42 days in Italy Itinerary

42 days in Italy Itinerary

Created using Inspirock Italy holiday builder

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Route & dates

Start: New York City
Bus + Fly:  11 h 30 min
1
Venice
— 5 nights
Bus:  1 h 30 min
2
Verona
— 5 nights
Train:  1 h 45 min
3
Florence
— 5 nights
Bus:  1 h 15 min
4
Siena
— 5 nights
Drive:  1 h 45 min
5
Assisi
— 4 nights
Drive:  4 h 30 min
6
Ravello
— 5 nights
Drive:  1 h 15 min
7
Naples
— 5 nights
Train:  1 h 15 min
8
Rome
— 6 nights
+2
Fly + Train + Subway:  13 h 15 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.
Let the collections at Doge's Palace and La Biennale di Venezia - Arsenale capture your imagination. Get some cultural insight at Piazza San Marco and Gallerie dell'Accademia. Step out of Venice to go to Valdobbiadene and see PDC Cartizze, which is approximately 1h 15 min away. There's still lots to do: admire the landmark architecture of Basilica di San Marco, view the masterpieces at Giudecca 795 Art Gallery, explore the activities along Canal Grande, and browse the exhibits of Palazzo Cavalli-Franchetti.

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

New York City, USA to Venice is an approximately 11.5- hour combination of bus and flight. You can also do a combination of subway, train, and flight; or do a combination of train and flight. The time zone difference moving from Eastern Standard Time (EST) to Central European Standard Time (CET) is 6 hours. Expect a bit cooler evenings in Venice when traveling from New York City in August, with lows around 66°F. Wrap up your sightseeing on the 9th (Fri) early enough to take a bus to Verona.

Things to do in Venice

Museums Shopping Historic Sites

Side Trip

PDC Cartizze
Find places to stay Aug 3 — 9:
Highlights from your plan
Basilica di San Marco
Basilica di San Marco
Doge's Palace ©
Doge's Palace
Piazza San Marco ©
Piazza San Marco

5
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.
For shopping fun, head to Piazza delle Erbe or Fondazione Bisazza. Get some cultural insight at Arena di Verona and Villa Calicantus. Venture out of the city with trips to Gardaland Park (in Castelnuovo del Garda) and Il Vittoriale degli Italiani (in Gardone Riviera). Next up on the itinerary: contemplate in the serene atmosphere at Basilica di San Zeno Maggiore, learn about winemaking at Bertani, enjoy breathtaking views from Torre dei Lamberti, and take in the architecture and atmosphere at Basilica di Santa Anastasia.

To find traveler tips, other places to visit, where to stay, and more tourist information, use the Verona trip planning site.

Take a bus from Venice to Verona in 1.5 hours. Alternatively, you can drive; or take a shuttle. In August, daytime highs in Verona are 86°F, while nighttime lows are 64°F. Cap off your sightseeing on the 14th (Wed) early enough to catch the train to Florence.

Things to do in Verona

Museums Historic Sites Theme Parks

Side Trips

Gardaland Park, Il Vittoriale degli Italiani, Villa Calicantus, Fondazione Bisazza
Find places to stay Aug 9 — 14:
Highlights from your plan
Fondazione Bisazza ©
Fondazione Bisazza
Arena di Verona ©
Arena di Verona
Piazza delle Erbe ©
Piazza delle Erbe

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 Art Gallery Studio Iguarnieri and M.G. Design. Florence Academy of Fine Arts and Gallerie Degli Uffizi will appeal to museum buffs. Get out of town with these interesting Florence side-trips: Castello del Trebbio (in Santa Brigida), Leaning Tower of Pisa (in Pisa) and Castello di Verrazzano (in Greve in Chianti). There's still lots to do: contemplate the long history of Cathedral of Santa Maria del Fiore, contemplate in the serene atmosphere at The Baptistery of St. John, do a tasting at Poggio al Bosco, and ponder the world of politics at Palazzo Vecchio.

