Tuscany is where Italy’s Renaissance genius meets rolling vineyards and stone towns that glow at golden hour. Florence still hums with the energy of the Medici and the masters they patronized, while Siena keeps the rhythm of the Middle Ages alive in its shell-shaped square and storied Palio traditions.

Across seven days, you’ll walk in the footsteps of Michelangelo, gaze over cypress-lined hills, sip Sangiovese where it’s born, and learn to make pasta like a Tuscan nonna. Expect slow meals, vivid frescoes, and streets designed for lingering. This itinerary focuses on two essential bases—Florence and Siena—to keep travel smooth and your days full.

Practical notes: Reserve time-slot tickets for major museums weeks ahead, especially in spring–fall. Many museums close on Mondays. Driving in city centers is restricted (ZTL zones); park outside the historic cores or rely on trains and buses. Tuscan cuisine favors seasonal produce, grilled meats, hearty soups, and handmade pastas—come hungry.

Florence

Florence is the cradle of the Renaissance, a compact city where Brunelleschi’s dome crowns the skyline and the Arno divides elegant boutiques from artisan workshops. It’s walkable, photogenic, and dense with masterpieces—meaning a smart plan helps you savor it without the crowds.

Top sights include the Duomo complex, Uffizi Gallery, Accademia (for Michelangelo’s David), Ponte Vecchio, Boboli Gardens, and the Oltrarno’s ateliers. Food-wise, this is the land of bistecca alla fiorentina, lampredotto sandwiches, and gelato worth detouring for.

• Where to stay: Browse central apartments and boutique stays near the Duomo, Santa Croce, or Oltrarno for easy walking access:
  • VRBO: Florence vacation rentals
  • Hotels.com: Florence hotels
• How to arrive: Fly into Florence (FLR) or Pisa (PSA). Compare flights to Europe on Omio. If you’re flying from outside Europe, also check Kiwi.com or Trip.com. From Pisa Airport, trains to Florence take about 1 hour 20 minutes—search schedules on Omio Trains.

Day 1: Arrival in Florence, first strolls and steak

Morning: Travel day. If you’re arriving from abroad, aim for midday/early afternoon to shake off jet lag with a walk rather than a nap. Compare flight options on Omio (Europe) or Kiwi.com/Trip.com (global).

Afternoon: Check in and go for an easy loop: Piazza del Duomo (admire the polychrome marble), down Via Calzaiuoli to Piazza della Signoria (open-air sculptures under the Loggia), then the Arno and Ponte Vecchio’s glittering goldsmiths. Espresso and cannolo at Caffè Gilli or a specialty pour-over at Ditta Artigianale. Gelato stop: Gelateria dei Neri (classic pistachio, salted caramel).

Evening: Dinner options: Trattoria Sostanza (butter chicken and artichoke omelet; book ahead), Ristorante del Fagioli (for bistecca), or Sabatino (old-school, wallet-friendly). Nightcap at Le Volpi e l’Uva wine bar—ask for a Chianti Classico from a small producer and a slab of pecorino with honey.

Day 2: Masterpieces of the Renaissance

Morning: Meet your guide for a small-group deep dive that pairs Florence’s two essential museums in one efficient block:

Uffizi & Accademia Timed Entry: Small Group Walking Tour

See Michelangelo’s David up close, then Botticelli’s Birth of Venus and Primavera with context that brings them alive. Timed entries and a guide save hours and give structure.

Afternoon: Lunch: I’ Girone De’ Ghiotti for a crowd-beating schiacciata sandwich (try finocchiona and pecorino) or a sit-down plate of pappardelle al cinghiale at Trattoria Mario near San Lorenzo. Walk the artisan-lined Borgo Santi Apostoli and Via Tornabuoni’s high-fashion windows. Espresso at Rivoire overlooking Piazza della Signoria.

Evening: Cross to the Oltrarno for aperitivo at Pitti Gola e Cantina (by the Pitti Palace). Dinner at Trattoria 4 Leoni (pear and pecorino ravioli) or Cammillo (time-honored Florentine fare). Gelato at La Carraia before a riverside stroll.

Day 3: Markets, Santa Croce, and a Tuscan farm cooking class

Morning: Breakfast at S. Forno (schiacciata and jam, superb cornetti) or Ditta Artigianale (flat whites and eggs). Explore Basilica di Santa Croce (tombs of Michelangelo and Galileo) and the leather school nearby to see artisans at work. Snack at Mercato Centrale—try Da Nerbone for bollito or lampredotto (tell them “con salsa verde”).

Afternoon: Head just outside the city for a hands-on culinary experience set on a Tuscan estate:

Florence Pizza or Pasta Class with Gelato Making at a Tuscan Farm

Roll dough, shape pasta or pizza, spin gelato, and feast on your creations with local wine. It’s equal parts delicious and insightful—great for couples and families.

Evening: Return to town for a gentle passeggiata. If you still have room, grab a late-night cantucci with vin santo near Santa Croce, or a simple plate of ribollita at Da Ruggero for a humble, homey finish.

Day 4: Chianti vines and Florentine views

Morning: Leisurely start in the Oltrarno: cappuccino at Ditta Artigianale (Via dello Sprone), then the Boboli Gardens for Renaissance landscaping and Medici vistas. Peek into the costume museum at Pitti Palace if fashion history calls.

Afternoon: Spend your afternoon in the hills of Chianti learning why Sangiovese thrives here:

Chianti Wine Tour from Florence

Visit wineries for cellar tours and tastings of Chianti Classico, often paired with pecorino and olive oil. Expect cypress-dotted ridgelines and postcard villages.

