A Taste of Le Marche

Another secret region, nestled along Italy’s Adriatic coastline

The idea of visiting “the homeland” of a country is easily eclipsed by the idea of exploring a borderland. It’s where cultures collide or might collide at any moment. This is where the tension is … and tension is the source of those unforgettable feelings you get when you read an epic story or see a great movie.

Le Marche region is a different Italy in much the same way that the Molise is. The people are friendly toward the curious traveler, and the secrets that open doors are more apparent, even when language insists on throwing up barriers to understanding.

In medieval Europe, a march (marche) was, broadly, any kind of borderland. More specifically, a march was a border between realms, and/or a neutral zone under joint control of two states, where differing laws might apply. In both of these senses, marches served a political purpose, like providing warning of military incursions, or regulating cross-border trade, or both. This background provides loads of history … and mystery.

Come explore with us what this means in a 21^st century slice of the Marche region. You will not be disappointed.

DAY 1 –  Ascoli: hippest town in the region

Welcome to the region’s hippest town: Ascoli Piceno. Don’t worry about pronouncing it, just settle in and fall in love! Our travertine tower hotel is right off the main square, the perfect base from which to explore the city with our private guide. She will unveil the town’s long history starting from the Sabine tribe in the 9th century. Locally-guided immersion into some artisan bottegas rounds out the day.

Ascoli (as it’s known locally) is like the long-lost cousin of ancient Rome, heavy on history and food. Weary legs will appreciate its lack of hills and all travelers will appreciate its historical riches, excellent pinacoteca (art gallery), trendy bars and restaurants, one of Italy’s unsung perfect piazzas and the calorific treat, olive all’ascolana (veal-stuffed fried olives). A final treat: the historic Caffè Meletti. Aperitivo at the hotel followed by dinner tonight in a splendid location. 

Welcome to the hippest town in Le Marche!

Accommodation for the next 3 nights: Historic Hotel and Spa Palazzo Mercanti or similar. Meals included: Welcome drink, D.

Day 2 – Hill towns between mountains and sea

Enjoy breakfast and a free morning to explore Ascoli and have lunch on your own. 

The rest of today will be dedicated to ancient hilltop villages. First stop: Ripatransone. Perched only a few miles from the Adriatic Sea, the historic center of the town is a succession of elegant buildings, flower-filled views, and walks among stairways and alleys (including the narrowest alley in Italy!). We’ll stop at the studio of artist Mario Vespasiani, the town’s de facto cultural center. Mario’s studio is a place for meeting and reflection, exchange, and deep assimilation of art. Ripatransone also boasts another small gem: Teatro Mercantini. Learn why Le Marche is known as the “land of 100 historic theaters”, nearly all intimate and very beautifully crafted. 

We will close the day discovering Offida. If Ascoli Piceno is one of Italy’s top hidden treasures (and it is), then little Offida, with its prehistoric origins and elegant Renaissance centro, has to be one of Italy’s top villages. This is the home of traditional bobbin lace-making, which we’ll watch firsthand. Just down the street sits 14th-century Santa Maria della Rocca, stunningly nestled on a rocky promontory with an interior awash with well-preserved ancient frescoes.

The day will wrap with dinner at a gourmet restaurant under the vaulted ceilings of former stables in one of Offida’s beautiful palazzos. Chef Daniele Citeroni will wow you! B, D

Day 3 – Women and Wine 

This morning we head to the hills to discover woman-owned-and-operated Cocci Grifoni Winery. Here Marta guides us through the labyrnth of 85 years of history, recounting how Grandpa Guido sensed that this land was perfect to salvage the native Pecorino grape. From his wisdom comes their enchanting white wine, which seems to pull flavors right out of these breathtakingly gorgeous hills. Light lunch on the panoramic terrace offers us the chance to taste and pair the local creations.

The afternoon is free to wander independently and discover the many charms of Ascoli. Instagram moments abound! Most shops are open from 4-8pm today for your final souvenir purchases.

Explore some of the many trendy bars and restaurants for dinner tonight: B,L

Day 4 – Ascoli Piceno to Rome

Departure for Rome after an early breakfast; please book flight departures AFTER 1PM TODAY.  B

Consider this 3-day mini-tour as a follow-up to our Molise tour, which runs from September 13-19, 2026.