Medieval Tuscany Tour: Monteriggioni, Montalcino & Pienza
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USD 64.74
Journey through the medieval heart of Tuscany on the Medieval Tuscany Tour from Florence — a beautifully paced full-day trip through three of the region's most captivating and historic destinations. Walk the intact walls of Monteriggioni, wander the wine-scented streets of Montalcino, and stroll the Renaissance piazzas and Pecorino-filled shops of Pienza — all set against the extraordinary UNESCO-listed landscape of theVal d'Orcia, travelling in comfort aboard a fully equipped GT coach from Florence.
Key Highlights
- Explore Monteriggioni — one of the best-preserved fortified medieval villages in Italy, whose ring of intact ancient walls and 14 towers have stood unchanged since 1203
- Visit the Templar Museum inside Monteriggioni and admire panoramic views from the ancient walls
- Discover Montalcino — the hilltop medieval village internationally renowned for Brunello di Montalcino, one of Italy's greatest red wines, with an optional wine tasting of two wines with cold cuts and cheeses
- Wander Pienza — the UNESCO-listed Renaissance ideal city, famous for its romantic cobbled streets, panoramic Val d'Orcia views, and the irresistible Pecorino di Pienza cheese
- Journey through the stunning Val d'Orcia — a UNESCO World Heritage Site of emerald hills, golden fields, cypress trees, and rolling vineyard landscapes immortalised in films and paintings
About Medieval Tuscany Tour: Monteriggioni, Montalcino & Pienza
This full-day tour through medieval Tuscany journeys into some of the most beautiful and historically resonant landscapes in Italy — travelling through the breathtaking scenery of theVal d'Orcia to discover medieval villages, ancient walls, Templar legends, and the authentic flavours of Tuscany's most celebrated food and wine.
The first stop is Pienza — a charming UNESCO-listed village in the heart of theVal d'Orcia, designed in the 15th century as the ideal Renaissance city by Pope Pius II and still perfectly preserved today. Free time to stroll the romantic cobbled streets — including the Via del Bacio (Kiss Street) — and browse the many shops scented with Pecorino di Pienza, one of Tuscany's most iconic and beloved cheeses. The tour then continues to Montalcino — a fortified medieval hill town perched above sweeping vineyard views, internationally renowned as the home of Brunello di Montalcino, one of the world's most prestigious red wines. An optional tasting of one Brunello di Montalcino and one Rosso di Montalcino with local cold cuts and cheeses can be added — one of the most genuinely memorable food and wine experiences available on any Tuscany day trip.
The final stop is Monteriggioni — a perfectly intact medieval fortified village whose ring of ancient walls and 14 towers have remained virtually unchanged since the village was built in 1203 as a Sienese defensive outpost against Florence. Walking inside the walls feels like stepping directly into the 13th century, and an upgrade option gives access to the Templar Museum and panoramic views from the ancient walls themselves — available from March to October. The tour returns to Florence in the early evening with the golden Val d'Orcia light on the rolling hills behind you. Note that from 29 March onwards, the order of visits changes to Pienza first, then Montalcino, then Monteriggioni. Book your Medieval Tuscany Tour from Florence now on Thrillark.
The first stop is Pienza — a charming UNESCO-listed village in the heart of theVal d'Orcia, designed in the 15th century as the ideal Renaissance city by Pope Pius II and still perfectly preserved today. Free time to stroll the romantic cobbled streets — including the Via del Bacio (Kiss Street) — and browse the many shops scented with Pecorino di Pienza, one of Tuscany's most iconic and beloved cheeses. The tour then continues to Montalcino — a fortified medieval hill town perched above sweeping vineyard views, internationally renowned as the home of Brunello di Montalcino, one of the world's most prestigious red wines. An optional tasting of one Brunello di Montalcino and one Rosso di Montalcino with local cold cuts and cheeses can be added — one of the most genuinely memorable food and wine experiences available on any Tuscany day trip.
The final stop is Monteriggioni — a perfectly intact medieval fortified village whose ring of ancient walls and 14 towers have remained virtually unchanged since the village was built in 1203 as a Sienese defensive outpost against Florence. Walking inside the walls feels like stepping directly into the 13th century, and an upgrade option gives access to the Templar Museum and panoramic views from the ancient walls themselves — available from March to October. The tour returns to Florence in the early evening with the golden Val d'Orcia light on the rolling hills behind you. Note that from 29 March onwards, the order of visits changes to Pienza first, then Montalcino, then Monteriggioni. Book your Medieval Tuscany Tour from Florence now on Thrillark.
