Pienza is a charming and picturesque town known for its Renaissance architecture, stunning views of the surrounding countryside, and delicious local food. Here are some things you can do in Pienza: Visit Pienza's Historic Center: Pienza is a UNESCO World Heritage Site and its historic center is a delight to explore. Walk through its narrow streets, admire the well-preserved Renaissance architecture, and discover charming squares. Piazza Pio II: This central square is the heart of Pienza and is surrounded by important buildings, including the Cathedral of Santa Maria Assunta and the Palazzo Piccolomini. Relax in the square's ambiance and enjoy the beautiful architecture. Palazzo Piccolomini: Explore this elegant palace that was once the residence of Pope Pius II. The palace is a prime example of Renaissance architecture and offers insights into the history of the region. Local Food and Wine: Pienza is famous for its pecorino cheese, so be sure to taste some of this local delicacy.
Idyllium Cocktail Bar: Best cocktail bar in Pienza. Picturesque panoramic views of the Val D'Orcia valley and a vast aperitivo menu. Great music at night too. Cordial Cocktail Bar: CCB is in the gardens of a 15th-century monastery. Great apertivo menu and cocktails. Great music playing and outdoor views are amazing. Pienza 491: Come during the day to see the views from its elevated terrace; stay on after sunset for peak vibes. Bar Il Casello: Another great location to sit outside and enjoy the Tuscan scenery. Grab a cappuccino or a beer and enjoy the views. La Bandita Townhouse: A boutique hotel with a lovely cafe that offers a modern twist on classic Tuscan dishes. Trattoria Latte di Luna: Known for its traditional Tuscan dishes, it's a great place to try the local pasta with wild boar sauce. Osteria Sette di Vino: A cozy place offering a menu of regional classics. Il Rossellino: Another favorite spot for traditional Tuscan cuisine.
Montepulciano is a medieval town known for its historic architecture, wine production, and stunning vistas. Here are some things you can do in Montepulciano: Piazza Grande: This central square is the heart of Montepulciano. It's surrounded by historical buildings, including the town hall, the Cathedral of Santa Maria Assunta, and the Palazzo Comunale. Church of San Biagio: A short walk from the hotel block, this Renaissance church is considered one of the most beautiful churches in Italy. Its stunning architecture and scenic location make it a must-visit. Wine Tasting and Cellar Tours: Montepulciano is renowned for its wine, particularly Vino Nobile. Take advantage of the many wineries and wine cellars in the area offering guided tours and tastings. Visit a Viewpoint: Veduta Panoramica is a beautiful viewpoint at the edge of the historic center walls. It’s the perfect place to come for incredible views over the Tuscan countryside, especially at sunset.
Ristorante La Grotta: Next to the Temple of San Biagio, La Grotta offers refined Tuscan cuisine with an emphasis on local ingredients. The courtyard seating offers a beautiful view of the temple. Osteria Porta di Bacco: Chef Rachael Ray's favorite restaurant for a reason! The best pasta Dalton and I had in Montepulciano. Incredible dishes at an affordable price that can be paired with a wine next door at the Porta di Bacco wine shop. Highly recommend if you are in the area! Contucci Winery: The winery is over 1000 years old, and the Contucci family are recognized as one of the "founding fathers" of the famous Vino Nobile wine. De Ricci Winery: Located in the heart of Montepulciano, be sure to stumble into this winery and visit the wine cellar - which dates back to 500BC! Icario Winery: Beautiful, modern winery producing some of the best wine in the region. Enoteca Osteria del Borgo: A cozy wine bar with an extensive wine list. Great food and great views.
If you plan to extend your trip either before or after the wedding weekend, we recommend checking out the following nearby cities: - San Gimignano / Known for it's skyline featuring towers built as early as the 14th century, the "Manhattan of the Middle Ages" is a UNESCO World Heritage site that is worth checking out for it's quaint town center and unique history. - Cinque Terre / Stunning seaside town built onto steep cliffs on the coastline of Italy. - Florence / Beautiful city full of history, art, architecture and food. - Siena / Larger Tuscan city with a lot of medieval charm, check out the historic town center which is a UNESCO World Heritage site.
Biking is a great way to enjoy the breathtaking views of Val d'Orcia. There's a few routes we would recommend, such as the Pienza Route (an asphalt route that takes you to/from Pienza and Montepulciano). Please reach out if you'd like to rent either bikes or e-bikes during your trip and we would be happy to get you in touch with a local vendor! E-Bikes will generally cost around 60 Euros per day from local vendors.