Tuscany & Florence Bespoke Tours ✈ 2027

Q: How Many Days Do You Need in Tuscany?

Four to five days is the realistic minimum to see both Florence and the Tuscan countryside, and a full week lets you slow down and truly enjoy it. Most travelers spend between five and nine days in Tuscany. Our sample 10-day itinerary combines three days in Florence with a week in Chianti, Siena, Val d'Orcia and Lucca.

Q: Is 2 Days Enough for Florence?

Two full days covers Florence's essentials: the Duomo, the Uffizi, Michelangelo's David at the Accademia, the Oltrarno and sunset at Piazzale Michelangelo. Three days gives you breathing room. The Uffizi and the Accademia are closed on Mondays, so book timed entries in advance.

Q: Can Tourists Drive in Florence?

Not freely. The historic center of Florence is a camera-controlled restricted traffic zone (ZTL). Entering without a permit triggers a fine of roughly 80 to 335 euros per entry, often mailed months later through your rental company. Siena, Pisa and Lucca have similar zones, so private transfers are the simplest solution.

Q: Is Tuscany Good for Families with Kids?

Yes. Children love hands-on experiences like truffle hunting with trained dogs and making fresh pasta in a Tuscan family kitchen. Countryside villas with pools and walled towns like Lucca, where families can cycle on the Renaissance walls, make Tuscany easy to enjoy at a child's pace.

Q: Should You Stay in Florence or the Tuscan Countryside?

For most trips the best answer is both: two to three nights in Florence for art and restaurants, then a villa or agriturismo in Chianti or Val d'Orcia as a base for wine tastings, cooking classes and day trips to Siena, San Gimignano, Pienza and Montalcino.

Q: What Is the Best Time to Visit Tuscany?

The best times are April to June and September to October. Summer is hot and busy in Florence and Siena, and Siena's Palio is held on July 2 and August 16. Autumn brings the grape harvest and the start of the white truffle season. We recommend booking 6 to 12 months ahead.

Q: Do You Need a Car in Tuscany?

Not necessarily. Trains and buses work between Florence, Pisa, Lucca and Siena, but not for Chianti, Val d'Orcia or most wineries. Driving brings ZTL fines, limited parking in hill towns and wine tastings that make driving a bad idea, so we organize countryside days with a private driver.

Q: What Are the Must-See Places in Tuscany?

Florence, Siena, San Gimignano, Chianti, the UNESCO-listed Val d'Orcia, Pienza, Montalcino and Montepulciano, Lucca and Pisa.

Q: When Is Truffle Season in Tuscany?

Truffles are found in Tuscany all year. The white truffle season runs from October to December, peaking in November, when San Miniato hosts its white truffle market on the last three weekends of the month. The winter black truffle follows from about December to March, and the summer black truffle is found from late spring to summer.

Italy Bespoke Tours is a boutique travel agency founded by Italian travel designer Fabio Ilardi.

We design custom travel itineraries across Florence and Tuscany, helping international travelers explore Renaissance cities, hilltop villages and family-run wineries with clear planning and reliable ground support.

We organize private drivers, licensed guides, wine and food experiences, and hotel bookings, from boutique hotels in Florence to restored countryside villas, all tailored to your schedule.

With 24/7 local support throughout your stay, we ensure your trip across Tuscany is comfortable, simple, and well-coordinated from start to finish.

Florence skyline at dusk with Palazzo Vecchio and the Duomo

Wooden door framed by pink hydrangeas in Pienza, Tuscany

Chianti vineyards and rolling hills between Florence and Siena

Piazza dell'Anfiteatro in Lucca with its curved medieval houses

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A NOTE FROM THE FOUNDER
Fabio Ilardi - Founder & Travel Agent

Having lived in six countries across Europe, Asia, and Oceania, and traveled to nearly fifty more, I bring a global perspective to local travel design.

I understand the standards international travelers expect when booking high-end accommodations, private driver services, and well-organized day tours.

Tuscany combines Renaissance art, rolling vineyards, medieval hill towns and some of Italy's finest food and wine. My focus is simple: to use local knowledge and reliable ground support to build a clear, personal itinerary tailored to your schedule.

Consider me your direct contact on the ground, handling all local transport and logistics so you can enjoy Florence and the Tuscan countryside comfortably.

Get in touch to start planning your trip.

The Step-by-Step Process

1. Initial Inquiry & Discovery
Once we receive your request via contact form, email, or WhatsApp, we will reach out to understand your expectations, preferences, and budget.
This discovery phase allows us to design not just where you’ll go, but how you’ll experience Florence & Tuscany.

2. Preliminary Bespoke Proposal
Based on our conversation, we will create a first draft of your personalized itinerary, along with an initial cost estimate. This serves as the creative foundation of your journey.

3. Refinement & Personalization
We will review the proposal together and refine it as needed, until it feels just right.

4. Your Journey: 24/7 On-Site Assistance
Once we finalize the itinerary together, we will take care of everything for you and remove the stress of having to book everything on your own. We work closely with our trusted partners and arrange every detail for you.
We provide all the essential information needed to ensure a smooth and stress-free journey. We also include curated recommendations for restaurants and local specialties in each destination and region you’ll visit. During your stay in Italy, you will always have our dedicated support.

Tuscan farmhouse surrounded by cypress trees in Val d'Orcia, