Things To Do
Monte Oliveto Maggiorenza
✨ Please try to arrive before 6:00 PM so we can welcome you properly. 👕 Modest dress is appreciated inside the church and sacred spaces. 🤫 Quiet hours begin in the evening — it’s the perfect time to unwind and soak in the calm surroundings. 🚗 Parking is available near the main entrance, so no long hikes with luggage!
Siena
Walk, wander, repeat — Siena is wonderfully walkable (and quite hilly), so take your time and enjoy every cobblestone corner. Head to Piazza del Campo, the heart of the city, and soak in the atmosphere. Don’t miss the stunning Duomo and the views from Torre del Mangia — the climb is worth it. Save space for pici, ricciarelli, and a glass of Tuscan wine — local flavors are part of the experience. If you’re visiting on July 2 or August 16, you may catch the famous Palio horse race — plan ahead, as the city becomes especially lively. Just so you know: Parking in the city centre is limited, as the old town is mostly pedestrian-only. For maps and helpful advice, you can stop by the Tourist Information Office at Piazza del Campo. Enjoy exploring the art, history, and hidden alleyways of Siena, and take time to sit in a café and simply watch the world go by.
Osteria Le Logge in Siena
Typical Opening Hours: Monday – Saturday: ~12:00 PM – 2:45 PM and 7:00 PM – 10:45 PM Sunday: Closed About the Restaurant: Osteria Le Logge is a beloved restaurant in Siena’s historic centre, just steps from Piazza del Campo. It combines traditional Tuscan cuisine with refined seasonal cooking, a thoughtful wine list, and the charm of a historic osteria space (once a grocery shop). Dining here is often described as a memorable experience, with dishes that reflect local ingredients and creative preparation.
Osteria da Divo in Siena
Friday: 12:00 – 14:30 & 19:00 – 22:30 Saturday: 12:00 – 14:30 & 19:00 – 22:30 Sunday: 12:00 – 14:30 & 19:00 – 22:30 🍽️ About the Restaurant Osteria da Divo offers refined Tuscan and Italian cuisine in a historic atmosphere carved into ancient Etruscan and medieval stone beneath Siena’s city centre. It’s known for dishes inspired by local traditions, seasonal ingredients, and an exceptional wine list — all served in intimate dining rooms that reflect centuries of history. Reservations are highly recommended, especially for dinner or weekend dining, as this is a popular spot just steps from the Duomo and Piazza del Campo.
Hotel Athena Terrace Bar in Siena
About the Terrace Bar & Views Hotel Athena features a panoramic terrace bar on its rooftop where guests can enjoy drinks, aperitifs, or dinner with sweeping views over Siena’s rooftops and the Tuscan countryside beyond. Terrace service is usually available in the warmer months and showcases beautiful sunset views paired with local wines and cocktails — it’s a highlight for many visitors.
Volterra
A Few Tips to Make Your Visit Even Better: Take a stroll through Piazza dei Priori, one of Tuscany’s most impressive medieval squares. Visit the Roman Theatre and imagine performances from nearly 2,000 years ago. Browse the local alabaster workshops — Volterra is famous for this traditional craft. Wander without a strict plan; some of the best discoveries are found in quiet side streets. Pause for a leisurely meal and enjoy local specialties paired with Tuscan wine. Just so you know: The town is built on a hill, so comfortable shoes are highly recommended. Parking is located outside the historic centre — follow signs to the designated lots. Shops may close for a midday break, especially outside peak season. Enjoy the history, the views, and the slower rhythm of Volterra. Take your time — this is a place meant to be savored.
San Gimignano
ake your time wandering through Piazza della Cisterna, the heart of the town and a perfect place to pause for a coffee or gelato. Climb Torre Grossa for sweeping views over rolling vineyards and olive groves — the panorama is unforgettable. Explore the quiet side streets beyond the main squares to discover artisan shops and peaceful corners. Sample Vernaccia di San Gimignano, the town’s celebrated white wine. Visit early morning or later in the afternoon for a more relaxed atmosphere. Just so you know: The historic center is pedestrian-only, and parking is located outside the town walls. The streets are cobbled and occasionally steep — comfortable shoes will make all the difference. Shops may close briefly in the early afternoon. Enjoy the towers, the views, and the timeless charm of San Gimignano. It’s a place where history rises quite literally all around you.
