Tuscany, Italy · Route map
Tuscan Flavors and Renaissance Gems
This relaxed loop blends the high culture of Florence with the slow-paced food traditions of the Tuscan countryside. Seven days is a tight squeeze for Italy, so we have focused entirely on Tuscany to give you the relaxed, local experience you crave.
- 1
Florence
3 nights
Renaissance icons and vibrant neighborhood food markets
- 2
Siena
1 night
Medieval lanes and intimate local osterias
- 3
Val d'Orcia
2 nights
Classic Tuscan landscapes and Brunello wine estates
- ✦3 stops · 6 nights
A sample from our journal — written by Waypora, kept as inspiration
Use this as a starting pointThe day-by-day
Arrival in Florence
Arrive into Florence Peretola Airport
Flight · Morning · Florence Airport
Take local tram to the city center
Transfer · Morning · Florence
The clean, modern T2 line takes you straight to Santa Maria Novella station in twenty minutes.
Afternoon at leisure around Oltrarno
At leisure · Afternoon · Oltrarno
Cross the Arno river to find the workshops, families, and wine bars where Florentines actually live.
Overnight in Florence
Accommodation · Evening · Oltrarno
Renaissance Icons and Local Flavors
Fast-track entry to the Uffizi Gallery
Excursion · Morning · Centro Storico
Pre-booked morning tickets let you beat the longest queues.
Head straight to the top floor Botticelli rooms before the general crowd spreads out.
Street food crawl in Sant'Ambrogio Market
Excursion · Afternoon · Sant'Ambrogio
Skip the tourist-heavy Central Market and try Da Rocco inside this neighborhood market for genuine trippa.
Overnight in Florence
Accommodation · Evening · Oltrarno
Panoramic Views and Quiet Corners
Climb up to San Miniato al Monte
Excursion · Morning · San Miniato
It is much higher and far less crowded than nearby Piazzale Michelangelo, offering better views.
Leisurely stroll through Boboli Gardens
At leisure · Afternoon · Oltrarno
Overnight in Florence
Accommodation · Evening · Oltrarno
Southward to Medieval Siena
Regional train from Florence to Siena
Transfer · Morning · Tuscany
The scenic rail journey takes roughly one hour and thirty minutes.
Explore Piazza del Campo and Duomo
Excursion · Afternoon · Siena
Buy the Opa Si Pass to see the Cathedral's unbelievable inlaid marble floors.
Overnight in Siena
Accommodation · Evening · Siena Centro
Into the Val d'Orcia
Pick up rental car in Siena
Car hire · Morning · Siena
Collect your hire car from the city center depot to begin driving south.
Self-drive Siena to Pienza
Self-drive · Morning · Val d'Orcia
Drive takes just over one hour through classic Tuscan hill country.
Pecorino cheese tasting in Pienza
Excursion · Afternoon · Pienza
Stop at Caseificio Cugusi just outside town to pick up cheeses and olives for a picnic.
Overnight in Val d'Orcia agriturismo
Accommodation · Evening · Pienza countryside
Thermal Springs and Brunello Wine
Soak in Bagno Vignoni hot springs
Excursion · Morning · Bagno Vignoni
While the ancient central pool is off-limits, head to Parco dei Mulini below for free bathing.
Brunello tasting in Montalcino
Excursion · Afternoon · Montalcino
Book ahead at small, family-run organic wineries like Sesti for a truly personal tasting.
Overnight in Val d'Orcia agriturismo
Accommodation · Evening · Pienza countryside
Return to Florence for Departure
Self-drive Val d'Orcia to Florence
Self-drive · Morning · Tuscany
The scenic northward run back to Florence takes about two hours.
Drop off rental car at airport
Car hire · Afternoon · Florence Airport
Return your vehicle directly to Florence Peretola Airport.
Departure flight from Florence Airport
Flight · Afternoon · Florence Airport
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