26 days in Italy Itinerary

26 days in Italy Itinerary

Created using Inspirock Italy tour builder

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Route & dates

26 days in Italy Itinerary

Start: New York City
Bus + Fly:  11 h 30 min
1
Venice
— 3 nights
Bus:  1 h 30 min
2
Verona
— 2 nights
Train:  1 h 45 min
3
Florence
— 3 nights
Drive:  2 h 15 min
4
Assisi
— 2 nights
Drive:  4 h 30 min
5
Ravello
— 4 nights
Drive:  1 h 15 min
6
Naples
— 3 nights
Train:  1 h 15 min
7
Rome
— 4 nights
Train:  3 h
8
Milan
— 3 nights
Fly:  12 h 30 min
End: New York City

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.
Popular historic sites such as Piazza San Marco and Peggy Guggenheim Collection are in your itinerary. Doge's Palace and Palazzo Cavalli-Franchetti will appeal to museum buffs. There's lots more to do: explore the activities along Canal Grande, admire the landmark architecture of Basilica di San Marco, shop like a local with Max Studio, and pause for some serene contemplation at Basilica dei Santi Giovanni e Paolo.

For ratings, photos, and tourist information, use the Venice journey 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. Traveling from New York City in October, Venice is little chillier at night with lows of 51°F. Finish your sightseeing early on the 8th (Thu) so you can take a bus to Verona.

Things to do in Venice

Museums Historic Sites Shopping
Find places to stay Oct 4 — 8:
Highlights from your plan
Canal Grande ©
Canal Grande
Doge's Palace ©
Doge's Palace
Piazza San Marco ©
Piazza San Marco

2
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.
On the 9th (Fri), enjoy some music at Arena di Verona, pause for some serene contemplation at Cappella dei Notai, admire the landmark architecture of Casa di Giulietta, take in panoramic vistas at Torre dei Lamberti, then take a stroll through Piazza delle Erbe, and finally shop like a local with Galleria Dello Scudo. On the 10th (Sat), you'll have a packed day of sightseeing: take in the architecture and atmosphere at Basilica di Santa Anastasia, take in the architecture and atmosphere at Chiesa di San Giorgetto o San Pietro Martire, take in the architecture and atmosphere at chiesa di San Lorenzo - Verona, then explore the historical opulence of Museo di Castelvecchio, and finally explore the historical opulence of Piazzale Castel San Pietro.

Plan my trip to Verona with suggested itineraries provided by Inspirock.

Getting from Venice to Verona by bus takes about 1.5 hours. Other options: drive; or take a shuttle. In October, plan for daily highs up to 66°F, and evening lows to 50°F. Cap off your sightseeing on the 10th (Sat) early enough to catch the train to Florence.

Things to do in Verona

Historic Sites Museums Shopping
Find places to stay Oct 8 — 10:
Highlights from your plan
Arena di Verona ©
Arena di Verona
Piazza delle Erbe ©
Piazza delle Erbe
Basilica di San Zeno Maggiore ©
Basilica di San Zeno Maggiore

3
nights
Florence

Florence ©
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Academy Of Florence Art Gallery and M.G. Design will appeal to museum buffs. Your cultural itinerary includes sights like Piazzale Michelangelo and Basilica of Santa Croce. Next up on the itinerary: contemplate in the serene atmosphere at Cathedral of Santa Maria del Fiore, admire the landmark architecture of The Baptistery of St. John, admire the masterpieces at Pitti Palace, and appreciate the extensive heritage of Piazza del Duomo.

To see more things to do, reviews, photos, and more tourist information, go to the Florence itinerary builder site.

You can take a train from Verona to Florence in 2 hours. Alternatively, you can drive; or take a bus. In October, daily temperatures in Florence can reach 71°F, while at night they dip to 54°F. Finish your sightseeing early on the 13th (Tue) to allow enough time to drive to Assisi.

Things to do in Florence

Museums Historic Sites Shopping
Find places to stay Oct 10 — 13:
Highlights from your plan
Cathedral of Santa Maria del Fiore ©
Cathedral of Santa Maria del Fiore
Academy Of Florence Art Gallery ©
Academy Of Florence Art Gallery
Pitti Palace ©
Pitti Palace

2
nights
Assisi

Assisi ©
Rich in culture and religious tradition, Assisi is known as the birthplace of St.
Start off your visit on the 14th (Wed): learn about winemaking at Tili Vini Societa Agricola, see the interesting displays at Museo della Porziuncola, do a tasting at Bibenda Assisi, contemplate in the serene atmosphere at Eremo delle Carceri, then get to know the fascinating history of Piazza Superiore di San Francesco, and finally pause for some serene contemplation at Basilica Papale e Sacro Convento di San Francesco d'Assisi. Keep things going the next day: learn about winemaking at Vineria del Carmine, then get to know the fascinating history of Centro Storico di Assisi, then step into the grandiose world of Rocca Maggiore, and finally steep yourself in history at San Damiano.

For ratings, reviews, where to stay, and tourist information, read Assisi day trip planning app.

Getting from Florence to Assisi by car takes about 2.5 hours. Other options: take a train. In October, plan for daily highs up to 70°F, and evening lows to 51°F. Finish your sightseeing early on the 15th (Thu) to allow enough time to drive to Ravello.

