When is the best time to visit Tuscany?

April–June and September–October are ideal — warm, green, and without the July–August crowds. The harvest in September–October adds a living layer to the wine estate visits. Winter in Florence is cold but beautiful — far fewer tourists, and the museums are peaceful.

Can we add Rome or Venice to this itinerary?

Yes. The most natural extension adds 3 nights in Rome at the end — a high-speed train from Florence takes 1h30m. Venice can be added at the start or end, also by high-speed train. We'll build the extension seamlessly.

What happens after I request this trip?

You'll complete a short planning form with your dates, group size, and any preferences. A travel specialist will respond within one business day with a personalised proposal and exact pricing. No obligation — it's a conversation.

7-Day Small Group Journey

Essence of Tuscany

Florence, Siena, San Gimignano & Chianti

Available as Private Semi-Private Self-Guided

From €2,690 per person 7 days / 6 nights

View Itinerary

Tour Overview

7 days across Italy.

Tuscany is not a destination so much as a state of mind — the particular pleasure of a landscape where beauty has been cultivated for so long that the hills, the vine rows, the medieval towers, and the food all feel like expressions of the same ancient sensibility. This seven-day private journey moves through the region at the pace Tuscany itself suggests: unhurried, curious, and always moving toward the next view. Florence provides the Renaissance foundations; Pisa and Lucca offer the medieval northwest; San Gimignano and Siena anchor the south; and the Chianti countryside — rolling hills, warm stone farmhouses, a glass of something local — is the reward for making it this far.

Trip Quick Look

Duration: 7 Days / 6 Nights
Destinations: Florence, Siena, San Gimignano & Chianti
Group Size: 2–10 guests (private)
Dates: Year-round, flexible
Tour Type: Private Package
Accommodation: 4–5★ hotels and countryside villas
Meals: Daily breakfast
Transport: Private vehicles throughout

From €2,690 per person, based on double occupancy

Activity Level

Moderate

Florence involves 3–4 hours of walking on city streets and museum floors. Tuscany's hill towns (Siena, San Gimignano) require some steep climbs on medieval cobblestones. The Chianti day is largely by vehicle with gentle walks around the estate. Comfortable walking shoes are essential throughout.

Detailed Itinerary

Your journey, day by day.

Every day is designed with breathing room. Sleep in, take a detour, linger at lunch — the itinerary flexes around you, not the other way around.

Day 1

Arrival in Florence

The cradle of the Renaissance, still warm.

Your private driver meets you at Florence airport or Santa Maria Novella station and delivers you to your hotel in the historic centre — a location that puts the Duomo, the Arno, and the best gelato in the city within ten minutes of your door. The rest of the afternoon is yours to settle in: walk across the Ponte Vecchio and look down at the jade-green water of the Arno, find a table at a trattoria in the Oltrarno for ribollita and a carafe of house Chianti, or simply wander the illuminated streets as Florence transitions from a city of tourists by day to a city of locals by evening.

Private transfer to Florence
Ponte Vecchio and Arno River at leisure
First evening in the historic centre

4★ centrally located hotel, Florence historic centre

Day 2

Florence Renaissance Highlights

The Medici built this city — and never let you forget it.

Your private guide — an art historian who has been interpreting this city for foreign visitors for twenty years — meets you after breakfast for a morning that begins where the Renaissance effectively began: outside the Baptistery of San Giovanni, whose gilded doors Michelangelo called the Gates of Paradise. From there the route winds through Piazza della Signoria — the political heart of the Florentine republic, still presided over by a copy of David — and along the embankment to the Ponte Vecchio, the medieval bridge lined with goldsmiths whose shops have occupied these wooden cabinets since the sixteenth century. The Uffizi Gallery, if you choose to enter, contains the densest concentration of Renaissance masterpieces on earth: Botticelli's Birth of Venus, Leonardo's Annunciation, Raphael's portraits — paintings that reproduce so perfectly on postcards that seeing them in person is a surprise each time. The Accademia — home to the original David — is an alternative. The afternoon returns you to the streets for the Medici chapels, the San Lorenzo market, or a long coffee in Piazza della Repubblica as the city moves around you.

Baptistery Gates of Paradise and the Duomo complex
Piazza della Signoria and Palazzo Vecchio
Uffizi Gallery or Accademia with David
Ponte Vecchio and the Arno embankment

Meals: Breakfast 4★ centrally located hotel, Florence historic centre

Day 3

Chianti Wine Region

Rolling hills, warm stone, and the wine that defines a landscape.