To find where to stay, ratings, traveler tips, and more tourist information, use the Florence attractions site.

You can take a train from Verona to Florence in 2 hours. Alternatively, you can drive; or take a bus. In August, daytime highs in Florence are 86°F, while nighttime lows are 64°F. Finish up your sightseeing early on the 19th (Mon) so you can catch the bus to Siena.

Things to do in Florence

Historic Sites Wineries Museums

Side Trips

Greve in Chianti, Castello del Trebbio, Leaning Tower of Pisa, Poggio al Bosco
Find places to stay Aug 14 — 19:
Highlights from your plan
Cathedral of Santa Maria del Fiore ©
Cathedral of Santa Maria del Fiore
Gallerie Degli Uffizi ©
Gallerie Degli Uffizi
Florence Academy of Fine Arts ©
Florence Academy of Fine Arts

5
nights
Siena

Siena ©
Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
Get a sense of the local culture at Guardastelle Vineyard and Ciacci Piccolomini d'Aragona. Shop till you drop at Siena Tartufi (truffle hunting) and Silvia Tanganelli. Venture out of the city with trips to Historic Centre of San Gimignano (in San Gimignano), San Quirico d'Orcia (in San Quirico d'Orcia) and Cascate del Mulino (in Saturnia). Next up on the itinerary: don't miss a visit to Piazza del Campo, get a sense of history and politics at Palazzo Pubblico and Museo Civico, indulge your taste buds at Food & Drink, and take in the architecture and atmosphere at Duomo di Siena.

To see reviews, ratings, maps, and tourist information, go to the Siena road trip planning app.

Traveling by bus from Florence to Siena takes 1.5 hours. Alternatively, you can drive; or take a train. Expect a daytime high around 89°F in August, and nighttime lows around 67°F. Finish your sightseeing early on the 24th (Sat) so you can drive to Assisi.

Things to do in Siena

Tours Historic Sites Wineries

Side Trips

San Gimignano, San Quirico d'Orcia, Ciacci Piccolomini d'Aragona, Cascate del Mulino
Find places to stay Aug 19 — 24:
Highlights from your plan
Guardastelle Vineyard ©
Guardastelle Vineyard
Ciacci Piccolomini d'Aragona ©
Ciacci Piccolomini d'Aragona
Duomo di Siena ©
Duomo di Siena

4
nights
Assisi

Assisi ©
Rich in culture and religious tradition, Assisi is known as the birthplace of St.
Museo della Porziuncola and Museo della Memoria will appeal to museum buffs. Your cultural itinerary includes sights like Basilica Papale e Sacro Convento di San Francesco d'Assisi and Eremo delle Carceri. Change things up with these side-trips from Assisi: Castello Monte Vibiano Vecchio (in Mercatello), Civita di Bagnoregio (in Bagnoregio) and Casa del Cioccolato Perugina (in Perugia). There's lots more to do: do a tasting at Tili Vini Societa Agricola, get a taste of the local shopping with Assisi Galleria 6C, take in the exciting artwork at B.A.T. Assisi, and step into the grandiose world of Rocca Maggiore.

To find more things to do, reviews, maps, and tourist information, go to the Assisi online itinerary planner.

You can drive from Siena to Assisi in 2 hours. Other options are to take a bus; or take a train. Expect a daytime high around 88°F in August, and nighttime lows around 63°F. Wrap up your sightseeing on the 28th (Wed) to allow time to drive to Ravello.

