Hidden On Italy's Adriatic Coast Is An Under-The-Radar Lively City For An Authentic Cultural Vacation

If Rome is the Eternal City and Venice is the floating one, then Ancona is the Adriatic's best-kept secret. Here, you'll be trading tourist traps for overlooked piazzas and timeless history that comes alive with every step you take. And if there's anything we've learned about visiting Italy the first time, it's to not make the mistake of renting a car and opt instead for exploring it all on foot.

Once the economic backbone of Adriatic trade routes, this port town hums with life and culture without trying too hard. Defined by a natural elbow-shaped promontory, Ancona has always been tied to the Adriatic. The unique shape of the land caught the attention of Greek settlers from Syracuse, who named it "Ankon," or "elbow," in 387 B.C. The town's harbor quickly became a valuable asset thanks to its strategic location and protective waters. Later, during the Middle Ages, Ancona emerged as a maritime powerhouse that challenged the city of Venice for dominance over the sea. Today, the Adriatic remains central to the city's character.

Since Rome is the best place to kick off your Italian vacation, it provides convenient access to cities like Ancona — a train ride takes anywhere between three and a half to four and a half hours. And when you're done indulging in all the good food in Milan, which is ranked the second most walkable city in the world, catch a train to this destination, which takes about the same amount of time as the capital city. If you're coming from abroad, fly into Ancona Airport (AOI) — the closest air hub — or Bologna Airport for more international options.

Just as Amalfi is the Instagram poster child of Italy, Ancona is that indie destination that gains a cult following over time, and it's all thanks to its authentic, historical soul. The first stop in the city is the Ancona Cathedral, also known as Cattedrale di San Ciriaco. Originally built over a Greek temple, its architecture combines Byzantine and Gothic styles, and the crypt here hides the painting "Maria di San Ciriaco." When standing in the heart of this place of worship, the intricate details and carvings of the cathedral will take your breath away.

You can't miss the Arch of Trajan, a Roman marvel that's still standing tall. Built in 115 A.D., this arch is a symbol of Ancona's significance in Roman times. Known for its elegant proportions and coastal location, the arch is believed to have been surrounded by statues of gods and emperors back in the day. Then, make your way to Piazza del Plebiscito, one of the town's oldest squares. From medieval executions to the local hangouts of today, this space has seen it all. Although the piazza is brimming with cafes and shops, take a moment to admire the monumental Church of San Domenico and the Baroque statue of Pope Clement XII.

Next, head to the Mole Vanvitelliana, or the Lazzaretto of Ancona. This massive pentagonal building was originally built as a quarantine station; since, it has served several purposes, from military use to sugar refineries. Now, the Lazzaretto is one of the city's standout landmarks, with incredible views of the harbor.

If you're craving an arts and culture fix, Ancona has you covered. Whether you're into archaic artifacts, fine art, or something truly extraordinary, this city will leave you inspired. The National Archaeological Museum, located in the stunning Palazzo Ferretti, is a treasure trove of artifacts that span from the Paleolithic era to the Middle Ages. Walking through its halls, you'll find everything from prehistoric tools to antique weapons. The Frasassi Venus, a remarkable Paleolithic figurine, is just one of the museum's must-see pieces.

For art lovers, the Civic Art Gallery is a dream. Housed in Palazzo Bosdari, this gallery features an impressive collection that goes all the way back to the Middle Ages. Wander through the rooms and you'll find masterpieces by Titian, Carlo Crivelli, and Lorenzo Lotto. The gallery also showcases works by modern artists, including Bartolini, Bucci, and Enzo Cucchi. But if you're looking for something different, visit Museo Omero, or Homer Museum. This incredible space allows you to interact with art through touch. From ancient Greek sculptures to contemporary pieces by De Chirico and Pistoletto, you'll be able to feel the textures and intricacies of the works — it's accessible art in a whole new way.

Wait till you see what's hiding beneath the city: Miles of tunnels stretch through the center. These dark, secret passages were once used as water tanks, though their exact history is unknown. Make sure to book a tour with Ancona Sotterranea, because this just might be the highlight of your trip.

What's a visit to a port town without catching the waves? La Marina Dorica, with more than 1,300 in-water berths and tons of amenities, is the perfect spot to kick back and enjoy the view. Whether you're sipping a drink at a waterfront cafe or catching the sunset over the sea, this marina pairs scenic seaside beauty with lively energy. You can even watch boats getting repaired or take part in some sailing activities. The marina offers a full calendar of cultural events and nightlife that just keeps going, so there's never a dull moment.

Strolling along Ancona's Old Port is a soothing way to connect with the sea and its past. This harbor was first established by the Picentes and their dealings with the Greeks. You'll find the remains of the old Roman port, with sections of 2nd-century B.C. city walls. Also standing here is the Captain's House, a medieval gem that survived WWII bombings, complete with Romanesque details and arches looking out over the water.

Don't forget about Passetto Beach. This is where locals come to relax and unwind. But it's the caves that truly steal the show. These rock cavities were created by fishermen over several decades and provide an amazing backdrop for those looking to experience the shoreline like never before. Do witness the caves at night when they're lit up — it's a magical sight you won't forget. With a complete itinerary and top-tier hacks for your Italian vacation, your Ancona trip is all set for an unforgettable adventure.