Hilltop towns, warm sunshine, castles, villas, wineries….Tuscany has it all! This is one of the most romantic places I have ever been to. It truly is like living a dream. I had heard these phrases used about Tuscany before I went, and I was worried the area would be a little cliche. It is not. It is anything but. It truly is everything you dream it will be.
The Tuscany region is a series of beautiful small towns, many of which are located on hilltops. These hilltop towns usually have a fortress, castle or cathedral at the top which serve as a lookout for the town. Two of my favourite hilltop towns are Montalcino and Cortona.
- Montalcino is a beautiful walled medieval hilltop city, less than an hours’ drive south of Siena. It is in the Val d’Orcia region, a region renowned for its production of Brunello wine. Think Brunello di Montalcino… This is a great town to visit to try this delicious wine, and enjoy the quaint restaurants and shops of local artisans. There is also a large fortress that has been mostly intact since the Middle Ages, so you can really feel the history here. I recommend at least a half day to visit.
- Cortona came to fame when it was featured in the “Under the Tuscan Sun” movie with Diane Lane. However, I don’t feel the movie did it justice! This town is also on a hilltop and is very steep to both arrive by vehicle and walk around when you are in town. There is a beautiful main square which has lovely church and great restaurant overlooking the square. Small alleyways, cute wine shops and artisans fill the streets and make visiting a delight. There is a lovely lookout area as well, which gives unobstructed views of the gorgeous Tuscan countryside. If you’re feeling energetic, take the 20 minute walk uphill to the Girifalco castle, the highest point in the city.
When in Tuscany, you must stay in a Villa and a Castle! Really, it doesn’t get more unique or romantic than this. Here are my top picks for this area:
- Villa Fontelunga – This is the perfect escape. This is what you think of when you think of a villa in Tuscany. Fontelunga is a homestyle villa, with a family feel. At only 9 rooms and 2 private villas, you will never feel crowded here. You enter into the main floor and it immediately feels like home. Friendly staff, open kitchen, serve yourself. This is a perfect place to explore the region, and come home to your sanctuary. The bedroom windows open to gorgeous views of the valley, and there is a lovely lawn and olive tree grove to really immerse you in a natural setting. The pool and hot tub are a great addition as well, and I enjoyed my late nights in the hot tub with a glass of wine! This is perfect for couples and families looking to explore Tuscan while having a true villa experience.
- Castello di Velona – Authentic Castle luxury!! This castle estate is on a hilltop and produces its own wine. Its also a thermal hot springs hotel, which means that their spa and large pools are all heated with naturally sourced hot spring water. And the pools are open all night!! I have to admit that I enjoyed a bottle of wine in the pool late into the night on more than a few occasions while staying here. This hotel is all about pampering! Staff are attentive, food is locally sourced and superb, wine is delicious. You can even do a private wine tasting in their wine cellar. Not to mention the view! Every morning you can have breakfast on the terrace overlooking the Val d’Orcia. Stunning. Perfect for honeymoons and couples looking to be spoiled.
To truly appreciate Tuscany, I recommend a private driver, or renting your own vehicle. This is a large region and distances between towns can be quite large. There is taxi service, however can be spotty depending where you’re going. The best places here are off the beaten path.
Having been here myself, I am happy to share the best places to stay, things to do and tips for the region. Contact me today to get started planning your Tuscan escape!