Inclusions
- Round-trip transport to and from the meeting point
- English-speaking guide commentary throughout
- Free time in Pienza, Montalcino, and Monteriggioni
- Entrance to Monteriggioni walls and Templar Museum
- Wine tasting at Montalcino
Exclusions
- Personal expenses
- Lunch
Insiders' Tips
Bring cash for Pecorino cheese shopping in Pienza — the small shops along the main street are the best places to buy directly from local producers and prices are very reasonable. In Montalcino, add the wine tasting if you enjoy Italian red wine — the Brunello is extraordinary and the local cold cuts and cheeses served alongside it make for a wonderful informal lunch. The Monteriggioni walls upgrade is worth adding between March and October for the panoramic views.
Additional Information
Child policy
- Children under 4 years are free of charge, but no seats will be reserved.
- Visitor Center in the ticket office atrium of Santa Maria Novella Railway Station.
- Lunch is not included — free time in each village allows for independent lunch
- Wine tasting is an optional upgrade
- Tour operates aboard a fully equipped modern GT coach
- Air-conditioned GT coach throughout
- Pienza, Montalcino, and Monteriggioni involve cobblestone walking — comfortable flat-soled shoes recommended
- Restrooms available in each village during free time
Cancellation Policy
- Full refund for cancellations made at least 48 hours before the travel date
Frequently Asked Questions
What is the Medieval Tuscany Tour from Florence?
The Medieval Tuscany Tour from Florence is a full-day guided trip visiting three of Tuscany's most historic and atmospheric medieval destinations — Pienza, Montalcino, and Monteriggioni — through the UNESCO-listed Val d'Orcia landscape by fully equipped GT coach. Optional upgrades include entrance to the Monteriggioni walls and Templar Museum, and a wine tasting of Brunello di Montalcino with local produce.
What is Pienza and why is it called the ideal city?
Pienza is a UNESCO-listed Renaissance village designed in the 15th century by Pope Pius II as a model of the ideal Renaissance city, and it remains one of the most perfectly preserved small historic towns in Italy. It is equally famous for Pecorino di Pienza — a sheep's milk cheese produced in the surrounding Val d'Orcia countryside and sold in the many characterful shops lining the cobbled streets.
What is Montalcino famous for?
Montalcino is a fortified medieval hill town internationally renowned as the home of Brunello di Montalcino — consistently ranked among Italy's greatest and most prestigious red wines, produced from Sangiovese grapes grown in the surrounding hills. The optional wine tasting included with selected tour options allows guests to sample one Brunello di Montalcino and one Rosso di Montalcino alongside local cold cuts and cheeses.
What is Monteriggioni and what can I see there?
Monteriggioni is one of Italy's best-preserved medieval fortified villages — a perfectly intact ring of ancient walls with 14 towers built by Siena in 1203 as a defensive outpost against Florence. Walking inside the walls feels like stepping directly into the 13th century, and the upgrade option includes entrance to the Templar Museum and panoramic views from the walls — available from March to October when the site is open.
What is theVal d'Orcia and why is it UNESCO-listed?
TheVal d'Orcia is a UNESCO World Heritage Site covering a uniquely beautiful stretch of the Tuscan countryside south of Siena — characterised by gentle rolling hills, golden wheat fields, cypress trees, medieval hilltop villages, and vineyard landscapes that have been celebrated in Italian Renaissance painting for centuries. The entire day tour takes place within or adjacent to theVal d'Orcia, and the countryside views throughout the journey are as much a highlight as the villages themselves.
Is the wine tasting included in all tour options?
The wine tasting is an optional upgrade — available as an add-on to the standard tour ticket. It includes a tasting of one Brunello di Montalcino and one Rosso di Montalcino with local cold cuts and cheeses at Montalcino, and is one of the most consistently praised inclusions by guests who select it.
When is the Monteriggioni walls entry available?
Entrance to the medieval walls and Templar Museum of Monteriggioni is available from March to October only — from November to March this option is not available and the upgrade ticket cannot be used. The walls are also currently undergoing maintenance — always confirm availability at the time of booking before selecting the upgrade option.
Does the tour order change throughout the year?
Yes — from 29 March onwards, the order of visits changes to Pienza first, then Montalcino, then Monteriggioni. Before this date, the order begins with Monteriggioni. The guide will confirm the day's schedule at the meeting point and the overall experience remains consistent regardless of the order.
Is lunch included in the Medieval Tuscany Tour?
Lunch is not included in the standard tour price — free time in Pienza and Montalcino provides ample opportunity to purchase lunch independently from the many local restaurants, cafes, and Pecorino and charcuterie shops in both villages. The optional wine tasting with cold cuts and cheeses in Montalcino provides a satisfying informal food experience if selected.
Do I need to book the Medieval Tuscany Tour from Florence in advance?
Advance booking is recommended, particularly during peak season from April to October when spots fill quickly and the most popular tour options — especially the combined walls entry and wine tasting upgrade — sell out ahead of time. Booking through Thrillark saves up to 16% on the standard rate with instant confirmation. Arrive at Santa Maria Novella Railway Station by the confirmed departure time as the coach departs on schedule.
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