Things To Do
Antinori nel Chianti Classico Winery
(Kat's favorite winery in the area!) Antinori is one of the most iconic wine families in Italy. Their stunning, modern winery is built directly into the hillside and offers curated tastings, guided tours, and a fantastic on-site restaurant. Perfect if you’re looking for a slightly more elevated wine experience. ~20 min away
Conte Ferdinando Guicciardini Castello Di Poppiano Winery
A historic estate owned by one of Florence’s oldest noble families. Tastings here include guided visits through ancient cellars, the olive mill, and the Vin Santo aging tower, finished with panoramic views and thoughtfully paired wines, olive oil, cheeses, and traditional Tuscan treats. ~8 min away
Fattoria San Michele a Torri Winery
A warm, rustic, and approachable experience focused on organic farming. Tastings feature Chianti wines alongside local cured meats, pecorino cheeses, fresh bread with olive oil, and even eggs from their free-range hens — perfect if you want something authentic and unfussy. ~15 min away
Frescobaldi Winery - Villa Castiglioni
A refined but relaxed introduction to one of Tuscany’s most important wine families. Tastings are paired with local cheeses, cured meats, and olive oil, set against classic vineyard views. ~10 min away
Scenic Walk: Via di Castiglioni
A beautiful, easy countryside walk that begins directly at the castle. This historic path winds through vineyards, old farmhouses, churches, and cypress-lined hills — essentially an open-air museum showcasing centuries of Tuscan life and land use. Perfect for a slow morning stroll. Text us for a suggested route!
Tennis Courts
Covered courts that remain open on the sides during summer. Equipment is available, and it’s easy to book — a great low-commitment way to move a little before aperitivo. ~5 min away
Montelupo Fiorentino Golf Club
9 holes. Relaxed and scenic. ~20 min away
Golf Club Ugolino
18 holes. A more traditional and well-known course. ~35 min away
Horseback Riding
Guided outdoor rides through the rolling Tuscan countryside, suitable for beginners and experienced riders alike. ~8 min away
Massages & Yoga
Treat yourself to a relaxing massage or yoga session set against the Tuscan hills. Options range from deep tissue and shiatsu to kobido facial massage and private or small-group yoga classes — ideal for unwinding after travel or resetting before wedding festivities. ~8 min away
Truffle Hunting
Join local truffle hunters and their dogs for a walk through the countryside, learning how truffles are found and harvested. Some experiences include an aperitivo or full lunch afterward — equal parts educational and delicious. ~25 min away
Cooking Classes
Hands-on classes focused on traditional Italian cuisine, from fresh pasta to classic sauces. ~30 min away
Pottery Workshop
Visit a working ceramics atelier and see traditional Tuscan pottery techniques in action — a great cultural stop if you enjoy art and craftsmanship. ~25 min away
Silver Jewelry Workshop
Create your own personalized silver charm or bracelet under the guidance of master silversmiths. No experience required, and you’ll leave with a meaningful keepsake. ~30 min away
Vespa Tours
Ride classic Italian Vespas through winding country roads, vineyards, and hill towns. Romantic, iconic, and incredibly fun. Start either at Castello di Poppiano (~10 min away) or directly from Montegufoni.
E-Bike Tours & Rentals
Electric bikes make it easy to explore the hills without the uphill struggle. Choose guided tours or go at your own pace with mapped routes. ~8 min away
Hot Air Balloon Ride Over Chianti
Sunrise balloon flights over vineyards and rolling hills, followed by breakfast. An unforgettable splurge. ~30 min away
Florence
(~30 min away) A perfect day trip if you’re craving art, history, shopping, or incredible food. • Visit the Duomo, Uffizi Gallery, or Accademia • Walk across Ponte Vecchio and explore Santo Spirito & Boboli Gardens • Lunch recs: All'Antico Vinaio, Pino's, Mercato Centrale, Gustapizza, Osteria Santo Spirito, Trattoria Za Za • Gelato recs: La Carraia, Gelateria dei Neri
San Gimignano
(~45 min away) A postcard-perfect medieval town known for its stone towers. • Wander the historic center • Stop for award-winning gelato • Pair with a nearby winery visit for a half-day outing
Siena
(~1 hour away) Elegant, historic, and slightly less hectic than Florence. • Explore Piazza del Campo • Visit Siena Cathedral • Enjoy a slower pace with incredible food and views