39 days in Italy Itinerary

39 days in Italy Itinerary

Created using Inspirock Italy sightseeing planner

Plan created by another user. Make it yours

Route & dates

1
Milan
— 9 nights
2
Florence
— 1 night
3
Cortona
— 1 night
4
Siena
— 1 night
5
Isola Del Giglio
— 1 night
6
Capoliveri, Elba Island
— 1 night
7
Bolgheri
— 1 night
8
Lucca
— 2 nights
9
Assisi
— 2 nights
10
Orvieto
— 3 nights
11
Castelluccio di Norcia
— 3 nights
12
Pisa
— 3 nights
13
Montepulciano
— 3 nights
14
Andora
— 2 nights
15
Genoa
— 2 nights
16
Cinque Terre
— 3 nights

9
nights
Milan

Milan ©
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.
Venture out of the city with trips to Gardaland Park (in Castelnuovo del Garda) and Verona (Museo Conte, Arena di Verona, &more). Next up on the itinerary: contemplate in the serene atmosphere at Duomo di Milano, see La Casa Maledetta, admire the masterpieces at Pinacoteca di Brera, and browse the different shops at Galleria Vittorio Emanuele II.

For ratings, where to stay, other places to visit, and more tourist information, go to the Milan trip planning website.

If you are flying in from United States, the closest major aiports are Malpensa International Airport, Milano Linate Airport and Il Caravaggio International Airport. In August, daytime highs in Milan are °F, while nighttime lows are °F. Finish up your sightseeing early on the 10th (Mon) so you can catch the train to Florence.

Things to do in Milan

Historic Sites Museums Tours

Side Trips

Verona, Gardaland Park
Find places to stay Aug 1 — 10:
Highlights from your plan
Duomo di Milano ©
Duomo di Milano
Arena di Verona ©
Arena di Verona
Galleria Vittorio Emanuele II ©
Galleria Vittorio Emanuele II

1
night
Florence

Florence ©
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Start off your visit on the 11th (Tue): appreciate the history behind Ratto di Polissena, explore the world behind art at Florence Academy of Fine Arts, make a trip to Piazzale Michelangelo, thensnap pictures at Ponte Vecchio, thenget to know the fascinating history of Piazza del Duomo, and finally take in the spiritual surroundings of Cathedral of Santa Maria del Fiore.

To see where to stay, reviews, other places to visit, and tourist information, go to the Florence day trip planner.

Getting from Milan to Florence by train takes about 2.5 hours. Other options: drive; or fly. In August in Florence, expect temperatures between °F during the day and °F at night. Wrap up your sightseeing on the 11th (Tue) early enough to drive to Cortona.

Things to do in Florence

Historic Sites Museums
Find places to stay Aug 10 — 11:
Highlights from your plan
Florence Academy of Fine Arts ©
Florence Academy of Fine Arts
Cathedral of Santa Maria del Fiore ©
Cathedral of Santa Maria del Fiore
Piazzale Michelangelo ©
Piazzale Michelangelo

1
night
Cortona

The hilltop town of Cortona gained international attention as the subject of the 2003 film "Under the Tuscan Sun." With the Chiana Valley and Lake Trasimeno as its backdrop, Cortona is one of Tuscany's hotspots for art and culture.
On the 12th (Wed), take in the spiritual surroundings of Eremo Le Celle, thenawaken your taste buds at some of the top wineries in the area, thenmake a trip to Piazza della Repubblica, and finally stop by Silvia Taccola Vanni - Laboratorio Stilistico.

For reviews, photos, more things to do, and more tourist information, you can read our Cortona online vacation builder.

Getting from Florence to Cortona by car takes about 2 hours. Other options: take a train. Finish your sightseeing early on the 12th (Wed) to allow enough time to drive to Siena.

Things to do in Cortona

Wineries Tours Historic Sites
Find places to stay Aug 11 — 12:
Highlights from your plan
Wine Tours & Tastings
Eremo Le Celle ©
Eremo Le Celle
Silvia Taccola Vanni - Laboratorio Stilistico ©

1
night
Siena

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 13th (Thu): don't miss a visit to Piazza del Campo, thendon't miss a visit to Centro Storico di Siena, and then enjoy breathtaking views from Torre del Mangia.

