Tuscany

Florence to

the vineyards

DAY ONE

ARRIVE IN FLORENCE

Arrival into Florence and check-in at the hotel. The afternoon opens with a private walking tour, led by a local host through the sun-drenched streets of Italy's Renaissance capital — the Duomo and Ponte Vecchio, but also the artisan quarter of Oltrarno and the vaulted medieval passage of Via dei Girolami, away from the crowds. Kaheen's own guide to Florence holds a further set of eating and drinking recommendations for the evening, left otherwise at leisure.
Overnight — Florence

DAY TWO

UFFIZI, ACCADEMIA AND THE TABLE

The morning begins at the Accademia Gallery, standing before Michelangelo's David, before continuing to the Uffizi's collection of Renaissance masterworks. The afternoon turns toward Florence's food and wine culture — a curated tasting through the city's Tuscan specialties and its iconic Negroni, moving between sit-down venues, a centuries-old wine cellar, and the story behind the city's wine windows. The evening is left open.
Overnight — Florence

DAY THREE

ANTINORI NEL CHIANTI CLASSICO

A visit to Antinori nel Chianti Classico, a house established in 1385 and among Italy's most historic wine producers — the label that redefined Chianti Classico from a table wine into a prestige one. Marco Casamonti's architecture for the estate matches the grandeur of what it holds, and lunch can be taken in its restaurant before the return to Florence in the evening.
Overnight — Florence

DAY FOUR

INTO CHIANTI

The road turns toward Chianti, unhurried, with room to stop along the way — Greve in Chianti, its central square lined with enotecas and artisan shops; Radda in Chianti, a hilltop village of cobbled streets and vineyard views; Gaiole in Chianti, its castles and quieter, more rustic character. A private winery visit can be woven into the route — a guided tour through historic aging cellars and a tasting of niche labels, or a fuller stop at a family-run estate for a Tuscan lunch built from homemade recipes and produce grown on-site. The day ends at your gorgeous Tuscan property.
Overnight — Tuscany

DAY FIVE

THE TRUFFLE HUNT

The morning begins with an expert truffle hunter and his trained dogs, leading a hunt through a private reserve — a rare window into one of Tuscany's oldest traditions. The estate's boutique winery follows, with a tasting of its finest labels, before a four-course truffle-inspired lunch paired with the estate's own wines. A private driver leads the return to the villa in the afternoon.
Overnight — Tuscany

DAY SIX

MONTEPULCIANO AND MONTALCINO

The day opens in Montepulciano, a short drive from your stay, with a private walking tour through one of Tuscany's best-preserved medieval towns — its ancient streets and the sweep of the Valdichiana countryside beyond. The road continues toward Montalcino, pausing at a boutique winery for a Tuscan lunch paired with Brunello di Montalcino, then a second estate for a private tour of the winemaking process and a tasting of its top labels. The evening returns to your Tuscan property.
Overnight — Tuscany

DAY SEVEN

TOWARD MILAN

The road turns north toward Milan, pausing along the way in Parma for a taste of the region — its cured hams and cheeses, built on patience as much as craft. A beautiful table booked at a restaurant of your choice or one from Kaheen’s recommendations.
Overnight — Milan

DAY EIGHT

HOMEWARD

A final morning in Milan before the flight home — the journey closing on the days behind it: Renaissance streets, cellars three centuries deep, a private truffle hunt, and roads that moved at exactly the pace they were meant to.

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