21 days in Italy Itinerary

21 days in Italy Itinerary

Created using Inspirock Europe trip planner
Make it your trip
Drive to Roanoke–Blacksburg Regional Airport, Fly to Venice
1
Venice
— 2 nights
Drive
2
Castelrotto
— 2 nights
Drive
3
Cinque Terre
— 1 night
Drive
4
Florence
— 2 nights
Train
5
Modena
— 5 nights
Drive
6
Siena
— 2 nights
Drive
7
Sorrento
— 2 nights
Train
8
Rome
— 3 nights
Fly to Roanoke–Blacksburg Regional Airport, Drive to Lynchburg

S M T W T F S
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Venice — 2 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.
Museum-lovers will appreciate Doge's Palace and Ca' d'Oro. Do some cultural sightseeing at Piazza San Marco and Peggy Guggenheim Collection. Venture out of the city with trips to Padua (Basilica of St. Anthony, Chiesa degli Eremitani - World Heritage Site, &more). Next up on the itinerary: admire the landmark architecture of Basilica di San Marco, see the interesting displays at Museo Ebraico di Venezia, take a stroll through Cannaregio, and enjoy breathtaking views from St Mark's Campanile.

To see ratings, photos, more things to do, and more tourist information, refer to the Venice day trip planning website.

Lynchburg, USA to Venice is an approximately 17.5-hour combination of car and flight. The time zone changes from Eastern Standard Time (EST) to Central European Standard Time (CET), which is usually a 6 hour difference. September in Venice sees daily highs of 77°F and lows of 59°F at night. Finish your sightseeing early on the 7th (Wed) to allow enough time to drive to Castelrotto.
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Historic Sites · Museums · Parks · Nature
Side Trip
Find places to stay Sep 5 — 7:

Castelrotto — 2 nights

On the 8th (Thu), you'll have a packed day of sightseeing: explore the world behind art at Tesoro Del Duomo, get engrossed in the history at South Tyrol Museum of Archaeology, then appreciate the extensive heritage of Merano Centro Storico, and finally admire the natural beauty at I Giardini di Castel Trauttmansdorff.

For photos, maps, where to stay, and tourist information, go to the Castelrotto road trip planning website.

Drive from Venice to Castelrotto in 3.5 hours. Traveling from Venice in September, expect Castelrotto to be a bit cooler, temps between 63°F and 46°F. Finish up your sightseeing early on the 9th (Fri) so you can go by car to Cinque Terre.
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Parks · Historic Sites · Trails · Outdoors
Side Trips
Find places to stay Sep 7 — 9:

Cinque Terre — 1 night

Italian Riviera

Made up of five picturesque towns on the Ligurian coast, Cinque Terre is Italy's answer to the French Riviera.
To see maps, reviews, other places to visit, and tourist information, read our Cinque Terre attractions website.

Getting from Castelrotto to Cinque Terre by car takes about 6 hours. In September, Cinque Terre is a bit warmer than Castelrotto - with highs of 78°F and lows of 59°F. Wrap up your sightseeing on the 10th (Sat) early enough to drive to Florence.
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Outdoors · Tours · Wildlife · Trails
Find places to stay Sep 9 — 10:

Florence — 2 nights

Birthplace of the Italian Renaissance

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Get ready for a full day of sightseeing on the next day: make a trip to Piazzale Michelangelo, snap pictures at Ponte Vecchio, appreciate the extensive heritage of Piazza del Duomo, then take in the spiritual surroundings of Cathedral of Santa Maria del Fiore, then steep yourself in history at Basilica of Santa Croce, and finally admire the masterpieces at Florence Academy of Fine Arts.

For ratings, maps, reviews, and tourist information, read our Florence holiday planning tool.

You can drive from Cinque Terre to Florence in 2.5 hours. Another option is to take a train. In September, daytime highs in Florence are 78°F, while nighttime lows are 59°F. You'll have a few hours on the 12th (Mon) to wrap things up before traveling to Modena.
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Historic Sites · Museums
Find places to stay Sep 10 — 12:

Modena — 5 nights

Capital of Engines

Deemed the Capital of Engines, Modena is the birthplace of Enzo Ferrari and the headquarters of Italian sports cars.
Do some cultural sightseeing at Castello Sforzesco and Pinacoteca Ambrosiana. Deepen your sense of the past at sights like Palazzo Ducale di Mantova and Duomo di Modena. Get out of town with these interesting Modena side-trips: Palazzo Te (in Mantua) and Milan (Galleria Vittorio Emanuele II, Civic Archaeological Museum, &more). There's still lots to do: examine the collection at Acetaia Giuseppe Giusti, make a trip to Piazza Grande - World Heritage Site, look and learn at Civico Planetario F. Martino, and explore the world behind art at Museo Civico d'Arte.

To find maps and more tourist information, use the Modena route planner.