To see photos, other places to visit, and tourist information, you can read our Siena travel route builder website.

You can drive from Cortona to Siena in 1.5 hours. Other options are to take a train; or do a combination of train and bus. August in Siena sees daily highs of °F and lows of °F at night. Finish your sightseeing early on the 13th (Thu) to allow enough time to travel to Isola Del Giglio.

Things to do in Siena

Historic Sites
Find places to stay Aug 12 — 13:
Highlights from your plan
Piazza del Campo ©
Piazza del Campo
Torre del Mangia ©
Torre del Mangia

1
night
Isola Del Giglio

Isola Del Giglio ©
Start off your visit on the 14th (Fri): tour the pleasant surroundings at Spiaggia delle Caldane, thenkick back and relax at La Playa del Carma, and then head off the coast to Giglio Island.

To see reviews, other places to visit, maps, and more tourist information, read our Isola Del Giglio trip planner.

Traveling by combination of car and ferry from Siena to Isola Del Giglio takes 3.5 hours. Alternatively, you can do a combination of bus and ferry; or do a combination of bus, train, and ferry. In August, plan for daily highs up to °F, and evening lows to °F. Cap off your sightseeing on the 14th (Fri) early enough to travel to Capoliveri.

Things to do in Isola Del Giglio

Parks Outdoors Beaches
Find places to stay Aug 13 — 14:
Highlights from your plan
Spiaggia delle Caldane ©
Spiaggia delle Caldane
Giglio Island ©
Giglio Island

1
night
Capoliveri, Elba Island

Capoliveri ©
Capoliveri is a comune (municipality) on the island of Elba in Italy. Start off your visit on the 15th (Sat): tour the pleasant surroundings at Spiaggia Della Biodola, kick back and relax at Spiaggia Di Sansone, and then don't miss a visit to Spiaggia di Lacona.

To see where to stay, other places to visit, photos, and tourist information, you can read our Capoliveri trip planner.

Getting from Isola Del Giglio to Capoliveri by combination of ferry, bus, and train takes about 9.5 hours. Other options: do a combination of ferry and bus. Traveling from Isola Del Giglio in August, expect nights in Capoliveri to be about the same, around °F, while days are a bit cooler, around °F. Wrap up your sightseeing on the 15th (Sat) early enough to travel to Bolgheri.

Things to do in Capoliveri

Outdoors Beaches Parks

Side Trip

Portoferraio
Find places to stay Aug 14 — 15:
Highlights from your plan
Spiaggia Di Sansone ©
Spiaggia Di Sansone
Spiaggia di Lacona ©
Spiaggia di Lacona
Spiaggia Della Biodola ©
Spiaggia Della Biodola

1
night
Bolgheri

Bolgheri ©
Start off your visit on the 16th (Sun): cruise along Viale dei Cipressi, take in the architecture and atmosphere at Chiesa dei Santi Giacomo e Cristoforo, do a tasting at Fattoria Terre del Marchesato, do a tasting at Batzella, thenget outside with Bagni Sirena, and finally don't miss a visit to Bolgheri - Borgo Medievale.

To see other places to visit, maps, more things to do, and other tourist information, refer to the Bolgheri planner.

Do a combination of car and ferry from Capoliveri to Bolgheri in 3 hours. Alternatively, you can do a combination of bus and ferry; or do a combination of bus, ferry, and train. In August, daytime highs in Bolgheri are °F, while nighttime lows are °F. Finish up your sightseeing early on the 16th (Sun) so you can go by car to Lucca.

