Florence and Tuscany in 5 days
Florence: Uffizi Gallery skip-the-line tickets
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Five days is the ideal first Tuscany trip: enough Florence to see the essentials properly, plus a day each for Siena, a Chianti tour and Pisa. This itinerary uses trains and buses throughout — you do not need a car, though Chianti becomes much richer if you hire one for a day. All day trips are structured to get you back in Florence for dinner.
Budget estimate: €320–450 per person over five days including Uffizi (€30), Accademia (€22), Duomo pass (€20), Pisa leaning tower ticket (€20), Siena guided tour (~€25–35), meals and transport. Costs vary significantly based on restaurant choices and whether you add wine tastings.
Advance bookings needed: Uffizi, Accademia, Duomo dome, Pisa leaning tower. Book all at least two weeks ahead in April–May and September.
Day 1: Arrival and the Uffizi
Use the arrival day to check in, orient yourself and visit the Uffizi if your slot permits. If arriving late or needing the afternoon to settle, walk Piazza della Signoria, cross Ponte Vecchio and have aperitivo in the Oltrarno.
Full day 1 plan: follow the Florence in one day structure: Uffizi morning, Duomo afternoon (or save Duomo for Day 2), Piazzale Michelangelo sunset.
Dinner:
- Buca dell’Orafo (Vicolo dei Girolami 28) — near the Uffizi, classic Florentine
- Il Latini (Via dei Palchetti 6) — communal tables, lively, book ahead
Day 2: Accademia, the Duomo and Florence essentials
Morning: Accademia and the David (9:15–11:30)
The Accademia and Michelangelo’s David take 2 hours. Book your timed entry slot for 9:15. After the Accademia, walk south to the Duomo.
Mid-morning to afternoon: Duomo complex (12:00–15:00)
The Brunelleschi dome climb (463 steps, no lift) takes 1–1.5 hours round-trip. Book your timed entry in the 12:00–14:00 window and combine with the baptistery. The Duomo guide explains what’s included in the complex pass.
Lunch near the Duomo:
- Trattoria Mario (Via Rosina 2, 15 minutes north) — best value in the centre, communal tables
- Mercato Centrale (ground floor vendors) — lampredotto, pasta, cheese; budget €10
Afternoon: San Lorenzo and Medici Chapels (15:30–17:30)
Visit the Medici Chapels (~€12, book ahead) for Michelangelo’s tomb sculptures. The adjacent Basilica di San Lorenzo (€8) has Brunelleschi’s serene interior and Donatello’s bronze pulpits.
Evening: Oltrarno aperitivo and dinner
Cross to the Oltrarno for aperitivo around Piazza Santo Spirito, then dinner:
- Trattoria Sostanza — butter pasta and Florentine classics; book ahead
- Il Santo Bevitore — wine-focused, seasonal menu
Day 3: Siena and San Gimignano day trip
Siena and San Gimignano make a natural pairing — many operators run a combined day trip, or you can use public transport independently.
Getting there
By organised tour: Several operators run Florence → San Gimignano → Siena → Chianti day trips (10–12 hours, ~€50–80 including transport). Check our Siena day trip guide and San Gimignano day trip for the best options.
By public transport:
- Florence → San Gimignano: SITA bus to Poggibonsi then local bus (1h30 total, €7 each way)
- San Gimignano → Siena: bus via Poggibonsi (1h, €5)
- Siena → Florence: SITA bus from Siena Piazza Gramsci (1h30, €9)
The bus journey is slower but gives you more flexibility. Total transit time: ~3 hours on an independent day.
In San Gimignano (9:30–12:30)
San Gimignano is the medieval Manhattan: 14 towers still stand (originally 72) above a perfectly preserved hilltop town. It gets crowded after 10:00 — arrive early for the best experience.
What to see:
- Piazza della Cisterna — the older of the two main squares; the medieval well at the centre is 13th century
- Collegiate Church (Duomo) — entry €5; Ghirlandaio’s frescoes in the Chapel of Santa Fina are among the finest in Tuscany
- Rocca di Montestaffoli — the ruined fortress above the town; panoramic view at no cost
Best gelato: Gelateria Dondoli on Piazza della Cisterna won the Gelato World Cup. The crema di Santa Fina (saffron and pine nut) is extraordinary.
In Siena (13:00–18:00)
Siena is Florence’s great rival city — Gothic where Florence is Renaissance, organised around its contrade (17 neighbourhood districts that still compete in the Palio horse race twice a year, July 2 and August 16).
What to see:
- Piazza del Campo — the fan-shaped medieval square; sit and watch for 20 minutes before moving
- Siena Duomo (€8–15 depending on pass) — the black-and-white marble floor (52 panels of narrative scenes), Nicola Pisano’s pulpit, and the dome
- Piccolomini Library (inside the Duomo) — Pinturicchio’s ceiling frescoes, vivid and well-preserved
- Torre del Mangia (€10, climb 400 steps) — best view of the Campo from above
Lunch in Siena:
- Osteria Nonna Gina (Pian dei Mantellini 7) — simple, cheap, local
- Osteria Il Carroccio (Via del Casato di Sotto 32) — slightly more polished, pici pasta with ragù
- A slice of panforte (spiced fruit cake) or ricciarelli (almond cookies) from any café is essential
Return bus to Florence by 18:30–19:00.
Dinner:
- Alla Vecchia Bettola (Viale Ariosto 32, Oltrarno) — bistecca alla Fiorentina for two, Tuscan wine
- Osteria dell’Enoteca (Via Romana 70) — more refined, seasonal
Day 4: Chianti half-day and Pitti Palace
Morning: Pitti Palace (9:15–12:00)
Visit the Pitti Palace — the Palatine Gallery holds Raphael, Titian and Rubens in Medici-period display rooms. Combine with 45 minutes in the Boboli Gardens. See the Pitti Palace guide.
