Sirolo
A suggestive village nestled like a pearl between the green of Mount Conero and the blue of the Adriatic. A labyrinth of alleys to explore on foot until reaching the enchanting viewpoint of the main square, where you can admire all the splendor of the coast and enjoy a relaxing dinner in one of the nearby restaurants. It is worth getting lost among picturesque corners and monuments such as the Church of San Nicola (1765), built on the remains of a pre-existing church dating back to 1230, the 18th-century Church of the Rosario, just steps from the medieval gate, and the Cortesi Municipal Theatre, a small architectural gem from the late 19th century.

Numana
A small historic center perched on the top of the promontory overlooking the port. On summer evenings, it comes alive with events and the lively strolling of vacationers. A gelato at “Morelli” in Piazza del Santuario is a treat not to be missed, as is a dinner with a spectacular view at La Torre restaurant. In the small square of the viewpoint stands “La Torre,” the remains of a bell tower or a lookout tower, from which you can admire one of the most beautiful panoramas in the region. La Costarella, with its limestone houses once inhabited mainly by fishermen, is the most characteristic street, the passage between the upper town and the sea.

Ancona
Founded by the Syracusans in the 4th century BC, it is the capital of the Marche and one of the most active ports in the Mediterranean. The ancient port area invites you on a path marked by significant stages, from historic walls to Roman ruins, from the Arch of Trajan to the Clementine Arch, all the way to the base of the Lantern. At the top of Guasco Hill, dominated by the Cathedral of San Ciriaco—one of the most beautiful Romanesque monuments in central Italy—the view is memorable. The famous Grotte del Passetto, located on one of the most evocative urban beaches in Italy, are well worth a visit. Once storage for fishermen's boats, they are now a colorful summer refuge for the “grottaroli,” a symbol of Ancona's social life.

Camerano and the Caves
The small hilltop village just a few kilometers from Conero hides one of the most mysterious and fascinating places in the region. Beneath the historic center lies an underground city carved into the sandstone and structured in a labyrinthine path of about three kilometers. Over the centuries, the hypogeum was expanded to reveal architectural ornaments, religious bas-reliefs, and circular rooms—evidence of a history not entirely deciphered, stretching from ancient pagan rites to the two World Wars. The town is also famous for the Rosso Conero festival at the end of summer, a popular and highly appealing event.

Osimo
An elegant town a few kilometers from Conero, where you can enjoy a pleasant summer visit, perhaps for an aperitif in the square or an evening stroll. From the gardens of Piazza Nuova, the view extends from the sea to the mountains. Roman Auximum is rich in ancient remains, such as the headless Roman statues kept in the Town Hall, which earned Osimo residents the nickname “headless.” In addition to important religious monuments like the Cathedral of San Leopardo and the Basilica of San Giuseppe da Copertino, the underground caves are also noteworthy—a labyrinthine complex of artificial tunnels carved into the rock that connect some of the town's noble palaces. Offagna: Dominated by the scenic square-plan Fortress with towers and an imposing keep. The medieval festival stands out among summer events, an appointment rich in atmosphere, historical reenactments, and street performances.

Loreto
A city linked to Italy's largest Marian sanctuary and the Holy House of Nazareth, a place of worship visited every year by millions of pilgrims from all over the world. Some of the greatest artists of the 15th and 16th centuries worked in the basilica: Melozzo da Forlì, Luca Signorelli, Bramante, Sansovino, and Lorenzo Lotto.

Recanati
The “native village” of Giacomo Leopardi, where you can explore the places of his life and the views where his verses still resonate. From the bell tower of the Church of Sant’Agostino (the tower of the solitary sparrow), passing through the square of Saturday in the Village with Palazzo Leopardi, the Church of Santa Maria di Monte Morello where he was baptized, the humble house of Silvia, all the way to the Hill of Infinity, with its «endless spaces» and «superhuman silences.» To conclude this fascinating itinerary, you can treat yourself to an exclusive visit with a tasting at the Fuselli olive mill.