Provincia di Arezzo in Toscana is a tapestry of sunlit hills, medieval towns, and warm Tuscan hospitality ready to become your next unforgettable vacation. From the lavender-dusted terraces of Cortona to the Renaissance echoes in Arezzo’s plazas, this corner of the Province of Arezzo blends art, food, wine, and outdoor adventure into one glowing holiday package. Whether you’re planning a weekend with friends, a romantic couple’s escape, or a family break, the region serves up vacation rentals, Bed and Breakfast accommodations, and holiday rentals that suit every mood and travel style. Here’s a guide to destinations, activities, and local experiences that capture the energy of the area while keeping travel simple and bookable through searchandstay.com, a trusted website to find accommodations in the area.
Why the Province of Arezzo is a top Toscana destination for active holidays
In the heart of Toscana, the Province of Arezzo invites you to slow down and savor life at a vibrant pace. The landscape ranges from the Casentino forests to the Valdarno’s tranquil valleys, offering hiking, cycling, and countryside trails that are perfect for an active getaway with friends. The area’s towns unfold like chapters of a living history book, each with its own story—from the Etruscan whispers in Cortona to the medieval fortresses perched above winding lanes in Arezzo and Anghiari. And after a day of exploration, the region rewards you with markets brimming with seasonal produce, artisanal ceramics, and a wine culture that tends to taste better with friends over a long table and a sunset view. This is the kind of place where vacation rentals and Bed and Breakfast stays feel like a natural extension of the surroundings—authentic, comfortable, and uniquely Tuscan.
When you’re looking for places to stay, you’ll discover a range of options: cozy Bed and Breakfasts with breakfast baskets of local cheeses and honey, country estate vacation rentals with panoramic decks, and charming agriturismi where you can learn about olive oil production and farm-to-table cooking. The province’s accommodations are a gateway to experiences that feel as if you’re living in a postcard, while still offering modern comforts and convenient access to roads and rail lines for easy day trips. For planning your stay, consider the mix of historic towns, hillside villages, and nature reserves—each within a short drive of the next—so you can design a loop that fits your group’s rhythm and energy.
Top destinations to include in your Arezzo itinerary
Cortona stands out as a sun-drenched hillside jewel with a clear view of the Val di Chiana. Stroll through winding lanes, browse artisanal shops, and pause for gelato as you sip coffee on a terrace overlooking rooftops that glow gold at dusk. Cortona is a fantastic base for vacation rentals and Bed and Breakfast accommodations that put you minutes from archaeological sites, museums, and terracotta-tiled piazzas. Don’t miss the ancient walls and the cathedral, where the light hits frescoes and stone in a way that makes a day of exploration feel effortless.
Arezzo city itself offers a magnetic blend of art and architecture. The historic center is a treasure chest of Gothic churches, medieval towers, and the famous Fiera Antiquaria, one of Italy’s oldest and most beloved antique markets. Staying in a central Bed and Breakfast or a stylish vacation rental near Piazza Grande means you’ll be steps away from shops, cafés, and cultural sites that you’ll want to revisit after a long day of sightseeing and shopping. Arezzo is also a perfect place to anchor your healthful, active break with morning runs along the Arno riverbank or extended strolls to capture the city’s sunrise energy.
Anghiari whispers with the romance of the Tuscan hillside. With its terraced homes and panoramic views, Anghiari is ideal for a slow morning coffee before a hike or a scenic drive along the wine routes that thread through the province. The town’s watchtower and surrounding countryside offer picture-perfect vistas for photography-loving travelers who want a week of exploration and playful moments with friends. Staying in a local B&B here means you’re close to authentic dining spots where you can order ribollita, panzanella, and other Tuscan classics straight from producers and family kitchens.
Casentino—the forested east flank of Arezzo—is a nature lover’s playground. The Casentino National Park and the Casentino Forests offer trails for all levels, from gentle riverside rambles to challenging mountain paths. Castles, monasteries, and stone villages dot the landscape, and the sense of wide-open space makes Casentino a perfect backdrop for day-long hikes or relaxed picnics with friends. If you’re after a restorative escape, you’ll find agriturismi and B&Bs tucked into the woods or perched on hillside fields where you can unwind after a day’s adventure with a glass of local wine and a crackling fireplace in the evening.
