Le Marche’s boasts up to 32 medieval hilltop town, voted the most beautiful in Italy offering a picturesque escape into history, culture, and stunning natural landscapes. Perched on rolling hills, these majestic old towns are rich in heritage, boasting centuries-old buildings and historic churches with sweeping views of the countryside, stretching from the lush Apennine Mountains to the Adriatic Sea. Each town is a charming blend of medieval architecture, cobbled streets, festivals and vibrant local life where you immediately feel at home in this slow way of life.
Whether you’re exploring quaint streets, soaking in breathtaking views, or enjoying traditional cuisine, these hilltop towns offer a rare and authentic experience of Italy, far from the tourist crowds, providing perfect destinations for anyone seeking beauty, culture, and peace in an unspoiled corner of Italy.
Here is our guide to some of the best hilltop towns to visit in Le Marche and what you can discover:
Urbino
A UNESCO World Heritage site, Urbino is a Renaissance treasure. The town is famed for its impeccable architecture, artistic history, and stunning views over the rolling hills of Le Marche. Visit the majestic Palazzo Ducale, home to art treasures, and the Casa di Raffaello, Raphael’s birthplace. The town exudes a scholarly atmosphere, making it perfect for those who appreciate art, culture, and history.
Highlights:
- The Palazzo Ducale
- The Galleria Nazionale delle Marche, with works by Piero della Francesca
- Raffaello’s birthplace
Perfect For: History buffs, art lovers, culture seekers.
Travel from Oliveto Estate: Approximately 1 hour 40 minutes (99 km) by car.
Ascoli Piceno
Ascoli Piceno is a beautiful, well-preserved medieval town known for its unique Piazza del Popolo—a grand travertine square, one of the oldest in Italy, surrounded by majestic palaces, with cafés and shops offering a taste of local life. The town is famous for its olive ascolane (stuffed olives) and other culinary delights. The charming atmosphere, combined with its historical richness, makes it an excellent spot for a day trip.
Highlights:
- Piazza del Popolo and the nearby Caffè Meletti
- The Cattedrale di Sant’Emidio
- Olive ascolane tasting
- Pair with our wine and olive oil tasting experience and a visit to Offida
Perfect For: Foodies, history lovers, families looking for a more relaxed day out.
Travel Time from Oliveto Estate: About 50 minutes (50 km) by car.
Sarnano
Sarnano is a peaceful, lesser-known gem with stunning medieval charm. It’s an ideal spot for a relaxing day, with cobbled streets, historic buildings, and an incredible view of the Sibillini Mountains. The town’s main square, Piazza Alta, is perfect for a quiet aperitivo. Perfect for a combined daytrip to the infamous nearby Sibillini National Park, this day trip makes for a great spot for nature lovers and and foodies alike seeking traditional Marchigiana cuisine.
Highlights:
- Piazza Alta with its charming cafes
- The Sibillini Mountains and access to hiking trails and the local waterfalls
- The Chiesa di San Francesco
Perfect For: Nature lovers, hikers, foodies and anyone seeking a tranquil atmosphere.
Travel Time from Oliveto Estate: Around 45 minutes (44 km) by car.
Offagna
Offagna is a small, perfectly preserved medieval town surrounded by impressive defensive walls. It’s less touristy, making it a perfect destination for those seeking authenticity and tranquillity. Visit the Castello di Offagna and enjoy panoramic views of the surrounding landscape. The quiet streets and welcoming locals make it feel like a step back in time.
Highlights:
- Castello di Offagna for panoramic views
- Medieval streets and architecture
- The town’s annual medieval festival
Perfect For: Couples, history enthusiasts, anyone looking for a peaceful retreat.
Travel Time from Oliveto Estate: About 30 minutes (27 km) by car.
Corinaldo
Corinaldo is an enchanting town with some of the best-preserved medieval walls in Italy. The town is famous for its narrow streets and vibrant color scheme—much of the architecture is in shades of pastel, creating a delightful and photogenic environment. It’s also home to the Madonna del Piano, a lovely church that hosts incredible festivals throughout the year.
Highlights:
- The well-preserved city walls
- The Madonna del Piano
- Strolling through the picturesque Via della Speranza
Perfect For: Families, photography enthusiasts, foodies and those looking for charm and tranquillity.
Travel Time from Oliveto Estate: Approximately 40 minutes (38 km) by car.
Fermo
Fermo is a stunning town with sweeping views of the Adriatic coast and is home to some fantastic historical sites, including the Roman Cisterns and the Cattedrale di Santa Maria Assunta. The charming medieval center boasts several squares perfect for enjoying coffee or aperitivo. The blend of Roman and medieval history here offers a rich cultural experience.
Highlights:
- Pair with a bike ride through the centre of Fermo
- The Roman Cisterns
- The Cattedrale di Santa Maria Assunta
- The lovely Piazza del Popolo where you can enjoy a delicious artisinal lunch or dinner or visit the antiques market on a Thursday evening.
