Hamilton & Chase Tours
Private tours in Tuscany, Italy — Florence, Siena, San Gimignano
All Italy Tours

Tuscany Tours

Renaissance cities, cypress-lined hills, and Chianti wine roads.

11 Tours Best April – October
Florence Siena San Gimignano Chianti Val d'Orcia Pisa & Lucca

Tailor-Made Travel

Private & custom Tuscany tours, designed around you.

Tuscany is the Italy of the imagination — Renaissance Florence, the medieval towers of San Gimignano, the vineyards of Chianti, and the golden hills of the Val d'Orcia. It rewards slow travel: long lunches at a family estate, cellar visits, and hill towns reached by winding country roads.

Every Hamilton & Chase Tuscany tour is private and fully custom. Whether you want a luxury Tuscany vacation of villa stays and Brunello tastings, a family trip through Florence, Siena, and Pisa, or a food-and-wine route through Chianti and the Val d'Orcia, we build the itinerary around your pace — with handpicked hotels, private guides, and drivers throughout. The best time to visit Tuscany is April to October, with the grape harvest arriving in September and October.

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Tuscany Collection

Tuscany tour packages & itineraries

Tours that feature Tuscany — every one private and adjustable to your dates, pace, and hotels.

Best of Italy — Private Package 9-day tour: Venice, Florence & Rome
9 Days
Private Semi-Private Self-Guided
From €3,400 per person

ITALY

Best of Italy

Venice, Florence & Rome

Year-round 2–12 guests
Culture Romance Foodie Family

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ITALY

Private Semi-Private Self-Guided

Best of Italy

Venice, Florence & Rome

Cities & Regions

Venice · Florence · Rome

Highlights

  • Skip-the-line Vatican & Sistine Chapel tour
  • Private gondola ride through the Venetian canals
  • Uffizi Gallery with a local art historian

What's Included

  • 8 nights in 4–5★ hand-picked hotels
  • All inter-city transfers in private vehicles
  • English-speaking expert guides in every city

9 Days / 8 Nights

From €3,400

Year-round
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Essence of Tuscany — Small Group 7-day tour: Florence, Siena, San Gimignano & Chianti
7 Days
Private Semi-Private Self-Guided
From €2,690 per person

ITALY

Essence of Tuscany

Florence, Siena, San Gimignano & Chianti

April – October 4–8 guests
Foodie Wellness Romance

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ITALY

Private Semi-Private Self-Guided

Essence of Tuscany

Florence, Siena, San Gimignano & Chianti

Cities & Regions

Florence · Siena · San Gimignano · Chianti

Highlights

  • Private cooking class in a Chianti farmhouse
  • Chianti vineyard tour with sommelier
  • Florence Renaissance walking tour

What's Included

  • 6 nights in countryside agriturismi and city hotels
  • Private vehicle and driver throughout
  • All cooking and wine experiences

7 Days / 6 Nights

From €2,690

April – October
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Essence of Italy — Private Package 7-day tour: Venice, Florence & Rome
7 Days
Private Semi-Private Self-Guided
From €2,490 per person

ITALY

Essence of Italy

Venice, Florence & Rome

Year-round 2–10 guests
Culture Romance Foodie

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ITALY

Private Semi-Private Self-Guided

Essence of Italy

Venice, Florence & Rome

Cities & Regions

Venice · Florence · Rome

Highlights

  • Private water taxi arrival through the Venetian canals
  • Uffizi Gallery with Botticelli and Leonardo
  • Colosseum and Roman Forum with archaeologist guide

What's Included

  • 6 nights in 4–5★ centrally located hotels
  • Private water taxi and all station transfers
  • High-speed train tickets between cities

7 Days / 6 Nights

From €2,490

Year-round
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Epic Italy — Private Package 11-day tour: Rome, Florence, Tuscany & Venice
11 Days
Private Semi-Private Self-Guided
From €4,490 per person

