A traveler holding up two glasses of wine on a narrow stone-paved Oltrarno street, with shuttered buildings on both sides and evening light on the facades at the far end
Ciao, Firenze

4 Day Florence Itinerary: Duomo, David & Chianti Wineries

Book before you go

Must See Attractions

A Little About This Trip

Four days in Florence is my favorite version for a first trip because you get three full city days and then a complete change of scenery in Chianti! 🍷 The route starts with the Duomo and historic center, crosses the Arno for Pitti Palace and the Boboli Gardens, and dedicates day three to the Uffizi, Palazzo Vecchio, Santa Croce, and Michelangelo’s David. You can see the major Renaissance sights without stacking every timed museum reservation into the same day. 🏛️

Save energy—and room—for the food. Osteria Pastella’s truffle tagliatelle was the best meal we had in Florence, All’Antico Vinaio’s La Beatrice sandwich was a 10 out of 10, and sunset from Piazzale Michelangelo was the BEST decision for photos. 📸 The final day takes you into the Tuscan hills for winery tastings and a village stop. If you need a shorter trip, use my 3-day Florence itinerary. If museums and Medici history matter more than wine country, choose the 4-day art and history itinerary.

Itinerary Map Overview

Filter:
View nearby:

Day OneThe Classic Centre

  • Duomo · Piazza della Repubblica
  • 7 stops
Stop 1~ 2 hours

Train to Florence

Why this stop?

  • A scenic high-speed ride brings you straight into central Florence in about two hours
  • We caught a beautiful waterfront sunrise along the way 🌅
Practical Tips
  • Choose Firenze Santa Maria Novella to arrive in the middle of the city
Stop 2~ 1 hour

Massimo Leather

Why this stop?

  • A family-owned shop packed with leather jackets, bags, wallets, and purses
  • The kind staff helped us find jackets we still love
  • Excellent quality at a very reasonable price
Practical Tips
  • Closed all day Sunday
Stop 3~ 1 hour

Cathedral of Santa Maria del Fiore

Why this stop?

  • Green, pink, and white marble unlike any cathedral I’ve seen
  • One of my favorite cathedrals from our entire Italy and Spain trip!
  • The landmark dome dominates Florence’s skyline from every angle
Practical Tips
  • Free interior entry cannot be reserved, so holiday queues can stretch for hours
  • Closed to visitors on Sundays
Stop 4~ 1 hour

Climb of Brunelleschi's Dome

Why this stop?

  • Climb between Brunelleschi’s two dome shells for a truly unique perspective
  • The lantern terrace is the highest public viewpoint over Florence’s historic center
  • Up-close dome frescoes make the ascent feel even more special
Practical Tips
  • Leave medium bags and backpacks at the free Piazza Duomo luggage store
Stop 5~ 1 hour

Piazza della Repubblica

Why this stop?

  • Live buskers and a merry-go-round make the square feel SO lively
  • The Column of Abundance marks the Roman city’s central crossroads
  • A beautiful place to absorb Florence’s yellow architecture and cobblestone streets
Stop 6~ 1 hour

All'Antico Vinaio

Why this stop?

  • Freshly baked schiacciata stuffed generously with salumi, cheeses, spreads, and vegetables
  • The truffle-beef La Beatrice was PHENOMENAL—10 out of 10!
  • You can watch steaming bread come straight from the oven
Practical Tips
  • Compare the adjacent Via dei Neri queues before joining one
Stop 7~ 1 hour

Ponte Vecchio

Why this stop?

  • A 1345 bridge lined end to end with goldsmiths’ shops
  • It feels like a shopping street floating above the Arno!
  • Look up for the Medici family’s Vasari Corridor above the storefronts

Day TwoGardens, Wine, and Sunset

  • Oltrarno · San Frediano · Piazzale Michelangelo
  • 5 stops
Stop 1~ 3 hours

Palazzo Pitti (Galleria Palatina)

Why this stop?

