Florence · Chianti · Siena · Val d’Orcia · Montalcino
Your Tuscan journey begins in Florence, the birthplace of the Renaissance and the gateway to Italy's most celebrated wine and food region. A private driver meets you at the airport and delivers you to your hotel in the Oltrarno — the artisan quarter south of the Arno, where workshops still line the streets and the restaurants serve the neighbourhood rather than the tourist trail.
The rest of the day is yours. Walk across the Ponte Vecchio at sunset, find a trattoria for your first bistecca alla fiorentina, and settle into the Florentine rhythm. Tomorrow the cooking begins.
Morning at the Mercato Centrale di San Lorenzo — Florence's historic covered market, where butchers, cheese makers, and produce vendors have traded since 1874. Your guide introduces you to the best stalls: fresh porcini, hand-rolled pici, aged pecorino, and the lampredotto sandwich that Florentines queue for.
Afternoon, a private guided tour of the Uffizi Gallery — Botticelli, Leonardo, Raphael — the greatest collection of Renaissance painting in the world, experienced without queues. Late afternoon, a hands-on pasta-making class in a centuries-old kitchen: fresh tagliatelle, ravioli with ricotta and sage, tiramisu. Dinner is what you've made, paired with a Chianti Classico chosen by your instructor.
Leave Florence behind as your driver takes you south into the Chianti hills. Within thirty minutes the landscape transforms: cypress-lined roads, olive groves on every slope, vineyards stretching to the horizon. Your accommodation is a private estate in the heart of Chianti Classico — stone buildings, a pool overlooking the valley, and a cellar that's been producing wine since the 15th century.
Afternoon, a private olive oil tasting at the estate — learn to distinguish early-harvest from late, peppery from buttery, Tuscan from Umbrian. This evening, a chef-prepared dinner on the terrace: local produce, estate wines, the kind of meal that only happens when the kitchen and the vineyard are in the same postcode.
Your guide drives you to Siena, one of Italy's best-preserved medieval cities. Climb the Torre del Mangia for sweeping views of the Val d'Orcia, then walk the sloping Piazza del Campo where the Palio thunders each summer. Lunch in a 16th-century courtyard — fresh pici with wild boar ragù, the pasta Siena is famous for.
Continue to San Gimignano, the 'Manhattan of Tuscany,' where fourteen stone towers pierce the sky. Sample the town's award-winning gelato, visit a saffron farm. Late afternoon, a private wine tasting at a small-production Chianti estate — three generations of winemaking explained by the owner, with cheese and cured meats laid out beside the barrels.
Rise early for a truffle hunt in the Val d'Orcia with a local forager and his trained dog. Walk through oak forests, learning to read the subtle signs of buried treasure. When the dog stops, you dig — sometimes nothing, sometimes black gold worth more than its weight. The silence of the forest, the anticipation, the earthy perfume when the truffle breaks the surface — it's a meditation on patience and the generosity of the land.
Return to the estate where a chef transforms your truffles into a multi-course feast: truffle butter on fresh bread, truffle-shaved pasta, truffle-infused pecorino. Afternoon free for rest, photography, or a walk through the surrounding vineyards. This is Tuscany as you've imagined it — unhurried, generous, impossibly beautiful.
A day exploring the Val d'Orcia — the landscape that appears on every Tuscany postcard. Your driver takes you through rolling hills dotted with lone cypress trees, past the thermal baths of Bagno Vignoni, and into the hilltop town of Pienza, famous for its pecorino cheese and Renaissance town square.
Continue to Montalcino, home of Brunello — one of Italy's most celebrated wines. A private tasting at a Brunello estate reveals why these wines command such reverence: the terroir, the ageing process, the difference between a young Rosso and a five-year Brunello Riserva. Lunch at the estate, overlooking vineyards that have produced wine for centuries. Return to your accommodation as the golden light of late afternoon settles over the valley.
A final Tuscan breakfast at the estate — fresh bread, local honey, estate olive oil, espresso in the garden. Your private driver returns you to Florence for your departure flight, or onward to Rome, the Amalfi Coast, or the Cinque Terre if you've extended your journey.
You depart carrying the rhythms of Tuscany: the taste of hand-rolled pasta still on your tongue, the scent of truffle and rosemary in your memory, the golden light of the Val d'Orcia still warm behind your eyes. The Taste of Tuscany is a beginning — the flavours will call you back.
This is a sample luxury custom route — a starting point, not a fixed package. Many clients travel something very close to this. Book a free consultation and a specialist will build from here.
Your specialist pre-arranges the right luxury experiences based on your interests and travel style. These are the custom experience types available on this route — specific choices are made with you, not for you.
Activities are selected and pre-booked with your specialist based on your interests — not all activities are included in every trip version. Availability varies by season.
You work directly with a specialist who knows Italy deeply — not a call center or booking agent. Every consultation is with someone who has been there, stayed in those hotels, and knows the country inside out.

Florence and Austria-based, Lexi brings on-the-ground expertise across Southern Europe’s most sought-after destinations. Every recommendation comes from personal experience — the estates in Chianti, the truffle foragers in the Val d’Orcia, the winemakers who open their cellars to Juniper clients.
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25 years designing European trips, with a deep network across Italy’s regions. CMSC certified and former Peace Corps. Ideal for multi-country trips combining Italy with Ireland, Scotland, or beyond.
Book a Consultation“Juniper Tours did an amazing job booking our vacation to Italy. Lexi Blade helped us schedule our dream vacation from Venice all the way to Sorrento on the Amalfi coast, with stops in Florence and Rome. Lexi was phenomenal and made changes for us many times to assure we got the most out of our trip.”
Nikki Walls · Taste of Tuscany · Verified Google Review
30 minutes, completely free. Walk away with a clear picture of what your luxury custom Tuscany trip could look like — dates, route, 4 and 5-star accommodations, and all.