Things to do in Assisi

Museums Historic Sites Wineries

Side Trips

Azienda Agraria Guerrieri, Castello Monte Vibiano Vecchio, Civita di Bagnoregio, Palazzo Ducale di Urbino, Casa del Cioccolato Perugina
Find places to stay Aug 24 — 28:
Highlights from your plan
Museo della Porziuncola ©
Museo della Porziuncola
Tili Vini Societa Agricola ©
Tili Vini Societa Agricola

5
nights
Ravello

Ravello ©
Best known for its celebrated terraced gardens, Ravello is a hidden gem of Italy's Amalfi Coast.
Ceramiche D'Arte Pascal and Villa Cimbrone Gardens are good opportunities to explore the local culture. You'll explore and learn at Museo della Carta and Ceramiche d'Arte Carmela. Change things up with these side-trips from Ravello: Torre di Grado (in Praiano), Positano (Il Sentiero Degli Dei, Fornillo, &more) and Le Vigne di Raito (in Vietri sul Mare). There's lots more to do: kick back and relax at Spiaggia di castiglione, take in the spiritual surroundings of Duomo di Ravello, stroll through Lido Capo di Conca, and pause for some serene contemplation at Duomo di Sant'Andrea.

To see reviews, photos, other places to visit, and more tourist information, you can read our Ravello day trip planner.

You can drive from Assisi to Ravello in 4.5 hours. Other options are to do a combination of train and subway; or do a combination of train and bus. Expect a bit warmer evenings in Ravello when traveling from Assisi in August, with lows around 76°F. Wrap up your sightseeing on the 2nd (Mon) early enough to drive to Naples.

Things to do in Ravello

Parks Outdoors Beaches

Side Trips

Positano, Amalfi, Conca dei Marini, Torre di Grado, Le Vigne di Raito
Find places to stay Aug 28 — Sep 2:
Highlights from your plan
Fornillo ©
Fornillo
Le Vigne di Raito ©
Le Vigne di Raito
Ceramiche D'Arte Pascal ©
Ceramiche D'Arte Pascal

5
nights
Naples

Naples ©
Naples is the capital of the Italian region Campania and the third-largest municipality in Italy after Rome and Milan. Do your shopping at Museodivino and Archivio Fotografico Parisio. Pompeii Archaeological Park and Museo Archeologico Nazionale di Napoli are good opportunities to explore the local culture. You'll find plenty of places to visit near Naples: Ischia (Maronti Beach & Castello Aragonese d'Ischia). There's much more to do: take in the spiritual surroundings of Museo Cappella Sansevero, explore the world behind art at Museo del Tesoro di San Gennaro, take an in-depth tour of Museo e Real Bosco di Capodimonte, and steep yourself in history at Parco Acheologico di Ercolano.

To find ratings, traveler tips, photos, and tourist information, read Naples trip itinerary app.

Traveling by car from Ravello to Naples takes 1.5 hours. Alternatively, you can do a combination of taxi and subway; or take a bus. Traveling from Ravello in September, expect little chillier with lows of 64°F in Naples. Wrap up your sightseeing on the 7th (Sat) early enough to take a train to Rome.

Things to do in Naples

Historic Sites Museums Shopping

Side Trips

Ischia, Parco Acheologico di Ercolano, Pompeii Archaeological Park
Find places to stay Sep 2 — 7:
Highlights from your plan
Pompeii Archaeological Park ©
Pompeii Archaeological Park
Museo Cappella Sansevero ©
Museo Cappella Sansevero
Museo Archeologico Nazionale di Napoli ©
Museo Archeologico Nazionale di Napoli

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.
For shopping fun, head to Via Condotti or Body Worlds - Il Ciclo della Vita. Let the collections at Vatican Museums and Galleria Borghese capture your imagination. And it doesn't end there: contemplate the long history of St. Peter's Basilica, take a stroll through Trastevere, explore the ancient world of Colosseum, and make a trip to Piazza Navona.

For reviews, more things to do, maps, and tourist information, read Rome trip itinerary planning website.

Getting from Naples to Rome by train takes about 1.5 hours. Other options: drive; or take a bus. In September, plan for daily highs up to 81°F, and evening lows to 60°F. Wrap up your sightseeing on the 13th (Fri) to allow time to travel back home.

Things to do in Rome

Museums Historic Sites Shopping

Side Trip

Vatican City
Find places to stay Sep 7 — 13:
Highlights from your plan
Colosseum ©
Colosseum
Vatican Museums
Vatican Museums
Pantheon ©
Pantheon

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