Best Towns to Visit in Tuscany this Summer

Tuscany offers two perfect landscapes for nature lovers: the inland countryside—with its hilltop towns, vineyards, cypress-lined paths, and a slower pace that invites you to walk, eat well, and enjoy the silence—and the coast, where free beaches, hidden coves, pine forests, and crystal-clear waters await.

Here are ten of the most enchanting stops in central-southern Tuscany — some nestled in the hills, others overlooking the sea — all sharing a slower, truer summer deeply connected with nature.

10 Unmissable Tuscan Destinations for Summer

For lovers of hilltop villages and fresh air:

• Montepulciano
• Pienza
• Pitigliano
• Castiglione d’Orcia
• Montepescali

For those seeking sea breezes:

• Porto Ercole
• Castiglione della Pescaia
• Golfo di Baratti
• Marina di Alberese
• San Vincenzo

1. Montepulciano

Montepulciano is a classic hilltop town in the province of Siena, surrounded by vineyards that produce one of Italy’s finest red wines: Vino Nobile di Montepulciano. Its elevated position at 600 meters above sea level offers expansive views over the Val d'Orcia and Val di Chiana, especially breathtaking in summer when the landscape glows golden.

Wander its steep cobbled streets and you’ll find Renaissance palaces, artisan shops, and welcoming enotecas (wine bars). The town centers around Piazza Grande, where the imposing Palazzo Comunale echoes Florence’s Palazzo Vecchio. Just below the surface, cellars carved into ancient volcanic rock invite you to sample robust reds aged in oak barrels.

• Best for: Wine tasting, historical architecture, views
• Summer Tip: Book a tasting tour early in the morning to enjoy cooler temperatures and fewer crowds.

2. Pienza

Pienza is one of the most architecturally harmonious towns in Italy. Redesigned in the 15th century by Pope Pius II, the town was intended as the embodiment of Renaissance urban planning. It remains a UNESCO World Heritage Site today, drawing travelers who appreciate both its aesthetic precision and its gastronomic fame.

Walking through Corso Rossellino, you’ll encounter elegant palazzi, the majestic Cathedral of Santa Maria Assunta, and sweeping views over the Val d'Orcia. But just as notable is the aroma of Pecorino di Pienza, the town’s signature sheep’s milk cheese. Delis, bakeries, and gelaterias specialize in it, sometimes even turning it into gelato.

• Best for: Lovers of art, symmetry, cheese, and countryside charm
• Summer Tip: Visit during one of the town’s food festivals (usually held in late August) for live music and cheese tastings in the piazza.

3. Pitigliano

Often referred to as “La Piccola Gerusalemme” (Little Jerusalem), Pitigliano sits atop a volcanic tufa cliff. Its skyline appears sculpted from the very rock it stands on, and its streets hold stories from Etruscan times to the Jewish communities that shaped it in the Middle Ages.

Pitigliano’s layered identity is best explored on foot. You can visit the Jewish Quarter, the ancient Orsini Fortress, and the intricate network of vie cave—narrow Etruscan paths carved into stone. The town also boasts one of the most photogenic old towns in Tuscany, especially striking in the golden light of a summer afternoon.

• Best for: History lovers, photographers, curious travelers
• Summer Tip: Explore early or late in the day to avoid the mid-afternoon heat and capture the best photos.

4. Castiglione d’Orcia

If you’re seeking tranquility and timeless landscapes, Castiglione d’Orcia is a peaceful alternative to more touristed towns like Montalcino or San Quirico. Set within the UNESCO-listed Val d’Orcia, this town offers unspoiled views, historic charm, and a slower rhythm of life.

The central Piazza Vecchietta, named after the local painter and sculptor, is framed by rustic stone buildings and a small church. Above the town looms the Rocca di Tentennano, a medieval fortress with panoramic views over the valley—a perfect vantage point for golden hour in summer.

• Best for: Serenity, cultural immersion, outdoor exploration
• Summer Tip: Combine a visit with a stop in nearby Bagno Vignoni, famous for its natural thermal baths.