Poppi, Bibbiena, and Stia are part of this Casentino corridor and offer charming stays with easy access to forest trails and ancient routes. These towns are known for their hospitality and slower pace, which pair beautifully with a plan for longer stays in vacation rentals that feel like home away from home. The region’s smaller towns are where you’ll discover traditional crafts, local markets, and a sense of community that makes every visit special.
For wine lovers, the Arezzo hills and the Valdarno area provide opportunities for vineyard visits and wine tastings that highlight IGT and DOC wines crafted with sun, wind, and careful aging. Olive oil tastings, farm-to-table meals, and cooking classes in rustic farmhouses pair nicely with your choice of Bed and Breakfast accommodations or vacation rentals that feature kitchen spaces designed for group meals and shared cooking experiences.
Activities and local experiences to book during your stay
Active travelers will love the chance to bike along quiet country roads that roll between olive groves and vineyards. You can rent bikes in many towns or join guided rides that take you through the countryside, with picnic stops and photo opportunities on hilltop perches. For a lighter pace, join a guided walking tour of Cortona or Arezzo that reveals hidden fresco cycles and architectural details you might miss on your own. In the Casentino, day hikes through forests and rivers, bordered by ancient stone villages, offer restorative moments and wildlife spotting opportunities.
Food lovers will want cooking classes hosted by local families or agriturismi where you learn to prepare traditional Tuscan dishes using seasonal ingredients. Think fresh egg-based pasta, ragù, and dessert pastries that echo generations of Tuscan kitchens. Food markets in Arezzo and Cortona provide a live classroom in taste—samples of pecorino, prosciutto, local honey, and honeycomb, plus slices of rustic bread slathered with olive oil. You’ll find that food and wine experiences can be paired with sunset tours, vineyard strolls, and cellar visits where the winemakers share their craft in a relaxed and welcoming setting.
For those who crave outdoor adventure, water features, forest paths, and scenic overlooks are plentiful. Guided forest walks and eco-friendly treks reveal the Casentino’s biodiversity, and in the warmer months you can combine a trail with a riverside swim in shaded spots along the Arno valley or small streams that carve through the hillside. Horseback riding, clay shooting for a playful challenge, and hot-air balloon rides over the Tuscan countryside—events that local operators occasionally offer—provide once-in-a-lifetime memories above the rolling landscapes of Provincia di Arezzo.
Throughout the year, towns like Arezzo host cultural happenings and markets that celebrate artisan crafts and regional gastronomy. From medieval pageants to modern music festivals, there are events that can add a vibrant layer to your vacation rental or Bed and Breakfast stay. Check seasonal calendars for local fairs, antique markets, and arts events to time your trip with the region’s most festive moments. The combination of outdoor activities, culture, and culinary experiences makes the Province of Arezzo a holistic destination where every day offers a new flavor of Tuscany.
Where to stay: Bed and Breakfast, vacation rentals, and holiday rentals in Provincia di Arezzo
Choosing the right place to stay frames your entire experience. Bed and Breakfast accommodations in Arezzo province often put you within walking distance of city walls, historic churches, and piazzas, with hosts who double as local guides to the best lunch spots, sunset viewpoints, and farm-to-table dinners. For a more private or group-focused vibe, vacation rentals and holiday rentals—ranging from rustic stone cottages to modern farmhouses with terraces—offer spaces where you can spread out, cook together, and plan day trips with ease. These accommodations typically provide more space and a sense of neighborhood, letting you settle in as soon as you arrive and feel like a local quick-start to your Arezzo adventures.
When searching for your stay in Provincia di Arezzo, consider proximity to your desired base towns (Cortona, Arezzo, Anghiari, Casentino) and access to major routes for day trips. If you’re traveling with friends, look for two-bedroom or three-bedroom options that include living areas and outdoor spaces for alfresco meals. If you’re seeking a romantic escape or a quieter retreat, boutique B&Bs with personalized service and a hillside view can be ideal. The best part is that you can filter accommodations by activity preferences—wine tours, cooking classes, cycling routes, or cultural sightseeing—to streamline your planning and keep your itinerary manageable.