ITALY

Epic Italy

Rome, Florence, Tuscany & Venice

Year-round 2–10 guests
Culture Foodie Romance Family

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ITALY

Private Semi-Private Self-Guided

Epic Italy

Rome, Florence, Tuscany & Venice

Cities & Regions

Rome · Florence · Siena · San Gimignano · Venice

Highlights

  • Three full days in Rome — ancient, baroque, and Vatican
  • Tuscany day with Siena, San Gimignano, and Chianti tasting
  • Four nights in Florence with a free day

What's Included

  • 10 nights in 4–5★ centrally located hotels
  • Private water taxi and all transfers
  • High-speed train tickets between all cities

11 Days / 10 Nights

From €4,490

Year-round
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North of Italy — Private Package 9-day tour: Milan, Lake Como, Venice & Florence
9 Days
Private Semi-Private Self-Guided
From €3,520 per person

ITALY

North of Italy

Milan, Lake Como, Venice & Florence

Year-round 2–10 guests
Culture Romance Wellness

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ITALY

Private Semi-Private Self-Guided

North of Italy

Milan, Lake Como, Venice & Florence

Cities & Regions

Milan · Lake Como · Venice · Florence

Highlights

  • Private boat tour of Murano and Burano
  • Verona's Roman Arena and Juliet's House
  • Leonardo da Vinci's Last Supper in Milan

What's Included

  • 8 nights in 4–5★ hotels and lakeside villa
  • Private water taxi and all transfers
  • Private expert guides in Venice, Verona, and Milan

9 Days / 8 Nights

From €3,520

Year-round
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Best of Italy & Assisi — Private Package 9-day tour: Rome, Assisi, Florence & Venice
9 Days
Private Semi-Private Self-Guided
From €3,610 per person

ITALY

Best of Italy & Assisi

Rome, Assisi, Florence & Venice

Year-round 2–10 guests
Culture Wellness Romance

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ITALY

Private Semi-Private Self-Guided

Best of Italy & Assisi

Rome, Assisi, Florence & Venice

Cities & Regions

Rome · Assisi · Florence · Venice

Highlights

  • Giotto's fresco cycle in the Basilica of St. Francis
  • Colosseum and Vatican with specialist guides
  • Uffizi Gallery and Michelangelo's David in Florence

What's Included

  • 8 nights in 4–5★ centrally located hotels
  • Private water taxi and all transfers
  • High-speed train and private vehicles

9 Days / 8 Nights

From €3,610

Year-round
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Best of Italy from Rome — Private Package 9-day tour: Rome, Florence, Tuscany & Venice
9 Days
Private Semi-Private Self-Guided
From €3,490 per person

ITALY

Best of Italy from Rome

Rome, Florence, Tuscany & Venice

Year-round 2–10 guests
Culture Foodie Romance

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ITALY

Private Semi-Private Self-Guided

Best of Italy from Rome

Rome, Florence, Tuscany & Venice

Cities & Regions

Rome · Florence · Siena · San Gimignano · Venice

Highlights

  • Colosseum, Forum, and Vatican in Rome
  • Uffizi Gallery and Ponte Vecchio in Florence
  • Tuscany day — Siena, San Gimignano, and Chianti wine tasting

What's Included

  • 8 nights in 4–5★ centrally located hotels
  • Private motorboat and all station transfers
  • High-speed train tickets between cities

9 Days / 8 Nights

From €3,490

Year-round
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The Truffle Hunter's Italy — Bespoke 8-day tour: Black truffles in Norcia, white truffles in San Miniato, Brunello in Montalcino.
8 Days
Private Semi-Private Self-Guided
From €4,290 per person

ITALY

The Truffle Hunter's Italy

Black truffles in Norcia, white truffles in San Miniato, Brunello in Montalcino.

September – November 2–8 guests
Foodie Culture

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ITALY

Private Semi-Private Self-Guided

The Truffle Hunter's Italy

Black truffles in Norcia, white truffles in San Miniato, Brunello in Montalcino.

