25 days in Italy Itinerary

Created using Inspirock Italy tour itinerary builder
Make it your trip
Fly
1
Florence
— 4 nights
Drive
2
Siena
— 3 nights
Drive
3
Assisi
— 1 night
Drive
4
Rome
— 4 nights
Drive
5
Positano
— 4 nights
Fly
6
Venice
— 4 nights
Drive
7
Verona
— 2 nights
Drive
8
Milan
— 1 night
Fly

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

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.
Get out of town with these interesting Florence side-trips: Leaning Tower of Pisa (in Pisa) and Castello del Trebbio (in Santa Brigida). Dedicate the 5th (Tue) to wine at some of the top wineries in the area. There's much more to do: explore the world behind art at Florence Academy of Fine Arts, contemplate in the serene atmosphere at Cathedral of Santa Maria del Fiore, take in the views from Ponte Vecchio, and pause for some photo ops at Campanile di Giotto.

To find traveler tips, other places to visit, photos, and more tourist information, refer to the Florence trip planner.

Vancouver, Canada to Florence is an approximately 16-hour flight. The time zone difference moving from Pacific Standard Time to Central European Standard Time is 9 hours. Traveling from Vancouver in September, you will find days in Florence are a bit warmer (30°C), and nights are about the same (17°C). Wrap up your sightseeing on the 9th (Sat) to allow time to drive to Siena.
more
Wineries · Historic Sites · Tours · Museums
Side Trips
Find places to stay Sep 4 — 9:

Siena — 3 nights

Cultural Heart of Tuscany

Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
Go for a jaunt from Siena to San Gimignano to see Guardastelle Vineyard about 52 minutes away. There's lots more to do: savor the flavors at Food & Drink, take in the spiritual surroundings of San Francesco, take in the architecture and atmosphere at Duomo di Siena, and indulge in some culinary diversions at a local gastronomic tour.

Take the guesswork out of planning a Siena vacation by using our trip itinerary maker.

You can drive from Florence to Siena in 1.5 hours. Alternatively, you can take a bus; or take a train. In September in Siena, expect temperatures between 32°C during the day and 19°C at night. Finish your sightseeing early on the 12th (Tue) to allow enough time to drive to Assisi.
more
Tours · Wineries · Historic Sites · Museums
Side Trip
Find places to stay Sep 9 — 12:

Assisi — 1 night

City of Peace

Rich in culture and religious tradition, Assisi is known as the birthplace of St.
Start off your visit on the 13th (Wed): do a tasting at Tili Vini Societa Agricola, contemplate in the serene atmosphere at Eremo delle Carceri, step into the grandiose world of Rocca Maggiore, then take in the architecture and atmosphere at Basilica Papale e Sacro Convento di San Francesco d'Assisi, and finally do a tasting at Azienda Agraria Saio.

For other places to visit, ratings, traveler tips, and tourist information, refer to the Assisi trip planner.

Drive from Siena to Assisi in 2 hours. Alternatively, you can take a bus; or take a train. In September, daytime highs in Assisi are 30°C, while nighttime lows are 16°C. Wrap up your sightseeing on the 13th (Wed) early enough to drive to Rome.
more
Historic Sites · Wineries
Find places to stay Sep 12 — 13:

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, sightseeing, and nightlife. Your trip includes some of its best attractions: contemplate the long history of St. Peter's Basilica, make a trip to Trevi Fountain, let your taste buds guide you at a local gastronomic tour, and explore the world behind art at Vatican Museums.

For other places to visit, reviews, more things to do, and other tourist information, read our Rome trip itinerary builder tool.

