Sample Itinerary · Italy

Taste of
Tuscany

Florence · Chianti · Siena · Val d’Orcia

Duration
7 Days · 6 Nights
Accommodations
4-Star or Higher
Transport
Private Transfers
Best For
Foodies · Wine Lovers · Cooking Enthusiasts

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This is a sample itinerary — for inspiration only. Every Juniper trip is designed from scratch around you. Many clients travel a very similar route — if this resonates, book a free consultation and an Italy specialist will build something just like it (or better) specifically for your travel style, dates, and group.

1
Day One

Arrive in Florence

Florence

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 neighborhood 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.

Private airport transfer
Oltrarno neighborhood
Arrive Florence

Overnight: Florence

2
Day Two

Florence — Food, Art & Market

Florence

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.

Mercato Centrale tour
Uffizi Gallery (skip-the-line)
Cooking class

Overnight: Florence

3
Day Three

Florence to Chianti Estate

Chianti Classico Region

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.

Private transfer to Chianti
Estate check-in
Olive oil tasting

Overnight: Tuscan Estate

4
Day Four

Siena & San Gimignano

Siena & San Gimignano

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.

Siena guided tour
San Gimignano
Private wine tasting

Overnight: Tuscan Estate

5
Day Five

Truffle Hunt & Farm-to-Table Feast

Val d’Orcia

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.

Truffle hunting experience
Chef-prepared truffle lunch
Estate afternoon

Overnight: Tuscan Estate

6
Day Six

Val d’Orcia & Montalcino

Val d’Orcia & Montalcino

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.

Val d’Orcia scenic drive
Pienza cheese tasting
Brunello wine estate

Overnight: Tuscan Estate

7
Day Seven

Departure

Florence Airport

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 flavors will call you back.

Private transfer to Florence
App support throughout

Overnight: Depart from Florence

Love this itinerary? Make it yours.

This is a sample luxury custom route — a starting point, not a fixed package. Many clients travel something very close to this, customized for their travel style, group, and dates. Book a free consultation and a specialist will build from here.

Accommodations
Historic estates, boutique agriturismos, or Chianti villas — chosen based on your preferences and travel style.
Transportation
Private driver through the hills, self-drive option, or a mix — all confirmed before you travel.
Experiences
Pre-arranged tours and activities built around your interests — entrance tickets sorted, no queuing.

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Activities on this itinerary

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.

Truffle HuntVal d’Orcia

Mercato Centrale TourFlorence

Uffizi GalleryFlorence

Truffle HuntVal d’Orcia

Olive Oil TastingChianti Estate

Chianti Wine TastingChianti Classico

Brunello Estate VisitMontalcino

Siena Guided TourSiena

San Gimignano VisitSan Gimignano

Pienza Cheese TastingPienza

Vineyard DinnerChianti Estate

Saffron Farm VisitSan Gimignano

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.

The people who will design your Italy trip

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.

Italy · Switzerland · Portugal · Spain

Lexi Blade

Florence and Austria-based, Lexi brings on-the-ground expertise across Southern Europe’s most sought-after destinations. Every recommendation comes from personal experience.

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Ireland · Scotland · UK · Iceland

Taryn Harrison

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.

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About this itinerary

Is this good for food and wine lovers?


Yes — the Taste of Tuscany is Juniper Tours’ dedicated food and wine itinerary to the country. The route covers Italy’s most iconic regions in a logical sequence: Venice’s canals, Florence’s Renaissance art, Tuscany’s rolling countryside, Rome’s ancient monuments, and the Amalfi Coast’s dramatic cliffs. It’s Juniper’s most popular Italy itinerary precisely because it works well for first-time visitors without feeling rushed.

Can I customise this itinerary?


Yes — this is a sample for inspiration. Every Juniper trip is designed from scratch. You can add regions (Umbria, the Cinque Terre, Rome), swap experiences, extend vineyard stays, or focus entirely on wine, olive oil, or cooking. Your specialist builds the actual itinerary around your tastes during the free consultation.

Is 7 days enough for Tuscany?


7 days is the right length for this focused food and wine route — it covers Florence and the Tuscan countryside in depth without feeling rushed. Clients who want more time often add Rome or the Amalfi Coast. Your specialist builds the timing around you.

Is this itinerary good for a honeymoon?


This route works well as a honeymoon base — the intimate canals of Venice, Tuscan estate stays, and the romantic Amalfi Coast are all genuinely well-suited to couples. That said, our dedicated Amalfi Coast with Capri itinerary (7 days) is specifically designed for honeymoons and couples and covers the most romantic coastal regions and properties in more detail.

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“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  ·  Verified Google Review

Build your luxury custom Tuscany trip with one of our top travel specialists.

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.

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