How to Spend a Weekend in Tuscany

Rolling hills of picture perfect countryside, dotted with small villages you’ve only seen in movies, and in between those villages – a vineyard or two. And the food, well… What’s not to like about Italian food?

I think Tuscany is the perfect getaway and here’s how I suggest you route it!


Fly into Pisa – there are many airports around to choose from but Pisa tends to be less expensive than others, and the town (sorry Pisa) is less exciting than others in the area. Why not land here, visit the Leaning Tower as a starter after breakfast?


From Pisa drive to Florence – oh yes, rent a car. You’ll want full freedom once you see what’s out there. The drive is about 45 minutes. Spend the day exploring Florence. There’s so much to see from Ponte Vecchio, to the Basilica, Piazza della Signora, or the Baptistery. You can choose to spend the night in Florence, but I’d rather grab a pizza and then opt for the country side. So we keep driving…

Into the countryside we go and stop by the various perched villages, starting with Siena, where I recommend booking a table for dinner at Osteria Antica da Divo (Via Franciosa, 25, 53100 Siena SI, Italy / +39 0577 286054). Other favourites include Arezzo (where the town is taken over by antique stalls every first Sunday of each month – an amazing experience) and Cortona (famous for its appearance in the movie Under The Tuscan Sun!). Smaller town options to visit include San Gimignano, Monteriggioni, and Pitigliano.

For wine, I strongly recommend driving through Chianti, Montepulciano and Montalcino as they are all quite different in terms of wineries and setting – and all are equally important to see!

Between Montepulciano and Montalcino is the Val d’Orcia area, famed for its true beauty that you always see in Tuscan postcards and ads. It’s the perfect place for a picturesque drive – you’ll find it difficult not to stop many times along the way! In this area are also a number of “thermal” towns with hot springs, including the picturesque and tiny Bagno Vignoni which is just what dreams are made of! About 30 minutes away is the Bagni di San Filippo which is set in a forest surrounded by waterfalls and cliffs – great for a dip in the hot springs while Bagno Vignoni doesn’t allow swimming!

A bit of shopping in mind? Okay, it’s not as picturesque as the Tuscany you came here to see, but Space (a Prada Outlet located at Via Levanella Becorpi, Localita Levanella, SS 69, Montevarchi / +39 055 978 94 81) and The Mall (Via Europa 8, 50066 Leccio Reggello / +39 055 8657 775) have some serious steals on the shelves. It’s only about 30 minutes driving from Florence. Why not grab a new Prada clutch for your Tuscan sunset dinner tonight?


Relais La Suvera – perfection in every sense of the word. Book a dinner at Ristorante Oliviera, as you’ll be so remote and enchanted that a drive elsewhere won’t even stand a chance!

Via della Suvera, 53030, Pievescola SI, Italy / +39 057 7960 300

Villa Sassolini – perfectly located between Florence and Siena, this villa located in a beautiful perched village named Moncioni with views of the rolling hills below. Great location to explore Chianti, Arezzo, Cortona and Montepulciano in one go!

Via del Solatio Moncioni, 85, 52020 Montevarchi AR, Italy / +39 055 970 2246

Locanda al Colle – a seaside option in Tuscany, perfectly located for exploring both the Tuscany countryside as well as Cinque Terre and the fabulous beaches around Locanda al Colle!

Via La Stretta, 231, Camaiore LU, Italy / +39 0584 915195

Salcheto – a winery with an option to stay. Just at the base of Montepulciano itself with sweeping views of the countryside as well as the town!

Via Villa Bianca, 15, Provincia di Siena, Italy / +39 0578 798046



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