Ready for a roadtrip in Tuscany? These are my highlights!

#mediterranean Ready for a Tuscany adventure with seriously epic views? 😍 This whirlwind trip will have you strolling Siena’s ancient roads, climbing medieval walls in Monteriggioni, and unwinding in the heart of Chianti wine country—all with plenty of unforgettable panoramas. Top Spots to Visit 1. Via Romana, Province of Siena (Via Ferruccio, 44, 53011 Castellina in Chianti SI) Start the day with a peaceful walk along this historic road—it’s lined with classic Tuscan charm and gives you a taste of local life. Plus, it’s the perfect sunrise or sunset photo op! 2. Mura di Monteriggioni - Camminamento Sud (Via I° Maggio, 53035 Monteriggioni SI, 09:30-13:30, 14:00-18:00) Get up on Monteriggioni’s iconic medieval wall for jaw-dropping countryside views. My tip: go early or late to avoid crowds and snap that “King of the Castle” selfie. 3. Porta Franca (Via I° Maggio, 53035 Monteriggioni SI, open all day) Walk through this ancient stone gateway—one of Tuscany’s best-preserved. It’s like stepping inside a Renaissance painting. 4. Hotel Palazzo Squarcialupi (Via Ferruccio, 22, Castellina in Chianti) This hotel is next-level with its reserved parking, wine tastings, and a dreamy wellness area you can use even after check-out. The staff go above and beyond, making every traveler feel VIP. 5. La Castellina (Via Ferruccio, 26, Castellina in Chianti) Pop in for a top-tier wine tasting with sweeping Tuscan views. Staff love to chat about local vintages! Getting Around: Rent a car for max flexibility—village-to-village buses are limited. Most towns have paid parking near the center. Food Picks: Try wild boar pasta (“pappardelle al cinghiale”) in village trattorias. For wine and local fare, La Taverna Squarcialupi is a standout. Key Tips: Pack light layers—weather changes quick in the hills. Bring cash for small shops and parking. #tuscanyviews #chiantiwine #monteriggioni #sienadiaries #tripdotcom