31 days in Italy Itinerary

31 days in Italy Itinerary

Created using Inspirock Italy tour planner

Plan created by another user.Make it yours

Route & dates

Start: Positano
1
Positano
— 4 nights
Drive:  1 h 30 min
2
Naples
— 4 nights
Drive:  1 h 45 min
3
Ischia
— 3 nights
+2
Ferry + Subway + Train:  2 h 45 min
4
Rome
— 4 nights
Drive:  2 h
5
Montepulciano
— 2 nights
Drive:  30 min
6
Pienza
— 3 nights
Drive:  30 min
7
Bagno Vignoni
— 2 nights
Drive:  30 min
8
Montalcino
— 3 nights
Drive:  2 h
9
Florence
— 5 nights
Train:  1 h 45 min
End: Milan

4
nights
Positano

Positano ©
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.
You've now added Walk of the Gods to your itinerary. Venture out of the city with trips to Amalfi (Duomo di Sant'Andrea & Museo della Carta) and Ravello (Villa Cimbrone Gardens, Villa Rufolo, &more). And it doesn't end there: take some stellar pictures from Il Sentiero Degli Dei, look for gifts at Nana' Positano, let your taste buds guide you at a local gastronomic tour, and contemplate in the serene atmosphere at Church of Santa Maria Assunta.

To see traveler tips, other places to visit, more things to do, and more tourist information, read our Positano online trip maker.

If you are flying in from United States, the closest major aiport is Naples International Airport. In May, daytime highs in Positano are 74°F, while nighttime lows are 60°F. You will have some time to spend on the 20th (Wed) before leaving for Naples.

Things to do in Positano

Outdoors Tours Wildlife

Side Trips

Amalfi, Ravello, I Suoni degli Dei - Pelagos
Highlights from your plan
Fornillo ©
Fornillo
Villa Cimbrone Gardens ©
Villa Cimbrone Gardens
Il Sentiero Degli Dei ©
Il Sentiero Degli Dei

4
nights
Naples

Naples ©
Naples is the capital of the Italian region Campania and the third-largest municipality in Italy after Rome and Milan. You've now added Free Tour Taste of Naples’ History and Limoncello to your itinerary. You'll find plenty of places to visit near Naples: Vesuvio National Park (in Ottaviano) and Reggia di Caserta (in Caserta). The adventure continues: examine the collection at Museo Archeologico Nazionale di Napoli, pause for some serene contemplation at Cloister of Santa Chiara, stroll the grounds of Catacombe di San Gennaro, and get to know the fascinating history of Underground Naples.

For reviews, photos, other places to visit, and more tourist information, read Naples trip maker website.

Drive from Positano to Naples in 1.5 hours. Alternatively, you can take a bus; or do a combination of bus and subway. Expect a daytime high around 74°F in May, and nighttime lows around 58°F. On the 24th (Sun), wrap the sightseeing up by early afternoon so you can drive to Ischia.

Things to do in Naples

Historic Sites Museums Parks

Side Trips

Parco Acheologico di Ercolano, Vesuvio National Park, Reggia di Caserta
Highlights from your plan
Miglio Sacro ©
Miglio Sacro
Museo Archeologico Nazionale di Napoli ©
Museo Archeologico Nazionale di Napoli
Museo Cappella Sansevero ©
Museo Cappella Sansevero

3
nights
Ischia

Ischia ©
Ischia is a volcanic island in the Tyrrhenian Sea. Venture out of the city with trips to The Port of Corricella (in Procida) and Baia di Sorgeto (in Panza). There's still lots to do: make a trip to Castello Aragonese d'Ischia, contemplate the long history of Sant'Angelo (Serrara Fontana), enjoy the sand and surf at Maronti Beach, and tour the pleasant surroundings at Spiaggia di Citara.

To find ratings, photos, and other tourist information, go to the Ischia travel itinerary planner.