Traveling by train from Florence to Modena takes 2 hours. Alternatively, you can drive. In September, daily temperatures in Modena can reach 78°F, while at night they dip to 59°F. Cap off your sightseeing on the 17th (Sat) early enough to go by car to Siena.
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Museums · Historic Sites · Childrens Museums · Shopping
Side Trips
Find places to stay Sep 12 — 17:

Siena — 2 nights

Cultural Heart of Tuscany

Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
On the 18th (Sun), get a sense of history and politics at Palazzo Pubblico and Museo Civico, don't miss a visit to Piazza del Campo, don't miss a visit to Centro Storico di Siena, pause for some serene contemplation at Duomo di Siena, then enjoy breathtaking views from Torre del Mangia, and finally get engrossed in the history at MOnd - Museo della Contrada Capitana dell'Onda. On the 19th (Mon), you'll have a packed day of sightseeing: steep yourself in history at Torre Grossa, then steep yourself in history at Historic Centre of San Gimignano, then take in the architecture and atmosphere at Duomo di San Gimignano, and finally explore the world behind art at Museo dell'Opera Metropolitana.

To find reviews, maps, ratings, and other tourist information, refer to the Siena driving holiday planner.

Getting from Modena to Siena by car takes about 2.5 hours. Other options: take a train; or do a combination of train and bus. In September, daytime highs in Siena are 81°F, while nighttime lows are 61°F. Cap off your sightseeing on the 19th (Mon) early enough to go by car to Sorrento.
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Historic Sites · Museums
Side Trip
Find places to stay Sep 17 — 19:

Sorrento — 2 nights

Land of the Sirens

A lovely town easily accessible from almost anywhere in the country, Sorrento overlooks the Bay of Naples and sits right on the Amalfi Drive.
Start off your visit on the 20th (Tue): take an in-depth tour of Museobottega della Tarsialignea, view the masterpieces at Marcello Aversa Studio d'Arte, indulge your taste buds at Food & Drink, then view the masterpieces at SyArt, then contemplate in the serene atmosphere at St Francis Church and Convent, and finally don't miss a visit to Piazza Tasso. Keep things going the next day: get engrossed in the history at MAR - Museo Archeologico Romano Positano, then take in the exciting artwork at Absolute Positano, then view the masterpieces at Miniaci Art Gallery, and finally take a tour by water with Boat Tours & Water Sports.

To find reviews, where to stay, more things to do, and tourist information, use the Sorrento online tour itinerary planner.

Traveling by car from Siena to Sorrento takes 5 hours. Alternatively, you can take a train; or take a bus. Traveling from Siena in September, expect somewhat warmer with lows of 68°F in Sorrento. Wrap up your sightseeing on the 21st (Wed) to allow time to take a train to Rome.
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Tours · Museums · Shopping · Outdoors
Side Trip
Find places to stay Sep 19 — 21:

Rome — 3 nights

Eternal City

Aptly nicknamed the Eternal City, Rome is the birthplace of the Roman Empire, one of the world's greatest civilizations ever.
Kick off your visit on the 22nd (Thu): explore the world behind art at Vatican Museums, steep yourself in history at St. Peter's Basilica, then enjoy breathtaking views from Museo Nazionale di Castel Sant'Angelo, and finally explore the ancient world of Colosseum. Here are some ideas for day two: explore the world behind art at Galleria Borghese, pause for some serene contemplation at Church of St. Louis of the French, get to know the fascinating history of Piazza Navona, then delve into the distant past at Pantheon, and finally don't miss a visit to Trevi Fountain.

To see maps, ratings, where to stay, and more tourist information, you can read our Rome trip itinerary planner.

Getting from Sorrento to Rome by train takes about 3 hours. Other options: drive; or take a bus. Traveling from Sorrento in September, expect little chillier with lows of 60°F in Rome. Cap off your sightseeing on the 24th (Sat) early enough to travel back home.
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Historic Sites · Museums
Side Trip
Find places to stay Sep 21 — 24:

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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Tuscany travel guide

4.4
Landmarks · Art Museums · Sacred & Religious Sites
Birthplace of the Italian Renaissance
Known for its landscapes, traditions, and history, Tuscany possesses an unparalleled artistic legacy that continues to influence world culture. Regarded as the birthplace of the Italian Renaissance, the region boasts a lengthy list of attractions, including world-class museums, art galleries, and archeological sites. With a distinct culture and a very strong linguistic identity, this region is sometimes referred to as a nation within a nation. A land of picture-postcard areas, Tuscany contains plenty of places to visit on your holiday, with seven World Heritage Sites, including the historic town centers of Florence and Siena. With more than 120 protected nature preserves, Tuscany is not only a land of culture and historic monuments, but also a great place to discover and enjoy the Italian outdoors. Take it slowly here (as the locals do), and give yourself plenty of time to get to know the local culture and cuisine of Tuscany's medieval towns and ancient villages.
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