Tuscany (Toscana) is the cradle of the Renaissance and a patchwork of soft hills, cypress-lined lanes, and villages frozen in golden light. From Florence’s masterpieces by Michelangelo and Botticelli to Val d’Orcia vineyards producing Brunello and Vino Nobile, this region marries culture and countryside with effortless grace.

Fun fact: Tuscany pioneered modern banking in the Middle Ages, financed explorers in the 1400s, and perfected the bistecca alla fiorentina. Today it’s equally famous for Chianti Classico, thermal baths like Bagno Vignoni, and hill towns such as Pienza and Montepulciano.

Practical notes: You’ll base in just two places—Florence and Pienza—and explore by car. Watch for ZTL (limited-traffic zones) in historic centers, reserve museum tickets in advance, and book tastings/cooking classes ahead of time, especially in spring–fall. For flights and trains within Europe, compare on Omio; for hotels or apartments, browse Hotels.com and VRBO.

Florence (Firenze)

Florence is a living museum where cathedral domes and artisan workshops share streets with lively osterie. Stroll over the Ponte Vecchio at sunset, sip Tuscan reds in tiny wine bars, and let the Uffizi and Accademia remind you why the Renaissance still matters.

• Top sights: Duomo and Brunelleschi’s dome, Uffizi Gallery, Accademia (David), Ponte Vecchio, Boboli Gardens, Basilica di Santa Croce.
• Neighborhoods: Oltrarno (artisans, cool bars), Santa Croce (foodie haven), Duomo (central and walkable). Avoid driving inside the center’s ZTL.
• Food & drink: Trattoria Sostanza for butter chicken, Enoteca Pitti Gola e Cantina for wine flights, Caffè Gilli for historic pastries, Gelateria dei Neri for gelato.

Where to stay: For mid-range charm near the river, consider Hotel Balestri or Plaza Hotel Lucchesi; boutique style in Oltrarno at Hotel Lungarno or Hotel Calimala. Compare rates on Hotels.com or browse apartments on VRBO. Tip: If you’ll rent a car, delay pickup until the day you leave Florence.

Getting there: Fly into Florence (FLR), Pisa (PSA), or Rome (FCO/CIA). Compare flights and trains on Omio. From PSA to Florence SMN by train takes ~1h15 from Pisa Centrale (~€10–18 on Omio trains).

Day 1: Arrive in Florence

Afternoon: Arrive and check in. Shake off jet lag with a stroll via Piazza della Signoria to the Arno. Coffee pick-me-up at Ditta Artigianale (specialty espresso and signature Negroni if you dare) or a pastry at Caffè Gilli.

Evening: Golden-hour walk over Ponte Vecchio to the Oltrarno. Dinner at Trattoria Cammillo (old-school Florentine, excellent pappardelle al cinghiale) or Osteria dell’Enoteca (steak specialists; reserve). Gelato at La Carraia on your way home.

Day 2: Duomo, Uffizi, and Historic Core

Morning: Duomo Complex: visit the cathedral interior, then climb Brunelleschi’s Dome or Giotto’s Bell Tower for skyline views (reserve timed entry). Quick schiacciata sandwiches from I’ Girone De’ Ghiotti or I Fratellini.

Afternoon: Uffizi Gallery (2–3 hours). Prioritize Botticelli’s Birth of Venus and Primavera, then Titian, Caravaggio. Espresso at Caffè Scudieri or a sweet stop at Procacci for truffle panini.

Evening: Aperitivo at Le Volpi e l’Uva (by-the-glass gems, crostoni). Dinner at Trattoria Sostanza (butter chicken, artichoke omelet; tiny, book ahead) or Trattoria Da Burde (classic cucina outside the center). Nightcap on the Arno.

Day 3: Accademia, Oltrarno Artisans, Boboli Gardens

Morning: Accademia Gallery to meet Michelangelo’s David (early slot to avoid queues). Cappuccino and cornetto at Pasticceria Nencioni. Wander the San Lorenzo and Sant’Ambrogio markets for produce, pecorino, and cured meats.

Afternoon: Cross to the Oltrarno: artisan studios on Via Maggio and around Santo Spirito. Pizza at Gustapizza or sourdough pies at SimBIOsi. Stroll the Boboli Gardens and Pitti Palace courtyard for Medici grandeur.

