Many people dream of a vacation in Tuscany. Maybe you’ve been before and can’t wait to get back. Or maybe you’ve always wanted to go and are finally planning a trip. Whatever the case may be, we have thousands of incredible vacation rentals in Tuscany and villas in Tuscany to choose from. From villas with pools in Tuscany to holiday rentals in Florence, right in the centre of the city, we have a range of different options to suit your needs and tastes. However, it doesn’t just stop at helping you find an ideal villa in Tuscany. Here at Tuscany Villas, we want to help you all throughout the entire booking process and your holiday itself – from finding the rental that is just right, to managing payments, to having a smooth arrival, to finding plenty of things to see and do in the area.
As we really want to help you make the most of your time in the region and make that dream vacation happen – whether you’re a seasoned visitor to Tuscany, it’s that first time, or it’s a once-in-a-lifetime blow-out experience – we established this blog years ago to keep guests abreast of the best things to see and do in Tuscany. There are endless articles about famous attractions, what to visit and when, places to eat, unique curiosities that you won’t want to miss, traditions and festivals, special events, hidden gems, and more. So, if you want to know what to eat, where to go wine-tasting, when you should visit the Leaning Tower of Pisa or what to do this spring, you’ll find the answers on our blog – it’s a great resource for planning your itinerary!
If you are planning your trip in a hurry or you simply want the highlights, however, you’re in luck, as we are beginning a new series of bucket lists based on destinations, themes, and times of the year. These are perfect little cheat sheets and one-stop shops for everything you need to know to plan perfect outings, all in one handy little list. So, find your villa in Tuscany and be sure to check them out as they appear on the blog!
Here’s the first of them... unique wine experiences in Tuscany that you shouldn’t miss...
1. Wine Windows
If you book a villa in Florence and wander around, you might spot tiny little windows in the walls of some of the Renaissance palaces. These buchette del vino, or wine windows, were once all over the city and date back to when the noble families who lived in those palaces used them to sell wine from their wineries directly to customers, maximising profit. Customers could pass a few coins through the window in exchange for a jug, flask, or bottle of wine that was then passed back out to them through the opening. Over the centuries, most of these wine windows disappeared but then the restaurant Babae in the Santo Spirito neighbourhood opened in 2019 and reopened the wine window in their building. Now a few wine windows are back in use. Definitely a trend reinforced by social media and getting that snap, it is a little touristy but is also the rebirth of a real tradition in the city so we think it’s worth experiencing for yourself!
2. Orcia Wine Festival
On the last weekend of April each year, the town of San Quirico d'Orcia hosts the Orcia Wine Festival in the 18th century Palazzo Chigi as well as various other spots across the charming historical centre of town. With tastings, talks from experts, visits to local wineries in the surrounding area, cooking classes, a Gala Dinner, and more, it is the ultimate way to familiarise yourself with the wines of the Orcia Valley. For the serious wine-lover, it is also one of the major events in the wine calendar in Tuscany. So, if you’re considering a vacation rental in the Orcia Valley towards the end of April, be sure to swing by!
3. Sit Out In A Piazza In The Sun
Less specific, this can be done in any town or city in the entire region but is definitely worth actually setting aside time for. Find a pretty piazza, sit in a sunny spot (or in a shaded spot on a really hot day), order a glass of wine, lean back, relax, and watch the world go by as you sip – now that sounds like an excellent way to spend a few hours on vacation in Tuscany...
4. Visit One Of The Oldest Wineries In The World
Contucci, the oldest wine producer in Montepulciano, is also one of the oldest wineries in the entire world, with records showing its existence since at least 1000AD. From the 1st of April 2025, it reopens for tours, on Tuesdays and Saturdays at 11am and 3.30pm. These tours bring guests to some of the rooms of the Palazzo Contucci, which is still home to the Contucci family and built in 1517 by Antonio da San Gallo the Elder, with rooms decorated in paintings by the likes of Andrea Pozzo. Then you go down into the historic wine cellars, part of the oldest city walls of Montepulciano and dating to the Middle Ages. Next, is a stop at the panoramic gardens, which boast views over the surrounding area and the Valdichiana. Then, you will finish up in their on-site restaurant with a wine-tasting of some of their incredible and award-winning wines, paired with local meats, wines, bread, and their own Extra Virgin Olive Oil. A villa in Montepulciano is ideal for wine-lovers as it is a major wine centre in the region and a visit to Contucci is the ultimate wine experience in the town!
5. Watch The Sun Set Over Florence While Sipping Wine
The Piazzale Michelangelo is famously one of the best spots to admire the iconic skyline of Florence and it draws crowds each evening to watch the sun set, listen to buskers, dance, eat slices of pizza while sitting on the steps, and generally enjoy the show. We suggest heading a little bit earlier, grabbing a seat at one of the tables outside the restaurant and bar in the square, and enjoying some wine and conversation with your travel companions as you take in the magic of the sun dipping behind the impressive dome of Santa Maria del Fiore – quite possibly the best way to experience the skyline while staying in a vacation rental in Florence.
6. See Chianti From Above
Want to take in the patchwork of green vineyards across the famous wine region of Chianti? Well, then be sure to hitch a ride on a hot air balloon – it’s the best way to see it all! Head on a hot air balloon outing while you are staying in one of our incredible villas in Chianti and start your day with breath-taking views and then a Prosecco breakfast. Then, head to one of those wineries that you just sailed over and taste some of those world-famous Chianti wines. If there’s a dreamier itinerary for a day in Chianti, we haven’t heard of it yet!
7. Sample A Tuscan Orange
Red, white, sparkling, Vin Santo, and rosé are all wines that you can find in wineries all throughout Tuscany. However, orange wine, popularised increasingly in recent years, is something that is generally associated with the region of Friuli-Venezia Giulia, further north in Italy. This is due to the fact that this type of wine – made like red wine by retaining the skins but by using white grapes to create a complex and interesting kind of wine somewhere between the two – traces its origins to the region and to Slovenia and has hundreds of years of history in that part of Italy. However, this trending wine can be found in Tuscany as well! So, if you’re a fan and you have found a holiday rental in Pisa, then you’re in luck. Produced by Cosimo Maria Masini in San Miniato, in the Pisan hills, their orange wine is called the Daphné. A scenic place to dine at their restaurant, take cooking lessons, or go wine tasting (they have nine different wines in total to sample), it is well-worth a visit, particularly to try that orange wine while admiring the gorgeous historic villa, gardens, and stunning surrounding scenery.
