings in Ravello when traveling from Rome in December, with lows around 49°F. Finish your sightseeing early on the 8th (Tue) to allow enough time to drive to Naples.

Things to do in Ravello

Historic Sites Parks Trails

Side Trips

Amalfi, Maiori, S.Maria Maddalena, Chiesa San Pietro Apostolo, Badia della Santissima Trinita'
Find places to stay Dec 3 — 8:
Highlights from your plan
Duomo di Ravello ©
Duomo di Ravello
Duomo di Sant'Andrea ©
Duomo di Sant'Andrea

6
nights
Naples

Naples ©
Naples is the capital of the Italian region Campania and the third-largest municipality in Italy after Rome and Milan. Shop till you drop at Centro Commerciale Campania and Caseificio La Pagliara. You'll discover tucked-away gems like Galleria Borbonica and Museo Archeologico Nazionale di Napoli. Explore Naples' surroundings by going to Santuario dell'Addolorata di Castelpetroso (in Castelpetroso), Lupanar (in Pompeii) and Door Terravecchia - Excavations of Saepinum at Altilia (in Sepino). The adventure continues: contemplate the long history of Catacombe di San Gaudioso, delve into the distant past at The Neapolis Buried, take in the architecture and atmosphere at Sant'Anna dei Lombardi (Monteoliveto), and see the interesting displays at Museo Nazionale Ferroviario di Pietrarsa.

For traveler tips, more things to do, where to stay, and tourist information, read Naples travel app .

Getting from Ravello to Naples by car takes about 1.5 hours. Other options: do a combination of taxi and subway; or take a bus. Expect slightly colder evenings in Naples when traveling from Ravello in December, with lows around 42°F. Finish your sightseeing early on the 14th (Mon) so you can travel to Palermo.

Things to do in Naples

Historic Sites Museums Shopping

Side Trips

Pompeii, Caseificio La Pagliara, Centro Commerciale Campania, Santuario dell'Addolorata di Castelpetroso, Door Terravecchia - Excavations of Saepinum at Altilia
Find places to stay Dec 8 — 14:
Highlights from your plan
Galleria Borbonica ©
Galleria Borbonica
Catacombe di San Gaudioso ©
Catacombe di San Gaudioso
Pompeii Archaeological Park ©
Pompeii Archaeological Park

5
nights
Palermo, Sicily

Palermo ©
The capital of Sicily, Palermo was founded by the Phoenicians under the name of Ziz.
Eschew the tourist crowds and head to Oratorio di Santa Cita and Museo dell'Acciuga. Give yourself a bit of retail therapy at Museo Diocesano di Palermo (Le Stanze dei Vescovi) and Mose since 1970. And it doesn't end there: contemplate the long history of Palazzo Steri - Chiaramonte - Carcere dei penitenziati, contemplate in the serene atmosphere at Chiesa di S. Domenico e Chiostro, take in the architecture and atmosphere at Chiesa Inferiore della Cappella Palatina, and don't miss a visit to Cattedrale di Palermo.

For ratings, photos, maps, and other tourist information, go to the Palermo trip planner.

You can fly from Naples to Palermo in 4 hours. Alternatively, you can do a combination of flight and bus; or ride a ferry. You will have some time to spend on the 19th (Sat) before leaving for home.

Things to do in Palermo

Historic Sites Museums Shopping

Side Trip

Museo dell'Acciuga
Find places to stay Dec 14 — 19:
Highlights from your plan
Palazzo Conte Federico ©
Palazzo Conte Federico
Oratorio di Santa Cita ©
Oratorio di Santa Cita
Santuario Santa Rosalia ©
Santuario Santa Rosalia

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