29 days in Italy Itinerary

29 days in Italy Itinerary

Created using Inspirock Italy tour planner

Make it your trip
Fly
1
Rome
— 5 nights
Train
2
Milan
— 2 nights
Drive
3
Bellagio
— 4 nights
Drive
4
Venice
— 3 nights
Train
5
Florence
— 8 nights
Train
6
Rome
— 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

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.
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, stop by Trastevere, appreciate the extensive heritage of Piazza Navona, and admire the masterpieces at Vatican Museums.

To see reviews, maps, ratings, and tourist information, read our Rome itinerary builder website.

Singapore, Singapore to Rome is an approximately 16.5-hour flight. Traveling from Singapore to Rome, you'll gain 7 hours due to the time zone difference. Plan for cooler temperatures traveling from Singapore in December, with highs in Rome at 16°C and lows at 4°C. Finish your sightseeing early on the 27th (Mon) so you can fly to Milan.

Things to do in Rome

Historic Sites · Museums · Neighborhoods

Side Trip

Find places to stay Dec 22 — 27:

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.
Kick off your visit on the 27th (Mon): take in the architecture and atmosphere at Basilica San Lorenzo Maggiore and then get to know the fascinating history of Piazza del Duomo. Get ready for a full day of sightseeing on the 28th (Tue): admire the striking features of Galleria Vittorio Emanuele II, then step into the grandiose world of Castello Sforzesco, then take an in-depth tour of Basilica di Sant'Ambrogio, and finally pause for some serene contemplation at Duomo di Milano.

For other places to visit, more things to do, photos, and tourist information, go to the Milan trip planner.

Fly from Rome to Milan in 3 hours. Alternatively, you can take a train; or drive. In December, Milan is little chillier than Rome - with highs of 9°C and lows of 1°C. You will leave for Bellagio on the 29th (Wed).

Things to do in Milan

Historic Sites · Shopping · Museums
Find places to stay Dec 27 — 29:

Bellagio

— 4 nights

Pearl of Lake Como

Known as the pearl of Lake Como for its luxury accommodations, high-end shops, and fine dining options, Bellagio serves as the lake's premiere resort town.
Get out of town with these interesting Bellagio side-trips: Como (Cathedral of Como (Duomo), Tea World, &more). There's much more to do: take in the pleasant sights at La Perla del Lago, surround yourself with nature on Walking Tour Bellagio - Lake of Como, take in nature's colorful creations at I Giardini di Villa Melzi, and don't miss a visit to Borgo di Pescallo.

To find other places to visit, where to stay, maps, and tourist information, you can read our Bellagio trip planning tool.

Traveling by car from Milan to Bellagio takes 2 hours. Alternatively, you can take a train. In December, plan for daily highs up to 8°C, and evening lows to -1°C. Finish up your sightseeing early on the 2nd (Sun) so you can go by car to Venice.

Things to do in Bellagio

Historic Sites · Parks · Wildlife · Outdoors

Side Trip

Find places to stay Dec 29 — Jan 2:

Venice

— 3 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.
Venice is known for historic sites, nature, and museums. Your trip includes some of its best attractions: explore the activities along Canal Grande, snap pictures at Ponte di Rialto, explore the world behind art at Peggy Guggenheim Collection, and see the interesting displays at Doge's Palace.

For ratings, reviews, where to stay, and other tourist information, read Venice trip itinerary builder app.

Drive from Bellagio to Venice in 3.5 hours. Alternatively, you can take a train; or do a combination of bus and train. Expect a daytime high around 9°C in January, and nighttime lows around 0°C. You'll set off for Florence on the 5th (Wed).

Things to do in Venice

Historic Sites · Museums · Nature · Parks
Find places to stay Jan 2 — 5:

Florence

— 8 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 these side-trips from Florence: Siena (Basilica Cateriniana San Domenico, Palazzo Pubblico and Museo Civico, &more). There's lots more to do: admire the masterpieces at Florence Academy of Fine Arts, don't miss a visit to Piazzale Michelangelo, pause for some serene contemplation at Cathedral of Santa Maria del Fiore, and appreciate the extensive heritage of Piazza della Signoria.

To see maps, traveler tips, other places to visit, and other tourist information, use the Florence tour planner.

You can drive from Venice to Florence in 3 hours. Alternatively, you can take a train; or take a bus. Expect somewhat warmer weather when traveling from Venice in January: highs in Florence hover around 13°C, while lows dip to 3°C. Finish your sightseeing early on the 13th (Thu) to allow enough time to take a train to Rome.

Things to do in Florence

Historic Sites · Museums · Tours · Parks

Side Trip

Find places to stay Jan 5 — 13:

Rome

— 4 nights

Eternal City

Go for a jaunt from Rome to Tivoli to see Villa d'Este about 48 minutes away. Explore Rome further: take an in-depth tour of Musei Capitolini, appreciate the history behind Monumento a Vittorio Emanuele II, make a trip to Centro Storico Associazione Centro Storico, and take in the architecture and atmosphere at Arcibasilica di San Giovanni in Laterano.

To find other places to visit, reviews, ratings, and tourist information, you can read our Rome day trip planning website.

Take a train from Florence to Rome in 2.5 hours. Alternatively, you can fly; or drive. Cap off your sightseeing on the 17th (Mon) early enough to catch the flight back home.

Things to do in Rome

Historic Sites · Museums · Spas · Parks

Side Trips

Find places to stay Jan 13 — 17:

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.