When is the best time to visit Tuscany?

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

Can we add Rome or Venice?

Yes. The most natural extension adds 3 nights in Rome at the end or Venice at the start — both connected by 90-minute 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.

8-Day Private Package Journey

Florence & Tuscany

Florence, Pisa, Lucca, Chianti, Siena & San Gimignano

Available as Private Semi-Private Self-Guided

From €2,960 per person 8 days / 7 nights

View Itinerary

Tour Overview

8 days across Italy.

Eight days based in Florence with the whole of Tuscany at your feet. This private journey uses the Renaissance capital as your home base while the private driver takes you into the countryside that inspired it: Pisa's improbable tower and Lucca's walled medieval city, the Chianti wine estates where fourth-generation winemakers pour their family's life work, the medieval towers of San Gimignano and the extraordinary Piazza del Campo in Siena. Two unhurried days in Florence itself give the Uffizi, the Duomo, and Michelangelo's David the time they deserve. Every guide is a specialist, every transfer is private, and breakfast is included daily.

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 transfers 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, browse the leather workshops of the Oltrarno, or simply find a table in Piazza Santo Spirito as the neighbourhood comes alive in the evening. We'll share our curated list of favourite restaurants nearby — the trattorias where ribollita and bistecca alla fiorentina are still made the way they've always been.

Private transfer to Florence
Ponte Vecchio and Arno River at leisure
Curated restaurant recommendations for your first evening

4–5★ centrally located hotel, Florence

Day 2

Florence Renaissance Highlights

The Medici built this city — and every detail shows it.

Your private guide — an art historian who has been interpreting this city for two decades — meets you after breakfast. The morning begins where the Renaissance effectively began: outside the Baptistery of San Giovanni, whose gilded doors Michelangelo called the Gates of Paradise. From there through Piazza della Signoria — the political heart of the republic, still presided over by a copy of David — along the embankment to the Ponte Vecchio, lined with goldsmiths whose shops have occupied these wooden cabinets since the sixteenth century. The Uffizi Gallery follows: Botticelli's Birth of Venus, Leonardo's Annunciation, Caravaggio's Medusa — the densest concentration of Renaissance masterpieces on earth. Or the Accademia for Michelangelo's David and the unfinished Prisoners. The afternoon is free: the Medici Chapels, the San Lorenzo market, or a long coffee in Piazza della Repubblica.

Baptistery Gates of Paradise and Duomo complex
Piazza della Signoria and Palazzo Vecchio
Uffizi Gallery or Accademia with David
Free afternoon in Florence

Meals: Breakfast 4–5★ centrally located hotel, Florence

Day 3

Pisa & Lucca

The tower that shouldn't stand, and the walls that always have.

Your private driver heads west through the Arno valley to Pisa. The Piazza dei Miracoli — the Cathedral, the Baptistery, and the Tower together on a lawn of impossible green — is more extraordinary in person than any photograph: the Tower does lean, more than seems structurally plausible, and the Cathedral's Romanesque facade is one of the finest in Italy. Your guide puts it all in context, including the physics of how the lean came to be and why it has been stabilised. After Pisa, the road curves north to Lucca — a city of warm red brick enclosed by Renaissance walls so broad the locals walk and cycle along the top. Inside, Lucca is a medieval city whose Roman grid is still legible, its churches and tower-houses remarkably intact. The afternoon returns you to Florence with the evening free to explore the city's restaurant scene.

Pisa's Piazza dei Miracoli and the Leaning Tower
Pisa Cathedral — Romanesque masterpiece
Lucca's Renaissance city walls
Lucca medieval centre and tower-houses

Meals: Breakfast 4–5★ centrally located hotel, Florence

Day 4

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. 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 or return to Florence at your leisure.

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★ centrally located hotel, Florence

Day 5

Siena & San Gimignano

Medieval towers and the most beautiful piazza in Italy.