5. Montepescali

Tucked away in the hills above Grosseto, Montepescali is often called the “Balcony of the Maremma” thanks to its commanding views over the plains and the Tuscan Islands beyond. Unlike more polished tourist towns, Montepescali retains a rustic, local charm with minimal development—making it ideal for travelers seeking an authentic and uncrowded experience.

The town’s medieval walls, narrow lanes, and scenic towers offer a sense of stepping back in time.

• Best for: Scenic detours, quiet reflection, road-trip travelers
• Summer Tip: Pack a picnic and stop here during a drive through the Maremma countryside.

6. Porto Ercole

While many associate Tuscany with vineyards and rolling hills, the region also has a beautiful coastline. Porto Ercole, located on the Monte Argentario peninsula, is a historic fishing village that now blends relaxed seaside life with refined hospitality.

Summer here means clear waters, pine-shaded trails, and afternoons on the beach. The town is also rich in history, with Spanish fortresses like Forte Stella and Forte Filippo offering views over the Tyrrhenian Sea. 

• Best for: Beachgoers, history lovers, glamour villages 
• Summer Tip: Visit the nearby Feniglia Nature Reserve, a long sandy beach bordered by forest, ideal for walking and cycling.

7. Castiglione della Pescaia

Castiglione della Pescaia offers the perfect blend of unspoiled nature, modern comforts, and medieval charm. A beloved destination in the Maremma region, it boasts a long stretch of golden sand, crystal-clear waters, and a historic hilltop village that watches over the coast.

The old town, enclosed by ancient walls and crowned by a castle, provides romantic vistas and inviting sea-view restaurants. Just outside the village lies the Diaccia Botrona Nature Reserve — a paradise for hikers and birdwatchers.

• Perfect for: Families, couples, nature enthusiasts
• Summer tip: Begin your day with a peaceful walk through the pine forest, then cool off with a dip in the sea.

8. Golfo di Baratti

Near Populonia, the Gulf of Baratti offers a captivating blend of history and natural beauty. Its dark, iron-rich sands contrast strikingly with the crystal-clear waters, creating a dramatic coastal landscape. Just a short distance away, the Baratti and Populonia Archaeological Park invites visitors to explore ancient Etruscan tombs and centuries-old stone quarries.

Baratti’s unspoiled charm and absence of urban development make it an ideal destination for those seeking an authentic, tranquil seaside escape.

• Perfect for: Archaeology lovers, nature enthusiasts
• Summer tip: Pack your snorkel — the gulf’s underwater scenery is stunning.

9. Marina di Alberese

Set within the protected Maremma Natural Park, Marina di Alberese is a true escape into the wild. Visitor numbers are limited daily to preserve its pristine character, and the expansive sandy beach is bordered by pine forests home to deer, wild boars, and herons.

There are no beach clubs or kiosks here — just raw, unspoiled beauty. It’s a peaceful retreat, even at the height of summer.

• Perfect for: Hikers, photographers, solitude seekers
• Summer tip: Reserve parking in advance or rent a bike in Alberese for a more sustainable experience.

10. San Vincenzo

San Vincenzo strikes the perfect balance between seaside relaxation and modern amenities. Located along the scenic Etruscan Coast, it’s well-suited for families yet romantic enough for couples.

Enjoy long stretches of sandy beach, boat excursions, and the nearby Rimigliano Nature Reserve. Savor fresh seafood by the water, or venture inland to explore the charming villages of Bolgheri and Suvereto.

• Perfect for: Families, active travelers, food lovers
• Summer tip: Sip an aperitivo at sunset along the harbor promenade — the soft pink glow over the calm sea is unforgettable.

LA ROQQA’s Experiences

If you're planning to explore both inland towns and the coast, Porto Ercole offers a convenient and beautiful base. Located on the Monte Argentario peninsula, it gives easy access to beaches, hilltowns, and regional highlights.

Nestled in Porto Ercole, LA ROQQA sustainable design hotel is your gateway to exploring the best of southern Tuscany, from inland hilltowns to the Tyrrhenian coast.

Explore LA ROQQA’s Experiences and Porto Ercole guide to begin your summer journey.