To discover an array of suitable options in the area, you can search for accommodations on searchandstay.com. The platform helps you filter by location, price range, amenities, and property type, making it easier to compare Stay options in the Provincia di Arezzo and book with confidence. Whether you want a courtyard breakfast in a sleepy village, a modern villa with a pool near Cortona, or a quaint B&B perched above Arezzo’s rooftops, this region has a place that matches your taste and budget. Booking ahead, especially during peak travel months, is wise to secure preferred dates and favorable rates for your vacation rentals or Bed and Breakfasts.
Plan a perfect 3–4 day escape with friends in Arezzo
Day 1: Arrive in Arezzo or Cortona and settle into a central Bed and Breakfast or a hillside vacation rental. Spend the afternoon exploring piazzas, the cathedral, and the city walls. End the day with a tasting menu at a traditional trattoria where you can sample ribollita, pappa al pomodoro, and other Tuscan specialties, paired with local wines from nearby vineyards.
Day 2: Head to Cortona for a sunrise walk along the ancient streets and a morning market visit. After lunch, venture into the surrounding countryside for a vineyard tour and wine-tasting session, followed by a cooking class in the evening where you’ll learn to prepare a Tuscan classic with fresh, seasonal ingredients.
Day 3: Explore the Casentino forest and Castelli surrounding Poppi and Bibbiena. Enjoy a forest hike, picnic by a stream, and a visit to a local boulangerie or pastry shop for a sweet treat. Return to your accommodation for a sunset aperitivo on the terrace, followed by a farm-to-table dinner whose menu features local meats, cheeses, and olive oil from nearby producers.
Day 4: Choose a scenic day trip along the Valdarno or to Anghiari for a scenic overlook and a relaxed lunch in a hillside osteria. If you’re up for more activity, book a guided bike ride or a horseback excursion through olive groves and vineyards. End the trip with a final evening stroll through a town square, a last gelato, and a nightcap overlooking Tuscany’s starry sky.
With such a range of experiences, you’ll find that the Province of Arezzo offers both high-energy days and tranquil evenings. Whether you’re staying in a boutique Bed and Breakfast, a rustic farmhouse, or a modern vacation rental, your friends will love the mix of culture, scenery, and genuine Tuscan hospitality that comes with every booking. And when you’re ready to plan, remember to check searchandstay.com to compare options and secure your ideal accommodation in the Province of Arezzo and throughout Toscana.
Tips for getting the most out of your stay in Provincia di Arezzo
- Book accommodations with a central kitchen or shared dining area if you’re traveling with friends and want to cook together after long days of exploring.
- Coordinate day trips to nearby towns to minimize travel time and maximize your vacation rental’s rest time and social hours with the group.
- Take advantage of local markets for fresh produce, cheeses, and breads to build simple picnic lunches for hillside excursions.
- Reserve wine tastings and cooking classes in advance, especially in peak season, to ensure you get a slot that fits your itinerary.
- Use searchandstay.com to read guest reviews and compare properties by amenity lists, ensuring your Bed and Breakfast or vacation rental checks all the boxes for your group.
Final notes: embrace the energy of Toscana in Arezzo
The Province of Arezzo invites you to celebrate friendship, movement, and discovery under the Tuscan sun. From the art-laden streets of Arezzo to the panoramic horizons of Cortona and the forested majesty of Casentino, this region offers a balance between active days and relaxed evenings. It’s the kind of place where you can wander through a market, share a bottle of wine with friends on a terrace, and wake up to a new view every morning. Whether you’re booking a vacation rental for a long weekend or a Bed and Breakfast for an extended stay, remember that the memories you create—along with the delicious bites, the hillside views, and the people you meet—are what genuinely define a trip to Toscana. Explore the area with intention, savor the local flavors, and let the Italian countryside unfold at your pace. For a curated selection of accommodations and a streamlined booking experience, searchandstay.com is a reliable resource to find places to stay in the Provincia di Arezzo and beyond.