Things to do in Bolgheri

Wineries Outdoors Scenic Drive

Side Trips

Castagneto Carducci, Bagni Sirena
Find places to stay Aug 15 — 16:
Highlights from your plan
Batzella ©
Batzella
Fattoria Terre del Marchesato ©
Fattoria Terre del Marchesato
Bagni Sirena ©
Bagni Sirena

2
nights
Lucca

Lucca ©
Lucca, famous for its intact Renaissance-era city walls, remained an independent city-state until the end of the 18th century.
Kick off your visit on the 17th (Mon): appreciate the extensive heritage of Montecatini Alto, don't miss a visit to Piazza Giuseppe Giusti, don't miss a visit to Torre delle Ore, thenadmire the landmark architecture of St Martin Cathedral, thentake in the spiritual surroundings of San Michele in Foro, and finally take in panoramic vistas at Torre Guinigi.

To see traveler tips, maps, ratings, and tourist information, read Lucca vacation maker tool.

Traveling by car from Bolgheri to Lucca takes 1.5 hours. Alternatively, you can do a combination of bus and train; or take a bus. In August, daytime highs in Lucca are °F, while nighttime lows are °F. Wrap up your sightseeing by early afternoon on the 18th (Tue) to allow enough time to drive to Assisi.

Things to do in Lucca

Historic Sites

Side Trip

Montecatini Terme
Find places to stay Aug 16 — 18:
Highlights from your plan
Le mura di Lucca ©
Le mura di Lucca
Torre Guinigi ©
Torre Guinigi
San Michele in Foro ©
San Michele in Foro

2
nights
Assisi

Assisi ©
Rich in culture and religious tradition, Assisi is known as the birthplace of St.
On the 18th (Tue), pause for some serene contemplation at Chiesa di San Giacomo De Muro Rotto and then take in the spiritual surroundings of Eremo delle Carceri. Get ready for a full day of sightseeing on the next day: do a tasting at Azienda Agraria Saio, learn about winemaking at BIBENDA ASSISI WINE BAR-WINE VINO, CHOCOLATE, OLIVE OIL,TRUFFLE TASTING, take in the spiritual surroundings of Basilica di Santa Chiara, thentake in the architecture and atmosphere at Basilica Papale e Sacro Convento di San Francesco d'Assisi, and finally make a trip to Piazza Inferiore di San Francesco.

To see photos, more things to do, traveler tips, and more tourist information, go to the Assisi trip planner.

Traveling by car from Lucca to Assisi takes 3 hours. Alternatively, you can take a train; or take a bus. Expect a daytime high around °F in August, and nighttime lows around °F. Finish your sightseeing early on the 20th (Thu) so you can drive to Orvieto.

Things to do in Assisi

Historic Sites Wineries Museums
Find places to stay Aug 18 — 20:
Highlights from your plan
Tili Vini Societa Agricola ©
Tili Vini Societa Agricola
Azienda Agraria Saio ©
Azienda Agraria Saio

3
nights
Orvieto

Orvieto ©
The striking town of Orvieto, perched on a volcanic cliff overlooking the Umbrian countryside, is known as the Green Heart of Italy.
Kick off your visit on the 21st (Fri): take in the architecture and atmosphere at Chiesa di Santa Maria e San Rocco, take in the natural beauty of Cascate del Mulino, examine the collection at Museo Civico Archeologico della Civilta Etrusca, see the interesting displays at Etruscan Museum "Claudio Faina", thenHead underground at Orvieto Underground, and finally admire the striking features of Duomo di Orvieto. On the next day, learn about winemaking at Decugnano dei Barbi, thensteep yourself in history at Porta Romana, thenadmire the sheer force of Cascata delle Marmore, and finally take in the architecture and atmosphere at Chiesa San Francesco d’Assisi.

To find maps, more things to do, other places to visit, and other tourist information, go to the Orvieto online road trip planner.

You can drive from Assisi to Orvieto in 1.5 hours. Alternatively, you can take a train; or take a bus. In August, daytime highs in Orvieto are °F, while nighttime lows are °F. On the 23rd (Sun), wrap the sightseeing up by early afternoon so you can drive to Castelluccio di Norcia.