Cities & Regions

Rome · Spoleto · Norcia · Perugia · Siena · Florence

Highlights

  • Private truffle hunt with fourth-generation hunter and trained Lagotto
  • San Miniato White Truffle Fair
  • Private Brunello estate barrel tasting

What's Included

  • 7 nights in 4–5★ hotels
  • 7 breakfasts, 4 lunches, 3 dinners
  • All truffle hunts and market visits

8 Days / 7 Nights

From €4,290

September – November
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Italian Opera & the Performing Arts — Bespoke 9-day tour: La Scala, the Arena di Verona, and music in the country that invented it.
9 Days
Private Semi-Private Self-Guided
From €5,190 per person

ITALY

Italian Opera & the Performing Arts

La Scala, the Arena di Verona, and music in the country that invented it.

June – October 2–8 guests
Culture Romance

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ITALY

Private Semi-Private Self-Guided

Italian Opera & the Performing Arts

La Scala, the Arena di Verona, and music in the country that invented it.

Cities & Regions

Milan · Cremona · Verona · Bologna · Florence · Rome

Highlights

  • Evening performance at La Scala with private morning tour
  • Opera under the stars at the Arena di Verona
  • Private luthier workshop in Cremona

What's Included

  • 8 nights in 5★ hotels
  • 8 breakfasts, 2 lunches, 4 dinners
  • Three evening performances

9 Days / 8 Nights

From €5,190

June – October
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The Grand Tour: Palaces & Private Collections — Bespoke 10-day tour: Turin to Rome, with access to collections that rarely open their doors.
10 Days
Private Semi-Private Self-Guided
From €5,890 per person

ITALY

The Grand Tour: Palaces & Private Collections

Turin to Rome, with access to collections that rarely open their doors.

April – June · September – October 2–6 guests
Culture

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ITALY

Private Semi-Private Self-Guided

The Grand Tour: Palaces & Private Collections

Turin to Rome, with access to collections that rarely open their doors.

Cities & Regions

Turin · Genoa · Portofino · Florence · Siena · Rome

Highlights

  • Private Florentine aristocratic collection not open to public
  • Uffizi and Palazzo Pitti Palatine Gallery after-hours
  • Sienese Contrada museum private access

What's Included

  • 9 nights in 5★ historic palace hotels
  • 9 breakfasts, 3 lunches, 5 dinners
  • Private access arrangements throughout

10 Days / 9 Nights

From €5,890

April – June · September – October
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Florence & Tuscany — Private Package 8-day tour: Florence, Pisa, Lucca, Chianti, Siena & San Gimignano
8 Days
Private Semi-Private Self-Guided
From €2,960 per person

ITALY

Florence & Tuscany

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

Year-round 2–10 guests
Culture Foodie Romance

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ITALY

Private Semi-Private Self-Guided

Florence & Tuscany

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

Cities & Regions

Florence · Pisa · Lucca · Siena · San Gimignano

Highlights

  • Uffizi Gallery with a private art historian
  • Chianti vineyard tour and wine tasting
  • Siena's Piazza del Campo and Duomo

What's Included

  • 7 nights in 4–5★ hotels or countryside villa
  • Private driver for all excursions
  • Expert guides in Florence and Tuscan towns

8 Days / 7 Nights

From €2,960

Year-round
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Good to Know

Tuscany tours — your questions answered

What is the best time to visit Tuscany?

April to October is the best time to visit Tuscany. May, June, and September offer warm weather and quieter roads, while September and October bring the grape harvest and the first olive oil — ideal for food and wine.

How many days do you need in Tuscany?

Four to five days lets you pair Florence with the countryside; a week adds Siena, San Gimignano, and the Val d'Orcia at an unhurried pace. Many travelers combine Tuscany with Rome or Venice.

Are your Tuscany tours private and customizable?

Yes — every Tuscany tour is private and fully custom. We tailor the route around Florence's art, Chianti's cellars, and the hill towns, with villa or country-house stays and private guides.

How do you get around on a Tuscany tour?

A private driver is the best way to reach Tuscany's hill towns and wine estates, which are hard to visit by public transport. We use trains for the Florence–Pisa–Lucca corridor and arrange every guide and tasting.

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