Today belongs to the Chianti Classico region — the corridor of hills between Florence and Siena that produces the wine the world associates with Tuscany. Your private driver takes the old Via Chiantigiana through Greve in Chianti and Panzano, the landscape changing with every kilometre as vineyards replace wheat fields and farmhouses become grander and more stone-built. At a family-run estate, your host — often a fourth-generation winemaker — walks you through the vineyards and the cantina before settling around a table for a tasting that works through the estate's range: the younger Chianti Classico, the Riserva aged in oak, and perhaps a single-vineyard selection that captures a particular slope in a particularly good year. The afternoon is yours to enjoy the estate grounds, take a swim if there's a pool, or simply sit among the vines with a glass of something you've just learned to appreciate on a deeper level.

Greve in Chianti and the Via Chiantigiana
Private estate wine tasting — Chianti Classico and Riserva
Cantina tour with the winemaker
Tuscan countryside at its most quintessential

Meals: Breakfast 4–5★ boutique hotel or countryside villa, Chianti

Day 4

San Gimignano & Siena

Medieval towers and the most beautiful piazza in Italy.

The road south from Florence enters the heartland of the Sienese republic — a landscape of cypress-lined roads, honey-coloured hill towns, and vineyard slopes that look exactly like they do in Renaissance painting, because they are: the same hills, the same light, the same towers on the horizon. San Gimignano arrives first: fourteen medieval towers still standing above a hill town whose walls are intact, whose streets are barely wide enough for two people, and whose vernaccia wine is one of Tuscany's oldest and best. Your guide explains the tower-building arms race that made medieval San Gimignano look like Manhattan in miniature: families competed in height as a display of wealth and power. After lunch, the road continues to Siena — the great rival of Florence, and by almost every architectural measure its equal. Piazza del Campo, the fan-shaped central square where the Palio horse race takes place twice a year, is one of the most beautiful civic spaces in Europe. Your guide leads you into the Duomo — where the marble floor is inlaid with narrative scenes — and through the medieval contrade neighbourhoods before the return to Florence.

San Gimignano — medieval towers and hilltop views
Vernaccia wine tasting in San Gimignano
Siena's Piazza del Campo
Siena Cathedral's marble floor and interiors

Meals: Breakfast 4★ centrally located hotel, Florence historic centre

Day 5

Val d'Orcia

The landscape that gave Tuscany its postcard — and it's even better in person.

Your private driver takes you south into the Val d'Orcia — the UNESCO-protected landscape that defines the Tuscan imagination: cypress-lined roads, golden wheat fields, solitary farmhouses on hilltops, and a quality of light that painters have been trying to capture since the Renaissance. The morning begins in Pienza, the tiny town Pope Pius II commissioned as an 'ideal city' in the fifteenth century and whose central piazza is a masterclass in Renaissance proportion. Montalcino follows — the hilltop fortress town that produces Brunello di Montalcino, one of Italy's greatest wines. Between the towns, the road winds through a landscape that looks staged but isn't: every curve reveals another composition of hill, cypress, and stone that seems designed for a photograph. The afternoon returns you to your hotel with time to spare for a final Tuscan stroll, a gelato in the piazza, or simply the pleasure of watching the evening light do its work on the terracotta rooftops.

Val d'Orcia — UNESCO World Heritage landscape
Pienza — Pope Pius II's ideal Renaissance town
Montalcino and Brunello wine country
Iconic Tuscan cypress-lined roads

Meals: Breakfast 4–5★ boutique hotel or countryside villa

Day 6

Florence — Free Day

The city gives back what the itinerary hasn't had time for.

Florence has been your base for six days, and today it asks nothing of you — no guides, no museums, no schedules. Use the day however Tuscany has taught you to: sleep until the church bells make it impossible, walk to the Boboli Gardens above the Palazzo Pitti for a morning in the most cinematic garden in Italy, cross the river to Oltrarno and spend an hour watching a bookbinder or a frame-maker work in one of the artisan workshops that are increasingly rare even here. Or take the short train to Fiesole, the hilltop Etruscan town above Florence, and look down at the city from the altitude the Medici summer retreats gave them. For your final Tuscan evening, your Hamilton & Chase booklet has recommendations for neighbourhood restaurants where the tagliatelle al ragù and bistecca alla fiorentina are still made the way they've always been.

Free day in Florence — no schedule
Optional: Boboli Gardens and Palazzo Pitti
Optional: Fiesole hilltop views
Oltrarno artisan workshops

Meals: Breakfast 4★ centrally located hotel, Florence historic centre

Day 7

Departure

Tuscany travels home with you — in the wine, the light, the stone.