Things to do in Orvieto

Nature Parks Historic Sites

Side Trips

Pitigliano, Terni, Cascate del Mulino, Porta Romana
Find places to stay Aug 20 — 23:
Highlights from your plan
Decugnano dei Barbi ©
Decugnano dei Barbi
Cascata delle Marmore ©
Cascata delle Marmore
Cascate del Mulino ©
Cascate del Mulino

3
nights
Castelluccio di Norcia

Castelluccio di Norcia ©
Change things up with these side-trips from Castelluccio di Norcia: Chiesa di Sant'Agata (in Arquata del Tronto), Visso (Santuario di Macereto, Museo Civico Diocesano - Museo dei Manoscritti Leopardiani, &more) and Abbazia di S. Eutizio (in Preci).

For other places to visit, maps, photos, and more tourist information, use the Castelluccio di Norcia visit planner.

You can drive from Orvieto to Castelluccio di Norcia in 3 hours. While traveling from Orvieto, expect cooler days and slightly colder nights in Castelluccio di Norcia, ranging from highs of °F to lows of °F. Wrap up your sightseeing on the 26th (Wed) early enough to travel to Pisa.

Things to do in Castelluccio di Norcia

Parks Nature Historic Sites

Side Trips

Visso, Chiesa di Sant'Agata, Gole dell’Infernaccio, Castelluccio, Lago di Pilato
Find places to stay Aug 23 — 26:
Highlights from your plan
Piana di Castelluccio di Norcia ©
Piana di Castelluccio di Norcia
Lago di Pilato ©
Lago di Pilato
Parco Nazionale dei Monti Sibillini ©
Parco Nazionale dei Monti Sibillini

3
nights
Pisa

Pisa ©
Known worldwide for the Leaning Tower of Pisa, the city of Pisa historically served as a maritime power in the heart of Tuscany.
Explore Pisa's surroundings by going to Livorno (Acquario di Livorno, Terrazza Mascagni, &more). Next up on the itinerary: enjoy breathtaking views from Leaning Tower of Pisa, take in the spiritual surroundings of Duomo di Pisa, admire the striking features of Baptistery of St. John, and don't miss a visit to Basilica romanica di San Piero a Grado.

To find more things to do, reviews, and other tourist information, refer to the Pisa journey builder tool.

You can drive from Castelluccio di Norcia to Pisa in 4.5 hours. Traveling from Castelluccio di Norcia in August, expect nights in Pisa to be somewhat warmer, around °F, while days are much warmer, around °F. Cap off your sightseeing on the 29th (Sat) early enough to go by car to Montepulciano.

Things to do in Pisa

Historic Sites Zoos & Aquariums Parks

Side Trip

Livorno
Find places to stay Aug 26 — 29:
Highlights from your plan
Leaning Tower of Pisa ©
Leaning Tower of Pisa
Piazza dei Miracoli ©
Piazza dei Miracoli
Duomo di Pisa ©
Duomo di Pisa

3
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.
On the 30th (Sun), indulge in some personalized pampering at some of the best spas, look for all kinds of wild species at Fosso Bianco - Bagni San Filippo, contemplate the long history of Historic Centre of the City of Pienza, thendo a tasting at Cantina Fattoria della Talosa, thendon't miss a visit to Piazza Grande a Montepulciano, and finally view the masterpieces at Quinteaquadri Lab Gallery. Get ready for a full day of sightseeing on the 31st (Mon): do a tasting at Podere Il Cocco, thentake in the architecture and atmosphere at Abbazia di Sant'Antimo, thenlearn about winemaking at Ciacci Piccolomini d'Aragona, and finally take in panoramic vistas at Fortezza di Montalcino.

To see where to stay, reviews, traveler tips, and other tourist information, use the Montepulciano trip itinerary app.

Traveling by car from Pisa to Montepulciano takes 2.5 hours. Alternatively, you can take a bus; or take a train. In August, daily temperatures in Montepulciano can reach °F, while at night they dip to °F. On the 1st (Tue), wrap the sightseeing up by early afternoon so you can travel to Andora.

