7 Days Hidden Italy

After arriving in Perugia, your private guide will meet you and bring you into the historic center to begin your time in Umbria. Perugia sits high on a hill overlooking the surrounding countryside, with stone streets, medieval buildings, and small local cafés spread through the center.

After checking into your accommodation, head out with your guide to explore Perugia’s historic center on foot. Walk through stone streets and covered archways before arriving at Piazza IV Novembre, the city’s main square, where cafés and historic buildings surround the center of town. 

Continue through the old center with your guide, passing churches, food shops, and smaller side streets, then stop for dinner later in the evening. Umbrian cuisine is known for truffle dishes, cured meats, local wines, and handmade pasta, giving you a good introduction to the region on your first night.

This morning, your private guide will drive you from Perugia to Assisi. After arriving, spend time exploring the town on foot, walking through narrow stone streets lined with churches, local shops, cafés, and small squares looking out across the Umbrian countryside below. 

Visit the Basilica of St Francis, known for its frescoes and connection to Saint Francis of Assisi, before continuing through the town on foot. There will be time to stop at cafés or local shops before leaving Assisi later in the day.

Continue onward to nearby Spello, a smaller hill town with narrow, flower-lined streets and quiet stone alleyways. Spend time walking through the center with your guide before returning through the Umbrian countryside in the afternoon.

Today you’ll leave the larger towns behind and head into the Umbrian countryside with your private guide, driving through vineyard areas, olive groves, and smaller hill towns on the way to Montefalco. 

Start in Montefalco, where you’ll walk through the small historic center and see the surrounding countryside from viewpoints around the town walls. The streets here are lined with wine shops, cafés, and local restaurants, with views stretching across the Umbrian hills below.

Later, visit a local vineyard with your guide to learn more about the wines produced in this part of Italy. After the tasting, continue to Bevagna, a quieter medieval town with stone streets, old churches, and small piazzas in the center.

Spend time walking through Bevagna before returning through the Umbrian countryside later in the afternoon.

Today you leave Umbria and continue east into Le Marche, a region of hill towns, farmland, and smaller historic cities between the Apennine Mountains and the Adriatic coast.

Arrive in Urbino, a historic university town best known for its Renaissance architecture and steep stone streets. Walk through the old center with your guide before visiting Palazzo Ducale, one of the region’s main historic buildings.

Spend the afternoon exploring more of the town, with time to stop at cafés or local restaurants before continuing through the surrounding countryside. The roads around Urbino pass farmland, vineyards, and smaller hill villages as you continue through Le Marche.

Begin the day at the Frasassi Caves, a large underground cave system in the Marche region. Follow the walking route through a series of enormous chambers filled with stalactites, stalagmites, and rock formations, while your guide explains how the caves were formed and discovered. 

After visiting the caves, continue toward Gubbio, one of Umbria’s best-preserved medieval towns. The town climbs up the hillside with steep streets, stone buildings, and open squares connected by stairways and archways.

Spend time exploring the historic center with your guide before stopping for lunch in one of the town’s local restaurants. Later in the afternoon, return through the mountain roads and countryside surrounding the town.

Today, your private guide takes you toward the Adriatic coast, where the scenery changes again from hill towns and countryside to beaches, harbors, and coastal roads overlooking the sea.

Start the day in Ancona, where your private guide will take you through parts of the historic center and down toward the harbor area. Spend time walking around the waterfront, seeing the fishing port, local cafés, and older streets near the sea before continuing south along the Riviera del Conero coastline. 

Spend the afternoon visiting small seaside towns along the coast, with time for lunch overlooking the water before continuing between beaches, marinas, and cliffside roads beside the Adriatic Sea.

On your final day, head south toward Ascoli Piceno, one of the most attractive historic towns in central Italy. The town is known for its large stone piazzas, historic buildings, and long café-lined streets running through the center.

Walk through Piazza del Popolo with your private guide before exploring more of the old town on foot. There will be time to stop for coffee or lunch before continuing onward toward your departure point.

After time in Ascoli Piceno, your private guide will transfer you to your airport or onward destination, bringing your time in Umbria and Le Marche to a close.