Best Arezzo Day Trips in 2026

Arezzo , Tuscany

From $ 217.59

- Guaranteed departure with 4+ guests. - This is a bike tour, so it’s important that you feel confident riding for your safety and the group’s. Please contact us before booking to avoid any issues during the tour. This is a shared tour. We limit the group to a maximum of 2–3 bookings to ensure everyone’s comfort. The eBike Ride: Set off to explore the Val di Chiana near Cortona, guided by local experts along breathtaking routes. The tour ends at a boutique winery for lunch and a tasting of selected wines (€40 extra, not included in the price). Riding Comfort: Our eBikes provide powerful pedal assistance, so you can enjoy the Tuscan countryside without the physical effort of a traditional bike. The tour lasts about 3 hours, 25 km (15 mi), and we always adjust the route based on our guests. Tours are also available around Cortona and in Pienza.

Arezzo , Tuscany

From $ 349.07

2022 and 2025 EUROPEAN TRAVEL AWARD WINNER - Our photography journey offers a unique opportunity to explore and capture the most captivating landscapes of Tuscany, from early morning light to sunset and dusk. It is a truly life-changing experience, revealing the breathtaking beauty and hidden secrets. During the Tour, you will be immersed in nature and in the authentic Tuscan culture and lifestyle, where history and art blend with outstanding food and wine. Guided by Marco Bulgarelli, an award-winning photographer, you will photograph both iconic views and lesser-known locations: magical landscapes, charming churches, vineyards, rolling green hills, and medieval hill towns and villages. The tour focuses on the finest viewpoints of Val d’Orcia and its surroundings, Crete Senesi, Montepulciano, Chianti, and Montalcino. We will always be in the right place at the right time. Participants will improve their photography skills and take home unforgettable images.

Arezzo , Tuscany

From $ 477.07

Kick off your day with a comfortable ride through the stunning Tuscan countryside. First, we’ll arrive in Siena, one of Tuscany’s most beautiful towns. Explore Piazza del Campo, famous for the Palio di Siena horse race, admire the breathtaking Duomo (Cathedral), and wander through the charming, narrow streets of the historic center. Wine Tasting & Light Lunch Next, we’ll head to a renowned winery for a light lunch paired with an amazing wine tasting experience. A sommelier will guide you through five exceptional wines, plus an olive oil tasting. After lunch, we’ll continue our journey with a spectacular drive through the rolling Vernaccia di San Gimignano vineyards, home to Tuscany’s most famous white wine. Stop in San Gimignano you’ll have free time to explore this medieval gem, known for its 14 towers dating back to the 13th century. The town’s atmosphere will transport you back to the Middle Ages! And of course, you can’t miss the world’s best gelato at Gelateria Dondoli.