Start the day late, like a Florentine mamma, and don’t get up until ten at the earliest. Make espresso with a thirties-designed Bialetti Espresso Maker ($30 at williams-sonoma.com) and Illy Fine Grind Espresso ($11.50). Knock it back in one shot—con un sorso.
Dress in tie-up espadrilles, Capris, a linen blouse, and a Pucci handkerchief around your hair. Rent a Bianchi Milano bicycle ($30 at Gotham Bikes; 212-732-2453) and cycle away, waving Ciao bello! to gawking neighbors. Enjoy the catcalls; on any other morning, it’s harassment, but today, it’s spontaneous courtship.
Stop at Sant Ambroeus (259 W. 4th St., nr. Perry St.; 212-604-9254) for brioche and Nutella. Lean your bike by the tree on Perry Street and sit outside. Read Corriere della Sera and La Repubblica. By now, you’re late for Mass. A few blocks away is the beautiful church of Our Lady of Pompeii (25 Carmine St., at Bleecker St.; 212-989-6805), where Father Massari gives a mellifluous Italian sermon.
At noon, take a whirlwind picnic-shopping tour. Stop by ’ino (21 Bedford St., nr. Downing St.; 212-989-5769) for ricotta fresca, truffle oil, and Parmesan bruschetta to go. While they prepare the food, take a lap around the pasticcerias near Bleecker and Carmine and grab a bag of biscotti. Buy a half-bottle of Querciabella Chianti Riserva ($21.56 at Italian Wine Merchants, 108 E. 16th St., nr. Park Ave.; 212-473-2323) and a couple of blood oranges from the Union Square Greenmarket for dessert. Rent Franco Zeffirelli’s Romeo and Juliet from Evergreen Video (37 Carmine St., nr. Bleecker St.; 212-691-7362), and pick up Dante’s Inferno from Biography bookshop (400 Bleecker St., at 11th St.; 212-807-8655).
Take the northbound bike path along the Arno—scusi, the Hudson—toward the Cloisters (212-923-3770; metmuseum.org; Tues.–Sun. 9:30–5:15), which resembles the buildings around the Piazza della Signoria. The hilly oasis is a dead ringer for San Miniato al Monte, a popular picnicking spot above the Arno’s banks. Spread your checkered blanket. Read Dante aloud.
Inspired, scribble eloquent thoughts onto beautiful Italian stationery—put your notes into a matching envelope (from Papyrus, 2157 Broadway, at 76th St.; 212-501-0102) and seal it with wax, as you imagine Dante did for Beatrice. Doze for an hour or two, then ride to the boccie courts at James J. Walker Park (Clarkson St. and Seventh Ave). If you’ve been practicing ($99 for balls at Restoration Hardware), you’re ready to smoke the old men before night falls. On your way back home, stop by Otto Enoteca Pizzeria (1 Fifth Ave., at E. 8th St.; 212-995-9559) and get hazelnut stracciatella gelato in a little metal cup for later.
Meet a group of amici at Palma (28 Cornelia St., nr. Bleecker St.; 212-691-2223), a Tuscan restaurant with a stunning private room in a farmhouse at the back of the garden ($85 per person, ten to sixteen people). Pace yourself for a multicourse marathon, and cap it off with grappa or vin santo with cantucci—sweet Tuscan biscuits.
End the day in bed, watching Romeo and Juliet, a 1968 classic set in Pienza. Indulge yourself one last time with the hazelnut stracciatella gelato. Collapse into a blissful Tuscan sleep.