Five days split between Florence and the Tuscan hills.
Art and countryside in equal measure.
Renaissance art masterpieces Medieval hill towns Chianti wine tastings Sunset viewpoints over Florence First-time Florence visitors Art and wine lovers Couples on romantic getaways
Key Facts
Renaissance Heart
Florence, Tuscany
Climb the 463 steps of the cupola for a close look at the dome's construction.
Florence, Tuscany
Admire the open-air sculptures, then step inside the Medici's seat of power.
Florence, Tuscany
Cross the jewellers' bridge at golden hour, then climb for the classic skyline view.
Gallery Day
Florence, Tuscany
The elegant Uffizi Gallery in soft morning light, its long arcaded corridor lined with classical statues, frescoed ceilings, visitors viewing the collection, museum architecture photography
Florence, Tuscany
Michelangelo's David standing in the Galleria dell'Accademia, soft gallery light, visitors gathered beneath the towering marble sculpture, unfinished prisoners along the walls, fine art photography
Florence, Tuscany
Cross the Arno to Santo Spirito for a trattoria dinner away from the crowds.
Siena Day Trip
Siena, Tuscany
The scallop-shell square hosts the Palio; climb the Torre del Mangia for the view.
Siena, Tuscany
A black-and-white striped cathedral with library frescoes and a marble floor.
Florence, Tuscany
Grab a table in Santa Croce or a wine bar off Piazza della Signoria.
Chianti Wine Route
Chianti, Tuscany
Browse the arcaded piazza and taste Chianti Classico at a winery along the SR222.
Chianti, Tuscany
Book a cellar tour near Castellina or Radda, then linger over a countryside lunch.
Florence, Tuscany
Stroll Piazza Santo Spirito for an aperitivo and a final gelato.
San Gimignano Day
San Gimignano, Tuscany
Fourteen medieval towers survive; climb the Torre Grossa for valley views.
San Gimignano, Tuscany
Lunch on the triangular square and taste the DOCG Vernaccia white wine.
Florence, Tuscany
Watch the city from Ponte Santa Trinita or a riverside wine bar.
Transport Between Stops
Regional Train
Direct Florence to Siena runs about 1 hour 30 minutes
Rental Car
Best for the Chianti road and San Gimignano's hill country
Bus
SITA lines connect Florence, San Gimignano and Greve in Chianti
Where to Stay
Base in Florence's center for easy day trips.
$ Budget
$$ Mid-Range
$$$ Luxury
Typical cost per person
Accommodation
€110–€280 per night
Food
€45–€85 / day
Entry Fees
€70–€100
Transport
€40–€90
Total Estimated
€900–€1,800
What This Itinerary Skips
One region, done well
This plan keeps you based in Florence rather than hopping hotels across Tuscany. It skips Pisa, Lucca and the Val d'Orcia, which are all rewarding but would spread five days thin. The trade-off is a deeper look at Siena, Chianti and San Gimignano without repacking your suitcase every night.
Customize This Itinerary
- Add 1 Day: Val d'Orcia or Pisa day trip
- Swap Day Trip: Lucca instead of San Gimignano
- Skip Wine Route: Second Florence museum afternoon
Seasonal Adjustments
- Summer: Book Uffizi and Accademia; skip midday heat.
- Spring / Fall: Golden light in Chianti; fewer tourists.