Food and Wine Lover's Tour of Tuscany

Florence

• See David at Galleria dell’Accademia di Firenze.

• Walk by the Duomo and admire the craftsmanship or go all in on a tour and climb to the top.

• Walk across the bridge and enjoy the quieter feel. Shop for cashmere and leather goods without as many crowds.

Siena

• Piazza del Campo and Fonte Gaia: Explore the streets and alleys surrounding del Campo. There’s a great little row of bars and restaurants on Via dei Rossi, and you can search for the “Naked Lady in the Window”.

• Torre del Mangia: Tickets can be purchased onsite. Opens at 10 am. I would start your morning here so you can beat the crowds to the top and the hot weather.

• Siena Cathedral (Duomo): There are several tours available. Tickets can be purchased here. The Gates of Heaven tour offers the best views from the top.

• Piccolomini Library and Santa Maria Della Scala showcase gorgeous and historical artwork.

• Take a local cooking class from Scuola di Cucina di Lella or Marta's Cooking Classes

• Stroll the markets: Open most of the year on Sundays and Wednesdays, offering everything from food and wine to clothing and antiques

• Explore the surrounding provinces of Colle Val D’Elsa, San Gimignano or Monteriggioni

Val D'Orcia:

Take a private wine tour or make your own! These wineries combine the best views with a glimpse into authentic, Italian wine-making.

• Palazzo Vecchio: Gorgeous estate

• Villa S. Anna Winery: Women run/owned. Not as expansive but has beautiful gardens and its own lemon grove

• Il Molinaccio di Montepulciano: This baby is RUS-TIC. As traditional as it gets.

• Boscarelli Winery: Hidden gem in Montepulciano's countryside

• Manvi Winery: Small, family-owned farm winery with gorgeous views of the town of Montepulciano

• Le Berne: Vineyard and olive grove tours available.

Explore the Hot Springs of Bagno Vignoni. There are a few ways to enjoy:

• Get a family pass through the Hotel Posta Marcucci to their pool, Val Di Sole. 150 euros for 5–6 people.

• Visit the Bagni San Filippo: There’s a path to follow through the woods and entry is free if you stop at the first few pools. If you choose to walk further, there’s a nominal fee (2 euros/pp). The waters here should be a little cooler since they mix with the river.

• For a more upscale experience, you can buy tickets to enjoy the pools and park at Terme San Giovanni. On Saturday nights, they offer a Night at the Spa experience that makes a perfect getaway for couples.

Day Trips

Day trip to Arezzo - Arezzo Cathedral, Casa Vasari (Home of artist/ architect contributing to the Duomo in Florence), Clock Tower, Piazza Grande. Eat at Dal Moro, Ristorante da Muzzicone, Antica Fonte, Antica Osteria L’Agania, La Tua Piadina, Le Chiavi d’Oro, Octavin, or Saffron.

Day trip to Pienza- Home of Pecorino cheese. Marusco e Maria is a great spot to pick up some samples to bring home. Park just outside the Porta al Murello. Walk to Via del Bacio, Via dell’Amore and Via dell Fortuna back to the Main Piazza. Eat at Sette di Vino, La Buca di Enea or Ristorante dal Falco.

Day trip to Montichiello - smaller and more relaxed. Eat at either La Taverna di Moranda or Osteria La Porta. The Teatro Povero, “Poor Theatre” has nightly performances in Italian where the entire town gets involved in pulling off the show.

Florence

• Trattoria 4 Leoni: Get a table on the patio for great people watching and order the pear ravioli.

• La Menagere: Best for a brunch or breakfast stop. Hearty dishes for the mornings when you need a little more than a pastry and espresso.

• Aqua Al 2: Romantic, intimate steakhouse.

• Mangia Pizza: My favorite pizza spot in Florence! Unique flavor combinations.

• Trattoria Nella: Rustic, authentic dining in a no-frills setting. Stop in for lunch while you're touring the historic monuments. Order a liter of the house wine and the walnut ravioli.

• Loggia Rooftop Bar: Get some fresh air while catching amazing views and cocktails.

Siena

• Torrefazione Fiorella: Original espresso bar, serving pastries and croissants.

• Gino Cacino: Amazing paninis just off the Piazza.

• Osteria degli Svitati: Cozy, relaxed with exposed brick walls offering traditional dishes.

• Menchetti 1948: Yummy pizzas and specialty grocery store.

• Ristorante La Locanda dei Tintori Siena: Unpretentious regional dishes in an intimate setting.

• Il Pomodorino: Wood-fired pizzas and craft beers with views of the Duomo.

• La Finestra: Traditional Italian in a mild venue with vaulted brick ceiling.

• Il Morbidi: Great for quick aperitivos.

• Osteria La sosta di Violante: A favorite for families.

• Osteria Nonna Gina: Feels like eating at your grandmother's house.

• La Taverna di San Giuseppe: Reservations here are a hot commodity, but I would try to get one.

• Antica Osteria Da Divo: High-end dining & fine wines in a vaulted medieval hall with cave-like cellars.

• Salefino bottiglieria / Salefino Cuisine and Wine: Modern, fine-dining with coursed menus and wine pairings.