The road south enters the heartland of the old Sienese republic — cypress-lined roads, honey-coloured hill towns, and vineyard slopes that look exactly like Renaissance painting backgrounds, because they are. San Gimignano arrives first: fourteen medieval towers still standing above a hill town whose walls are intact 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. After exploring the town, continue to Siena — the great rival of Florence and by almost every architectural measure its equal. Piazza del Campo, the fan-shaped square where the Palio horse race runs twice a year, is one of the most beautiful civic spaces in Europe. The Duomo's marble-inlaid floor — fifty-six panels of narrative scenes — is a world in itself. Return to Florence in the evening.

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 4–5★ centrally located hotel, Florence

Day 6

Florence — Free Day

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

Florence has been your base all week, and today it asks nothing of you — no guides, 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 the Oltrarno and spend an hour watching a bookbinder or frame-maker work in one of the artisan workshops that are increasingly rare even here. The Brancacci Chapel contains Masaccio's frescoes that Michelangelo came to study as a student. Or take the short bus to Fiesole — the hilltop Etruscan town above Florence — and look down at the city from the altitude the Medici used for their summer retreats. The evening is yours to explore our restaurant recommendations.

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

Meals: Breakfast 4–5★ centrally located hotel, Florence

Day 7

Optional Excursion or Florence Leisure

A final day shaped entirely by your curiosity.

Your last full day offers several paths. A drive to Volterra and Montepulciano takes you to the southern Tuscan towns the standard itinerary doesn't reach: Etruscan Volterra on its dramatic hilltop and the Vino Nobile vineyards of Montepulciano. Alternatively, a cooking class at a farmhouse in the Chianti hills — fresh pasta by hand, a table under the olive trees, and wine from the estate. Or stay in Florence: the Bargello museum's Donatello and Verrocchio collections, Santa Croce where Michelangelo is buried, or the climb to the top of the Duomo dome for the panoramic view that makes the whole week make sense. For your final Tuscan evening, your Hamilton & Chase booklet has a recommendation that won't disappoint.

Optional: Volterra and Montepulciano day trip
Optional: Tuscan cooking class
Optional: Duomo dome climb for panoramic views
Final evening in Florence

Meals: Breakfast 4–5★ centrally located hotel, Florence

Day 8

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 something to carry on the journey. 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

7 nights

4–5★ centrally located hotel or countryside villa

Historic centre or Chianti hillside

Florence as a base allows daily excursions across all of Tuscany; villa alternatives in the Chianti hills are available for those who prefer a rural setting

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

7 nights in 4–5★ hotel or countryside villa (double occupancy)
Daily breakfast at the property
Airport meet & greet on arrival
Private airport or station transfer
Private driver for all Tuscany excursions
Private expert guides in Florence, Pisa, Lucca, San Gimignano, and Siena
Private Chianti estate wine tasting and cantina tour
Skip-the-line access at major Florence sites
All entrance fees included in guided visits
All scheduled tours and transport as per itinerary
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 all of Tuscany; alternatively, we can split accommodation between Florence and a Chianti villa.
All guides and experiences are arranged exclusively for your group — never shared with other travellers.
Comfortable walking shoes are essential — cobblestones and medieval paving are the norm in every town.
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 before general opening — the Botticelli rooms or the David are yours alone for the first hour

From €95 pp

Tuscan cooking class

A morning at a family cooking school: market visit, pasta making, and a proper sit-down meal with paired wines

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 meal where truffles appear in every course

From €175 pp

Volterra and Montepulciano day trip

The southern Tuscan towns: Etruscan Volterra's dramatic hilltop and the Vino Nobile vineyards of Montepulciano

From €165 pp

Professional photo session

Portrait session at the Duomo, Ponte Vecchio, or a Chianti vineyard with a local photographer

From €350

"Eight days in Tuscany was exactly right. The Chianti winemaker was extraordinary, Siena took our breath away, and having a free day to just wander Florence made all the difference. We came home with twelve bottles of wine and plans to return."

Anne & Robert K.

Toronto, Canada · Florence & 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. Florence is 30–45 minutes by car. We'll find the right property and adjust the itinerary.

How does this differ from the Essence of Tuscany 7-day tour?

This 8-day version adds a full day for Pisa and Lucca, plus an extra leisure day that can be used for a cooking class, Volterra, or simply more Florence time. It's the more complete Tuscany experience.

Private Package Journey

Florence & Tuscany

8 days / 7 nights

From €2,960

per person

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