Traveling by car from Naples to Ischia takes 2.5 hours. In May, daily temperatures in Ischia can reach 74°F, while at night they dip to 60°F. On the 27th (Wed), you'll have the morning to explore before heading off to Rome.

Things to do in Ischia

Parks Historic Sites Nature

Side Trips

Forio, Sant'Angelo (Serrara Fontana), The Port of Corricella, Baia di Sorgeto
Highlights from your plan
Maronti Beach ©
Maronti Beach
Castello Aragonese d'Ischia ©
Castello Aragonese d'Ischia
The Port of Corricella ©
The Port of Corricella

4
nights
Rome

Rome ©
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 plan includes some of its best attractions: explore the ancient world of Colosseum, explore the world behind art at Vatican Museums, make a trip to Piazza Navona, and indulge in some culinary diversions at a local gastronomic tour.

To see where to stay, traveler tips, and tourist information, go to the Rome trip itinerary maker.

You can do a combination of ferry and train from Ischia to Rome in 4 hours. Other options are to do a combination of ferry and car; or do a combination of ferry and bus. In May, plan for daily highs up to 75°F, and evening lows to 58°F. Finish your sightseeing early on the 31st (Sun) so you can drive to Montepulciano.

Things to do in Rome

Historic Sites Museums Tours

Side Trip

Vatican City
Highlights from your plan
Colosseum ©
Colosseum
Pantheon ©
Pantheon
Trevi Fountain ©
Trevi Fountain

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.
On the 1st (Mon), make a trip to Piazza Grande a Montepulciano, don't miss a visit to Terrazza Del Palazzo Comunale, thenindulge in some personalized pampering at some of the best spas, thencontemplate in the serene atmosphere at Eremo Le Celle, and finally do a tasting at Azienda Agricola Leuta. On the 2nd (Tue), you'll have a packed day of sightseeing: contemplate in the serene atmosphere at Tempio di San Biagio, do a tasting at Tenuta Valdipiatta, do a tasting at Az. Agr. Poliziano, thenget engrossed in the history at MAEC - Museo dell'Accademia Etrusca, and finally see the interesting displays at Museo Diocesano.

To find more things to do, traveler tips, maps, and tourist information, read our Montepulciano day trip site.

Drive from Rome to Montepulciano in 2 hours. Alternatively, you can take a bus; or take a train. Traveling from Rome in May, plan for little chillier nights in Montepulciano, with lows around 53°F. Cap off your sightseeing on the 2nd (Tue) early enough to go by car to Pienza.

Things to do in Montepulciano

Wineries Historic Sites Spas

Side Trips

Cortona, Spas
Highlights from your plan
Azienda Agricola Leuta ©
Azienda Agricola Leuta
Tenuta Valdipiatta ©
Tenuta Valdipiatta
Eremo Le Celle ©
Eremo Le Celle

3
nights
Pienza

Pienza ©
Pienza, a town and comune in the province of Siena, in the Val d'Orcia in Tuscany (central Italy), between the towns of Montepulciano and Montalcino, is the "touchstone of Renaissance urbanism."In 1996, UNESCO declared the town a World Heritage Site, and in 2004 the entire valley, the Val d'Orcia, was included on the list of UNESCO's World Cultural Landscapes.HistoryBefore the village was renamed to Pienza its name was Corsignano. Pienza is known for historic sites, museums, and shopping. Your plan includes some of its best attractions: appreciate the views at Val d'Orcia, learn about winemaking at Enoteca Di Ghino, look for gifts at Zazzeri Pienza, and experience rural life at Podere Il Casale.

To find maps, traveler tips, more things to do, and more tourist information, read our Pienza online trip builder.

Pienza is just a short distance from Montepulciano. In June, daytime highs in Pienza are 84°F, while nighttime lows are 61°F. Cap off your sightseeing on the 5th (Fri) early enough to travel to Bagno Vignoni.