Your last Tuscan morning: a coffee in Piazza della Repubblica, a final walk past the Duomo's white-and-green marble, perhaps a stop at the Mercato Centrale for a sandwich to carry on the road. At the agreed time, your private driver delivers you to Florence airport or Santa Maria Novella station. Your travel specialist is reachable until you're home — and a few days later will be in touch to hear which corner of Tuscany has already claimed a place in your regular conversation.

Final morning in Florence at leisure
Private transfer to airport or station

Meals: Breakfast

Where You'll Stay

Hand-picked hotels, every night.

We choose properties for character, location, and the kind of service that makes you feel looked after — not just checked in. Every hotel can be swapped for an alternative if you prefer.

Florence

6 nights

4★ centrally located hotel or countryside villa

Historic centre or Chianti hillside

Florence as a base allows daily excursions across Tuscany; villa alternatives in the Chianti hills are available for guests who prefer a rural base with a car

Hotels shown are indicative of the standard we book. Upon request, we will provide a detailed itinerary with specific hotel options tailored to your preferences and budget.

What's in the Price

Included

6 nights in 4–5★ boutique hotels or countryside villas (double occupancy)
Daily breakfast at each property
Airport meet & greet on arrival
Private airport or station transfer
Private driver for all Tuscany excursions
Private expert guides in Florence, San Gimignano, and Siena
Private Chianti estate wine tasting and cantina tour
Val d'Orcia guided excursion
Skip-the-line access at major Florence sites
All entrance fees included in guided visits
24/7 local support throughout your trip
Hamilton & Chase digital travel booklet with restaurant and local recommendations

Not Included

International flights to/from Florence
Travel insurance (required — we can arrange coverage on request)
Lunches and dinners
Personal expenses (shopping, additional tastings, spa treatments)
Gratuities for guides and drivers (optional but appreciated)
City tax (collected directly by hotels, typically €3–5 per person per night)

Good to Know

This itinerary is a starting point — days can be reordered, towns swapped, and the pace adjusted to suit your group.
Florence is an excellent base for Tuscany; alternatively, we can split accommodation between Florence and a Chianti villa for a more rural experience.
All guides and experiences are arranged exclusively for your group — never shared with other travellers.
Siena and San Gimignano on the same day is full but rewarding — guests who want more time in Siena can split this across two days with an overnight.
Flexible booking: adjust or postpone your dates up to 60 days before departure at no charge.

Make It Yours

Optional add-ons & upgrades.

Every trip is different. These extras can be woven into your itinerary — just let your travel specialist know what catches your eye.

Private Uffizi or Accademia early access

Skip-the-queue access to the Uffizi or Accademia before general opening — the rooms are yours alone for the first hour

From €95 pp

Florentine cooking class

A morning at a family cooking school: market visit, pasta making, braised meats, and a proper sit-down lunch with the wine that goes with each dish

From €130 pp

Truffle hunting in Mugello

A morning in the woods north of Florence with a truffle hunter and his dog — followed by a lunch where truffles appear in every course

From €175 pp

Private Chianti vineyard lunch

A longer tasting experience at a premium Chianti estate — four courses paired with the estate's full range by the winemaker

From €145 pp

Volterra and Montepulciano extension

The southern Tuscan towns that the standard itinerary doesn't reach: Etruscan Volterra and the Vino Nobile vineyards of Montepulciano

From €165 pp

Professional photo session

A portrait session at the Duomo, Piazza della Signoria, or a Chianti vineyard with a local photographer

From €350

"The Chianti day was the best of the whole trip — the winemaker was extraordinary, the estate was beautiful, and the lunch lasted three hours. Siena on the same trip as San Gimignano is a lot but Hamilton & Chase paced it perfectly. We came home with twelve bottles of wine."

Anne & Robert K.

Toronto, Canada · Essence of Tuscany, September 2025

Common Questions

Questions about this trip.

Can we base ourselves in the Chianti countryside instead of Florence?

Yes — and many guests prefer it. A Chianti agriturismo or villa gives you sunsets over the vines, olive oil pressed on the property, and a very different rhythm from city hotels. Florence is 30–45 minutes by car. We'll find the right property for your group and build the itinerary around it.

Is the Chianti wine tasting included in the base price?

Yes — a private estate tasting and cantina tour is included. For a more elaborate tasting lunch with multiple courses, we can upgrade to the Chianti vineyard lunch add-on at an additional cost.

Small Group Journey

Essence of Tuscany

7 days / 6 nights

From €2,690

per person

Ready to go?

Share a few details and a specialist will reply within one business day.

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