4-Day Tuscan Itinerary: Florence, Chianti and Siena

We started with a direct flight from Madrid—Iberia IB3286, about two and a half hours—landing at noon at Florence's small airport, a short distance from the center. Flying direct saved us an entire morning: by early afternoon we were already checking in to our hotel.

We stayed at Hotel Brunelleschi, a boutique set inside a 6th-century bell tower two hundred meters from the Duomo (it cost us about €148 a night). We left the first afternoon unscheduled on purpose: the historic center can be crossed entirely on foot and deserves getting lost in. To start our trip with authentic Florentine flavor, we went to Trattoria Mario—an institution since 1953 famous for its bistecca alla fiorentina—; it only opens at lunch and doesn't take reservations, so we arrived early and ended up sharing a table with strangers.

The second day was dedicated to art, which in Florence is almost like breathing. We started early at the Galleria degli Uffizi with a skip-the-line ticket and a reserved time slot: with Botticelli, Leonardo, and Caravaggio under the same roof, three hours felt too short, and arriving early spared us the queues that wrapped around the piazza.

Then, crossing the Arno, we went to see the original David at the Galleria dell'Accademia (watch out for Mondays, when it's closed). At lunchtime we stopped at Mercato Centrale in San Lorenzo: fresh produce downstairs; upstairs, a food court where you can grab pasta or bistecca without any fuss. And to finish the day, we walked up—no tour bus, no shortcuts—to Piazzale Michelangelo, the classic postcard view of Florence from above. We arrived just as the sun was setting, with the Duomo glowing in the distance, and it was probably the moment we remember most vividly from the trip.

If you're coming to Tuscany for wine, this is your day. We booked a visit to Castello di Verrazzano in Greve in Chianti, with a shuttle from Florence so neither of us had to worry about driving. It included a tour of the cellars and a tasting of five wines paired with cheese, cured meats, and focaccia: about €85 per person, which felt justified the moment we saw rows of vines rolling down the hillside.

Delegating the transport had its rewards: we returned to Florence without rush or worries. Back in the city, we finished with artisan gelato from Gelateria dei Neri—Sicilian pistachio, ricotta with figs—before a relaxed dinner.

The last full day we reserved for the Tuscany of postcards, with a full-day tour. In the morning, San Gimignano, the town of towers: fourteen still stand out of the more than seventy it once had, and its narrow streets demand a slow pace and a stop for the award-winning gelato from Dondoli (we went back twice).

In the afternoon, Siena. Piazza del Campo, with its scallop-shell shape where people sit directly on the paving stones, is one of those spaces that explains why the Middle Ages were also art. For dinner nearby we chose Osteria Le Logge, a couple of minutes from the square: traditional Tuscan cuisine in a historic setting that we booked a couple of days in advance.

Rather than a food destination, Tuscany felt to us like a permanent excuse to sit down at a table. We alternated between two styles: the informal—the bistecca at Trattoria Mario, the quick lunch at Mercato Centrale, gelato in the middle of the afternoon—and the formal, like dinner in Siena.

Two things we learned the hard way. First: book your important dinners in advance, because good places fill up even outside peak season (the first night we couldn't get into the restaurant we wanted). And second: leave room in your budget for spontaneity, because in Tuscany it's usually the best—a cone of olives, a glass of Chianti in a piazza, gelato that wasn't on the plan.

All in, we spent between €1,500 and €2,200 for two people, depending on how much we left on tables and wine tastings. The big budget items: the Iberia direct flight was around €424 round-trip for both of us; four nights at Hotel Brunelleschi, about €592; the Chianti tasting and the San Gimignano and Siena tour, around €75–85 per person each. On top of that, we had small expenses that save headaches, like a private taxi to the airport and cancellation insurance.

The core idea, and what we took home: four days get you a lot if you have a good base in Florence and you outsource the transportation for day trips. We came away with the feeling that we'd seen the essentials without rushing, which was exactly what we wanted from a couple's getaway.