Tuscany has been setting trends since the Renaissance, when the Medici funded geniuses who redrew the boundaries of art and science. Today, the region’s spirit lives in frescoed chapels, frescoed palazzi, and in humble bowls of ribollita served in trattorie that feel like living rooms.

Its landscapes are as storied as its museums: cypress-lined lanes, stone hilltowns, sunflower fields, and vineyards producing Chianti Classico, Vino Nobile, and Brunello di Montalcino. In five days, you’ll savor Florence’s masterworks, Siena’s brick-and-contrada soul, and the cinematic Val d’Orcia.

Practical notes: Historic centers enforce ZTL (limited traffic zones)—park outside the walls and walk in. Reserve major museums ahead (Uffizi, Accademia, Florence Duomo Cupola) and consider a Siena cathedral pass. Trains connect cities easily; countryside day trips work best by car or a small-group tour. Tipping is modest (round up or add 5–10% for great service).

Florence

Renaissance Florence is a living museum: the Duomo’s audacious dome, Botticelli’s Birth of Venus at the Uffizi, and Michelangelo’s David at the Accademia. Cross the Ponte Vecchio to the artisan ateliers of the Oltrarno, then watch sunset wash the city gold from Piazzale Michelangelo.

• Top sights: Duomo complex (Cathedral, Dome, Baptistery), Uffizi Gallery, Accademia, Palazzo Vecchio, Boboli Gardens, Santa Croce, Piazza della Signoria, Ponte Vecchio.
• Food & drink: Trattoria Mario (lively lunch spot for bistecca and soups), Trattoria Sabatino (old-school, budget-friendly Tuscan fare), Buca Lapi (historic cellar steakhouse), Gusta Pizza (chewy, wood-fired pies), Ditta Artigianale (specialty coffee), Gelateria dei Neri or La Carraia (top gelato).
• Fun to know: The dome’s herringbone brick pattern was a Renaissance engineering revolution; Florence’s “aperitivo hour” is practically a local ritual—go for spritzes and Tuscan salumi.

Where to stay: Browse Florence stays on VRBO or find hotels near the Duomo, Oltrarno, or Santa Croce on Hotels.com.

Getting there: Fly into Florence (FLR) or Pisa (PSA) using Omio (flights). From Pisa airport or Rome, trains to Florence Santa Maria Novella typically take 1–1.5 hours from Pisa and ~1.5–2 hours from Rome; check schedules and prices on Omio (trains) or Omio (buses).

Siena

Siena is all warm brick and medieval pride, organized into 17 contrade (neighborhoods) that animate the famous Palio horse race each summer. Piazza del Campo, the scallop-shaped heart of the city, invites lingering with a coffee while life swirls around you.

• Top sights: Piazza del Campo, Torre del Mangia (tower climb), Duomo di Siena and the inlaid marble floor, Piccolomini Library, Baptistery, Museo dell’Opera (panoramic terrace).
• Food & drink: La Taverna di San Giuseppe (Tuscan classics in stone-vaulted rooms), Osteria Le Logge (refined seasonal cuisine near the Campo), Trattoria Papei (casual local favorite by the market), Pasticceria Nannini (ricciarelli, panforte, espresso).
• Fun to know: Siena’s marble mosaic floor—revealed fully in select periods—is one of Italy’s finest; contrada museums display centuries of banners and Palio lore.

Where to stay: Explore Siena apartments and countryside agriturismi on VRBO or book hotels inside the city walls on Hotels.com.

Getting there from Florence: Trains take ~1h30 with a change at Empoli and usually cost ~€9–12; buses are ~1h15–1h30. Compare times and prices on Omio (trains) and Omio (buses).

Day 1: Arrive in Florence — Duomo, Aperitivo, and an Evening Stroll

Morning: Fly into Florence (FLR) or Pisa (PSA) via Omio (flights). If landing in Pisa or Rome, ride the train to Firenze S. M. Novella (about 1–2 hours total from Pisa, ~1.5–2 hours from Rome) using Omio (trains). Drop bags at your hotel in the historic center or Oltrarno.

Afternoon: Orient yourself around the cathedral square. Admire the Baptistery’s bronze doors and the Duomo’s green-white-pink marble; consider the Duomo combo ticket if you plan to climb Brunelleschi’s Dome on Day 2 (~€30; timed entry required). Coffee at Caffè Gilli (Belle Époque vibe) or Ditta Artigianale (excellent espresso and filter).

Evening: Walk Via Calzaiuoli to Piazza della Signoria for the open-air sculpture gallery. Cross the Ponte Vecchio at twilight. Dinner at Trattoria Sabatino (homey Tuscan classics like peposo and ribollita) or Buca Lapi (historic cellar for bistecca alla fiorentina; reserve). Gelato at Gelateria dei Neri—try pistachio and crema di Firenze.

Day 2: Florence Masterpieces — Uffizi, Accademia, and Oltrarno Artisans

Morning: Pre-book the first Uffizi slot (~€25 high season). See Giotto, Botticelli’s Birth of Venus and Primavera, and Caravaggio in digestible bites—pause on the Arno-facing corridors for river views. Espresso and a sfoglia at Caffè Scudieri or a light breakfast at Ditta Artigianale.

