Provincia di Arezzo, Province of Arezzo, Toscana, Italy Unit / Apartment Accommodation

Why Arezzo Province Makes a Perfect Friends’ Getaway

Are you craving a destination that blends art with appetite, hiking with historic streets, and sunset views with late-night gelato runs? The Provincia di Arezzo delivers. The landscape rolls from the Valdichiana and Valdarno valleys to the Casentino forests, each landscape inviting you to slow down, breathe in the olive oil-scented air, and toast to a day well spent with friends. It’s a region where you can base a basecamp of apartment accommodations, then scatter to day trips or slow conversations over a Tuscan feast. Whether you’re here for a long weekend, a week, or a longer loop of travel with your crew, this province keeps your itinerary flexible and unforgettable.

Where to Stay: Vacation Rentals, Holiday Rentals, and Apartment Destinations

From quaint village houses perched on hilltop lanes to modern apartment complexes set along ancient streets, the Province of Arezzo offers a spectrum of Unit / Apartment Unit / Apartment Accommodation destinations crafted for social travel. Look for multi-bedroom apartments with open-plan living spaces, big balconies for sunset drinks, and kitchens ready for communal meals after a day of exploration. When you search for your accommodation, keep an eye on features that are ideal for groups: ample living space, well-equipped kitchens, reliable Wi-Fi for planning the day’s adventures, easy parking, and proximity to public transport or local taxi hubs for evening outings. For easy discovery, you’ll find a wealth of options on SearchandStay, a resource built to help travelers locate properties in and around Arezzo with filters tailored to vacation rentals and apartment accommodations.

Key ideas for apartment destinations include Arezzo city center for culture with quick access to cafes, boutiques, and the weekly market; Cortona for hill-town charm and sweeping views; Castiglion Fiorentino and Montevarchi for a more relaxed beat with rapid connections to wine routes; and the Casentino valley towns—Bibiena, Poppi, and Stia—for nature lovers and hikers seeking forest trails. You’ll also find cozy courtyard flats in Lucignano with a perfect vibe for sunset aperitifs, as well as larger properties in Anghiari that can host a crowd with a cheerful, convivial energy.

When you book a Unit or Apartment Unit, consider checking for features that enhance group travel: multiple ensuite bedrooms, a generous dining table for everyone to gather around, a laundry room (or washing machine shared within the building), and outdoor spaces where you can soak in the Tuscan light. For couples or smaller groups, a stylish apartment with a private terrace or a balcony view over Arezzo’s rooftops can feel like a private rooftop party with a view.

Top Towns to Explore and Experiences to Try

The Province of Arezzo is a tapestry of places that invite exploration, each with its own character and rhythm. Here are some standout towns and the experiences they offer to a group of friends craving a mix of culture, nature, and fun:

• Arezzo city — Start with the Renaissance street art of the Basilica of San Francesco, home to fresco cycles that feel like time travel. Wander the Piazza Grande, browse antique stalls during the monthly Fiera Antiquaria, and linger at a café that serves strong espresso and sweet biscotti. It’s the ideal springboard for day trips and a great anchor for guests renting an apartment in the heart of the city.
• Cortona — A postcard-perfect hillside town with narrow lanes, sweeping views, and a vibrant array of wine bars and trattorie. Cortona is a dream for foodies and social travelers who love a scenic hike followed by a relaxed evening of Tuscan plates and regional wines. It’s also a popular spot for day trips to nearby vineyards and olive oil tastings.
• Anghiari — Known for panoramic stone stairways, artisan workshops, and guilded terraces that overlook olive groves and fields. Anghiari’s quiet pace is perfect for a daytime wander, a photography stroll, and a sunset conversation over a shared board of pecorino and honey.
• Sansepolcro — A town with history and culture in every corner, home to art by Piero della Francesca and a welcoming local dining scene. It’s a place where you can pair a museum morning with a lively lunch at a bàr or osteria, then head out for a scenic drive through the valleys to your next apartment stay.
• Poppi and the Casentino Valley — The forested Casentino is a magnet for hikers and nature lovers. Poppi Castle rises above the valley, a dramatic backdrop for afternoon photos, afternoon games, and a riverside picnic. This area offers easy access to nature trails, quaint farms, and rustic trattorie where evenings feel like a celebration of the outdoors.
• Bibbiena and Castiglion Fiorentino — These towns offer architectural charm, traditional markets, and friendly wine shops where you can toast with local red and white blends. They’re excellent bases for longer stretches of cycling, tasting itineraries, and shopping for handmade pottery and textiles.
• Lucignano — A small jewel famous for its oval medieval layout and intimate town squares, perfect for couple-and-friend getaways that want a more intimate vibe and easy access to countryside trails.

