14 days in Italy Itinerary

14 days in Italy Itinerary

Created using Inspirock Tuscany tour itinerary planner

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Route & dates

14 days in Italy Itinerary

Start: San Quirico d'Orcia
1
San Quirico d'Orcia
— 3 nights
bus:  30​min
2
Montalcino
— 3 nights
Drive:  1​h 15​min
3
Cortona
— 2 nights
Drive:  45​min
4
Montepulciano
— 2 nights
Drive:  30​min
5
Pienza
— 3 nights
End: San Quirico d'Orcia

3
nights
San Quirico d'Orcia

San Quirico d'Orcia ©
San Quirico d'Orcia is a comune (municipality) of about 2,500 inhabitants in the Province of Siena in the Italian region Tuscany, located about 80km southeast of Florence and about 35km southeast of Siena inside the Valdorcia landscape. Step off the beaten path and head to San Quirico d'Orcia and Parco Archeologico Citta del Tufo. Explore San Quirico d'Orcia's surroundings by going to Chiesa di Santa Maria Maggiore (in Sovana), Piancastagnaio (Rocca degli Aldobrandeschi & Piancastagnaio) and Azienda Vitivinicola Villa Corano (in Pitigliano). There's lots more to do: make a trip to Piazza delle Sorgenti, get in on the family fun at Indiana Park Amiata, pause for some serene contemplation at Chiesa di San Giovanni Battista, and take some stellar pictures from Cipressi di San Quirico d'Orcia.

To find more things to do, ratings, reviews, and tourist information, read San Quirico d'Orcia online day trip planner .

If you are flying in from United Kingdom, the closest major airports are Perugia San Francesco d'Assisi – Umbria International Airport, Peretola Airport and Pisa International Airport. In May in San Quirico d'Orcia, expect temperatures between 27°C during the day and 13°C at night. Finish your sightseeing early on the 8th (Wed) to allow enough time to drive to Montalcino.

Things to do in San Quirico d'Orcia

Wineries Historic Sites Museums

Side Trips

Sovana, Bagno Vignoni, Piancastagnaio, Fortress of Tentennano, Azienda Agricola Santa Giulia
Find places to stay May 5 — 8:
Highlights from your plan
Azienda Vitivinicola Villa Corano ©
Chiesa di Santa Maria Maggiore ©
Chiesa di Santa Maria Maggiore
Parco Archeologico Citta del Tufo ©
Parco Archeologico Citta del Tufo

3
nights
Montalcino

Montalcino ©
In the heart of wine country, the hill town of Montalcino offers a glimpse of untouched medieval-era Tuscany.
Start off your visit on the 9th (Thu): do a tasting at Mate Winery, then learn about winemaking at Enoteca di Piazza Wine Room, then indulge your senses at some of the top wineries in the area, and finally learn about winemaking at Azienda Agricola Patrizia Cencioni Solaria. On the next day, do a tasting at Podere Le Ripi, then admire the natural beauty at Il giardino di Daniel Spoerri, then pause for some serene contemplation at Chiesa di Santa Maria e San Rocco, and finally contemplate in the serene atmosphere at Chiesa di San Giorgio.

To find photos, other places to visit, maps, and more tourist information, you can read our Montalcino day trip tool .

Montalcino is very close to San Quirico d'Orcia. May in Montalcino sees daily highs of 27°C and lows of 13°C at night. Wrap up your sightseeing by early afternoon on the 11th (Sat) to allow enough time to drive to Cortona.

Things to do in Montalcino

Wineries Tours Parks

Side Trips

Chiesa di San Giorgio, Il giardino di Daniel Spoerri, Chiesa di Santa Maria e San Rocco, Borgo Medievale Cinto da Mura
Find places to stay May 8 — 11:
Highlights from your plan
Mate Winery ©
Mate Winery
Wine Tours & Tastings
Chiesa di San Giorgio ©
Chiesa di San Giorgio

2
nights
Cortona

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 11th (Sat), look for gifts at Giancarlo Rossi and then learn about winemaking at Tenimenti d'Alessandro. On the 12th (Sun), you'll have a packed day of sightseeing: contemplate in the serene atmosphere at Santa Maria del Calcinaio, explore and take pictures at Tipografia Grifani Donati, and then take in the architecture and atmosphere at Cattedrale dei Santi Florido e Amanzio.

Discover how to plan a Cortona trip in just a few steps with Inspirock's itinerary builder.

You can drive from Montalcino to Cortona in 1.5 hours. Other options are to do a combination of bus and train; or take a bus. On the 13th (Mon), wrap the sightseeing up by early afternoon so you can drive to Montepulciano.

Things to do in Cortona

Historic Sites Wineries Shopping

Side Trip

Citta di Castello
Find places to stay May 11 — 13:
Highlights from your plan
Santa Maria del Calcinaio ©
Santa Maria del Calcinaio
Tenimenti d'Alessandro ©
Tenimenti d'Alessandro
Azienda Agricola Baldetti Alfonso ©
Azienda Agricola Baldetti Alfonso

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 13th (Mon): do a tasting at De' Ricci, do a tasting at Cantina Fattoria della Talosa, and then learn about winemaking at Azienda Agricola Ercolani. Keep things going the next day: admire the natural beauty at La Foce, then do a tasting at Gattavecchi Winery, then do a tasting at Contucci, and finally do a tasting at Tenuta Valdipiatta.

Plan a trip to Montepulciano easily and quickly by telling Inspirock to suggest an itinerary.

Traveling by car from Cortona to Montepulciano takes an hour. Alternatively, you can take a bus; or do a combination of train and bus. In May in Montepulciano, expect temperatures between 27°C during the day and 13°C at night. Finish your sightseeing early on the 15th (Wed) to allow enough time to take a bus to Pienza.

Things to do in Montepulciano

Wineries Museums Parks

Side Trips

Chianciano Terme, Vicolo Baciadonne, Museo Archeologico Nazionale, Fortezza di Radicofani
Find places to stay May 13 — 15:
Highlights from your plan
Cantina Fattoria della Talosa ©
Cantina Fattoria della Talosa
Tenuta Valdipiatta ©
Tenuta Valdipiatta
Contucci ©
Contucci

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. Kick off your visit on the 16th (Thu): learn about winemaking at Enoteca Di Ghino, shop like a local with Artemisia Gallery, look for gifts at La Taverna del Pecorino, pause for some photo ops at Pozzo dei Cani, then don't miss a visit to The Checche Oak Tree, and finally wander the streets of Monticchiello. On the 17th (Fri), you'll have a packed day of sightseeing: identify plant and animal life at Riserva Naturale Lucciolabella, explore the historical opulence of Castello di Montorio, and then don't miss a visit to Masso Leopoldino.

To find more things to do, photos, ratings, and other tourist information, go to the Pienza travel planning website .

Pienza is very close to Montepulciano. In May in Pienza, expect temperatures between 27°C during the day and 13°C at night. On the 18th (Sat), wrap the sightseeing up by early afternoon so you can drive back home.

Things to do in Pienza

Historic Sites Parks Wildlife

Side Trips

Masso Leopoldino, Castello di Montorio
Find places to stay May 15 — 18:
Highlights from your plan
Monticchiello ©
Monticchiello
Enoteca Di Ghino ©
Enoteca Di Ghino
The Checche Oak Tree ©
The Checche Oak Tree