Top Things to Do in Cortona: 3 Unmissable Tuscan Experiences

Cortona is one of Tuscany’s most enchanting hill towns—a medieval gem frozen in time, overlooking the breathtaking Val di Chiana. If you are planning your getaway and wondering about the absolute best things to do in Cortona to experience the region like a local, you have come to the right place. This sun-drenched corner of Italy offers far more than postcard-perfect views and cobblestone alleys; it invites you to dive headfirst into centuries-old traditions. Whether you are a dedicated foodie, a wine enthusiast, or an outdoor adventurer, these curated experiences are designed to turn a standard vacation into the trip of a lifetime.

To make the most of your time and secure your spot, booking your Cortona activities well in advance is essential, especially during the peak travel seasons. Below, you will find our handpicked selection of the top 3 guided experiences, complete with pricing, practical details, and direct links to book securely.

The Best Experiences to Book in and Around Cortona

Choosing the right activity can completely elevate your Italian holiday. When deciding what to do in Cortona, comparing duration, budget, and the style of the experience is the best place to start. The Tuscan countryside provides the ultimate backdrop, whether you want to roll up your sleeves in a traditional kitchen under the guidance of local chefs or explore rolling hills on a premium electric bike.

All of our selected experiences offer maximum flexibility—a game-changer for stress-free travel. You can take advantage of free cancellation up to 24 hours in advance and a convenient “book now, pay later” option.

Here is a quick breakdown of prices and features to help you choose your perfect Tuscan adventure:

Cooking Class at a Beautiful Tuscan Villa Near Cortona

If your dream is to master the culinary secrets of authentic Italian grandmothers, this Tuscan cooking class is an absolute must. Picture yourself stepping onto the grounds of a gorgeous villa nestled on a hillside in the Val di Chiana, surrounded by a lush forest where deer and squirrels roam. Led by Chef Dandy and Chef Otilia—passionate, authentic Italian chefs—you will instantly feel at home in a warm, welcoming environment.

During this 5-hour immersive experience, you will make several types of fresh pasta, a traditional Tuscan ragù (meat sauce), and a classic Italian dessert from scratch. The real highlight? You will cook exclusively with high-quality, homegrown ingredients, including olive oil pressed from the villa’s own groves and fresh vegetables picked straight from their garden. Afterward, you will sit down to enjoy your culinary creations alongside unlimited red wine and water. This is a small-group experience (limited to 10 guests), ensuring plenty of hands-on attention.

• Price: From €115 per person.

• Traveler Tip: Be sure to notify the hosts of any dietary restrictions or allergies in advance. If your preferred date looks unavailable online, you can contact the provider (Dedalo Bellini) directly to check for extra openings.

Check prices and availability: Don’t risk missing out! Click below to secure your spot with zero commitment today.

👉 Check Availability & Book the Villa Cooking Class on GetYourGuide

Cortona: Hands-On Pasta and Pizza Cooking Class

Short on time but unwilling to compromise on an authentic Cortona cooking class? This 2.5-hour experience is tailor-made for you. Hosted at the beautiful Casa Bellavista estate, local cook Simonetta welcomes you into her kitchen to teach you the fine art of traditional Italian baking and pasta-making.

Once you throw on your apron, you will be guided through every single step of the process. You will learn the secrets behind the perfect focaccia, authentic Italian pizza dough, and fresh handmade pasta (choosing between ravioli and tagliatelle). After the hard work is done, you can unwind with a stroll through the estate’s stunning rose garden, which boasts a spectacular 360-degree panoramic view of the Valdichiana. Weather permitting, your meal is served on an open-air terrace—and if you book the evening slot, you will dine while watching the sunset over the Tuscan hills. You can also pair your meal with a selection from a wine list featuring over 85 local Tuscan wines.

• Price: From €110 per person.

• What to bring: Comfortable clothes and walking shoes. This intimate class is capped at 8 participants. Please note it is not suitable for individuals with mobility impairments, wheelchair users, or infants under 1 year old.

Book with total flexibility: This popular workshop sells out quickly due to the small group size. Take advantage of the risk-free cancellation policy.

👉 Check Timings & Book the Pizza & Pasta Class on GetYourGuide

Cortona: Val di Chiana Guided E-Bike Tour with Wine Tasting

For travelers looking to pair outdoor exploration with world-class wine, this Tuscany e-bike tour is the gold standard of Val di Chiana experiences. Run by the local experts at EpicBike, this tour lets you soak in the sublime beauty of the countryside rolling between Cortona and Montepulciano—all without breaking a sweat, thanks to premium, eco-friendly electric bicycles.

The 5-hour itinerary (which includes about 3.25 hours of actual riding time) takes you along peaceful, gravel “strade bianche” (white roads), far away from heavy traffic and tourist crowds. You will pedal past blooming wildflowers, golden wheat fields, and pristine vineyards. On the loop back, the tour stops at a local estate and winery for a fabulous wine tasting paired with a light lunch (available for an optional €40 per person, payable directly to the cellar). The package includes your e-bike rental, helmet, technical assistance, and a highly convenient hotel pick-up and drop-off service.

• Price: From €158 per person (wine tasting/lunch optional and extra).

• Important Requirements: You should feel confident and stable on a bicycle. This activity is not suitable for pregnant travelers, anyone with mobility impairments, or individuals over 120 kg (264 lbs). Closed-toe athletic shoes are required (no sandals or flip-flops).

Lock in your e-bike today: Tours require a minimum of 4 participants to run, and bike sizes must be arranged in advance. Secure your adventure now.

👉 Check Rates & Book the Val di Chiana E-Bike Tour on GetYourGuide

How to Choose the Perfect Cortona Activity for Your Group

Still undecided? Consider your schedule and your preferred pace. If you want a deeply relaxing, food-focused day, the 5-hour villa class offers an old-world atmosphere and unforgettable farm-to-table dining. If you want a fast-paced, highly dynamic session that leaves your afternoon free to explore Cortona’s historic center, the 2.5-hour class at Casa Bellavista is a perfect fit. Finally, if you want to balance your indulgence with active exploration and vineyard views, hop on an e-bike for an unforgettable ride through the valley.

Insider Tips for Booking Your Cortona Experiences

• Plan ahead: Small-group experiences (capped at 8–10 guests) offer incredible quality but sell out months in advance, particularly during the spring and summer.

• Use the cancellation policy to your advantage: All the provided links feature free cancellation up to 24 hours before your activity. This means you can lock in your spots today and adjust your itinerary if your plans or the weather forecast change.

• Keep your budget flexible: By utilizing the “Book Now & Pay Later” option, your card won’t be charged at checkout, letting you manage your travel expenses with total peace of mind.

Stay in Ultimate Luxury in the Heart of Tuscany

After a day spent rolling out fresh pici pasta or cycling through the iconic landscapes of the Val di Chiana, there is nothing quite like returning to an exclusive retreat to unwind. To truly immerse yourself in the timeless magic of the region, we invite you to discover the breathtaking properties of TuscanMansions. Staying in one of our private, masterfully restored villas—complete with top-tier modern amenities and authentic Tuscan charm—will elevate your journey into an experience of unparalleled luxury, privacy, and relaxation. Head over to the TuscanMansions website to find the perfect luxury estate for your next Cortona vacation.