Afternoon: Lunch near Mercato Centrale: Trattoria Mario (lively shared tables, daily pasta soups, bistecca; opens for lunch only) or Da Nerbone inside the market (lampredotto rolls and bollito). Walk to the Accademia to meet Michelangelo’s David (book timed entry; ~€16). Pop into Santa Croce for tombs of Michelangelo, Galileo, and Machiavelli, plus the Scuola del Cuoio leather workshop.

Evening: Cross to the Oltrarno: browse artisan studios on Via Maggio and Borgo San Jacopo, then head up to Piazzale Michelangelo for sunset over terracotta rooftops. Dinner at Trattoria 4 Leoni (pear-and-pecorino ravioli, Florentine staples) or Gusta Pizza (casual, share a table). Nightcap at Il Santino (tiny, atmospheric wine bar with crostini and salumi).

Day 3: Florence to Siena — Medieval Splendor and the Duomo’s Marble Floor

Morning: Travel to Siena. Take a Regionale train from Firenze S. M. Novella to Siena (~1h30, ~€9–12) via Omio (trains); or a direct bus from Florence’s bus station (~1h15–1h30) via Omio (buses). Check in within the city walls so you can walk everywhere.

Afternoon: Start at Piazza del Campo—its shell shape funnels the city’s energy. Climb Torre del Mangia for a skyline of sienna rooftops (~€10; allow 30–45 minutes). Explore the Duomo complex: zebra-striped columns, the Piccolomini Library’s vibrant Pinturicchio frescoes, and, when uncovered, the inlaid marble floor (look for the “Fortune” panel).

Evening: Aperitivo on the Campo, then dinner at La Taverna di San Giuseppe (pici all’aglione, aged pecorino in honey, Brunello by the glass) or Osteria Le Logge (seasonal tasting menu near the Campo). Finish with ricciarelli and a night espresso at Pasticceria Nannini.

Day 4: Val d’Orcia Day Trip — Montalcino, Pienza, and Storybook Vistas

Morning: Pick up a rental car in Siena (driving the countryside is straightforward; avoid ZTL when returning). Head 45 minutes to Montalcino for fortress views and a Brunello tasting—consider estates like Poggio Antico or Ciacci Piccolomini (reserve ahead). Detour 15 minutes to the Romanesque Abbey of Sant’Antimo, where Gregorian chants occasionally echo through stone.

Afternoon: Continue 35 minutes to Pienza, the “ideal Renaissance city,” for pecorino tastings along Corso Rossellino. Lunch at Trattoria da Fiorella (handmade pasta; book) or Ristorante La Porta in nearby Monticchiello (hilltop terrace with Val d’Orcia views). Grab classic postcard shots at the cypress-lined Cappella della Madonna di Vitaleta and the Belvedere viewpoint near San Quirico d’Orcia.

Evening: On the way back, stroll Bagno Vignoni’s steamy Renaissance pool (bathing is restricted in the main basin; hotel spas offer access). Return to Siena for a casual dinner at Trattoria Papei (pici cacio e pepe, grilled meats) and a final glass of Vin Santo with cantucci.

Day 5: Slow Siena Morning — Market Bites and Farewell

Morning: Coffee at Torrefazione Fiorella (tiny, beloved) and a gentle wander through contrada lanes. If you’re keen, visit a contrada museum for Palio history, or browse the mercato (market days vary) for pecorino, wild boar salumi, and Tuscan olive oil.

Afternoon: Climb the Museo dell’Opera terrace for a last panorama, then an early lunch at Osteria La Chiacchera (cozy, excellent pastas) or a panino from a salumeria near Via di Città. Depart: trains from Siena to Florence take ~1h30; Siena to Pisa airport ~2–2h30 (change at Empoli or Pisa Centrale); Siena to Rome ~3–3.5 hours via Chiusi. Compare routes and book on Omio (trains) or Omio (buses), and connect to flights via Omio (flights).

Evening: If your flight is late, enjoy a final gelato at Nannini or a stroll on the Campo as lights come on. Safe travels—arrivederci, Toscana!

Extra food and coffee picks to bookmark: All’Antico Vinaio (Florence; schiacciata sandwiches—go early), Trattoria Sostanza (Florence; butter chicken and bistecca, hard reservation), La Giostra (Florence; romantic, Tuscan with flair), Gelateria La Carraia (Florence; two locations by the river), Salumeria Il Cencio (Siena; panini), Enoteca I Terzi (Siena; deep wine list).

Transport snapshot and costs (approx., March 2025): Florence–Siena train ~1h30, €9–12; Florence–Siena bus ~1h15–1h30, €10–15; Pisa Airport–Florence train ~1–1.5h, €12–18; Siena–Rome (via Chiusi) ~3–3.5h, €20–35. Check live schedules on Omio (trains) and Omio (buses).

This 5-day Tuscany itinerary threads Renaissance icons with vineyard roads and small-town tables where recipes outlive empires. You’ll leave with museum highlights, new favorite wines, and a palate forever tuned to peppery olive oil and pecorino.