Welcome to Tuscan Hill Towns!
About Tuscany
As a top Italian tourist destination, Tuscany attracts millions of visitors annually to cities like Florence, Pisa, Siena, and Lucca. Coastal towns such as Castiglione della Pescaia, along with the Chianti wine region and Val d’Orcia, are also major draws. Seaside tourism accounts for about 40% of its visitors, while its countryside, dotted with cypress-lined hills, offers picturesque escapes. Tuscany’s ten provinces, including Siena, Livorno, and Grosseto, each contribute unique attractions.
Seven UNESCO World Heritage Sites are located in Tuscany, including Florence’s historic center, Pisa’s Cathedral Square, and the Val d’Orcia. Its rich cultural tapestry is complemented by over 120 protected nature reserves. With its Mediterranean coastline and vibrant landscapes, Tuscany provides an unforgettable experience, blending natural beauty with historical and artistic treasures.
Our Favorite Walking Tours
The best way to learn about a city is through local tours
Eat Play & Stay
There are so many amazing places to eat in Tuscany. The area is vast with many amazing small towns and wineries. The best places for wine are Montepulciano, San Gimignano, Montalcino, and Chianti. Always look for an authentic experience, and luckily there are many. Also consider a wine tasting on a vineyard with your meal. Terreno Restaurant is located on the Terreno estate, 25 km south of Florence. The 150 hectares estate has been making wine for hundreds of years. The Rudhne family from Sweeden purchased it in 1988.
The small town of Pienza is idyllic! It is not too far from the many wineries in the area. This restaurant was highly rated by Kimberly Holcomb, from the podcasts, Kimberly's Italy (find out more www.kimberleysitaly.com). She raves in a recent episode, and after looking at the reviews, we can see why. Put this on your itinerary while driving through the winding roads of Tuscany! you won't be disappointed.
You can easily look for a good winery tour on Viator, or AirBNB experiences, but if you have a car, you can make your own itinerary. There are so many wineries in Tuscany, many family owned, with tours, wine tastings, restaurants and even accomodation. Check out this list of the top wineries from Tripadvisor and make your own itinereary. It is best to reserve ahead, so they know you are coming! But sit with people and drink the most incredible wine in the world!
You will get some of th emost amazing recommendations if you listen to Kimberley's Italy Podcast. This is another that hits it right out of the park. There are many wonderful wineries in Tuscany, but this family run business will take you away from the commercial, big production feel, to like you are wine tasting with family. Kimberly mentions this on a recent episode, so we had to check it out! Wow, the setting is without words, and the hospitality and approach of the owners allows you to truly understand their passion for making wine.
If you are anywhere near Tuscany, YOU HAVE to stay here. The castle was purchased by Salvatore Gangale, and completely refurbished with the help of his son, Antonio. You will be hard pressed to find a review on tripadvisor below a 5. This is on our bucket list but dear friends have stayed and confirmed how amazing it is! Salvatore is a trained chef (spent time in San Diego and Cleveland). Be sure to ask about a dinner in with him! And take this place in. It is quite affordable considering the location. Ironically his sister had a restauant 5 minutes from our house and we live in Ohio! It truly is a small world...
This highly rated villa is set in one of the prettiest areas of Tuscany, Greeve in Chianti. It was an estate from the 15th century. Not only is it a working winery but the main building offers 11 rooms, a restaurant and even cooking classes! All are very affordable and worth a look.
Experiences with Viator
Local Spotlight
Tuscany Top 10
Ryan always delivers and wow this is a great one! Tuscany is beautiful beyond words and he brings that to life in this video. Really any hill town will be magical to visit but this gives you a great foundation.
Rok Goes Around
Rok is a cinematic vlogger with extensive experience as a tour guide. Here he gives us the top 10 of Tuscany. We love how he weaves in history and culture. He will help you narrow down your itinerary.
Tuscany Top 10
Epic Explorations
Rok Goes Around
Rok is a cinematic vlogger with extensive experience as a tour guide. Here he gives us the top 10 of Tuscany. We love how he weaves in history and culture. He will help you narrow down your itinerary.
Tuscany Road Trip
Suitcase Monkey gives an entertaining and realistic approach on a trip to Tuscany. He gives a great suggestion about driving and parking. Finding a spot outside of Florence is a wise thing to do. There are tram stops with vast parking lots located around the city.
Amateur Traveler
Hill Towns of Tuscany
Local Spotlight~ Hill Towns
San Gimignano
Rok, one of our favorites, is at it again…sharing some great tips on hill town of San Gimignano. That way you can decide if it is worth a visit. We vote yes! It is magical!
Must See Tuscany Hill Towns
Great video overview on some of the best hill towns in Italy. Put these places on your itinerary!
Off the Beaten Path
For a breathtaking view and incredible wine, sign up for a wine tasting at Tanuta di Fanti. There are many vineyards in Tuscany but if you get a chance to taste Brunello wine in Montalcino, it really is one a great experience.
A Guide to Vineyards
The Tour Guy has some very helpful videos about locations all over Italy. Before we went to Rome, we watched every one. He has a tour company that does affordable day trips.
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