16 days in Italy Itinerary

16 days in Italy Itinerary

Created using Inspirock Italy trip itinerary planner

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Route & dates

16 days in Italy Itinerary

Start: Boston
Fly + Drive:  17​h
1
Castelnuovo di Garfagnana
— 1 night
Drive:  2​h
2
Florence
— 3 nights
train:  1​h 45​min
3
Orvieto
— 2 nights
train:  3​h 45​min
4
Sperlonga
— 1 night
train + subway:  4​h 15​min
5
Sorrento
— 3 nights
Drive:  4​h 15​min
6
Montepulciano
— 3 nights
Drive + Fly:  21​h 45​min
End: Boston

1
night
Castelnuovo di Garfagnana

Castelnuovo di Garfagnana
Castelnuovo di Garfagnana is a town and comune in the province of Lucca, Toscana, central Italy. To find photos, reviews, more things to do, and more tourist information, read Castelnuovo di Garfagnana trip planning website .

Boston, USA to Castelnuovo di Garfagnana is an approximately 17-hour combination of flight and car. Due to the time zone difference, you'll lose 6 hours traveling from Boston to Castelnuovo di Garfagnana. Expect somewhat warmer temperatures when traveling from Boston in April; daily highs in Castelnuovo di Garfagnana reach 64°F and lows reach 50°F. You will leave for Florence on the 29th (Wed).

Things to do in Castelnuovo di Garfagnana

Historic Sites Parks Outdoors
Find places to stay Apr 28 — 29:

3
nights
Florence

Florence ©
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Deepen your sense of the past at sights like Cathedral of Santa Maria del Fiore and Abbazia di San Galgano. Discover out-of-the-way places like Pitti Palace and Food Tours. Venture out of the city with trips to Anghiari (in Anghiari), Musei San Domenico (in Forli) and Centro Storico di Siena (in Siena). Next up on the itinerary: get great views at Piazzale Michelangelo, admire the striking features of Loggia dei Lanzi, examine the collection at Museo di Palazzo Davanzati, and appreciate the extensive heritage of Centro Storico.

To find where to stay, reviews, photos, and other tourist information, read our Florence trip itinerary planner .

Drive from Castelnuovo di Garfagnana to Florence in 2 hours. Traveling from Castelnuovo di Garfagnana in May, expect a bit cooler with lows of 52°F in Florence. Finish up your sightseeing early on the 4th (Mon) so you can catch the train to Orvieto.

Things to do in Florence

Museums Historic Sites Tours

Side Trips

Anghiari, Musei San Domenico, Abbazia di San Galgano
Find places to stay Apr 29 — May 2:
Highlights from your plan
Academy Of Florence Art Gallery ©
Academy Of Florence Art Gallery
Abbazia di San Galgano ©
Abbazia di San Galgano
Anghiari ©
Anghiari

2
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.
To see maps, photos, reviews, and tourist information, read our Orvieto trip itinerary planning site .

Traveling by train from Florence to Orvieto takes 2 hours. Alternatively, you can drive; or take a bus. In May, plan for daily highs up to 71°F, and evening lows to 51°F. You'll have a few hours on the 6th (Wed) to wrap things up before traveling to Sperlonga.

Things to do in Orvieto

Historic Sites Parks Nature
Find places to stay May 2 — 4:
Highlights from your plan
Duomo di Orvieto ©
Duomo di Orvieto
Chiesa San Giovenale ©
Chiesa San Giovenale
Sant'Andrea, Orvieto ©
Sant'Andrea, Orvieto

1
night
Sperlonga

Sperlonga ©
Sperlonga is a coastal town in the province of Latina, Italy, about halfway between Rome and Naples.Surrounding towns include Terracina to the West, Fondi to the North, Itri to the North-East, and Gaeta to the East.HistoryLocated near the Via Appia, but also on the edge of the Pontine Marshes, Roman "Spelunca" (Latin for cave or grotto) was only known for the grotto on the coast, after which it was named. Start off your visit on the 6th (Wed): enjoy the sand and surf at Lido Beluga, then get outside with Roccia dei Falchi, and then explore the ancient world of Villa Di Tiberio.

