Things to do

Attractions

• Luca and Lorenzo’s cooking class in Chianti hills (Florence)

  • This is our highest recommendation of anything on this list. Luca and Lorenzo meet you at Florence’s Santa Maria Novello station, then you take a train to reach their beautiful home in the Tuscan hillside, where you spend the day learning to cook some of the most incredible food you’ll ever taste. Luca and Lorenzo are the best! You can also book through Airbnb Experiences, where they have been recognized as the best Airbnb Experience, literally in the entire world!

• The town of Arezzo

• Baptistery of San Giovanni (Florence)

  • The Brunelleschi Pass will also provide entry to the top of the Duomo, Giotto’s Bell Tower, the Opera del Duomo museum, Santa Reparata and the Baptistery of San Giovanni.

• Basilica Cateriniana San Domenico (Siena)

• Basilica of Santa Croce (Florence)

• Cappelle Medicee (Florence)

• Cathedral of Santa Maria del Fiore (Florence)

  • A bit touristy, but full rec to reserve a timeslot to take the 463 stairs to the top of the duomo to see Filippo Brunelleschi’s handiwork – the world’s largest masonry dome, even 500 years later – up close and get a view across the birthplace of the Renaissance.

• The town of Fiesole

  • Overlooking Florence, nearby Fiesole is a great day or half-day trip.

• Galleria dell’Accademia (Florence)

  • Home to Michelangelo’s famed statue, The David.

• Giotto’s Bell Tower (Florence)

  • Take the 414 steps to the top for a view of the famed Duomo.

• Il Mercato Centrale (Florence)

• Museo Nazionale del Bargello (Florence)

• Opera del Duomo Museum (Florence)

• Palazzo Piccolomini (Pienza)

• Piazza del Campo (Siena)

• Piazzale Michelangelo (Florence)

• Pieve di Corsignano (Pienza)

  • Russell Crowe once walked these hills during an iconic scene in the movie Gladiator. Pope Pius II and his nephew, Pope Pius III, were both baptized at the church as well.

• Poggio Covili viewpoint (Castiglione d'Orcia)

  • Straight out of a Tuscan postcard

• Ponte Vecchio

• The town of San Quirico d’Orcia

• Siena Cathedral

• Uffizi Gallery (Florence)

• Wine window (Florence)

• Vasari Corridor (Florence

  Wineries

• Azienda Agricola La Lastra (Siena)

• Azienda Agricola Poliziano (Montepulciano)

• Bindella (Montepulciano)

• Cantina Baldetti (Cortona)

• Castello Banfi (Montalcino)

• Fabbrica (Pienza)

• La Ciarliana (Montepulciano)

• Madonna Bella (Siena)

  • Highly recommend the four-course lunch and tour option.

• MonteRosola (Volterra)

• Palazzo Massaini (Pienza)

  • Be sure to enjoy the Cypress tree-lined driveway to the tasting room.

• Podere Le Ripi (Montalcino)

• Tenuta Torciano (San Gimignano)

Bars, cafés and restaurants

• Giotto Pizzeria (Florence)

  • Pizzeria that’s been recognized by Michelin(!).

• Idyllium (Pienza)

• Il Moro (Montalcino)

• La Taverna di San Giuseppe (Siena)

  • Michelin-recognized restaurant in a 950-year-old building with a wine cellar that once was a small chapel inside an original Etruscan home.

• La Strega Nocciola Gelateria (Florence)

  • Multiple locations, can’t go wrong.

• La Vineria di Montepulciano

• Pane Vino & Zucchero (Pienza)

• Parione (Florence)

• Particolare di Siena

  • A bit spendy but worth the splurge for a Michelin-recognized pre-fixe experience.

• Prosit (Pienza)

• Ristorante La Grotta (Montepulciano)

• Sette di Vino (Pienza)

• Trattoria Garga (Florence)

• View on Art (Florence)

  • Rooftop bar with incredible views of the iconic 15th-century dome of the Cathedral of Santa Maria del Fiore; service is slow and drinks are a bit pricey but it is well worth it for the view. Be sure to get a reservation.

• Vivoli Gelateria (Florence)