Evening: Rooftop aperitivo at La Terrazza (Hotel Continentale) with Ponte Vecchio views. Dinner in San Niccolò at La Beppa Fioraia (Tuscan plats du jour, lush garden) or wine-focused Fuori Porta. Gelato at Gelateria dei Neri.

Day 4: Chianti Classico by Car

Morning: Pick up your car outside the center (avoid ZTL). Drive the SR222 “Chiantigiana.” Stop in Greve in Chianti for the main piazza and Antica Macelleria Falorni (sample finocchiona). Winery tour at Antinori nel Chianti Classico (Bargino)—stunning architecture plus tastings (~€35–60; book ahead).

Afternoon: Continue to Panzano. Lunch with a view at La Cantinetta di Rignana or carnivore temple Dario Cecchini’s Solociccia (fixed menu). Optional tasting at Castello di Ama (art installations among vineyards) or Castello di Brolio (Gaiole; history-rich estate).

Evening: Return to Florence (~1–1.5 hours depending on route). Simple dinner near your stay—Osteria Santo Spirito (risotti in copper pans) or Trattoria La Casalinga (budget-friendly home cooking). Pack for tomorrow’s move.

Pienza (Val d’Orcia)

Pienza is Pope Pius II’s Renaissance “ideal city,” a honey-colored hill town surrounded by the iconic wheat fields and cypress spines you’ve seen on postcards. It’s romantic, tiny, and perfectly placed for day trips to Montalcino, Montepulciano, and thermal springs.

• Top experiences: Val d’Orcia scenic drives, Bagno Vignoni hot springs, Brunello tastings in Montalcino, Vino Nobile cellars in Montepulciano, Abbey of Sant’Antimo chants.
• Flavors: Pecorino di Pienza, pici pasta with ragù or cacio e pepe, honey, saffron, and robust Sangiovese reds.
• Vibe: Slow mornings, cinematic sunsets, starlit dinners—tailor-made for couples.

Where to stay: In Pienza, consider La Bandita Townhouse (stylish), Hotel Corsignano (great value), or countryside agriturismi with views. Search hotels on Hotels.com or villas on VRBO. Free parking sits outside the walls; the center is for pedestrians only.

Getting there from Florence: Drive ~120 km, 1h45–2h via Siena. Alternative without a car: train Florence–Chiusi-Chianciano Terme (~1h45, €12–20 on Omio trains), then a 40-minute taxi to Pienza.

Day 5: Florence → Siena (stop) → Pienza

Morning: Depart Florence around 9:00. Drive 1h15 to Siena. Park at a signed lot outside the walls. Explore Piazza del Campo and the striped Siena Duomo (opt for the Gate of Heaven rooftop tour if available).

Afternoon: Lunch at La Taverna di San Giuseppe (vaulted stone rooms; Tuscan classics) or the wallet-friendly Osteria Nonna Gina. Optional 20-minute detour to the walled hamlet of Monteriggioni for coffee and a walk on the ramparts.

Evening: Arrive Pienza by late afternoon, check in, and catch golden hour from the panoramic walls along Via dell’Amore. Dinner at La Bandita Townhouse Caffè (seasonal plates) or Trattoria Buca delle Fate (pici ragù). Gelato at Buon Gusto.

Day 6: Brunello Day—Montalcino and Sant’Antimo

Morning: Drive 35 minutes to Montalcino. Start at the Fortress for views and a flight at Enoteca la Fortezza. Pre-book one winery such as Poggio Antico, Castello Banfi, or Caparzo (typical tastings €30–60).

Afternoon: Picnic or lunch in Montalcino—Re di Macchia does excellent pici. Visit the Romanesque Abbey of Sant’Antimo (10 minutes south) and listen for Gregorian chant times when available.

Evening: Return via the iconic cypress lanes near Podere Baccoleno or the Gladiator road by Pienza (for photos, park only in marked spots). Dinner with a view at Osteria La Porta in Monticchiello—romance dialed up at sunset.

Day 7: Thermal Baths and Garden Strolls

Morning: Soak at Bagno Vignoni (15 minutes from Pienza). Consider day access at Hotel Posta Marcucci’s thermal pools (panoramic valley views) or the nearby ADLER Spa Resort Thermae; mid-range option: Terme Theia in Chianciano (family-friendly, ~€30–45 for day passes).

