29 days in Northwest Italy Itinerary

29 days in Northwest Italy Itinerary

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Route & dates

29 days in Northwest Italy Itinerary

Start: Charlotte
Fly:  14​h
1
Venice
— 2 nights
bus:  30​min
2
Padua
— 3 nights
3
Modena
— 1 night
Drive:  1​h 30​min
4
Ravenna
— 3 nights
5
Assisi
— 1 night
Drive:  1​h 15​min
6
Montepulciano
— 2 nights
7
Siena
— 2 nights
Drive:  45​min
8
San Gimignano
— 2 nights
Drive:  2​h 45​min
9
Cinque Terre
— 2 nights
10
Pisa
— 2 nights
11
Florence
— 6 nights
Fly:  15​h
End: Charlotte

2
nights
Venice

Venice ©
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.
Eschew the tourist crowds and head to Cannaregio and San Giorgio Maggiore. There's lots more to do: explore the activities along Canal Grande, take in the views from Ponte di Rialto, wander the streets of Dorsoduro, and admire the landmark architecture of Basilica di San Marco.

For maps, reviews, ratings, and tourist information, read our Venice trip planner.

Charlotte, USA to Venice is an approximately 14-hour flight. You can also do a combination of flight and train. Due to the time zone difference, you'll lose 6 hours traveling from Charlotte to Venice. Expect slightly colder weather when traveling from Charlotte in May: highs in Venice hover around 72°F, while lows dip to 55°F. Finish your sightseeing early on the 23rd (Thu) to allow enough time to take a bus to Padua.

Things to do in Venice

Historic Sites Neighborhoods Nature
Find places to stay May 21 — 23:
Highlights from your plan
Canal Grande ©
Canal Grande
Basilica di San Marco
Basilica di San Marco
Doge's Palace ©
Doge's Palace

3
nights
Padua

Padua ©
Padua is a picturesque city with a dense network of arcaded streets opening into large communal piazze (squares).
Start off your visit on the 24th (Fri): contemplate the long history of Piazza dei Signori, take in the spiritual surroundings of Battistero del Duomo, pause for some serene contemplation at Scrovegni Chapel, then get curious at MUSME - Museum of the History of Medicine of Padova, and finally take in the architecture and atmosphere at Basilica di Sant’Antonio. Keep things going the next day: step into the grandiose world of La Cinta Muraria - Camminamento di Ronda, pause for some serene contemplation at Santuario della Madonna di Monte Berico, then pause for some serene contemplation at Santuario Madonna della Salute Monteortone, and finally admire the natural beauty at Giardino di Valsanzibio.

To find more things to do, other places to visit, maps, and tourist information, go to the Padua road trip site .

Padua is very close to Venice. In May, daily temperatures in Padua can reach 70°F, while at night they dip to 59°F. Wrap up your sightseeing on the 26th (Sun) early enough to drive to Modena.

Things to do in Padua

Historic Sites Museums Childrens Museums

Side Trips

Santuario Madonna della Salute Monteortone, Santuario della Madonna di Monte Berico, Giardino di Valsanzibio, La Cinta Muraria - Camminamento di Ronda
Find places to stay May 23 — 26:
Highlights from your plan
Scrovegni Chapel ©
Scrovegni Chapel
Basilica di Sant’Antonio ©
Basilica di Sant’Antonio

1
night
Modena

Modena ©
Deemed the Capital of Engines, Modena is the birthplace of Enzo Ferrari and the headquarters of Italian sports cars.
Start off your visit on the 26th (Sun): examine the collection at Casa Museo Luciano Pavarotti, see the interesting displays at Panini Motor Museum, examine the collection at Acetaia Giuseppe Giusti, then examine the collection at MEF-Museo Enzo Ferrari, and finally appreciate the history behind Palazzo Ducale. Here are some ideas for day two: don't miss a visit to Piazza dei Martiri, contemplate the long history of Acetaia Villa San Donnino, get the adrenaline pumping with an extreme tour, see the interesting displays at Museo Ferrari, then contemplate the long history of Palazzo Ducale Piano Primo, and finally take in the spiritual surroundings of Duomo di Modena.

