There are few places in the world as dreamy as Tuscany. It’s almost as if there is a different energy in the atmosphere. There is something so alluring about the cascading hills of rustic farms lined with grape vines, towering cypress-lined driveways, and sun-soaked villages clinging to every hill. In my mind, it’s not a trip to Italy if you do not experience the sights and tastes of the Tuscan countryside.
I have had the fortune of visiting Tuscany during all four seasons. Winter is a nice time to visit because you’ll basically have the wineries to yourself – perfect for intimate wine tastings! Summer is gorgeous because it’s nice and warm and everything is in full bloom. But if you ask me, the best time of year to visit Tuscany is in September. It’s still beautiful and quite warm out, with a gentle fall breeze creeping in at night. The best part? You won’t have to deal with the summertime tourist crowds that flock to Tuscany from late spring through July.
Where to stay:
One of my favorite parts of any Tuscan vacation is finding a charming place to stay – and there is no shortage of adorable villas and boutique resorts. Here’s a few of my favorite places I’ve stayed over the past couple of years.
Laticastelli Country Relais: located in Rapolano, in the province of Siena
This is by far one of the most gorgeous places I have ever stayed. It was once a small Tuscan village that has now been transformed into a ‘Country Relais.’ The rooms are exceptionally clean and beautifully decorated in historic Tuscan style. One of my favorite memories is swimming in the infinity pool while admiring the stunning countryside views. We enjoyed an incredible moonlight dinner on the terrace of their restaurant, La Taverna di Laticastelli, which overlooks the gardens and majestic cypress trees.
I was especially blown away by the quality of the dishes – we enjoyed the most amazing Rosso di Montalcino, risotto, sea-salt encrusted bistecca alla Fiorentina (Florentine Steak), and decadent tortino al cioccolato (chocolate torte) for dessert. In the morning the restaurant served an immaculate spread of fruit, eggs, bacon, pastries, and other breakfast treats. It was truly an unforgettable experience all around. I highly recommend this place for a romantic couples retreat!
Villa Acquaviva Wine Resort: located in Manciano, in the hills of Tuscan Maremma
If you are visiting the famous Saturnia hot springs and looking for a villa located directly on top of a winery, then this is the place for you! You can imagine my delight when I realized I had stumbled upon quite literally a “wine resort.” Upon entering through the gates of Villa Acquaviva, you are taken along a dirt path with towering olive trees and breath-taking views of the surrounding vineyards. When we got to the villa, we were greeted by the family’s adorable pup, Arturo. I immediately knew I was going to love this place after seeing how dog-friendly it was!
The villa was once a noble residence, and today the hotel rooms are beautifully decorated with antique Tuscan furniture and beautiful linens. Our deluxe room had a spacious terrace overlooking the vineyards and rolling countryside. I highly recommend stargazing on this terrace with a bottle of wine. During our stay we really enjoyed their restaurant “La Limonaia,” which features a seasonal menu of food and produce directly from the agritourism’s vegetable garden. Some of the most memorable dishes we enjoyed were the fried zucchini flowers, bean soup with wild chards, homemade beef ragout, spinach and ricotta tortellini, beef with zucchini spaghetti, and last but not least, the delightful lemon tart. Y’all know I had to get the lemony dessert! During the day we enjoyed several leisurely walks through the vineyards. I cannot recommend this gorgeous place enough!
Wineries to visit:
Azienda Agricola La Lastra: located outside of Siena
We visited La Lastra at the end of July and it was perfect. We didn’t have a reservation but fortunately most of the Italian wineries do not require reservations like the ones in the States do (Napa, Charlottesville, etc.). The winery was covered in lush greenery, florals and the most beautiful assortment of succulents and cacti I’ve ever laid eyes on. We enjoyed a private tour of the vineyards followed by a wine tasting led by the most lovely woman. We will definitely be back!!
Boscarelli Winery: located in Montepulicano
We went to this winery during the off season right before COVID hit (February 2020) and pretty much had the entire winery to ourselves. It was amazing! The owner was incredibly kind and gave us a special wine tasting, including an assortment of snacks to pair with each wine. We really loved having the entire place to ourselves. While you may not get to enjoy the lush greenery of Tuscany in February, you will certainly get to enjoy your private wine tasting in peace. 10/10 recommend!
How to get there:
If you’re planning a trip to Tuscany, you’ll likely be coming from Rome or Florence. The easiest way to travel is by train of course – Trenitalia has a 1.5 hour train from Florence to Siena. Siena is a charming medieval village with a UNESCO historic center. You will definitely want to build in time to explore the cobblestone streets of this charming town on your way to the Tuscan wineries! Salute!
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