Perfect For: History lovers, anyone seeking a combination of art, culture, and scenic views.Travel Time from Oliveto Estate: About 5 minutes (3 km) by car.
Ripatransone
Ripatransone is a captivating hilltop town in Le Marche, offering a serene atmosphere perfect for those looking to unwind. Known as the “Balcony of the Marche,” it boasts sweeping views of the Adriatic Sea and the lush surrounding countryside. The town’s cobbled streets, medieval architecture, and charming piazzas invite visitors to explore its rich history and local culture. Whether strolling through the historic center or enjoying the picturesque landscapes, Ripatransone provides a peaceful escape into the heart of rural Italy.
Highlights:
- The historic centre with its medieval charm
- Panoramic views over the Adriatic Sea
- The Church of San Gregorio
- The narrowest street in Italy
Perfect For: Those seeking a quiet getaway, lovers of history and culture, and anyone wanting to experience authentic Italian village life. On the way back from Ascoli Piceno
Travel Time from Oliveto Estate: Approximately 45 minutes (50 km) by car.
Loreto
Loreto is one of the most significant religious sites in Italy, home to the Basilica della Santa Casa, which is believed to house the home of the Virgin Mary. The town’s spiritual aura, combined with the grandeur of the basilica and the surrounding historical buildings, makes it a must-visit for anyone interested in faith, healing and history. Its location also offers delightful panoramic views of the Adriatic coast.
Highlights
- The Basilica della Santa Casa
- Piazza della Madonna
- Panoramic views of the Adriatic Coast
- Perfect visit to pair with a visit to Sirolo or Portonovo beaches.
Perfect For: Pilgrims, history enthusiasts, and those seeking peace and inspiration.
Travel Time from Oliveto Estate: About 20 minutes (19 km) by car.
Recanati
Famous as the birthplace of poet Giacomo Leopardi, Recanati is an elegant town with stunning views of the surrounding countryside and the Conero Promontory. The town is brimming with literary and cultural history, making it a perfect spot for those interested in Italian poetry and arts. Recanati’s charming streets, panoramic views, and cultural attractions make it a must-visit for any traveller.
Highlights:
- The Leopardi House and Museum
- The Palazzo Comunale and Piazza Giacomo Leopardi
- Panoramic views of the Conero Promontory
Perfect For: Literature lovers, culture seekers, those who appreciate beautiful vistas.Travel Time from Oliveto Estate: Approximately 25 minutes (24 km) by car.
Gradara
Gradara is a medieval fortress town known for its well-preserved Castello di Gradara, which offers dramatic views and rich historical tales, especially regarding the tragic love story of Paolo and Francesca. The charming streets and atmospheric castle make it a fascinating place for history buffs and those looking for a romantic escape.
Highlights:
- The Castello di Gradara
- Paolo and Francesca’s tragic love story
- Panoramic views from the castle
Perfect For: History enthusiasts, couples, those seeking a romantic atmosphere.Travel Time from Oliveto Estate: Approximately 1 hour 45 minutes (105 km) by car.
Civitanova Alta
Civitanova Alta is a quaint 13th Century hilltop town offering sweeping views over the surrounding countryside and the Adriatic coast and the closest town to Oliveto Estate. With its charming medieval streets, narrow alleys, and historic architecture, this town is perfect for a peaceful stroll and a taste of traditional Italian village life. Here slow life abounds, with locals playing cards and enjoying freshly made gelatos whilst spending time with friends of old in the retro cafes, pizzerias and historic piazza.
Highlights:
- Piazza XX Settembre with panoramic views
- The historic Chiesa di San Bartolomeo
- Strolling through narrow medieval streets
Perfect For: Families, photographers, history enthusiasts and those wanting to stroll up to the village from Oliveto Estate.
Travel Time from Oliveto Estate: Only 2 minutes (1 km) by car
Civitanova Marche Porto
Civitanova Marche is a vibrant coastal town with a beautiful seafront and a lively atmosphere. While Civitanova Alta offers historical charm, the port of Civitanova Marche is perfect for enjoying beaches, boutique shopping, and local seafood restaurants and features in this list to showcase what Oliveto Estate’s local town has to offer. The contrast between Civitanova Alta & port provides those staying at Oliveto a complete Italian experience, minutes drive from each other.
Highlights:
- The beautiful beaches of Civitanova Marche
- The lively Piazza XX Settembre
- Local seafood dining experiences
Perfect For: Beach lovers, families, anyone looking for a mix of seaside charm and urban vibrancy.Travel Time from Oliveto Estate: Approximately 10 minutes (5 km) by car.
Each of these hilltop towns offers a unique experience, from medieval history and spiritual significance to panoramic views and literary heritage. Whether you’re seeking adventure, tranquility, or cultural discovery, these towns provide the perfect atmosphere for a memorable Italian vacation. They are all within a short drive from Oliveto Estate, making them ideal for day trips or leisurely exploration. Connect with us here to find out more about a stay at Oliveto Estate