To find more things to do, photos, where to stay, and other tourist information, you can read our Sperlonga vacation maker .

Traveling by car from Orvieto to Sperlonga takes 3 hours. Alternatively, you can take a train. Expect a daytime high around 74°F in May, and nighttime lows around 53°F. Finish your sightseeing early on the 6th (Wed) to allow enough time to drive to Sorrento.

Things to do in Sperlonga

Parks Outdoors Historic Sites

Side Trip

Old Town
Find places to stay May 4 — 5:
Highlights from your plan
Porto di Sperlonga ©
Porto di Sperlonga
Villa Di Tiberio ©
Villa Di Tiberio
Roccia dei Falchi ©
Roccia dei Falchi

3
nights
Sorrento

Sorrento ©
A lovely town easily accessible from almost anywhere in the country, Sorrento overlooks the Bay of Naples and sits right on the Amalfi Drive.
Get some historical perspective at Duomo di Sant'Andrea and Pompeii Archaeological Park. Explore hidden gems such as St Francis Church and Convent and Food Tours. You'll find plenty of places to visit near Sorrento: Cloister del Paradiso (in Amalfi) and Duomo di Ravello (in Ravello). There's lots more to do: make a trip to Piazza Tasso, walk around Villa Comunale, learn about winemaking at Limonoro, and take in the exciting artwork at Absolute Positano.

To find more things to do, photos, traveler tips, and tourist information, read Sorrento trip app .

Traveling by car from Sperlonga to Sorrento takes 3 hours. Alternatively, you can do a combination of train and subway; or do a combination of train and bus. Plan for somewhat warmer nights when traveling from Sperlonga in May since evenings lows in Sorrento dip to 60°F. Cap off your sightseeing on the 8th (Fri) early enough to travel back home.

Things to do in Sorrento

Historic Sites Parks Tours

Side Trips

Amalfi, Absolute Positano, Duomo di Ravello, Pompeii Archaeological Park
Find places to stay May 5 — 8:
Highlights from your plan
Duomo di Sant'Andrea ©
Duomo di Sant'Andrea
Pompeii Archaeological Park ©
Pompeii Archaeological Park
Duomo di Ravello ©
Duomo di Ravello

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.
Start off your visit on the 9th (Sat): contemplate in the serene atmosphere at Cathedral, steep yourself in history at Palazzo Piccolomini, look for gifts at La Taverna del Pecorino, then get to know the fascinating history of Montefollonico Centro Storico, then learn about winemaking at De' Ricci, and finally do a tasting at Azienda Agricola Ercolani. Keep things going the next day: make a trip to Terrazza Del Palazzo Comunale, learn about winemaking at Cantina Fattoria della Talosa, explore the world behind art at Museo Civico Archeologico delle Acque, appreciate the views at Val d'Orcia, then take in the architecture and atmosphere at Cappella della Madonna di Vitaleta, and finally do a tasting at Winery Solaria Patrizia Cencioni.

To see more things to do, ratings, traveler tips, and more tourist information, go to the Montepulciano vacation planner .

You can drive from Sorrento to Montepulciano in 4.5 hours. Other options are to do a combination of subway and train; or take a bus. Traveling from Sorrento in May, Montepulciano is slightly colder at night with lows of 53°F. Wrap up your sightseeing by early afternoon on the 11th (Mon) to allow enough time to travel back home.

Things to do in Montepulciano

Historic Sites Wineries Museums

Side Trips

Pienza, Museo Civico Archeologico delle Acque, Winery Solaria Patrizia Cencioni, Montefollonico Centro Storico, Val d'Orcia
Find places to stay May 8 — 11:
Highlights from your plan
Val d'Orcia ©
Val d'Orcia
Cappella della Madonna di Vitaleta ©
Winery Solaria Patrizia Cencioni ©
Winery Solaria Patrizia Cencioni

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