Tuscany blends vineyard-laced hills with the genius of the Renaissance. Florence—its spirited capital—has been a beacon of art since the Medici backed masters like Michelangelo and Botticelli. Today, trattorias hum with the scent of bistecca and sage butter as church bells mark the hours.

Food and wine are the region’s heartbeat. Chianti’s Sangiovese pairs beautifully with rustic soups like ribollita and pappardelle al cinghiale. Markets brim with Pecorino di Pienza, finocchiona, and seasonal truffles—ideal for a mid-range traveler who wants quality without overspending.

Practical notes: reserve major museums in advance (the Uffizi and Accademia often sell out and are typically closed on Mondays). Florence is a walkable city; trams and buses are reliable (single tickets ~€1.70). Expect a modest tourist city tax at hotels, and note that tipping is appreciated but not required—round up for great service.

Florence

Florence is a living museum with a convivial appetite. The Duomo’s polychrome marble glows at golden hour, the Arno turns rose just before dusk, and the Oltrarno quarter buzzes with artisans and wine bars. It’s an ideal base for a 3-day Tuscany itinerary focused on food, wine, and a taste of the countryside.

• Top sights: Duomo complex, Ponte Vecchio, Piazza della Signoria, Basilica of Santa Croce, Boboli Gardens.
• Eat & drink: Ribollita, pappa al pomodoro, lampredotto, bistecca alla fiorentina, Chianti Classico, Vin Santo with cantucci.
• Fun fact: Florence’s “wine windows” (buchette del vino) once served vino directly from palazzi during plagues—some still pour today.

How to get to Florence (FLR/Santa Maria Novella):

• Flights within or to/from Europe: search and compare on Omio. Typical nonstops arrive at Florence (FLR) or Pisa (PSA).
• Flights from outside Europe: compare global options on Trip.com.
• Trains in Europe: high-speed routes via Omio. Rome → Florence ~1h30–1h40 (from ~€20–50). Milan → Florence ~1h55–2h (from ~€25–60). Pisa Airport → Florence ~1h15 (from ~€12–15).
• Local transit: Tram T2 links FLR airport to Santa Maria Novella station in ~20 minutes (~€1.70). Taxis to center ~20–25 minutes.

Where to stay (mid-range to special splurge):

• Search apartments and villas on VRBO Florence (great for kitchens and longer stays).
• Compare hotels on Hotels.com Florence for central, walkable bases near the Duomo or Oltrarno.
• Dreamy countryside splurges (1–1.5 hours’ drive): Castello di Casole, A Belmond Hotel; Borgo Pignano. Rustic agriturismo favorite near Val d’Orcia (about 1.5–2 hours): Agriturismo Il Rigo.

Day 1: Arrival, Duomo District, and a Sunset Food & Wine Stroll

Afternoon: Arrive and drop bags. Shake off travel with a short loop: Piazza del Duomo to admire Brunelleschi’s dome and Giotto’s bell tower, then Via dei Calzaiuoli to Piazza della Signoria. Coffee and a sweet bite at Scudieri (classic Florentine counter) or Ditta Artigianale (specialty roaster).

Evening: Ease into Tuscany’s flavors with an acclaimed guided tasting walk.

Featured activity: Winner 2025 Florence Sunset Food & Wine Tour by Eating Europe

Discover wine windows, sip Chianti and Vernaccia, and taste zero-waste soups like ribollita alongside artisanal cheeses and salumi. This is perfect for a mid-range foodie: generous tastings stand in for dinner, and the storytelling adds rich context.

Late: If you still have room, share a gelato at Gelateria La Carraia (silky pistachio, salted caramel) and stroll the Ponte Vecchio by night for river reflections.

Day 2: Full-Day Tuscan Countryside—Siena, San Gimignano, Pisa + Winery Lunch

All day (no need to split by morning/afternoon/evening): Trade city stones for cypress-lined ridges and medieval skylines.

Featured activity: Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery

Walk Siena’s shell-shaped Piazza del Campo and peek into the striped Duomo. In San Gimignano, count medieval towers and try a scoop of saffron gelato. At a countryside winery, enjoy a guided tasting—look for Sangiovese cherry, violet, and savory herbs—paired with rustic courses. Cap your day beneath Pisa’s Leaning Tower for the classic photo.

Dinner back in Florence: Keep it light after a vineyard lunch: grab a panino at All’Antico Vinaio (try “La Favolosa” with Tuscan pecorino cream) or settle into Il Santo Bevitore for seasonal small plates and a well-priced Tuscan list.

Day 3: Markets, Hands-On Cooking, and Your Last Florentine Feast

Morning: Breakfast at Forno Pugi (schiacciata flatbread, warm from the oven) or Caffè Gilli for an elegant pastry. Browse Mercato Centrale: sample Pecorino di Pienza, truffle condiments, and olives; pick up edible souvenirs like cantucci and local olive oil. Walk across Ponte Vecchio to the Oltrarno side for artisan studios and a quiet espresso at Caffè degli Artigiani.

Afternoon: Roll up your sleeves for a Tuscan cooking experience that doubles as lunch.

Featured activity (hands-on): Florence Pizza or Pasta Class with Gelato Making at a Tuscan Farm

On a countryside estate, learn to hand-shape pasta or craft a blistered pizza, then churn gelato. You’ll feast on your creations with wine—an ideal finale for a foodie focused itinerary.

Alternative for wine lovers (half-day): Small-Group Wine Tasting Experience in the Tuscan Countryside

Evening: Early aperitivo at Le Volpi e l’Uva (expertly curated by-the-glass flights with crostini), then your farewell dinner. Consider Trattoria Mario for bistecca (lunch-only, queue early), Trattoria Sostanza for butter chicken and Florentine classics (book ahead), or Osteria del Cinghiale Bianco for pappardelle al cinghiale. Finish with Vin Santo and cantucci at Enoteca Pitti Gola e Cantina across from Palazzo Pitti.

Optional art add-on if time allows: For an efficient overview, consider a skip-the-line museum tour that pairs well with free mornings:
Uffizi Gallery Small Group Tour with Guide

Budget tips (50/100): Make lunch your main meal (fixed-price menus are common), snack on market bites, and opt for house wine (vino della casa) which is often excellent. Walk or use the tram, and book key activities in advance to lock in better prices.

Travel back: For flights in or to/from Europe, compare on Omio. For trains to major hubs like Rome or Milan, check Omio again for times and fares. If you’re flying long-haul beyond Europe, browse Trip.com for global options.

In three compact days, you’ll taste Florence’s culinary soul, sip Chianti among vineyards, and wander medieval lanes under Tuscan light. Expect to return—Tuscany rewards repeat visits with deeper flavors and ever-wider horizons.