Afternoon: Lunch at Osteria del Leone (homemade pastas) in Bagno Vignoni. Then wander the Horti Leonini gardens in San Quirico d’Orcia—an elegant 16th-century geometric park.

Evening: Back in Pienza, sample pecorino at La Taverna del Pecorino or Marusco & Maria, then an easy dinner at Il Rossellino Ristorante (tiny, book ahead) or the rustic Latte di Luna.

Day 8: Cooking Class and Montepulciano

Morning: Hands-on cooking class at a local farmhouse. Options include Podere Il Casale (organic farm near Pienza with cheese-making and pasta; ~€90–140) or Agriturismo Le Caggiole near Montepulciano (classic Tuscan recipes; similar pricing). You’ll make pici, ragù, and seasonal sides—then enjoy your creations with house wine.

Afternoon: Explore Montepulciano (15 minutes). Tour historic underground cellars—Cantina Contucci in Palazzo Contucci and De’ Ricci’s dramatic brick caverns—tastings ~€10–20. Espresso and a slice of torta at the Art Nouveau Caffè Poliziano overlooking the valley.

Evening: Sunset by the Temple of San Biagio below Montepulciano (lovely photo spot). Dinner near Pienza at Ristorante La Grotta (romantic, candlelit) or in town at La Bandita Townhouse Caffè. Toast with a glass of Vino Nobile.

Day 9: Slow Morning and Departure

Morning: Leisurely breakfast at Bar Il Casello (terrace views). Last stroll through Pienza’s tiny lanes—Via del Bacio lives up to its name. Pack pecorino and honey for home.

Afternoon: Drive to your departure city: Florence FLR ~1h45, Pisa PSA ~2h15, Rome FCO ~2h45 (allow time to return the car). Compare onward flights and trains on Omio and, if continuing within Europe, rail options on Omio trains or buses on Omio buses.

Dining Shortlist by City (Save These!)

• Florence coffee & breakfast: Ditta Artigianale (specialty roasts), Caffè Gilli (historic pastries), Pasticceria Nencioni (locals’ favorite).
• Florence lunch: I Fratellini (stand-up panini), All’Antico Vinaio (hearty schiacciata; expect a queue), Mercato Centrale food hall upstairs (varied, budget-friendly).
• Florence dinner: Trattoria Sostanza, Trattoria Cammillo, Osteria dell’Enoteca, La Beppa Fioraia.
• Wine bars Florence: Le Volpi e l’Uva (small, curated), Enoteca Pitti Gola e Cantina (by the Pitti Palace).
• Pienza coffee & snacks: Bar Il Casello (view), Dolce Sosta Pasticceria (sweets).
• Pienza/Val d’Orcia lunch & dinner: La Bandita Townhouse Caffè (seasonal), Trattoria Buca delle Fate (pici), Osteria La Porta (Monticchiello), Osteria del Leone (Bagno Vignoni), La Grotta (near San Biagio), Re di Macchia (Montalcino).
• Wine stops: Enoteca la Fortezza (Montalcino), Cantina Contucci and De’ Ricci (Montepulciano).

Logistics, Budget, and Booking Tips

• Car & ZTL: Historic centers in Florence and Siena have cameras and fines. Park on the edges (e.g., garages or lots by the walls) and walk in. Country roads are well signed; avoid unpaved lanes after rain.
• Budget (mid-range ~50/100): Expect €15–20 breakfasts for two in cafés, €25–35 pp lunches, €35–55 pp dinners without premium steak, winery tastings €25–60, spa day passes €30–80, cooking class €90–140.
• Accommodation searches: Compare across neighborhoods on Hotels.com and Hotels.com (Pienza), or browse entire homes on VRBO (Florence) and VRBO (Pienza).
• Tickets & transport: Reserve Uffizi/Accademia time slots; compare regional trains and buses on Omio trains and Omio buses. For intra-Europe flights, use Omio.

With Florence’s masterworks and the Val d’Orcia’s vineyards as your twin bases, this itinerary balances art with countryside bliss. Expect leisurely meals, warm hospitality, and panoramas you’ll remember long after the last sip of Brunello.