Pienza
Stroll through Piazza Pio II, the heart of the town, and admire the cathedral and surrounding Renaissance palaces. Walk along the panoramic viewpoints behind the town walls for breathtaking views over the Val d’Orcia countryside. Taste the famous Pecorino di Pienza — local sheep’s milk cheese that ranges from fresh and mild to aged and robust. Wander the charming side streets, many named after love, where small shops offer artisanal foods and local crafts. Pause for a leisurely lunch and enjoy the peaceful rhythm of village life. Just so you know: The historic centre is pedestrian-only, with parking located just outside the walls. The town is compact and easy to explore on foot. Shops and restaurants may close briefly in the early afternoon. Take your time in Pienza — it’s a place designed to be admired slowly, where every view feels like a postcard and every corner reflects thoughtful beauty.
Montepulciano
Make your way up to Piazza Grande, the town’s impressive main square, surrounded by historic palaces and the cathedral. Climb the tower of the Palazzo Comunale for panoramic countryside views that stretch for miles. Visit one of the historic underground wine cellars carved into the rock beneath the town. Sample Vino Nobile di Montepulciano, the area’s celebrated red wine. Take your time exploring the artisan shops and quiet side streets along the way. Just so you know: Montepulciano is built on a steep hill — comfortable walking shoes are essential. The historic center has restricted traffic, and parking is available below the town with escalators and shuttle options. Shops may close for a short break in the early afternoon. Enjoy the rhythm of Montepulciano — where grand architecture, rolling vineyards, and relaxed Tuscan living come together beautifully. If you'd like, I can create one for Montalcino to round out your wine-country collection.
De' Ricci Cantine Storiche in Montepulciano
🕒 Typical Opening Hours (daily): • Monday – Sunday: 10:30 AM – 7:00 PM (hours can vary by season and tours are by reservation) Visit Notes: • The cellar and wine tastings are generally by advance reservation, and slots often start around 10:30 AM, 12:30 PM, 3:00 PM, and 5:00 PM. • It’s highly recommended to book in advance, especially in peak travel months, as tours fill up quickly. Take time to explore the impressive underground chambers — they are among the most beautiful historic cellars in Tuscany. Sample Vino Nobile di Montepulciano, the estate’s signature wine, along with other carefully crafted selections. Ask about the aging process and the story behind each vintage — the experience is as much about heritage as it is about wine.
Enoliteca Consorzio Vino Nobile in Montepulciano
Opening Hours (typical) Hours can vary by season, but generally: Monday – Sunday: ~10:30 AM – 7:00 PM (some sources note extended hours later in season). What It Is Enoliteca is the wine bar and tasting facility of the Vino Nobile di Montepulciano consortium, located inside the old Fortezza di Montepulciano. Here you can sample a wide range of local Vino Nobile DOCG wines — often by the glass or tasting portions using a self-serve dispenser system — and enjoy beautiful views of the countryside and fortress gardens.
Ercolani Cellars - "Underground City" and Museum in Montepulciano
Cantina Ercolani offers: Guided tours of its historic underground cellars and “Underground City” featuring medieval and Etruscan elements. Wine tastings of the winery’s own Vino Nobile, Vinsanto, and other local products, often paired with pecorino cheese and cured meats. A direct shop where you can buy wines, olive oil, truffles, salami, and gift baskets. Typical Opening Hours According to local listings, Cantina Ercolani is generally open every day (except Christmas Day) from 8:00 AM to 10:00 PM with continuous hours. Visit Tips The tasting and cellar tours can often be free or included with a purchase, but reservations are recommended for full guided experiences. Comfortable shoes are helpful as you explore historic stone cellars and uneven surfaces.
