The Area

Enjoy a unique Tuscany wine tasting trip in a wonderful setting!


Created by the Romans, Florence is today the capital city of the region. But more than this, Florence is the cradle of the Renaissance with a unique heritage, most of it classified as UNESCO world sites. City of art, Florence boasts a wide range of museums with some of the world’s most famous works of art, many breath-taking palaces as well as stunning churches. Under the Medici’s family, the city blossomed and gained its artistic and cultural reputation.

Tuscany wine tasting - Credits Firenze Turismo
Chianti Wine Tour- Credits Firenze Turismo

Main sights include the Cathedral (also called il Duomo), the Uffizi Gallery, the Ponte Vecchio – the medieval bridge famous for its numerous jewellery stalls, the Galleria dell’Accademia, the Palazzo Pitti, the Basilica di Santa Croce, the Palazzo Vecchio and the Piazzale Michelangelo from where there is a breath-taking panoramic view over Florence, day and night.


Siena is a beautiful medieval city at the heart of the Tuscan region which is also definitely worth a visit. First established by the Etruscans and later developed by the Romans, legend says that Siena was founded by Senius and Aschius, the two sons of Remus and nephews of Romulus, the two brothers who, according to myths, founded Rome. Siena’s historic centre is a UNESCO World Heritage Site. The main square, il Campo, is where the Palio (the famous horse race), takes place twice every summer (as featured in the James Bond film Quantum of Solace). During the race the different districts of the city compete against each other.

Tuscany wine tasting - Credits Grand Hotel Continental Siena
Siena Wine Tasting Tour Credits Wine tour in Siena

Main sights include the Cathedral, also referred as il Duomo, the Palazzo Pubblico, the Bell Tower, Basilica di San Domenico and The Sanctuary of Saint Catherine amongst others. Siena is also renowned for being a city of water and has many enchanting fountains which are worth looking at.

San Gimignano

San Gimignano is a charming medieval town located between Florence and Siena. The place is famous for its impressive towers which offer charming views over the picturesque Tuscan countryside. There used to be about 70 of them, however today only 14 remain. San Gimignano is a UNESCO World Heritage Site also renowned for its white wine the Vernaccia di San Gimignano and its saffron.

Rome wine tour- Credits My Tour

Main sights include Piazza della Cisterna, the Piazza Duomo, the Collegiata and chiostro di Sant’Orso, the 14 towers including the Torre Grossa, the highest of San Gimignano’s remaining towers.


Pienza is a small hidden gem in the heart of the Val d’Orcia valley. Built on a hilltop, the village offers gorgeous views over the surrounding countryside.

Main sights include the Cathedral with its bell tower and fine paintings, the Papal or Piccolomini Palace with its charming loggia and garden (one of the filming locations of Zeffirelli’s Romeo and Juliet – 1968), the Town Hall, and the beautiful central square. The Romanesque church of Pieve di Corsignano is only a short walk from Pienza and is certainly worth a visit.

For food lovers the Pecorino cheese of Pienza is a must taste!


Montalcino is an enchanting little town with cobbled streets and surrounded by medieval walls. Famous for its Brunello wine, Montalcino is a must see. Its fortress, also called the Rocca was built in 1361. This impressive building offers astonishing views over the quaint surroundings including the exquisite hills of the Maremma. The Palazzo dei Priori with its clock tower overlooking the town’s main square, the Piazza del Popolo is absolutely gorgeous.


With its medieval palaces and ancient churches, Montepulciano is a truly beautiful medieval town. The views on the surrounding countryside are fabulous. Its main square, the Piazza Grande is famous for the barrel racing contest, Bravio delle Botti, which takes place every August.

Florence wine tour
Chianti Wine Tour- Credits Florence Town

Main sights include the palazzo comunale and the Sanctuary of San Biagio, just outside of the city, with a lovely view on the Tuscan countryside.

For food lovers, Montepulciano has some unique specialties that are definitely worth trying. The local wine is the famous Nobile di Montepulciano (not to be missed on your Tuscany wine tasting adventure!). Pork meat from Cinta Senese pigs is another local specialty. You may also want to try the Pici pasta, a long thick spaghetti often served with a tomato, garlic and meat stew. If you have a large appetite the Bistecca alla Fiorentina (steak) is the dish to try!

Tuscany wine tasting - Credits My Tour

All in all an excellent break and I would certainly recommend your tours to others. Many thanks for all your help and the help of your team to get all the arrangements in place. I hope that we will be able to use Grape Escapes again in the future.

Carol- West Sussex, UK

Get in Touch

Around half of our trips are completely bespoke. Our expert team would be delighted to discuss your requirements and create your perfect trip.

Contact Us

Grape Escapes Gifts

What to buy for the wine lover who has everything? We offer a variety of gift options, and vouchers are valid for two years.

Browse Gifts