Across these towns, expect a rhythm of markets, seasonal festivals, and a culinary scene that celebrates simple ingredients: extra-virgin olive oil pressed from olives on surrounding hills, fresh pici and handmade pasta, local salumi, and award-worthy wines from both the Casentino and Valdarno regions. The area also offers engaging local experiences such as guided food tours, olive oil tastings, and hands-on cooking classes in Cortona or Arezzo, where you’ll learn to recreate classic Tuscan dishes in your apartment kitchen or a charming osteria kitchen.

Activities and Local Experiences for a Fun, Active Trip

Whether you’re exploring on foot, two wheels, or with a camera slung over your shoulder, Arezzo Province invites you to move, sip, and savor. Here are some featured activities and experiences that pair perfectly with a group holiday renting an apartment in these towns:

• Hilltop hikes and forest walks — Start from Cortona’s old town or the Casentino forests near Poppi and Stia. Trails vary from gentle scenic strolls to more challenging routes that reward you with panoramic views of the Tuscan plains and distant hill towns.
• Wine and olive oil tours — The Valdarno and nearby hills host boutique vineyards and olive oil mills where you can learn about production, sample olive oils with diverse fruity notes, and toast with a glass of local wine in a sunlit courtyard.
• Cooking classes and market to table experiences — Join a hands-on afternoon in Cortona or Arezzo to learn traditional Tuscan recipes, then savor the finished dishes in your apartment’s dining area or on a shared terrace with friends.
• Antique markets and artisan shopping — If you’re visiting Arezzo during the Fiera Antiquaria, you’ll discover a treasure trove of vintage goods, crafts, and curated antiques. Even outside market days, the region’s small shops offer handmade leather goods, ceramics, and textiles perfect for group gifts or keepsakes.
• Bike riding and scenic drives — Secondary roads wind through olive groves and vineyards, offering scenic routes that are beginner-friendly or more challenging for experienced cyclists. Endpoints often feature hilltop towns with inviting cafes and gelaterias for a refreshing break.
• Historic site visits — The province is home to medieval castles, fortress towers, and churches with renaissance art. A thoughtfully planned itinerary can mix Arezzo’s fresco cycles with Cortona’s museums and Anghiari’s artistic lanes for a balanced cultural day.
• Wellness and spa days — Take a restorative day trip to a Tuscan wellness spot for thermal baths or spa treatments, pairing that with a relaxed lunch in a sunlit trattoria and a stroll through a nearby village.

Seasonal Itineraries and Practical Planning

Are you planning a September grape harvest trip, a spring flower-viewing weekend, or a summer escape that blends beach days with hill town exploring? The Province of Arezzo shines in every season. Here are quick seasonal ideas that work for groups renting apartment units:

• — Long days, blooming orchards, and markets full of fresh produce. Take a Cortona stroll, visit nearby wineries, and enjoy a picnic on a hillside with Tuscan cheeses and white wine from the area.
• Summer (July–August) — Warm evenings and open-air festivals. Consider a base in Arezzo or Cortona and plan late-afternoon hikes, sunset aperitifs on a terrace, and rooftop dinners with friends.
• Autumn (September–November) — Harvest time brings vibrant colors, seasonal menus, and a relaxed tempo. It’s perfect for a food-focused itinerary that pairs cooking classes with vineyard tours and truffle-hunting experiences in the Casentino.
• Winter (December–February) — Cozy apartment stays with access to nearby art galleries, wine bars, and candlelit dinners. It’s ideal for a slower pace and intimate group meals that celebrate Tuscan comfort food.

