Tuscany tour: Florence and countryside

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Claim your place on this Tuscany tour and transform your travel into a tailor-made Italian story. Savor private tastings, unlock hidden ateliers with local hosts, and let our expert planners craft every moment to reflect your tastes.

Act now to design a personalized Italy trip, secure exclusive access, and turn genuine Florentine charm and Tuscan countryside rhythms into lasting memories. Contact us to start your bespoke experience and travel the Italy you have always imagined.

Tuscany tour highlights

  • Florence Renaissance immersion: Explore Florence's masterpieces with a private guide, skip-the-line access, and tailor-made art tours.
  • Tuscan countryside drive: Drive through rolling vineyards in a customized itinerary, stopping at family-run estates.
  • Hands-on cooking experience: Join a local chef for a private class, crafting regional dishes from market to table.
  • Medieval hilltop villages: Wander secluded lanes and meet artisans in hand-picked villages.
  • Private wine and olive oil tastings: Savor rare vintages and estate-pressed oils in intimate settings.
DayMorningAfternoonEvening
Day 1Arrival in FlorenceGuided walk of Florence's iconic landmarksAuthentic aperitivo: local wine in a cozy bar
Day 2 Free day in Florence 
Day 3Group tour through the Chianti countrysideWinery visits and wine, olive oil, and balsamic tastings 
Day 4Siena, Cortona, and Montepulciano day tour Relaxed evening at your Chianti accommodation
Day 5 Afternoon hands-on Tuscan cooking class with tasting and wineReturn to Florence

Places you'll visit

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San Gimignano
San GimignanoTuscany
Day01

Day 1: Arrival in Florence

Arrive in Florence and settle into your accommodation. Join a guided walk to discover the Duomo, Ponte Vecchio, and Piazza della Signoria while uncovering hidden artisan workshops and the stories behind Renaissance masterpieces.

Toast the start of your Italy travel with an authentic aperitivo in a cozy bar, sipping local wine and sampling nibbles.

Florence
Day02

Day 2: Free day in Florence

Exploring Florence at your own pace. Marvel at masterpieces in the Uffizi Gallery and the Accademia Gallery, home to Michelangelo’s David. Climb Giotto’s Bell Tower or head to Piazzale Michelangelo for sweeping city views.

Wander the Ponte Vecchio, shop in artisan workshops, and dine in local trattorias for authentic flavors. Tailor-made optional tours and activities are available to create a personalized experience, from guided museum visits to countryside wine tastings.

Florence
Day03

Day 3: Group tour through the Chianti countryside

Join a small shared group tour through the Chianti countryside from 10:30 AM to 3:00 PM. Visit two acclaimed wineries, meet passionate winemakers, and taste Chianti Classico.

Enjoy tastings of truffle-infused olive oil and aged balsamic vinegar, plus insider stories that turn this Italy itinerary into an authentic, tailor-made experience.

Wine Tasting in Tuscany
Day04

Day 4: Siena, Cortona and Montepulciano tour

Today you’ll explore some of Tuscany’s most iconic hill towns. Start in Siena, where you’ll wander through the fan-shaped Piazza del Campo and take in the Gothic grandeur of the cathedral.

Then head to Cortona, with its narrow lanes and sweeping views that stole the show in Under the Tuscan Sun. In Montepulciano, sip Vino Nobile as you explore medieval streets and tucked-away piazzas. Finish your day back in your Chianti base, with a glass of wine in hand, of course.

Val D'Orcia
Day05

Day 5: Tuscan cooking class and return to Florence

Take a hands-on Tuscan cooking class led by a local chef, crafted for travelers seeking authentic, tailor-made experiences. Learn classic recipes using fresh regional ingredients, pick up local techniques and food stories, then savor your creations with a glass of Tuscan wine.

Return to Florence by 5:00 PM, carrying memories of Tuscany’s rich flavors, rolling landscapes, and warm culture.

Cooking Class