Why Florence and Tuscany
Florence is the most concentrated art city in the world — a historic center of roughly three square kilometers contains the Uffizi, the Accademia, the Bargello, the Brancacci Chapel, and more Renaissance painting and sculpture per square meter than anywhere else on earth. The challenge isn’t finding what’s worth seeing; it’s accepting that you cannot see all of it and deciding what to prioritize.
But Florence is also the gateway to a Tuscany that operates on a completely different register — the wine estates of Chianti, the cypress-lined roads of the Val d’Orcia, the medieval hill towns of San Gimignano and Volterra, the thermal spas of the Maremma. The guests who get the most out of this region are the ones who use Florence as the cultural anchor and let the countryside fill the rest.
Best for: Art and history travelers, wine and food focused itineraries, couples, guests combining city and countryside, and anyone who wants to understand the Renaissance as a physical experience rather than an art history concept.
When to go: April through June and September through October. The spring and autumn windows have the best light, manageable crowds, and the full restaurant season in operation. July and August in Florence are hot and very crowded; the Tuscan countryside is more forgiving in summer but the best hotels book out months ahead.
Best Luxury Hotels in Florence & Tuscany
Portrait Firenze (Florence) The Lungarno Collection’s finest property — a converted palazzo on the Arno with views straight to the Ponte Vecchio from the rooftop. Twenty rooms, apartment-style configuration, and the kind of service that makes it feel like you’ve borrowed a very well-connected friend’s Florentine residence. Best for: Couples, design travelers, guests who want Florence’s best view and the most residential feel in the luxury tier Pricing: From €700–2,000/night Full Italy guide →
Belmond Villa San Michele (Fiesole, above Florence) A 15th-century monastery on the hillside above Florence, with a façade attributed to Michelangelo and a garden terrace looking over the city and the Arno valley. 46 rooms; a pool; the most atmospheric setting in the greater Florence area. Best for: Guests who want altitude and quiet with Florence 20 minutes below, honeymooners Pricing: From €800–2,500/night
Castello di Casole (Sienese hills — Belmond) A 1,000-year-old estate in the Sienese hills converted into a Belmond property with 39 suites and 4,200 acres of Tuscan countryside. The spa is carved into the hillside; the restaurant uses the estate’s own olive oil and wine. Best for: Wine and farm-estate travelers, couples seeking seclusion, guests who want to base in Chianti and explore by car Pricing: From €600–1,500/night
AdAstra (Tuscany) One of the most talked-about Tuscan openings in recent years — intimate, design-considered, and a genuine alternative for guests who find the Belmond estate model too produced. Best for: Design-forward guests who want something genuinely new in the market Pricing: From €500–1,200/night
Borgo San Felice (Chianti Classico) A medieval hamlet converted into a Relais & Châteaux property in the heart of the Chianti Classico wine zone — 69 rooms across the original village buildings, a Michelin-starred restaurant, and estate wine production. The most complete wine-country hotel in Tuscany. Best for: Wine-focused travelers, guests who want to base in Chianti for cellar visits and countryside drives Pricing: From €400–900/night
Where to Eat in Florence & Tuscany
Buca Mario (Florence, near Piazza della Repubblica) The oldest restaurant in Florence, operating since 1886 — vaulted cellars, Florentine classics (bistecca alla Fiorentina, ribollita, lampredotto), and a wine list covering the Tuscan appellations in depth. The bistecca here is ordered by weight (minimum 800g for two) and is the correct benchmark for the dish. Pricing: €50–80 per person
Trattoria Mario (Florence, San Lorenzo market) The most famous lunch in Florence — a communal-table trattoria next to the San Lorenzo market that has been feeding Florentines since 1953. No reservations; arrive before noon and queue. Ribollita, pasta e fagioli, and the daily pasta. Cash only. Pricing: Lunch €15–20 per person
Buca dell’Orafo (Florence, near Ponte Vecchio) A historic Florentine trattoria in a medieval cellar steps from the Ponte Vecchio — the location that should make it a tourist trap and somehow doesn’t. The cooking is correct and the cellar setting is genuinely beautiful. Pricing: €45–65 per person
Enoteca Pinchiorri (Florence — 3 Michelin stars) The most serious restaurant in Florence — one of the finest wine cellars in Italy (over 150,000 bottles), and cooking that has held three Michelin stars since 1993. A special-occasion restaurant that earns its price. Pricing: €250–350 per person
Osteria di Passignano (Chianti — 1 Michelin star) Inside the cellars of the Antinori wine estate in Badia a Passignano — Tuscan cooking using estate ingredients, paired with Antinori wines. One of the best lunches in Tuscany if you’re driving the Chianti road. Pricing: €80–120 per person
Mercato Centrale (Florence, San Lorenzo) The covered food hall above the San Lorenzo market — the upstairs level (opened 2014) has an excellent selection of producers and prepared food stalls: pasta, truffles, lampredotto (the Florentine street food made from tripe), gelato, and wine by the glass. Good for lunch without a reservation. Pricing: €12–20 per person
Things to Do in Florence & Tuscany
The Uffizi — the most important collection of Renaissance painting in the world: Botticelli’s Primavera and Birth of Venus, Leonardo’s Annunciation, Raphael, Titian, Caravaggio. Book timed entry well in advance; a focused two-hour visit covers the essential rooms without the fatigue of trying to see everything. Go in the early morning or late afternoon when the light in the galleries is best.
The Accademia — Michelangelo’s David, in the room built specifically for it. The scale surprises everyone who has only seen it in photographs. The Prisoners (unfinished figures emerging from marble blocks) in the gallery leading to the David are as interesting as the David itself. Book timed entry; the queues without it are long.