Lunch:
- Il Guscio (Via dell’Orto 49, Oltrarno) — neighbourhood trattoria, seasonal dishes
- Fuori Porta (Via Monte alle Croci 10) — wine bar, crostini and full plates
Afternoon: Chianti half-day (13:30–18:30)
The Chianti wine region begins 15 km south of Florence. A half-day organised tour from Florence takes you to 1–2 wineries for tastings, olive oil sampling and the Chianti Classico production area.
What to expect on a half-day tour:
- Departure from Florence ~14:00
- 1–2 winery visits with cellar tour and tasting of 3–5 wines
- Some tours include Monteriggioni (a perfectly intact medieval walled town) or Greve in Chianti
- Return to Florence ~18:30–19:00
An independent alternative: train to Greve in Chianti is not direct; the organised tour is more practical for a half-day. See our Chianti day trip guide for the full options comparison.
Dinner:
- Il Santino (Via Santo Spirito 60) — natural wines and excellent salumi; perfect after a wine-focused afternoon
- Raspo di Uva (Via Maggio 18) — local aperitivo crowd, good Chianti by the glass, light food
Day 5: Pisa and departure
Pisa morning (8:00–13:00)
Pisa is 1 hour by direct train from Florence Santa Maria Novella (€9–15, runs hourly). First train recommended: 8:15 arrival ~9:15, leaving time before the Field of Miracles crowds arrive.
What to see at the Campo dei Miracoli:
- Leaning Tower — advance timed entry required (~€20). The 30-minute climb (294 steps) goes counterclockwise up the marble spiral staircase. The lean is visible and disorienting.
- Cathedral (Duomo) — free with tower ticket. Romanesque interior with a Pisano pulpit and mosaic ceiling. Allow 30 minutes.
- Baptistery — free with some ticket combinations; the acoustic demonstrations inside (guides demonstrate the echo) are a highlight
- Campo Santo (monumental cemetery) — Gothic cloister with fragments of medieval frescoes
The Pisa day trip guide covers the best routes from Florence and the tower booking system.
Lunch in Pisa:
- Osteria dei Cavalieri (Via San Frediano 16) — local favourite near the university, ribollita and pasta ~€15
- Il Montino (Vicolo del Monte 1) — cash-only, cecina (chickpea flatbread), a Pisan speciality
Return train by 13:30–14:00 for afternoon departure, or explore Pisa’s city centre (the medieval streets south of the river are rarely visited by tourists and very pleasant).
Afternoon: return to Florence or departure
If your flight or train departs from Florence in the evening, you have the afternoon for final wandering. Florence’s Santa Maria Novella church (free entry) is frequently overlooked in favour of the train station namesake — the interior holds Masaccio’s Trinity fresco (1427), a foundational document of perspective. Worth 20 minutes.
Final dinner:
- Buca Mario — dependable Florentine classic before departure
- Or a quick ribollita and Chianti at any of the Oltrarno spots you’ve grown to like
Logistics for five days
Transport:
- Siena: SITA bus from Santa Maria Novella coach station (~€9 each way, 1h30)
- San Gimignano: SITA bus via Poggibonsi (~€7, 1h30)
- Pisa: Trenitalia from Santa Maria Novella station (~€9–15, 1 hour)
- Chianti: organised tour is most practical; rental car possible but adds ZTL complexity
ZTL in Florence: Fines of €80–335 for unauthorised vehicles in the historic centre. Do not drive there. Full details: Florence ZTL explained.
Night stays: Stay in Florence all 5 nights. The day trips all return comfortably before 19:30. Staying in Florence means restaurant choice, no driving and no luggage logistics.
Frequently asked questions about this itinerary
Do I need a car for a 5-day Tuscany trip?
Not for this itinerary. All destinations are reachable by bus or train. A car adds flexibility for Chianti (you can stop at wineries and drive the scenic SR222 road independently) but creates ZTL complications in Florence city itself. Read our renting a car in Tuscany guide for the honest trade-offs.
Is Cinque Terre worth adding to a 5-day Florence trip?
Honest answer: Cinque Terre from Florence is 2.5 hours each way by train. You arrive tired, have perhaps 4–5 hours on the coast, and return exhausted. It’s beautiful, but it’s better as a separate trip (staying one or two nights) than a day trip from Florence. See our Cinque Terre day trip guide for the logistics if you want to try.
Is it worth booking a guide for Siena and San Gimignano?
Yes, for first-time visitors. The Palio’s history, the Contrade system and Siena’s rivalry with Florence are far richer with a local guide. San Gimignano’s tower-building oligarchies and the Ghirlandaio frescoes also come alive with context. An organised day tour is typically more cost-effective than a private guide.
What should I skip to save time?
If you are short on time, cut the Chianti half-day and use that afternoon to revisit Florence (Bargello, Galileo Museum, or a second Uffizi visit for rooms you rushed through). Pisa and Siena are the non-negotiable day trips for a first Tuscany visit.
How should I sequence the museums across 5 days?
Uffizi on Day 1 (always first — the foundation), Accademia on Day 2, Duomo on Day 2 afternoon, Pitti on Day 4. This spreads museum hours across the week and leaves room for the day trips’ natural rhythm. The how many days in Florence guide has more detail on museum sequencing.
Top experiences
Bookable activities with verified prices and instant confirmation on GetYourGuide.
Florence: Uffizi Gallery skip-the-line tickets
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- Free cancellation
Florence: Accademia Gallery — David skip-the-line ticket
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Florence: Siena, San Gimignano and Chianti day trip
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- Hotel pickup
Pisa: timed entry leaning tower and cathedral tickets
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Florence: ticket to Brunelleschi's Dome with panoramic views
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