If I were to compile a list of the highlights of Italy, I would easy rank Assisi up there with Rome, Florence, and Venice. The entire town can be considered a landmark, with its historical significance and its incredibly tranquil beauty.
Within Assisi, there are several "must-sees." On your way into town (assuming that you arrive by train), stop first by Santa Maria degli Angeli to see the humble chapel that Francis frequently attended, and you can stop by the room where St. Francis spent his last moments. Once you've made your way up the hill, the Basilica of Santa Chiara is also a worthwhile stop. The church itself is beautiful (the pink and white striped exterior seems to perfectly capture the town's simple charms), and it also contains the painted crucifix that supposedly spoke to a young, materialistic Francis, prompting his dramatic conversion. And, of course, there are the basilicas in honor of the man himself. The upper basilica is open and majestic, while the lower basilica is squat and round, giving a personal and cozy feeling. An even lower descent leads to a dim and simple chapel - Francis's final resting place.
Quick Tips:
If possible, visit Assisi n the spring. Not only will the town be full of flowers, but the surrounding vineyards and farmland will also be in bloom, and the elevation of the town makes for some incredible views. If you can be even more selective about the time of your visit, early May is the time of the Calendimaggio festival, when Assisi revisits its medieval roots with music and costumes. Unlike the Palio in Siena, not nearly as many tourists are aware of Assisi's signature festival (I learned about it when I wound up in the middle of it), so it can be enjoyed in a relatively authentic manner.
Best Way To Get Around:
Getting from Santa Maria degli Angeli requires a bus (unless you are into serious hiking), and tickets can be purchased at any tabacchaio (a tobacco shop). Once you're in Assisi, WALK! Assisi is fairly small, so you won’t have to cover any great distances. More importantly, the picturesque nature of Assisi's narrow streets makes Francis's leisurely, less-is-more lifestyle entirely understandable, and only a slow walk through the town can truly capture its comfortable tranquility. Plus, the steep inclines (Assisi is built at the top of a hill) will burn off all of those multiple-course Italian meals you've been enjoying on your vacation.