Best of Tuscany by Vespa: Siena, Chianti & Val d'Orcia

Gateway to Tuscany.

You'll be met at Poggibonsi train station and transferred to the Vespa office, where you'll receive your scooter, complete a safety and route briefing, and make sure your Vespa is comfortably fitted before setting off.

Once you're ready, enjoy a short introductory ride through the Tuscan countryside to Villa San Lucchese, your elegant 4-star boutique accommodation. Settle in and take some time to relax before joining a welcome dinner at the villa's restaurant, the perfect way to begin your Tuscan Vespa adventure.

Towers, Walls, and Renaissance Art.

Set out by Vespa through the rolling Tuscan countryside to San Gimignano, one of Italy's most iconic medieval hill towns. Instantly recognisable by its celebrated 13th- and 14th-century towers, the town is filled with atmospheric lanes, historic palazzi and beautifully preserved medieval architecture.

Take time to visit the magnificent Collegiata, whose richly decorated interior includes the Chapel of Santa Fina, adorned with remarkable frescoes by Domenico Ghirlandaio. The Civic Museum is also well worth exploring for its outstanding collection of medieval and Renaissance art.

Continue along quiet, scenic roads to Volterra, a spectacular hilltop town with roots stretching back to the Etruscans. Explore its ancient streets and historic walls, with sweeping views across the surrounding Tuscan countryside, before returning by Vespa to Villa San Lucchese for the evening.

Along the Ancient Via Cassia.

Leave Villa San Lucchese and follow a quiet, winding route through the Tuscan countryside to Monteriggioni, one of the region's finest-preserved medieval settlements. Encircled by imposing stone walls and crowned by its distinctive watchtowers, this tiny fortified village offers a fascinating glimpse into medieval Tuscany.

Continue to Siena, where you'll have time to explore the atmospheric Piazza del Campo, the famous shell-shaped heart of the city, and admire the extraordinary marble façade of the Siena Cathedral.

From Siena, turn south and follow sections of the ancient Via Cassia, the Roman road that once connected Rome with northern Italy. Continue through the rolling countryside to Buonconvento, where you'll settle into Pieve a Salti, a welcoming 3-star agriturismo surrounded by vineyards and farmland, with beautiful views towards the hills of Montalcino.

The UNESCO Val d'Orcia.

Ride deep into the UNESCO-listed Val d'Orcia, one of Tuscany's most iconic landscapes, where rolling hills, cypress-lined roads and vineyards create the postcard scenery for which the region is famous. Pass through the celebrated Brunello di Montalcino vineyards before reaching the magnificent Abbey of Sant'Antimo, a beautifully preserved Romanesque church set peacefully among the hills.

Continue along quiet, winding roads to Bagno Vignoni, a unique ancient thermal spa village built around its remarkable central pool. From here, ride onwards to Pienza, the celebrated "ideal Renaissance town" created in the 15th century by Pope Pius II.

Take time to sample some of the region's finest produce, including Pecorino di Pienza and local truffles, before continuing to Montepulciano. Your accommodation tonight is Villa Cicolina, an elegant 4-star country residence surrounded by vineyards and gardens. Relax by the pool or explore the grounds before enjoying dinner at the villa.

Overnight: Villa Cicolina

Vino Nobile & Culinary Secrets.

Today is yours to enjoy Tuscany at your own pace. Choose between a scenic Vespa loop to Montefollonico, a charming hilltop village known for its historic wine cellars and Vino Nobile di Montepulciano, or simply slow things down with a relaxing morning by the pool at Villa Cicolina.

In the afternoon, roll up your sleeves for an authentic hands-on Tuscan cooking class. Learn the secrets behind traditional local dishes before sitting down to enjoy the meal you've prepared, accompanied by the flavours of the region.

The Sienese Clays & Truffle Country.

Leave Montepulciano behind and ride through the extraordinary Crete Senesi, one of Tuscany's most distinctive landscapes. Rolling clay hills, sculpted ridges and solitary cypress trees create an almost lunar backdrop, with quiet roads winding through the countryside and very little traffic to interrupt the views.

Continue through the peaceful village of Trequanda to Asciano, a historic hill town at the heart of the Crete Senesi. Stop to savour authentic local specialities featuring the area's prized truffles, an essential taste of southern Tuscany.

From Asciano, continue north towards Siena, where you'll return your Vespa and settle into your centrally located hotel in the heart of the medieval city. With the evening free, step straight out into Siena's atmospheric streets, historic piazzas and lively restaurants.

The Chiantigiana Wine Road.

Take the morning to enjoy more of Siena before collecting your Vespa and heading north into the celebrated Chianti wine country. Follow the winding Chiantigiana Road, one of Tuscany's most scenic routes, through rolling vineyards, olive groves and wooded hills dotted with historic castles and farm estates.

Ride through some of Chianti's best-known wine villages, including Radda, Panzano and Castellina in Chianti, each offering its own character, ancient streets and welcoming piazzas.

Continue to the atmospheric Volpaia Castle, a beautifully preserved medieval village and renowned Chianti Classico estate. Take the opportunity to taste its celebrated Chianti Classico "Black Rooster" wines before continuing through the vineyards to Poggibonsi.

Return to Villa San Lucchese for your final evening, where you can relax and reflect on a memorable journey through the Tuscan countryside.