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Perched on a hillside overlooking the Umbrian countryside, wooded hills framing the background, Assisi is a perennially popular destination thanks to its attractive location, historic core, UNESCO-listed basilica and its associations with Saint Francis. Exploring with a private guide, spend your day discovering the history behind its Roman remains, medieval streets and renowned residents. Your guide will help you avoid the crowds at more popular attractions and leave you with enough time to explore at leisure the nearby medieval hilltown of Spello, a quiet tangle of winding laneways lined with stone houses and encircled by Roman walls.

Your private driver and guide will pick you up at your hotel on the morning of the tour, and if you’re not based in Assisi, take you there in a private vehicle. You’ll then set out on foot to explore the town, starting at the Saint Francis Basilica.

Construction began in 1228 after Saint Francis died on the two churches that make up the huge building. The Lower Church, home to Saint Francis’s tomb, was built in the heavy Romanesque style and is covered in frescoes spanning a century, including work by Simone Martini, Cimabue and Pietro Lorenzetti. In contrast, the Upper Church is in Gothic style, with high ceilings, large stained-glass windows and walls adorned with an extensive cycle of frescoes by Giotto.

Your guide will help you navigate the churches, explaining their ecclesiastical as well as architectural importance and introducing you to the highlights of the much-admired frescoes.

After your visit to the basilica, you’ll begin your walking tour of Assisi, passing through the narrow streets filled with shops and making your way to the Piazza del Comune, which is home to the 1st-century BC Temple of Minerva and local government buildings. Although only the façade of the temple remains, it’s possible to enter a system of tunnels beneath the square to explore the site of the town’s former Roman forum, located 5 m (16 ft) below the current ground level.

From here, continue your walk around the town, visiting the Piazza San Rufino and Piazza Santa Chiara, both home to Romanesque churches dedicated to Saint Clare and Saint Francis. Your guide will also take you to scenic lookouts around the town for unobstructed views of the surrounding countryside.

After the tour, say goodbye to your guide and meet your driver for the transfer to Spello, a small, medieval hilltown best known for its bright, flower-filled streets. Here you’ll have some free time to explore the little streets and alleyways lined with stone houses, dotted with churches and enclosed by intact Roman walls and medieval towers. The main street, Via Cavour, is filled with small shops, restaurants and wine bars where it’s easy to while away a few hours.

The tour is flexible and your guide in Assisi can help you decide where to eat lunch — we suggest waiting until you reach Spello, which is less crowded.