2025 Radda in Chianti Travel Guide: Must-see attractions, popular food, hotels, transportation routes (updated in October)

【Stunning Check-in Spots】✨ 1️⃣ Chianti Wine Region 📍Address: via Bolgherese, 174, 57022 Bolgheri 🍷Authentic Italian red wine! Highly recommend the wine tasting experience at Tenuta di San Guido winery, whose Sassicaia series is known as the "Italian Lafite"—a legendary wine～ 2️⃣ Volterra 📍Address: 53048 Volterra SI 🏛This Etruscan ancient city features a super cool underground tunnel system and handcrafted amber workshops, a must-visit for Harry Potter fans! 3️⃣ Pienza 📍Address: 53026 Pienza SI ♨️A stunning hot spring town! The hilltop viewing platform overlooks the entire Orcia Valley, every snapshot looks like a postcard🎑 4️⃣ Montepulciano 📍Address: 53045 Montepulciano SI 🌇A more niche wine town than Montalcino, the sunset at the square is breathtaking, perfect for watching the sunset with a slight buzz～ 🚗【Convenient Transportation Guide】🚗 ▫️Florence → Volterra: Train + shuttle bus (about 2 hours total)🚆 ▫️Chianti area: Strongly recommend renting an electric bike! Cycling between vineyards is super pleasant～🚴 ▫️Montepulciano: Free parking lot in the town center, arrive early during peak season to secure a spot🅿️ 🛍️【Must-Buy Souvenirs】🛍️ 🍷Chianti DOCG red wine: Sassicaia series from Tenuta di San Guido (90+ rating) 🧀Pecorino cheese: Handmade in Volterra’s old town workshops, perfect with local honey! 🕯️Handmade beeswax candles: Lavender scent from Pienza is the most popular, all-natural and additive-free 🍽️【Recommended Restaurants】🍽️ 📍 Trattoria da Pippo Address: via Chiantigiana, 33, 50026 San Casciano in Val di Pesa 🍝The century-old meat sauce pasta is a must-try! The noodles are chewy, and the sauce is so rich it brings tears～ 📍 La Bottega del Vino Address: via di Gracciano nel Corso, 93, 53045 Montepulciano 🍝The truffle pasta in the cave restaurant is stunning! Michelin-level quality at an affordable price～ 📍 Gelateria La Romana Address: via Matteotti, 4, 56048 Volterra 🍦Pistachio flavor is limited daily! Super creamy but not too sweet, definitely worth the queue! 🏡【Heavenly Accommodations】🏡 🍇 Tenuta di San Guido Winery Villa Address: via Bolgherese, 174, 57022 Bolgheri ✨Includes a private tasting room and vineyard spa, a paradise for wine lovers～ ♨️ Terme di Saturnia Hot Spring Resort Address: via della Follonata, 58014 Saturnia 🛁Natural sulfur pools + cliffside infinity pool, perfect for beauty and skin care! 🏰 Castello di Volpaia Castle Hotel Address: 53017 Radda in Chianti 🏰A medieval castle converted into a hotel, terrace breakfast overlooks the entire Chianti hills～ 🌟【Perfect 5-Day Itinerary】🌟 Day 1: Florence → Chianti (wine tasting + cycling) → Volterra (stay in the ancient city) Day 2: Volterra underground city → Pienza hot springs → Montepulciano (stay at winery) Day 3: Montepulciano square → Siena → return to Florence 💕【Tips】💕 ✔️Best travel season: September to October grape harvest season ✔️Must-bring items: Sunscreen + lightweight hiking shoes ✔️Hot spring secret: Sulfur pools are super good for the skin! ✔️Perfect ending: Chianti red wine + Tuscan bread = forever classic