Things to do in Montepulciano

Wineries Historic Sites Wildlife

Side Trips

Montalcino, Spas, Historic Centre of the City of Pienza, Fosso Bianco - Bagni San Filippo
Find places to stay Aug 29 — Sep 1:
Highlights from your plan
Ciacci Piccolomini d'Aragona ©
Ciacci Piccolomini d'Aragona
Podere Il Cocco ©
Podere Il Cocco
Tenuta Valdipiatta ©
Tenuta Valdipiatta

2
nights
Andora

Andora ©
On the 2nd (Wed), head outdoors with Bagni Regina, thentake advantage of the amenities at Bagni Costa d'Oro, thenenjoy the sand and surf at Bagni Colombo Andora, and finally appreciate the extensive heritage of Budello di Alassio. On the 3rd (Thu), you'll have a packed day of sightseeing: delve into the distant past at Old Bussana (Bussana Vecchia), thenstroll through Pista Ciclabile Area 24 - Sanremo, and then appreciate the extensive heritage of Centro Storico di Cervo.

To find traveler tips, photos, maps, and more tourist information, refer to the Andora route builder website.

Traveling by car from Montepulciano to Andora takes 5 hours. Alternatively, you can do a combination of car and flight. Expect a daytime high around °F in September, and nighttime lows around °F. Wrap up your sightseeing on the 3rd (Thu) to allow time to drive to Genoa.

Things to do in Andora

Outdoors Historic Sites Parks

Side Trips

Sanremo, Centro Storico di Cervo, Budello di Alassio
Find places to stay Sep 1 — 3:
Highlights from your plan
Bagni Costa d'Oro ©
Bagni Costa d'Oro
Bagni Regina ©
Bagni Regina
Budello di Alassio ©
Budello di Alassio

2
nights
Genoa

Genoa ©
Once the most important harbor in the Mediterranean Sea, Genoa has a long history as a rich and powerful trade center in northern Italy.
On the 4th (Fri), take in the spiritual surroundings of Cattedrale di San Lorenzo - Duomo di Genova, meet the residents at Aquarium of Genoa, thenexamine the collection at Galata Museo del Mare, and finally take in the waterfront at Old Port. Get ready for a full day of sightseeing on the next day: make a trip to Piazza Raffaele De Ferrari, browse for treasures at Rattopennugo, get to know the fascinating history of Via Giuseppe Garibaldi, thenget to know the fascinating history of Passeggiata Anita Garibaldi a Nervi, and finally visit Boccadasse.

Make your Genoa itinerary with Inspirock to find out what to see and where to go.

Traveling by car from Andora to Genoa takes 1.5 hours. In September, daily temperatures in Genoa can reach °F, while at night they dip to °F. Finish up your sightseeing early on the 5th (Sat) so you can catch the train to Cinque Terre.

Things to do in Genoa

Historic Sites Zoos & Aquariums Parks
Find places to stay Sep 3 — 5:
Highlights from your plan
Passeggiata Anita Garibaldi a Nervi ©
Passeggiata Anita Garibaldi a Nervi
Aquarium of Genoa ©
Aquarium of Genoa
Boccadasse ©
Boccadasse

3
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 6th (Sun), cruise along Ponte Thaon di Revel, thenvisit Portovenere, and then hike along Cinque Terre footpaths. Keep things going the next day: look for gifts at Fannys Bazar, hike along Cinque Terre Trails, explore the historical opulence of Castello Doria, thentrek along Footpath Monterosso - Vernazza, and finally get into the urban bustle at Vernazza.

To find ratings, where to stay, photos, and other tourist information, you can read our Cinque Terre trip itinerary maker tool.

You can take a train from Genoa to Cinque Terre in 2 hours. Alternatively, you can drive; or do a combination of bus and train. Plan for little chillier nights when traveling from Genoa in September since evenings lows in Cinque Terre dip to °F. On the 8th (Tue), wrap the sightseeing up by early afternoon so you can drive back home.

Things to do in Cinque Terre

Outdoors Historic Sites Trails

Side Trips

Portovenere, Ponte Thaon di Revel
Find places to stay Sep 5 — 8:
Highlights from your plan
Footpath Monterosso - Vernazza ©
Footpath Monterosso - Vernazza
Portovenere ©
Portovenere
Cinque Terre footpaths ©
Cinque Terre footpaths

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