To see maps and tourist information, read Modena trip builder app .

Traveling by car from Padua to Modena takes 2 hours. Alternatively, you can take a train; or take a bus. Traveling from Padua in May, expect little chillier with lows of 54°F in Modena. Finish up your sightseeing early on the 27th (Mon) so you can go by car to Ravenna.

Things to do in Modena

Museums Historic Sites Wineries

Side Trips

Maranello, Palazzo Ducale Piano Primo, Piazza dei Martiri
Find places to stay May 26 — 27:
Highlights from your plan
Acetaia Villa San Donnino ©
Acetaia Villa San Donnino
Museo Ferrari ©
Museo Ferrari
Duomo di Modena ©
Duomo di Modena

3
nights
Ravenna

Ravenna ©
Famous for its wealth of original mosaics, Ravenna is a hub of artistic and cultural heritage.
Start off your visit on the 28th (Tue): pause for some serene contemplation at Basilica di S. Giovanni Evangelista, explore the world behind art at Mar - Museo d'Arte della citta di Ravenna, contemplate the long history of Basilica di Sant'Apollinare Nuovo, explore the different monuments and memorials at Indian Army War Cemetery, then take in the architecture and atmosphere at San Mercuriale Abbey, and finally contemplate the long history of Basilica San Vitale. Here are some ideas for day two: don't miss a visit to Mausoleo di Galla Placidia, admire nature's wide array of creatures at Parco R.Bucci, see the interesting displays at Palazzo Milzetti Museo Nazionale dell'eta Neoclassica in Romagna, then don't miss a visit to Piazza del Popolo, and finally contemplate in the serene atmosphere at Battistero Neoniano (Battistero degli Ortodossi).

To find more things to do, traveler tips, other places to visit, and more tourist information, read Ravenna holiday app .

Getting from Modena to Ravenna by car takes about 1.5 hours. Other options: take a train. In May in Ravenna, expect temperatures between 73°F during the day and 58°F at night. Finish your sightseeing early on the 30th (Thu) so you can drive to Assisi.

Things to do in Ravenna

Historic Sites Museums Zoos & Aquariums

Side Trips

Faenza, Forli
Find places to stay May 27 — 30:
Highlights from your plan
Basilica San Vitale ©
Basilica San Vitale
Mausoleo di Galla Placidia ©
Mausoleo di Galla Placidia
Basilica di Sant'Apollinare Nuovo ©
Basilica di Sant'Apollinare Nuovo

1
night
Assisi

Assisi ©
Rich in culture and religious tradition, Assisi is known as the birthplace of St.
Start off your visit on the 30th (Thu): take in the spiritual surroundings of Basilica di Santa Maria degli Angeli - Porziuncola, see the interesting displays at Museo-Laboratorio di Tessitura a Mano Giuditta Brozzetti, learn about winemaking at Montioni Frantoio e Cantina, then examine the collection at Museo della Porziuncola, and finally steep yourself in history at San Pietro. Keep things going the next day: pause for some serene contemplation at Basilica inferiore di San Francesco d'Assisi, take in the spiritual surroundings of Santuario di Rivotorto, do a tasting at Arnaldo Caprai - Viticoltore in Montefalco, then pause for some serene contemplation at Santa Maria Maggiore, then look for gifts at La Bottega Di Teresa, and finally contemplate the long history of Eremo delle Carceri.

For more things to do, traveler tips, photos, and more tourist information, use the Assisi trip builder .

Getting from Ravenna to Assisi by car takes about 3 hours. Other options: take a train; or take a bus. Traveling from Ravenna in May, you can expect nighttime temperatures to be slightly colder in Assisi, with lows of 52°F. Finish your sightseeing early on the 31st (Fri) to allow enough time to drive to Montepulciano.