Evening: Sunset at Piazzale Michelangelo—walk up via the Rose Garden for blooms and views. Dinner at Osteria All’Antico Ristoro di’ Cambi (hearty Tuscan classics) or Trattoria Il Magazzino (tripe specialties and creative Tuscan plates). Nightcap along the Arno.

Siena

Siena is Florence’s medieval foil: a brick-red city of contrade (neighborhoods) whose identity is woven into the Palio horse races each July and August. Its heart, Piazza del Campo, is a perfect shell where time seems to slow.

Don’t miss the black-and-white striped Duomo and the jewel-box Piccolomini Library, the Torre del Mangia for views, and the OPA Museum terrace for a secret skyline. Between sights, nibble ricciarelli (almond cookies) and sip local Rosso di Montalcino or Vino Nobile from nearby hilltowns.

• Where to stay: Inside the historic walls for pure atmosphere, or in a countryside agriturismo for vineyard mornings.
  • Hotels.com: Siena hotels (intra-muros and nearby)
  • VRBO: Siena and countryside stays
  • Splurge retreat near Siena: Castello di Casole, A Belmond Hotel (storybook castle, spa, and estate trails).
  • Romantic agriturismo with Val d’Orcia views: Agriturismo Il Rigo (homemade breakfasts, golden fields).
  • Eco-chic country estate for design lovers: Borgo Pignano (near Volterra; infinity pool and organic gardens).

Day 5: Transfer to Siena, piazza life, and Tuscan comfort food

Morning: Travel from Florence to Siena. By train: about 1h30–1h45 with a change at Empoli, around €10—check times on Omio Trains. By bus: ~1h15 direct from Firenze Autostazione, roughly €8 via Omio Buses. If driving, beware Siena’s ZTL; park at “Il Campo” or “Santa Caterina” garages and walk in.

Afternoon: Settle in and orient yourself around Piazza del Campo. See the Fonte Gaia and note the shell’s nine sections—an ode to Siena’s medieval rule. Coffee and a slice of panforte at Pasticceria Nannini. If energy allows, climb the Torre del Mangia for sweeping hills.

Evening: Dinner at Taverna di San Giuseppe (arched stone cellar; pici cacio e pepe and bistecca) or Antica Trattoria Papei (local favorite for Tuscan staples just off the Campo). A glass of Brunello at Enoteca I Terzi. Gelato at La Vecchia Latteria.

Day 6: Siena’s Duomo treasures and medieval lanes

Morning: The Duomo complex rewards time. Admire the black-white marble stripes, Pisano’s pulpit, and the Piccolomini Library’s vivid frescoes. Continue to the Museo dell’Opera and the Facciatone terrace—one of Tuscany’s finest city views.

Afternoon: Explore Santa Maria della Scala, a former hospital turned museum with layered history and frescoed halls. Walk to the Sanctuary of Santa Caterina and Basilica of San Domenico for a window into Siena’s patron saint. Lunch at Osteria Le Logge (seasonal Tuscan with finesse) or Nonna Gina (home-style pici and ragù).

Evening: Sunset amble atop the Fortezza Medicea’s walls. Aperitivo at Bar Il Palio facing the square. Dinner at Osteria La Chiacchera (cozy, local) or circle back to whichever Siena classic you missed. Finish with ricciarelli and a night stroll under medieval lamps.

Day 7: Hilltown hop and departure

Morning: Quick foray to Monteriggioni, a perfectly preserved walled hamlet that feels plucked from a manuscript. Bus 130 from Siena takes ~25–30 minutes, about €4—search on Omio Buses. Espresso in the tiny piazza and a short wall walk before heading back. Prefer to linger in Siena? Visit a Contrada museum to understand Palio culture.

Afternoon: Depart for your onward flight or train. To Florence Airport: direct bus or bus+train combo in ~1.5–2 hours; to Pisa Airport: train via Empoli ~2–2.5 hours—check Omio Trains. For flights within Europe, compare on Omio; long-haul options on Kiwi.com or Trip.com.

Optional Florence evening add-on (foodie focus)

If you prefer a guided culinary immersion on your Florence nights, consider:

Winner 2025 Florence Sunset Food & Wine Tour by Eating Europe

Discover historic wine windows, neighborhood trattorie, and the stories behind iconic dishes with a local expert.

Need a second wine day?

Florence also offers intimate vineyard-focused outings:

Small-Group Wine Tasting Experience in the Tuscan Countryside

This is a great backup if your travel dates or pace call for a shorter excursion.

Where to caffeinate and eat (quick hits to bookmark):

• Florence coffee/breakfast: Ditta Artigianale (specialty coffee), S. Forno (bakery), Scudieri (classic bar by the Duomo).
• Florence lunch: Da Nerbone (Mercato Centrale, lampredotto), I’ Girone De’ Ghiotti (sandwiches), Trattoria Mario (pasta, bistecca).
• Florence dinner: Trattoria Sostanza, 4 Leoni, Cammillo, Ristorante del Fagioli.
• Florence gelato: Gelateria dei Neri, La Carraia.
• Siena coffee/pastry: Pasticceria Nannini.
• Siena lunch/dinner: Taverna di San Giuseppe, Antica Trattoria Papei, Osteria Le Logge, Nonna Gina.
• Wine bars: Le Volpi e l’Uva (Florence), I Terzi (Siena).

Booking tips: Reserve museum entries (Uffizi, Accademia) and popular trattorie 2–3 weeks ahead in high season (May–October). For the Palio (July 2 and August 16), book months in advance and expect some site closures on race days.

In one week you’ll have traced Renaissance brushstrokes, tasted Chianti at the source, and watched Siena’s brick lanes blush at sunset. This Tuscany itinerary balances art, cuisine, and countryside—leaving just enough unscripted moments for serendipity to find you.