27 days in Italy Itinerary

27 days in Italy Itinerary

Created using Inspirock Italy visit planner
Make it your trip
Fly
1
Amalfi
— 3 nights
Drive
2
Naples
— 3 nights
Train
3
Rome
— 5 nights
Drive
4
Assisi
— 1 night
Drive
5
Siena
— 4 nights
Drive
6
Florence
— 4 nights
Drive
7
Venice
— 4 nights
Drive
8
Milan
— 2 nights
Fly

S M T W T F S
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31
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Amalfi — 3 nights

Painted Town

Known for its impressive hillside cascade of colorful stone buildings down to the Mediterranean shore, Amalfi is the cultural and commercial heart of southern Italy's Amalfi Coast.
Your itinerary includes some good beach time at Fornillo and Spiaggia Grande. Villa Rufolo and Duomo di Ravello are good opportunities to explore the local culture. You'll find plenty of places to visit near Amalfi: Positano (Il Sentiero Degli Dei & Boat Tours & Water Sports). Next up on the itinerary: admire the natural beauty at Villa Cimbrone Gardens, see the interesting displays at Arsenale di Amalfi - antico Arsenale della Repubblica Marinara, take in the spiritual surroundings of Duomo di Sant'Andrea, and enjoy the sand and surf at Marina di Praia Beach.

To find traveler tips, more things to do, other places to visit, and more tourist information, read Amalfi online trip builder.

Bogota, Colombia to Amalfi is an approximately 16.5-hour flight. The time zone difference moving from Colombia Standard Time (COT) to Central European Standard Time (CET) is 6 hours. Plan for somewhat warmer temperatures traveling from Bogota in October, with highs in Amalfi at 26°C and lows at 20°C. Wrap up your sightseeing on the 15th (Sat) to allow time to drive to Naples.
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Outdoors · Historic Sites · Tours · Parks
Side Trips
Find places to stay Oct 12 — 15:

Naples — 3 nights

Naples is the capital of the Italian region Campania and the third-largest municipality in Italy after Rome and Milan. Pompeii Archaeological Park and Villa dei Misteri are good opportunities to explore the local culture. Parco Acheologico di Ercolano and Forum will appeal to history buffs. Explore the numerous day-trip ideas around Naples: Pompeii (Lupanar, Terme del Foro, &more) and Sorrento (Leonelli's Beach, Piazza Tasso, &more). There's still lots to do: take in the spiritual surroundings of Pontificio Santuario della Beata Maria Vergine del Santo Rosario di Pompei, explore the world behind art at Museo Cappella Sansevero, go for a walk through Lungomare Caracciolo, and appreciate the extensive heritage of Underground Naples.

To see reviews, maps, more things to do, and more tourist information, read our Naples trip maker website.

You can drive from Amalfi to Naples in 1.5 hours. Alternatively, you can take a bus; or do a combination of bus and train. Traveling from Amalfi in October, expect slightly colder with lows of 17°C in Naples. Finish your sightseeing early on the 18th (Tue) so you can take a train to Rome.
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Historic Sites · Museums · Beaches · Outdoors
Side Trips
Find places to stay Oct 15 — 18:

Rome — 5 nights

Eternal City

Aptly nicknamed the Eternal City, Rome is the birthplace of the Roman Empire, one of the world's greatest civilizations ever.
Deepen your sense of the past at sights like Colosseum and St. Peter's Basilica. Do some cultural sightseeing at Pantheon and Palatine Hill. Explore the numerous day-trip ideas around Rome: Tivoli (Villa d'Este & Villa Adriana). And it doesn't end there: explore the world behind art at Vatican Museums, steep yourself in history at Roman Forum, appreciate the extensive heritage of Piazza Navona, and pause for some serene contemplation at Church of St. Louis of the French.

To find reviews, more things to do, traveler tips, and tourist information, refer to the Rome online travel route planner.

Getting from Naples to Rome by train takes about 2 hours. Other options: drive; or fly. In October in Rome, expect temperatures between 26°C during the day and 15°C at night. Finish your sightseeing early on the 23rd (Sun) to allow enough time to drive to Assisi.
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Side Trips
Find places to stay Oct 18 — 23:

Assisi — 1 night

City of Peace

Rich in culture and religious tradition, Assisi is known as the birthplace of St.
To find ratings, photos, maps, and tourist information, read Assisi journey app.

