Why you'll love this tour
Get the best of Tuscany – in one day
For most of us, Tuscany perfectly embodies our most romantic dreams of Italy. The region’s mouth-watering cuisine, stunning scenery, fascinating historical heritage and wide range of cultural attractions make it a complete dream land for any bon vivant – and a must-visit destination for every self-respecting Italophile. On this 12-hour outing, you’ll get to visit two of the province’s most spectacular medieval towns and a hidden gem winery, where we'll treat you to a bounteous lunch and wine tasting session.
As you travel north through the Tuscan countryside in a deluxe air-conditioned van, your cheerful driver will entertain you with intriguing stories of historical happenings that took place in this very region as well as interesting tidbits about the local culture. Tune in as you soak up the beautiful vistas sweeping past the car window; a rolling landscape of vineyards and sunflower fields, dotted with Renaissance villages enthroned on green hilltops. While your driver won’t be wandering into the cities with you, he will provide you with plenty of background information on each place visited so that you'll be well-prepared to explore them independently.
Explore Siena – before wining and dining in Chianti
Our first destination is Siena. This medieval city had it’s heyday in the 1300 and 1400s and incredibly hasn’t changed much since. While brimming with architectural and artistic must-sees, this small town is easily manageable on foot. During the 2-hour stopover, you’ll have plenty time to cover all the major architectural highlights, such as the main square, Piazza del Campo, and the striking cathedral with its dramatically decorated interior of black and white marble stripes. A climb to the top of the Mangia Tower just down the road, offers a magnificent view of the brick laden city below (a sight well worth the 400-step climb!).
In a rural area, just north of Siena, we’ll stop for lunch at our very favorite "fattoria". Perched on a small hill in the very heart of the Chianti district, this family-run little winery is the perfect venue to get to know the Tuscan cuisine and wine tradition a little bit better. Your gracious hosts will show you how the wine is made – from grape to glass – through a thorough tour of the grounds. Naturally you’ll also get to try the farm’s own delicious produce! In the ever-romantic setting of a wine cellar dug into a tuff rock, you’ll be served an exquisite 4-course meal, perfectly paired with 7 wine tastings – all on the house!
Revel in the beauty of San Gimignano
We’ll cap our Tuscan day off with a stop in beautiful San Gimignano. This small hilltop village is especially famous for its many imposing towers, which create the unusual skyline that has earned the city its nickname – “the Medieval Manhattan". During the Renaissance, dozens of towers were built by aristocratic families who wanted to show off their economic and political success, but today only 14 of the original structures from the city’s golden age remain. Admiring the imposing monuments and meandering through the picturesque alleys, one can easily get a sense of what it was like to walk the very streets some 500 years ago.
No visit to San Gimignano would be complete without a refreshing visit to Gelateria Dondoli – voted “Gelato World Champion” for two consecutive years. Unsurprisingly, the lines to enter the tiny shop often stretch around the block; but the heavenly gelato is well worth the wait! Another top tip is to indulge in some shopping in the numerous shops selling typical Tuscan products such as handmade glass works, wooden goods, fine pottery, local wine, wild boar sausages, cured hams and cheeses. With so many quality products on offer, we’re sure you’ll find that perfect gift for your loved ones back home before embarking on your journey back to the Eternal City.
What you'll experience
Siena, today a medium-sized provincial city, was once one of the West's major powers that long fought against Florence for power over Tuscany. Siena lost this battle and, therefore, development almost stood still in the city – making this mini medieval metropolis a popular destination for visitors who want to soak up the historical atmosphere. Siena's main attractions are located around the fan-shaped Piazza del Campo, on which the "Palio” takes place every summer. This bareback horse race dates back to the 1600s and is still Italy’s most famous annual sporting event.