Things to do in Assisi

Historic Sites Wineries Museums

Side Trip

Vineria del Carmine
Find places to stay Oct 13 — 15:
Highlights from your plan
Tili Vini Societa Agricola ©
Tili Vini Societa Agricola
Museo della Porziuncola ©
Museo della Porziuncola

4
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 Duomo di Ravello are good opportunities to explore the local culture. Popular historic sites such as Villa Cimbrone Gardens and Villa Rufolo are in your itinerary. Change things up with these side-trips from Ravello: Positano (Fornillo, Bagni d'Arienzo Beach Club, Positano, &more).

To see reviews, more things to do, traveler tips, and tourist information, read our Ravello trip planner.

Traveling by car from Assisi to Ravello takes 4.5 hours. Alternatively, you can take a train; or do a combination of train and bus. Plan for somewhat warmer nights when traveling from Assisi in October since evenings lows in Ravello dip to 63°F. Wrap up your sightseeing on the 19th (Mon) to allow time to drive to Naples.

Things to do in Ravello

Parks Outdoors Beaches

Side Trips

Amalfi, Positano, Castello di San Nicola de Thoro-Plano, Lido Capo di Conca
Find places to stay Oct 15 — 19:
Highlights from your plan
Spiaggia di castiglione ©
Spiaggia di castiglione
Duomo di Ravello ©
Duomo di Ravello
Fornillo ©
Fornillo

3
nights
Naples

Naples ©
Naples is the capital of the Italian region Campania and the third-largest municipality in Italy after Rome and Milan. Popular historic sites such as Pompeii Archaeological Park and Cloister of Santa Chiara are in your itinerary. Appreciate the collections at Sol’Art Ceramiche and Museo e Real Bosco di Capodimonte. Change things up with a short trip to Spiaggia di Marina d'Albori in Vietri sul Mare (about 52 minutes away). And it doesn't end there: take in the spiritual surroundings of Museo Cappella Sansevero, contemplate the long history of Parco Acheologico di Ercolano, make a trip to Via San Gregorio Armeno, and appreciate the extensive heritage of Underground Naples.

For reviews, ratings, photos, and other tourist information, go to the Naples trip 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. Traveling from Ravello in October, plan for a bit cooler nights in Naples, with lows around 58°F. Finish your sightseeing early on the 22nd (Thu) so you can take a train to Rome.

Things to do in Naples

Historic Sites Museums Wineries

Side Trips

Vietri sul Mare, Pompeii, Parco Acheologico di Ercolano
Find places to stay Oct 19 — 22:
Highlights from your plan
Pompeii Archaeological Park ©
Pompeii Archaeological Park
Sol’Art Ceramiche ©
Sol’Art Ceramiche
Museo Cappella Sansevero ©
Museo Cappella Sansevero

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.
Give yourself a bit of retail therapy at Via Condotti and Vertecchi. Take a break from the city and head to Catacombs of Saint Callixtus and V Lounge Beach Club. And it doesn't end there: admire the masterpieces at Galleria Borghese, delve into the distant past at Pantheon, wander the streets of Trastevere, and appreciate the extensive heritage of Piazza Navona.

To see ratings, photos, where to stay, and tourist information, go to the Rome holiday planning site.

You can take a train from Naples to Rome in 1.5 hours. Alternatively, you can drive; or take a bus. In October, daily temperatures in Rome can reach 73°F, while at night they dip to 55°F. Finish your sightseeing early on the 26th (Mon) so you can take a train to Milan.

Things to do in Rome

Historic Sites Museums Neighborhoods

Side Trip

Vatican City
Find places to stay Oct 22 — 26:
Highlights from your plan
Pantheon ©
Pantheon
Vatican Museums
Vatican Museums
St. Peter's Basilica ©
St. Peter's Basilica

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.
Kick off your visit on the 27th (Tue): admire the landmark architecture of Galleria Vittorio Emanuele II, take in the spiritual surroundings of Duomo di Milano, don't miss a visit to Piazza del Duomo, then explore the world behind art at Pinacoteca Ambrosiana, and finally explore the different monuments and memorials at Monumental Cemetery. Get ready for a full day of sightseeing on the 28th (Wed): contemplate the long history of Il Cenacolo, take in the spiritual surroundings of Piazza di Santa Maria delle Grazie, 2, take an in-depth tour of Basilica di Sant'Ambrogio, then take in the architecture and atmosphere at Chiesa di San Maurizio al Monastero Maggiore, and finally see the interesting displays at Civic Archaeological Museum.

To see photos, more things to do, traveler tips, and other tourist information, read Milan trip itinerary builder.

You can take a train from Rome to Milan in 3 hours. Alternatively, you can fly; or drive. Traveling from Rome in October, expect nights in Milan to be about the same, around 52°F, while days are a bit cooler, around 65°F. On the 29th (Thu), wrap the sightseeing up by early afternoon so you can travel back home.

Things to do in Milan

Historic Sites Museums Shopping
Find places to stay Oct 26 — 29:
Highlights from your plan
Duomo di Milano ©
Duomo di Milano
Pinacoteca Ambrosiana ©
Pinacoteca Ambrosiana
Monumental Cemetery ©
Monumental Cemetery

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