Traveling by car from Assisi to Rome takes 2.5 hours. Alternatively, you can take a train; or take a bus. September in Rome sees daily highs of 32°C and lows of 18°C at night. Finish your sightseeing early on the 17th (Sun) to allow enough time to drive to Positano.
more
Historic Sites · Museums · Tours · Neighborhoods
Side Trip
Find places to stay Sep 13 — 17:

Positano — 4 nights

Often referred to as the gem of the Amalfi Coast, Positano remains one of southern Italy's most sought-after vacation locales, thanks to its hillside location and picturesque, pastel buildings.
Explore the numerous day-trip ideas around Positano: Ravello (Villa Cimbrone Gardens, Villa Rufolo, &more), Collegiate Santa Maria Maddalena (in Atrani) and Amalfi (Valle delle Ferriere, Duomo di Sant'Andrea, &more). There's lots more to do: cruise along Amalfi Coast, get great views at Il Sentiero Degli Dei, get a new perspective on things with Boat Tours & Water Sports, and view the masterpieces at Absolute Positano.

To find ratings, where to stay, traveler tips, and other tourist information, read Positano trip itinerary planning tool.

You can drive from Rome to Positano in 3.5 hours. Other options are to do a combination of train and bus; or take a bus. Traveling from Rome in September, Positano is somewhat warmer at night with lows of 23°C. Finish up your sightseeing early on the 21st (Thu) so you can catch the flight to Venice.
more
Outdoors · Parks · Historic Sites · Wildlife
Side Trips
Find places to stay Sep 17 — 21:

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.
Change things up with these side-trips from Venice: Prosecco Hills - World Heritage Site (in Susegana), Toni Doro - Il Prosecco (in Vittorio Veneto) and PDC Cartizze (in Valdobbiadene). Next up on the itinerary: explore the activities along Canal Grande, make a trip to Piazza San Marco, see the interesting displays at Doge's Palace, and pause for some serene contemplation at San Giorgio Maggiore.

To find maps, other places to visit, where to stay, and tourist information, refer to the Venice journey planner.

Traveling by flight from Positano to Venice takes 3 hours. Alternatively, you can drive; or do a combination of bus and train. Traveling from Positano in September, Venice is little chillier at night with lows of 17°C. Finish your sightseeing early on the 25th (Mon) to allow enough time to drive to Verona.
more
Historic Sites · Tours · Museums · Parks
Side Trips
Find places to stay Sep 21 — 25:

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.
Start off your visit on the 26th (Tue): contemplate the long history of Museo di Castelvecchio, contemplate in the serene atmosphere at Basilica di San Zeno Maggiore, examine the collection at Casa di Giulietta, don't miss a visit to Torre dei Lamberti, then shop like a local with Piazza delle Erbe, and finally enjoy some music at Arena di Verona. Get ready for a full day of sightseeing on the 27th (Wed): admire the natural beauty at Giardino Giusti, then explore the historical opulence of Piazzale Castel San Pietro, then pause for some serene contemplation at Basilica di Santa Anastasia, and finally make a trip to Piazza Bra.

To see reviews, photos, where to stay, and tourist information, you can read our Verona trip itinerary planner.

You can drive from Venice to Verona in 1.5 hours. Alternatively, you can take a shuttle; or take a train. In September, daytime highs in Verona are 30°C, while nighttime lows are 17°C. Cap off your sightseeing on the 27th (Wed) early enough to go by car to Milan.
more
Historic Sites · Parks · Shopping · Neighborhoods
Find places to stay Sep 25 — 27:

Milan — 1 night

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.
On the 28th (Thu), get engrossed in the history at Pinacoteca Ambrosiana, then take in the spiritual surroundings of Duomo di Milano, and then admire the landmark architecture of Galleria Vittorio Emanuele II.

For maps, traveler tips, photos, and more tourist information, you can read our Milan online trip maker.

You can drive from Verona to Milan in 2 hours. Alternatively, you can take a train. Expect a daytime high around 28°C in September, and nighttime lows around 16°C. Finish your sightseeing early on the 28th (Thu) to allow enough time to fly back home.
more
Museums · Historic Sites · Shopping
Find places to stay Sep 27 — 28:

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.
more