🍇🍷 Savor the Heart of Chianti: Medieval Walks and Wine Hideaways Kick off your journey in Castellina in Chianti, a dreamy Tuscan gem where vine-clad hills roll into centuries-old stone towns. Begin your day on Via delle Volte—this enchanting medieval tunnel street is pure magic! Stroll beneath stone arches, peek into artisan shops, and don’t miss the moody light for truly “insta-worthy” shots. Swing by the Church of Saint Salvador to take in its serene Romanesque charm. The simplicity here is a slice of Chianti’s soul and makes for peaceful, atmospheric photos, especially in the golden morning light. Next, walk Via Romana (Via Ferruccio, 44), the historic main street, perfect for window-shopping, local gelato, and candid snaps against terracotta facades. Tip: Wander here early before the day-trippers arrive for that tranquil, lived-in village vibe. Detour to Enoteca La Cantinetta on Via delle Volte for a cozy wine tasting—ask for local Chianti Classico and grab a patio seat if you can. The staff enjoys sharing insider stories on the region’s winemaking heritage! In the afternoon, head over to nearby Radda in Chianti and marvel at the Palazzo Del Podesta (Piazza Ferrucci). Its majestic arches and coat-of-arms–studded walls are a prime photo op, especially as late light hits the bricks. 📝 Practical Tips: - Both towns are best explored on foot—wear comfy shoes! - Via delle Volte and Via Romana are picturesque but can get slippery after rain. - Carry a light jacket, as tunnels and wine cellars stay cool year-round. - Many shops/attractions close for a long lunch (1–3 PM), so plan accordingly! #Chianti #Tuscany #MedievalTowns #WineLovers #TravelItaly

#mediterranean 🍷 Discover Tuscan Charm in Radda in Chianti! Immerse yourself in rolling vineyards, medieval squares, and authentic small-town magic—this is wine country at its dreamiest. Start your day at IV November Square, the beating heart of Radda, open all day and perfect for coffee and people-watching. Snap the colorful shopfronts and winding stone streets—prime spots for Insta-worthy shots of rustic Italian life. Stroll over to the nearby Palazzo Del Podesta on Piazza Ferrucci, whose noble façade and centuries-old loggias tell stories of Chianti’s rich past. Don’t miss the Propositura di San Niccolò: this Romanesque church on P.za Francesco Ferrucci is a gem for architecture lovers. The soft morning light streaming through the old windows makes for beautiful, atmospheric photos—visit early to enjoy quiet moments inside. For a taste of local life, wander through Giardino Azzurro Celestino—a peaceful park on Str. della Croce, ideal for a picnic lunch or a shady siesta under cypress trees. Recharge and soak in Chianti’s gentle landscapes, with panorama shots of vineyards rolling away beneath blue skies. Wrap up your afternoon at Podere L'Aja (Loc. L'aia, 156), open Monday–Friday from 9:00–17:00. This family-run winery is a must for sampling classic Chianti—and their terrace gives unbeatable vineyard views for your sunset photos. Quick Tips: - Radda’s stone streets can be steep—wear comfy shoes! - Most shops close mid-afternoon—plan meals ahead. - Bring cash: smaller spots may not accept cards. - Early evening is best for soft golden light and fewer crowds! #RaddainChianti #Tuscany #WineCountry #HiddenItaly #TravelTips

Nestled among olive groves and vineyards, Pieve Aldina Relais & Châteaux offers a serene escape in the heart of Tuscany. Located at Traversa del Chianti, Radda in Chianti, this newly opened gem may challenge your driving skills with its gravel approach, but the reward is a tranquil retreat amidst Italy's famed countryside. 🛏️ The hotel, a refurbished historic building, boasts a limited number of rooms, ensuring a peaceful stay. At night, the clear skies reveal a dazzling display of stars, perfect for romantics and dreamers alike. However, take note that the fresh renovations may leave a lingering scent, which might not sit well with the more scent-sensitive travelers. 🍴 Dining options for dinner are on the limited side, but what's available is sure to be curated to reflect the region's rich culinary heritage. Despite the teething issues of a new establishment, the allure of Pieve Aldina's setting is undeniable for those seeking a quiet corner under the Tuscan sun. #RaddaInChianti #TuscanyHotel #TuscanyTravel