This itinerary is designed for maximum impact. Think of it as rough draft for you to revise according to your own interests and time constraints.
Day 1: Venice
Arrive in Venice’s Marco Polo Airport (there are direct flights from the United States), hop on the bus into the main bus station in Venice, then check into your hotel, get out, and get lost in the back canals for a couple of hours before dinner. If you enjoy fish, you should indulge yourself at a traditional Venetian restaurant. There’s no better place for sweet, delicate Adriatic seafood.
Logistics: At the airport, avoid the Alilaguna boat into Venice on arrival. It’s expensive, slow, and singularly unromantic. The bus is quick and cheap—save the romance for later. When you get to the main station, transfer to the most delightful main-street “bus” in the world: the vaporetto ferry. Enjoy your first ride up the Grand Canal, and make sure you’re paying attention to the fermata (or stop) you need to get off at. As for water taxis from the airport to the city, they’re very expensive, although they’ll take you directly to your hotel.
Day 2: Venice
Begin by skipping the coffee at your hotel and have a real Italian coffee at a real Italian coffee shop. Spend the day at Venice’s top sights, including the Basilica di San Marco, Palazzo Ducale, and Galleria dell’Accademia; don’t forget Piazza San Marco, which is probably the most intense concentration of major artistic and cultural monuments in the world. The intense anticipation as you near the giant square through a maze of tiny shop-lined alleys and streets climaxes in the stunning vista of the Piazza (return at 7 am the next morning to see it “senza popolo” (without people) and it’ll look like a Canaletto painting come alive. Stop for lunch, perhaps sampling Venice’s traditional specialty, sarde in saor (grilled sardines in a mouthwatering sweet-and-sour preparation that includes onions and raisins), and be sure to check out the fish market at the foot of the Rialto Bridge, and sunset at the Zattere before dinner. Later, stop at one of the pubs around the Campo San Luca or Campo Santa Margarita, where you can toast to freedom from automobiles.
Logistics: Venice is best seen by wandering. The day’s activities can be done on foot, with the occasional vaporetto ride if you feel the urge to be on the water.
Day 3: Ferrara/Bologna
Get an early start and leave Venice on a Bologna-bound train. The ride to Ferrara—your first stop in Emilia-Romagna—is about an hour and a half. Visit the Castello Estense and Duomo before lunch; a panino and a beer at one of Ferrara’s cafés should fit the bill. Wander Ferrara’s cobblestone streets before hopping on the train to Bologna (a ride of less than an hour). In Bologna, check into your hotel and walk around Piazza Maggiore before dinner. Later you can check out some of northern Italy’s best nightlife.
Logistics: In Ferrara, the train station lies a bit outside the city center, so you may want to take a taxi into town (though the distance is easily walkable, too). Here and elsewhere in Italy, you may leave your bags at the station for a small fee. Going out, there’s a taxi stand near the back of the castle, toward Corso Ercole I d’Este. In Bologna the walk into town from the station is more manageable, particularly if you’re staying along Via dell’Indipendenza.
Day 4: Bologna/Florence
After breakfast, check out some of Bologna’s churches and piazzas, including a climb up the leaning Torre degli Asinelli for a red rooftop–studded panorama. After lunch, head back to the train station and take the short ride to Florence. You’ll arrive in time for an afternoon siesta and an evening passeggiata.
Logistics: Florence’s Santa Maria Novella train station is within easy access to some hotels, and farther from others. Florence’s traffic is legendary, but taxis at the station are plentiful; make sure you get into a licensed, clearly marked car; the taxi stand is just outside the station.