27 days in Italy Itinerary

27 days in Italy Itinerary

Created using Inspirock Italy trip planner

Make it your trip
Fly
1
Florence
— 3 nights
Drive
2
Assisi
— 3 nights
Drive
3
Rome
— 4 nights
Train
4
Naples
— 4 nights
Drive
5
Amalfi
— 2 nights
Fly
6
Venice
— 4 nights
Drive
7
Verona
— 2 nights
Drive
8
Milan
— 4 nights
Fly

S M T W T F S
19
20
21
22
23
24
25
26
27
28
29
30
31
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22

Florence

— 3 nights

Birthplace of the Italian Renaissance

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Change things up with a short trip to Leaning Tower of Pisa in Pisa (about 1h 20 min away). Next up on the itinerary: admire the masterpieces at Florence Academy of Fine Arts, enjoy breathtaking views from Campanile di Giotto, don't miss a visit to Piazzale Michelangelo, and pause for some serene contemplation at Basilica of Santa Croce.

To find other places to visit, photos, ratings, and tourist information, read Florence tour planner.

Singapore, Singapore to Florence is an approximately 18-hour flight. Traveling from Singapore to Florence, you'll gain 7 hours due to the time zone difference. Expect much colder temperatures when traveling from Singapore in December; daily highs in Florence reach 15°C and lows reach 4°C. Finish up your sightseeing early on the 25th (Sat) so you can go by car to Assisi.

Things to do in Florence

Side Trip

Find places to stay Dec 22 — 25:

Assisi

— 3 nights

City of Peace

Rich in culture and religious tradition, Assisi is known as the birthplace of St.
Take a break from Assisi with a short trip to Vineria del Carmine in La Bruna, about 46 minutes away. The adventure continues: pause for some serene contemplation at Basilica Papale e Sacro Convento di San Francesco d'Assisi, take in the spiritual surroundings of Basilica di Santa Chiara, don't miss a visit to Piazza del Comune, and see the interesting displays at Museo della Porziuncola.

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

Getting from Florence to Assisi by car takes about 2.5 hours. Other options: take a train. Traveling from Florence in December, you will find days in Assisi are slightly colder (11°C), and nights are about the same (2°C). Wrap up your sightseeing on the 28th (Tue) to allow time to drive to Rome.

Things to do in Assisi

Historic Sites · Wineries · Museums · Parks

Side Trip

Find places to stay Dec 25 — 28:

Rome

— 4 nights

Eternal City

Aptly nicknamed the Eternal City, Rome is the birthplace of the Roman Empire, one of the world's greatest civilizations ever.
Rome is known for historic sites, nightlife, and museums. Your trip includes some of its best attractions: take in the architecture and atmosphere at St. Peter's Basilica, admire the masterpieces at Galleria Borghese, explore the ancient world of Palatine Hill, and stop by Trastevere.

For more things to do, photos, traveler tips, and other tourist information, read our Rome trip itinerary planner.

Traveling by car from Assisi to Rome takes 2.5 hours. Alternatively, you can take a train; or take a bus. Traveling from Assisi in December, expect nights in Rome to be about the same, around 4°C, while days are a bit warmer, around 16°C. Finish your sightseeing early on the 1st (Sat) to allow enough time to take a train to Naples.

Things to do in Rome

Side Trip

Find places to stay Dec 28 — Jan 1:

Naples

— 4 nights
Naples is the capital of the Italian region Campania and the third-largest municipality in Italy after Rome and Milan. Change things up with these side-trips from Naples: Salerno (Centro Storico Salerno, Duomo di Salerno, &more) and Terme del Foro (in Pompeii). There's still lots to do: explore the ancient world of Pompeii Archaeological Park, steep yourself in history at Museo Cappella Sansevero, make a trip to Via San Gregorio Armeno, and take an in-depth tour of Museo e Real Bosco di Capodimonte.

To find maps, more things to do, reviews, and tourist information, refer to the Naples road trip planning site.

