Don't Miss in Ancona
Urbino: About 90 minutes outside Ancona, Urbino has everything you'd want in a historic Italian hilltop town. Beyond its attractive walls and massive Ducal Palace that contains an important collection of medieval and renaissance art, Urbino is also a university town, so it's chock full of cafes, restaurants and places to hang out. A must for art-lovers, Raphael's birthplace is also a small museum (just make sure you go in the morning, as it closes between 1 and 3 p.m. for lunch).
Riviera Conero: South of Ancona, the coastline stretches into gorgeous limestone cliffs and beaches, with Mount Conero rising above. Shore excursions often visit several towns -- Sirolo or Portonovo -- along the most picturesque stretches; some lines also offer beach stops in Numana or active excursions in Conero Regional Park. Don't miss the local wines: dry and citrus-inspired Verdicchio and spicy Rosso del Conero.
Ancona: If you're hesitant to leave the city limits, Ancona itself does have a few sites worth noting. High on the hill, the Cathedral of San Ciriaco is deceptively simple on the outside, but inside, you can view stones that date back to the 6th Century as well as a creepier relic: the mummified remains of Judas Cyriacus down in the crypt. In town, stroll through several piazzas where you'll find shopping and cute cafes for lunch, a drink or a snack.