Things to do in Pienza

Historic Sites Parks Wildlife

Side Trips

San Quirico d'Orcia, Tuscany
Highlights from your plan
Val d'Orcia ©
Val d'Orcia
Cappella della Madonna di Vitaleta ©
Cappella della Madonna di Vitaleta
Piazza Pio II ©
Piazza Pio II

2
nights
Bagno Vignoni

Bagno Vignoni ©
Start off your visit on the 6th (Sat): take in the natural beauty of Parco dei Mulini, thenget a taste of the local shopping with Librorcia Bagno Vignoni, thensteep yourself in history at Terme Bagno Vignoni, and finally visit Piscina Val di Sole. Here are some ideas for day two: admire the natural beauty at Il giardino di Daniel Spoerri, pause for some serene contemplation at Chiesa della Madonna dei Remedi, look for all kinds of wild species at Fosso Bianco - Bagni San Filippo, thentake a stroll around San Quirico d'Orcia, and finally take in the architecture and atmosphere at Chiesa di San Giovanni Battista.

To find maps, reviews, other places to visit, and more tourist information, read Bagno Vignoni trip planner.

Bagno Vignoni is just a short distance from Pienza. In June, plan for daily highs up to 84°F, and evening lows to 61°F. Wrap up your sightseeing on the 7th (Sun) to allow time to drive to Montalcino.

Things to do in Bagno Vignoni

Historic Sites Parks Shopping

Side Trips

San Quirico d'Orcia, Chiesa della Madonna dei Remedi, Fosso Bianco - Bagni San Filippo, Il giardino di Daniel Spoerri
Highlights from your plan
Terme Bagno Vignoni ©
Terme Bagno Vignoni
San Quirico d'Orcia ©
San Quirico d'Orcia
Il giardino di Daniel Spoerri ©
Il giardino di Daniel Spoerri

3
nights
Montalcino

Montalcino ©
In the heart of wine country, the hill town of Montalcino offers a glimpse of untouched medieval-era Tuscany.
You'll find plenty of places to visit near Montalcino: Crete Senesi (in Asciano) and Eremo di Montesiepi (in Chiusdino). And it doesn't end there: learn about winemaking at Ciacci Piccolomini d'Aragona, contemplate in the serene atmosphere at Abbazia di Monte Oliveto Maggiore, and steep yourself in history at Abbazia di Sant'Antimo.

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

Montalcino is just a short distance from Bagno Vignoni. In June, daytime highs in Montalcino are 84°F, while nighttime lows are 61°F. Finish up your sightseeing early on the 10th (Wed) so you can go by car to Florence.

Things to do in Montalcino

Wineries Historic Sites Wildlife

Side Trips

Asciano, Eremo di Montesiepi
Highlights from your plan
Ciacci Piccolomini d'Aragona ©
Ciacci Piccolomini d'Aragona
Castiglion del Bosco ©
Castiglion del Bosco
Mate Winery ©
Mate Winery

5
nights
Florence

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Step out of Florence to go to Pisa and see Leaning Tower of Pisa, which is approximately 1h 15 min away. There's much more to do: make a trip to Piazzale Michelangelo, pause for some serene contemplation at Basilica of Santa Croce, contemplate in the serene atmosphere at The Baptistery of St. John, and snap pictures at Ponte Vecchio.

To see other places to visit, traveler tips, where to stay, and other tourist information, use the Florence online trip itinerary maker.

You can drive from Montalcino to Florence in 2 hours. Other options are to take a bus; or do a combination of bus and train. In June, daily temperatures in Florence can reach 83°F, while at night they dip to 65°F. Finish your sightseeing early on the 15th (Mon) to allow enough time to take a train back home.

Things to do in Florence

Historic Sites Tours Museums

Side Trip

Leaning Tower of Pisa
Highlights from your plan
Food Tours
Piazzale Michelangelo ©
Piazzale Michelangelo
Florence Academy of Fine Arts ©
Florence Academy of Fine Arts

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