Things to do in Assisi

Historic Sites Wineries Museums

Side Trips

Spello, Montefalco, Perugia
Find places to stay May 30 — 31:
Highlights from your plan
Museo della Porziuncola ©
Museo della Porziuncola
Eremo delle Carceri ©
Eremo delle Carceri

2
nights
Montepulciano

Montepulciano ©
Perched on a limestone ridge in the heart of Tuscany, Montepulciano is known worldwide for its production of red wine, the Vino Noble.
Kick off your visit on the 1st (Sat): take in the architecture and atmosphere at Cappella della Madonna di Vitaleta, then learn about winemaking at Azienda Agricola Patrizia Cencioni Solaria, then do a tasting at Podere Il Cocco, and finally do a tasting at Ciacci Piccolomini d'Aragona. Here are some ideas for day two: don't miss a visit to Vicolo Baciadonne, soothe aching muscles at some of the top local wellness centers, then don't miss a visit to Piazza delle Sorgenti, then make a trip to Piazza Grande a Montepulciano, and finally learn about winemaking at Cantina Fattoria della Talosa.

To find maps, ratings, reviews, and more tourist information, go to the Montepulciano trip planner .

Traveling by car from Assisi to Montepulciano takes 1.5 hours. Alternatively, you can do a combination of train and bus; or take a bus. May in Montepulciano sees daily highs of 74°F and lows of 53°F at night. Finish your sightseeing early on the 2nd (Sun) so you can drive to Siena.

Things to do in Montepulciano

Wineries Spas Historic Sites

Side Trips

Montalcino, San Quirico d'Orcia, Vicolo Baciadonne, Spas & Wellness
Find places to stay May 31 — Jun 2:
Highlights from your plan
Podere Il Cocco ©
Podere Il Cocco
Piazza Grande a Montepulciano ©
Piazza Grande a Montepulciano

2
nights
Siena

Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
Kick off your visit on the 3rd (Mon): indulge your taste buds at Food & Drink. On the next day, take some stellar pictures from Volpaia, then learn about winemaking at Castello di Monterinaldi, then take in the architecture and atmosphere at Siena Cathedral, and finally contemplate the long history of Casa di Santa Caterina.

For traveler tips, ratings, and more tourist information, you can read our Siena trip builder website .

Getting from Montepulciano to Siena by car takes about an hour. Other options: take a train; or take a bus. June in Siena sees daily highs of 84°F and lows of 61°F at night. Wrap up your sightseeing on the 4th (Tue) to allow time to drive to San Gimignano.

Things to do in Siena

Tours Historic Sites Wineries

Side Trip

Radda in Chianti
Find places to stay Jun 2 — 4:
Highlights from your plan
Wine Tours & Tastings
Siena Cathedral ©
Siena Cathedral
Casa di Santa Caterina ©
Casa di Santa Caterina

2
nights
San Gimignano

San Gimignano ©
A historical gem in the heart of Tuscany, San Gimignano is known as the Town of Fine Towers for its jutting skyline of high city walls.
Kick off your visit on the 5th (Wed): contemplate the long history of Historic Centre of San Gimignano, make a trip to Piazza della Cisterna, and then learn about winemaking at Guardastelle Vineyard. Here are some ideas for day two: make a trip to San Gimignano Bell Tower, learn about winemaking at Fattoria Il Piano - Vineyard, get to know the fascinating history of San Gimignano 1300, then make a trip to Duomo di San Gimignano, and finally get engrossed in the history at Torre e Casa Campatelli.

To find traveler tips, where to stay, reviews, and tourist information, use the San Gimignano trip builder website .

Traveling by car from Siena to San Gimignano takes an hour. Alternatively, you can take a bus; or do a combination of train and bus. In June, daily temperatures in San Gimignano can reach 81°F, while at night they dip to 60°F. Finish up your sightseeing early on the 6th (Thu) so you can go by car to Cinque Terre.