Traveling by car from Rome to Assisi takes 2.5 hours. Alternatively, you can take a train; or take a bus. In October, daytime highs in Assisi are 24°C, while nighttime lows are 12°C. Finish your sightseeing early on the 24th (Mon) so you can drive to Siena.
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Historic Sites · Museums
Find places to stay Oct 23 — 24:

Siena — 4 nights

Cultural Heart of Tuscany

Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
Deepen your sense of the past at sights like Duomo di Siena and Duomo di San Gimignano. Get a sense of the local culture at Ciacci Piccolomini d'Aragona and Guardastelle Vineyard. Venture out of the city with trips to Walls of Monteriggioni (in Monteriggioni), Abbazia di San Galgano (in Chiusdino) and San Gimignano (La Bottega del Sale di Duccio Nacci photographer, Historic Centre of San Gimignano, &more). There's still lots to do: indulge your taste buds at Food & Drink, don't miss a visit to Centro Storico di Siena, take in the spiritual surroundings of Battistero di San Giovanni, and steep yourself in history at San Francesco.

For other places to visit, ratings, photos, and tourist information, refer to the Siena online trip builder.

Getting from Assisi to Siena by car takes about 2 hours. Other options: take a bus; or take a train. October in Siena sees daily highs of 26°C and lows of 15°C at night. Finish up your sightseeing early on the 28th (Fri) so you can go by car to Florence.
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Wineries · Historic Sites · Tours · Museums
Side Trips
Find places to stay Oct 24 — 28:

Florence — 4 nights

Birthplace of the Italian Renaissance

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Satisfy your inner culture vulture at Cathedral of Santa Maria del Fiore and Ponte Vecchio. Popular historic sites such as Basilica of Santa Croce and Campanile di Giotto are in your itinerary. You'll find plenty of places to visit near Florence: Castello di Verrazzano (in Greve in Chianti), A Solatio Organic Farm (in Certaldo) and Pisa (Duomo di Pisa & Leaning Tower of Pisa). There's still lots to do: admire the masterpieces at Florence Academy of Fine Arts, let your taste buds guide you at a local gastronomic tour, get a sense of history and politics at Museo Nazionale del Bargello, and get to know the fascinating history of Piazza della Signoria.

To find more things to do, maps, other places to visit, and other tourist information, read Florence tour itinerary site.

Drive from Siena to Florence in 1.5 hours. Alternatively, you can take a bus; or take a train. Expect a daytime high around 25°C in October, and nighttime lows around 14°C. Wrap up your sightseeing on the 1st (Tue) to allow time to drive to Venice.
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Historic Sites · Wineries · Museums · Tours
Side Trips
Find places to stay Oct 28 — Nov 1:

Venice — 4 nights

City of Romance

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.
Get some cultural insight at Piazza San Marco and Basilica di San Marco. Get some historical perspective at Doge's Palace and Scrovegni Chapel. Change things up with these side-trips from Venice: Padua (Piazza delle Erbe, Basilica of St. Anthony, &more) and Verona (Basilica di Santa Anastasia, Casa di Giulietta, &more). And it doesn't end there: contemplate the waterfront views at Canal Grande, pause for some serene contemplation at San Giorgio Maggiore, take in the views from Ponte dei Sospiri, and take in panoramic vistas at St Mark's Campanile.

To find traveler tips, photos, ratings, and other tourist information, refer to the Venice trip itinerary builder website.

Drive from Florence to Venice in 3 hours. Alternatively, you can take a train; or take a bus. Traveling from Florence in November, expect nights in Venice to be about the same, around 7°C, while days are slightly colder, around 15°C. Cap off your sightseeing on the 5th (Sat) early enough to go by car to Milan.
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Historic Sites · Museums · Neighborhoods · Parks
Side Trips
Find places to stay Nov 1 — 5:

Milan — 2 nights

Fashion Capital of World

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.
To see photos, other places to visit, reviews, and more tourist information, you can read our Milan trip itinerary tool.

Drive from Venice to Milan in 3 hours. Alternatively, you can take a train; or take a bus. In November, daily temperatures in Milan can reach 15°C, while at night they dip to 6°C. Wrap up your sightseeing by early afternoon on the 7th (Mon) to allow enough time to fly back home.
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Historic Sites · Tours · Wineries · Shopping
Find places to stay Nov 5 — 7:

Italy travel guide

4.6
Landmarks · Ruins · Beaches
Italy is a land of high fashion, fine art, exquisite architecture, luxury sports cars, outstanding cuisine--and an insatiable taste for "la dolce vita." It's also home to the greatest number of World Heritage Sites in the world, making it an ideal place for your next holiday. The country boasts a varied landscape of mountain ranges, alpine lakes, and coastal towns, so it's no wonder travelers often refer to it as the bel paese (beautiful country). With so many places to visit, visitors often have a difficult time planning their itinerary. The smaller villages each feature a distinct character and a blend of architecture, art, and cuisine. In the country, you'll find countless archeological sites dating back to Roman times and beyond. The country's cities and seaside resorts are cosmopolitan powerhouses with museums, galleries, restaurants, shops, open-air markets, and pedestrian-friendly historic areas.
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