The Bargello — the most underrated museum in Florence: the finest collection of Renaissance sculpture outside the Vatican, including Donatello’s David (the first freestanding male nude since antiquity) and works by Michelangelo, Cellini, and Verrocchio. Almost never crowded. Half a morning.
The Brancacci Chapel (Santa Maria del Carmine) — Masaccio’s frescoes of the life of St. Peter, painted in the 1420s and still the most radical paintings in Florence: the first fully realized perspective space in Western art, figures with weight and psychological depth that Michelangelo studied obsessively. Timed entry required; small groups only.
The Chianti Classico Wine Road — the SS222 from Florence to Siena runs through the heart of the Chianti Classico zone: Greve in Chianti, Panzano (home of the Antica Macelleria Cecchini, the most famous butcher in Italy — his lunch restaurants around the shop are the best value meals in Chianti), Castellina, Gaiole. A full day by car, stopping at two or three estates for tastings.
San Gimignano and Volterra — the two best-preserved medieval hill towns in Tuscany, an hour from Florence. San Gimignano for the towers (14 still standing of the original 72) and the Vernaccia wine grown on the surrounding slopes. Volterra for the Etruscan museum, the Roman theatre, and the alabaster workshops that have been operating since the Middle Ages. Neither requires more than a half-day.
Val d’Orcia — the UNESCO-listed landscape south of Siena: cypress allées, rolling hills, Romanesque churches, and the thermal baths at Bagno Vignoni (a medieval village built around a thermal pool rather than a piazza). The most photographed landscape in Italy for reasons that become obvious in person.
Sample 3-Day Florence & Tuscany Itinerary
Day 1: Florence Art Morning, Oltrarno Afternoon Morning: Uffizi at 9am (timed entry booked in advance) — Botticelli rooms, Leonardo, the Caravaggio at the end. Two hours maximum. Lunch near the Piazza della Signoria or at the Mercato Centrale upstairs.
Afternoon: Cross the Ponte Vecchio to the Oltrarno — the neighborhood south of the Arno that Florentines still actually live in. The Pitti Palace and Boboli Gardens (the garden is the best outdoor space in Florence). Walk back through the Santo Spirito neighborhood for aperitivo in the piazza. Dinner at Buca Mario or Buca dell’Orafo.
Day 2: Accademia, Bargello, and the Chianti Road Morning: Accademia at opening (8:15am; timed entry booked). An hour for the David and the Prisoners, then walk to the Bargello for the Donatello rooms — one of the great underused mornings in Florence.
Lunch: Drive south on the SS222 into Chianti. Lunch at Solociccia (one of Cecchini’s lunch restaurants in Panzano) — book ahead, fixed menu, one of the most fun lunches in Italy.
Afternoon: A wine tasting at Castello di Brolio (the Ricasoli estate, the oldest wine estate in Italy) or at Fontodi in Panzano. Drive back to Florence for dinner or stay in the Chianti countryside.
Day 3: Siena and the Val d’Orcia Leave Florence by 8:30am. Siena (1.5 hours) — the Piazza del Campo (the most beautiful medieval square in Italy), the Duomo (the most ornate Gothic cathedral in Italy, with the floor mosaics and the Piccolomini Library), and lunch in the city. Siena needs three hours minimum to feel it rather than pass through it.
Afternoon: Drive south into the Val d’Orcia — the cypress avenue at Monticchiello, the village of Pienza (the Renaissance ideal city, built in 10 years by Pope Pius II), and the thermal pool at Bagno Vignoni for a late afternoon soak. Return to Florence or stay in the Val d’Orcia.
Frequently Asked Questions About Florence & Tuscany
Do I need to book Florence museums in advance? Yes, for the Uffizi, the Accademia, and the Brancacci Chapel — all require timed entry and sell out in peak season. The Accademia in particular moves quickly; book as soon as your travel dates are confirmed. I handle all museum bookings as part of trip planning.
Is Florence worth combining with the Tuscan countryside? It’s the best structure for the region. Two to three nights in Florence for the art and the city, then two to three nights in a Chianti or Val d’Orcia property for the countryside. The contrast — the density of the city followed by complete agricultural quiet — is what makes a Tuscany trip memorable.
What is bistecca alla Fiorentina and should I order it? It is a T-bone steak from the Chianina breed of cattle, grilled over wood to rare (the Florentine position: it is not served well-done under any circumstances), salted after cooking, and served simply. It is ordered by weight, minimum 800g for two people, typically €50–70 per kilo. It is the correct dinner in Florence if you eat beef. Buca Mario and Trattoria Sostanza are the two most reliable versions in the city.
How far is the Tuscan countryside from Florence? The Chianti Classico zone begins 20 minutes south of Florence. Siena is 1.5 hours by car or 1.5 hours by bus (no direct train). The Val d’Orcia is 2 hours from Florence. A car is essential for any meaningful countryside exploration.
What wine should I drink in Tuscany? Chianti Classico (Sangiovese from the hills between Florence and Siena) for the fundamental Tuscan red. Brunello di Montalcino (from the hill town of Montalcino, south of Siena) for the finest and most age-worthy expression of Sangiovese in Italy. Vernaccia di San Gimignano for the local white — the first DOC wine in Italy. Super Tuscans (Sassicaia, Ornellaia, Tignanello) for the Bordeaux-influenced blends that changed the Italian wine landscape in the 1970s and 80s.
Plan Your Florence & Tuscany Trip with Paula Zambrano
A Florence and Tuscany itinerary built around the right sequence — which museums on which days, which wine estates are worth calling ahead, where to base in the countryside — is one of the most satisfying trips to put together. I handle the museum bookings, the cellar visits, and the hotel introductions across both the city and the countryside.