Take a train from Rome to Naples in 2 hours. Alternatively, you can drive; or fly. In January, daytime highs in Naples are 15°C, while nighttime lows are 6°C. Cap off your sightseeing on the 5th (Wed) early enough to go by car to Amalfi.

Things to do in Naples

Historic Sites · Museums · Parks

Side Trips

Find places to stay Jan 1 — 5:

Amalfi

— 2 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.
Kick off your visit on the 6th (Thu): don't miss a visit to Fiordo di Furore, take in the dramatic scenery at Valle delle Ferriere, then examine the collection at Museo della Carta, and finally take in the architecture and atmosphere at Duomo di Sant'Andrea. Get ready for a full day of sightseeing on the next day: explore the fascinating underground world of Cave of Smeraldo, kick back and relax at Spiaggia Grande, and then kick back and relax at Fornillo.

For traveler tips, maps, more things to do, and tourist information, use the Amalfi tour itinerary planner.

Getting from Naples to Amalfi by car takes about 1.5 hours. Other options: take a bus; or do a combination of train and bus. Traveling from Naples in January, expect somewhat warmer with lows of 10°C in Amalfi. Finish your sightseeing early on the 7th (Fri) to allow enough time to fly to Venice.

Things to do in Amalfi

Parks · Outdoors · Beaches · Nature

Side Trips

Find places to stay Jan 5 — 7:

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.
Venture out of the city with trips to Padua (Ragione Palace, Prato della Valle, &more). And it doesn't end there: explore the activities along Canal Grande, take in the views from Ponte di Rialto, take in the spiritual surroundings of Basilica di Santa Maria Gloriosa dei Frari, and pause for some serene contemplation at Basilica di San Marco.

For more things to do, traveler tips, reviews, and other tourist information, you can read our Venice travel route planner.

Getting from Amalfi to Venice by flight takes about 3 hours. Other options: do a combination of taxi and train; or drive. Traveling from Amalfi in January, expect Venice to be little chillier, temps between 9°C and 0°C. Finish up your sightseeing early on the 11th (Tue) so you can go by car to Verona.

Things to do in Venice

Historic Sites · Museums · Nature · Parks

Side Trip

Find places to stay Jan 7 — 11:

Verona

— 2 nights

City of Romeo and Juliet

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 12th (Wed), make a trip to Piazza Bra, take a stroll through Piazza delle Erbe, enjoy breathtaking views from Torre dei Lamberti, then browse the exhibits of Casa di Giulietta, then take in the spiritual surroundings of Basilica di San Zeno Maggiore, and finally contemplate the long history of Museo di Castelvecchio. Here are some ideas for day two: get to know the fascinating history of Centro Storico, then pause for some serene contemplation at San Fermo Maggiore, Verona, and then see the grandeur of opera at Arena di Verona.

For reviews, where to stay, photos, and tourist information, read our Verona road trip tool.

Traveling by car from Venice to Verona takes 1.5 hours. Alternatively, you can take a shuttle; or take a train. Wrap up your sightseeing on the 13th (Thu) to allow time to drive to Milan.

Things to do in Verona

Historic Sites · Nightlife · Museums · Neighborhoods
Find places to stay Jan 11 — 13:

Milan

— 4 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.
Explore the numerous day-trip ideas around Milan: Como (Basilica di Sant'Abbondio & Basilica di San Fedele). The adventure continues: contemplate in the serene atmosphere at Duomo di Milano, get a taste of the local shopping with Galleria Vittorio Emanuele II, explore the world behind art at Pinacoteca Ambrosiana, and take an in-depth tour of Basilica di Sant'Ambrogio.

To find traveler tips, photos, where to stay, and more tourist information, you can read our Milan road trip planning tool.

Traveling by car from Verona to Milan takes 2 hours. Alternatively, you can take a train. In January, daily temperatures in Milan can reach 9°C, while at night they dip to 0°C. Wrap up your sightseeing on the 17th (Mon) to allow time to fly back home.

Things to do in Milan

Historic Sites · Museums · Childrens Museums · Shopping

Side Trip

Find places to stay Jan 13 — 17:

Italy travel guide

4.6
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.