  • Walk through the Medici family’s enormous former palace
  • One ticket connects five collections spanning royal rooms, art, fashion, and icons
  • Each section reveals another era and style of the palace
Practical Tips
  • Closed every Monday
Stop 2~ 3 hours

Boboli Gardens

Why this stop?

  • A sprawling Renaissance garden of sculptures, fountains, hedges, and grottoes
  • Different sections unfold behind Palazzo Pitti as you climb
  • The grounds are beautiful, huge, and wonderfully well maintained
Practical Tips
  • Closed on the first and last Monday monthly
  • Last admission is one hour before closing
Stop 3~ 1 hour

Gelateria La Carraia

Why this stop?

  • A riverside gelateria serving Florence since 1990
  • The passion fruit and key lime double scoop was SO refreshing
  • House specialties extend beyond scoops to semifreddo cakes and zuccotti
Stop 4~ 1 hour

Babae Wine Window

Why this stop?

  • Sip wine through a tiny street window from Florence’s historic wine tradition
  • Babae revived its centuries-old buchetta in 2019
  • A fun little stop for wine and people-watching 🍷
Practical Tips
  • The wine window serves from 7–8 PM; outside that hour, order inside
Stop 5~ 1 hour

Piazzale Michelangelo

Why this stop?

  • A 10-out-of-10 panorama over Florence’s Duomo and red rooftops
  • The skyline absolutely screams Italy! 🇮🇹
  • Sunset brings locals, photographers, and engagement shoots to the terrace
Practical Tips
  • Arrive before summer sunset crowds if you want a place at the wall
Loading Klook recommendations…

Day ThreeDavid & Art Museums

  • Santa Croce · Piazza della Signoria · San Marco
  • 6 stops
Stop 1~ 1 hour

Vivoli Affogato and Gelato

Why this stop?

  • A family-run gelateria serving Florence since 1929
  • The classic affogato tastes like dessert and coffee in one
  • I loved the pistachio’s rich, nutty flavor!
Practical Tips
  • Closed Mondays
Stop 3~ 2 hours

Palazzo Vecchio & Arnolfo Tower

Why this stop?

  • Explore the Medici state rooms inside Florence’s still-working town hall
  • The Arnolfo Tower looks directly over Piazza della Signoria
  • Government history and city views come together in one landmark
Practical Tips
  • The tower needs a separate ticket and closes whenever it rains
Stop 4~ 1 hour

Pino's Sandwiches – Salumeria Verdi

Why this stop?

  • Crispy house-made schiacciata packed with genuinely high-quality ingredients
  • More than 30 made-to-order sandwiches, including vegetarian and vegan options
  • I even spotted Pino himself behind the counter! 🥪
Practical Tips
  • Closed all day Sunday
Stop 5~ 2 hours

Basilica di Santa Croce

Why this stop?

  • Michelangelo, Galileo, and Machiavelli are buried among nearly 300 memorials 🤯
  • Giotto, Donatello, and Vasari works fill the larger monastery complex
  • It feels like Florence’s true hall of fame
Loading GetYourGuide recommendations…

Day FourA Day in Chianti

  • Chianti wine country
  • 1 stop
Stop 1~ 6 hours

Chianti Wineries Tuscany Day Trip

Why this stop?

  • Escape Florence for Tuscany’s vineyard-covered hills
  • Visit two wineries for guided cellar tours and several tastings
  • Local wine comes with Tuscan bread, cheese, olive oil, and salami 🍷

Before You Go to Florence

Yes. Four days is enough for the Duomo, Uffizi, David and the Oltrarno without making every day another museum, and it leaves one complete day for the vineyards and villages of Chianti.

Start with the Brunelleschi’s Dome climb, the Uffizi and the Accademia because those timed visits shape your city days. Reserve the Chianti winery tour next; transportation and tasting places are limited, so it is not a good day to leave until arrival. 🍷

See the booking links above ↑

Choose Chianti if you want a change of pace, vineyard scenery and wine tasting after three city days. Choose the art and history version instead if the Bargello, Medici Chapels, Vasari Corridor and Palazzo Pitti collections are the reason you are visiting.

Loading GetYourGuide recommendations…