Local Cuisine, Markets, and Food Highlights

The Arezzo province is a paradise for food lovers. Expect hearty pasta dishes, rustic breads, and cheeses that pair beautifully with local wines. When you’re planning your apartment-based stay, these culinary experiences are easy to weave into your itinerary:

• Tagliata and Bistecca alla Fiorentina — Juicy steak cuts that deserve a share among friends, ideally from a local butcher and finished on a hot grill in your apartment’s outdoor or communal kitchen.
• Pici all’aglione and handmade pasta — Fresh pasta moments can be the highlight of a group cooking class or a fun competition among friends to craft the most delicious version with tomato, garlic, and olive oil.
• Olive oil tastings — The region’s olive oils have distinctive fruitiness and peppery finishes. Pair them with crusty bread and a flight of cheeses for a relaxed tasting session in your holiday rental.
• Markets and seasonal produce — Arezzo’s markets and the hill towns’ stalls overflow with seasonal fruit, vegetables, honey, and regional specialties. A market morning makes for a playful start to a day of exploring on foot or by bike, followed by a shared lunch back at your unit.
• Wine tasting routes — The vineyards of Valdarno and surrounding hills host intimate tastings that pair well with a private group tour. Finish with a sunset view over the vines as you sip a glass of local red or white.

Getting There, Getting Around, and Booking Your Stay

The Arezzo province is well connected by road and rail, making it an easy addition to a broader Tuscan itinerary. If you’re flying into Florence or Perugia, a quick train ride or a comfortable drive can place you in the heart of Arezzo’s city center or in the tranquil lanes of Cortona’s outskirts in under two hours. For a group that wants flexibility, renting a combined apartment unit with a central meeting point is ideal, letting you craft a flow that includes hill-town day trips, vineyard tastings, and lively evenings with friends.

To match your travel style—whether you want a modern apartment with contemporary amenities or a rustic villa-style unit with shared outdoor space—searchandstay.com is a practical ally. The site offers listings across Provincia di Arezzo and nearby areas, with filters designed for vacation rentals and apartment accommodations. Use it to compare options by price, location, and amenities, then book a property that fits your group’s rhythm. A well-chosen apartment rental can become the social hub of your trip, a place where memories are made, photos are shared, and plans for the next day take shape over a morning espresso or a late-night dessert.

When you’re exploring, consider staying in a central Arezzo city base for quick access to art, markets, and cafés, or choose Cortona or Anghiari if you want a quieter backdrop with sweeping views and easy countryside access. Look for properties that offer flexible bedding configurations, large common spaces, and outdoor areas where your group can gather after a day of adventures. If you’re traveling with friends who value nightlife or live music, pick a neighborhood with a lively but safe scene and easy transit options back to your apartment after an evening of exploring.

Find Your Ideal Arezzo Accommodation on SearchandStay

Searchandstay.com specializes in helping travelers find vacation rentals and apartment accommodations in and around the Province of Arezzo. Use the platform to filter by Unit / Apartment Unit / Apartment Accommodation destinations, bed configurations, pet-friendly options, and proximity to town centers, markets, and scenic trails. The listings include photos, precise locations, and booking details to simplify planning for a group trip. Whether you’re aiming for a chic urban apartment near Arezzo’s center or a countryside unit with open views and a shared garden, SearchandStay helps you compare prices, read guest reviews, and secure your preferred dates with confidence.

Pro tip: book a single base that’s close to the day’s chosen activities, so your group can easily assemble for sunrise hikes, market mornings, and sunset meals. If you’re unsure about the best neighborhood for your trip, you can search by experience—wine tasting, cooking classes, hill-town strolls, or forest hikes—and the site can suggest apartment destinations that align with those activities. This approach streamlines planning and ensures your Arezzo adventure stays social, affordable, and memorable.

To start exploring, visit SearchandStay and search for accommodations in Provincia di Arezzo. Look for a unit that offers the right blend of space, privacy, and shared spaces to keep your group energized, connected, and ready for the next day’s adventures. Whether you’re traveling with a small circle of friends or a larger group, you’ll find apartment accommodations that fit your travel style and budget, from snug courtyard flats to expansive multi-bedroom residences with outdoor terraces that become your evening gathering spot.

Plan Your Arezzo Adventure Today

Provincia di Arezzo is more than a destination; it’s a journey through time, flavor, and nature that invites you to live in the moment with friends. With a range of vacation rentals, holiday rentals, and Unit / Apartment Unit / Apartment Accommodation options, you can craft a stay that feels both luxurious and laid-back—perfect for days spent exploring art-filled streets, days spent cycling through olive groves, and evenings filled with shared meals and laughter. From the iconic rooftops of Arezzo to Cortona’s sunset terraces and the tranquil lanes of Anghiari, there is a place to call home for every group dynamic.

Ready to plan? Explore the offres in Provincia di Arezzo on SearchandStay, where you’ll find a variety of apartment destinations to suit your travel style. Book a social, stylish base, map out your day trips, and let the region’s beauty unfold around you as you travel with friends through one of Tuscany’s most charming corners.