We walked through a tall arched gate into the sleepy town of Montelupone, and it was like taking a step back into time. Actually, a lot of Le Marche region in Italy seems like it was frozen in time. But its pretty hilltop towns really reinforce that image. If you have seen pictures of a small Italian town with steep cobbled streets, lined with biscuit-coloured houses with green venetian blinds and perhaps a box of brightly coloured flowers in the window, it’s likely taken in Le Marche – the region boasts of 18 villages that have been conferred the orange flag, proclaiming them amongst the most beautiful villages of Italy.

On my recent trip to Italy, I explored two of these picturesque hilltop towns in Le Marche – Montelupone and Grottammare, both of which are an easy drive from the region’s capital Ancona (43 & 85 km respectively). You can even combine both the towns as a day trip from Ancona (115 km from Urbino, Le Marche’s Renaissance gem).

Montelupone is an ancient, walled town located in the Macereta province of Le Marche. Apart from a medieval palace and church, the town also has some ancient relics such as castle walls and four, well-preserved gates. At the heart of the town, in the main piazza, stands the imposing Palace of the Podestà, with its soaring civic tower topped with a battlement. It also displays the town’s old coat of arms, the town clock and a bronze bell. The palace itself is worth a visit, with its Gothic architecture and some interesting frescoes inside. The Palazzo Communale (Town Hall) is next door to the palace. This 19th century neo-classical building was built over an existing medieval structure, and it houses the historic Nicola Degli Angeli Theatre. More information on Montelupone here.

If you want to grab a quick coffee, or rest your feet and have a bite to eat, I’d recommend Bar Gelateria Boccanera on Via XXIV Maggio (it’s in the main square).

Grottammare is in the province of Ascoli Piceno and about 60 kilometres from Montelupone. It’s off the scenic A14, also known as Autostrada Adriatica, as it hugs the Adriatic coastline. Grottammare is perched on a hilltop and you can get a quick glimpse of the town from A14 – a glimpse that’s enough to make you take a detour and explore it! The drive up to the old hilltop town goes through the newer part of Grottammare, via a palm tree lined promenade (the palm trees were imported from Canary islands). 

 

 

In the old town, a maze of alleys lead you up to the remains of an 11th century fortress. A major part of the old walls was destroyed in the 16th century during multiple invasions. The Tower of the Battle (Torre della Battaglia) was built when the town walls were fortified in the mid-16th century. Parts of the old wall can still be seen, especially near the ancient lavatoio, or public laundry.

Grottammare has produced one pope, Pope Sixtus V (late 16th century), and is also the place where Hungarian composer and pianist Franz Liszt once lived, in the 18th century Palazzo Fenili. You can follow walking routes in the footsteps of these two illustrious people, or just ramble around Grottammare and stumble upon pretty piazzas – such as the atmospheric Piazza Peretti (which was the centre of the ancient village) with its Altana dell’Orologio (Arbour of the Clock). Nearby is the 19th-century Church of St. John the Baptist, built on the remains of an ancient church dating back to the 9th century. The 18th century Teatro dell’Arancio, one of the many historic theatres in Le Marche, is also located in the piazza.

 

PinThe arched Logge di Piazza Peretti gives a panoramic view of the Adriatic coastline – but you might find that some feline occupants have already grabbed the best seat in the house! Grottammare itself seems like a cat paradise, with tens of them lurking around (or just sunning themselves) in the piazzas and alleys.

PinA walk through the town will bring you to pretty houses fronted by colourful doors with quirky door knobs and decorations.

As you climb up the steep, cobbled road towards the castle, you get gorgeous views of the Adriatic and the sandy beaches below.

You will also pass the 16th century Church of St Lucia, commissioned by Pope Sixtus V, at the very place where he was born in Grottammare. The bell tower is quite stunning, with its stacked arches, from which are suspended the three bells of the church.

Cafes and osteria abound – some amidst picturesque piazzas, some with a sweeping view of the sea.

 

More information on Grottammare here.

A word of advice – rent a car to get around in, as most of these villages are not very well connected by public transport. Try and get your hands on the iconic Fiat 500 😉

PinIf you’re in Le Marche, don’t miss the chance to explore these and other small towns. They certainly live up to their title of the most beautiful villages in Italy!