Things to do in San Gimignano

Historic Sites Wineries Museums
Find places to stay Jun 4 — 6:
Highlights from your plan
Guardastelle Vineyard ©
Guardastelle Vineyard
Historic Centre of San Gimignano ©
San Gimignano 1300 ©
San Gimignano 1300

2
nights
Cinque Terre

Cinque Terre ©
Made up of five picturesque towns on the Ligurian coast, Cinque Terre is Italy's answer to the French Riviera.
On the 7th (Fri), don't miss a visit to Borgo Antico, make a trip to Chiesa di San Giovanni Battista, then hike along Footpath Monterosso - Vernazza, and finally take a stroll around Vernazza. Here are some ideas for day two: tour the pleasant surroundings at Levanto to Monterosso Trail, appreciate the extensive heritage of Borgo Storico di Corniglia, then explore the historical opulence of Castello Doria, and finally pause for some serene contemplation at Santa Margherita di Antiochia Church.

To find other places to visit, traveler tips, maps, and more tourist information, you can read our Cinque Terre road trip tool .

Drive from San Gimignano to Cinque Terre in 3 hours. Alternatively, you can take a train. June in Cinque Terre sees daily highs of 81°F and lows of 60°F at night. Wrap up your sightseeing on the 8th (Sat) to allow time to take a train to Pisa.

Things to do in Cinque Terre

Trails Parks Outdoors

Side Trip

Levanto to Monterosso Trail
Find places to stay Jun 6 — 8:
Highlights from your plan
Footpath Monterosso - Vernazza ©
Footpath Monterosso - Vernazza
Vernazza ©
Vernazza
Santa Margherita di Antiochia Church ©

2
nights
Pisa

Known worldwide for the Leaning Tower of Pisa, the city of Pisa historically served as a maritime power in the heart of Tuscany.
Kick off your visit on the 9th (Sun): admire the striking features of St Martin Cathedral, then take in the views from Ponte della Maddalena (detto Ponte del Diavolo), then awaken your taste buds at some of the top wineries in the area, and finally steep yourself in history at Chiesa di Santa Maria della Spina. Keep things going the next day: pause for some serene contemplation at Santuario di Montenero and then explore the gorgeous colors at Costiera di Calafuria.

For where to stay, reviews, more things to do, and more tourist information, read Pisa trip itinerary maker website .

Getting from Cinque Terre to Pisa by train takes about 2 hours. Other options: drive; or take a bus. June in Pisa sees daily highs of 81°F and lows of 60°F at night. Cap off your sightseeing on the 10th (Mon) early enough to catch the train to Florence.

Things to do in Pisa

Tours Historic Sites Parks

Side Trips

Livorno, Lucca, Ponte della Maddalena (detto Ponte del Diavolo)
Find places to stay Jun 8 — 10:
Highlights from your plan
Wine Tours & Tastings
St Martin Cathedral ©
St Martin Cathedral
Santuario di Montenero ©
Santuario di Montenero

6
nights
Florence

Florence ©
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
You'll discover tucked-away gems like Centro Storico and Museo Nazionale del Bargello. Dedicate the 15th (Sat) to wine at some of the top wineries in the area. There's still lots to do: explore the world behind art at Uffizi Galleries, examine the collection at Pitti Palace, get the lay of the land with Walking tours, and take some stellar pictures from Piazzale Michelangelo.

To find maps, more things to do, other places to visit, and other tourist information, refer to the Florence trip maker site .

Getting from Pisa to Florence by train takes about an hour. Other options: drive; or take a bus. In June, daytime highs in Florence are 83°F, while nighttime lows are 65°F. Finish up your sightseeing early on the 16th (Sun) so you can travel back home.

Things to do in Florence

Museums Historic Sites Tours
Find places to stay Jun 10 — 16:
Highlights from your plan
Uffizi Galleries ©
Uffizi Galleries
Academy Of Florence Art Gallery ©
Academy Of Florence Art Gallery
Centro Storico ©
Centro Storico

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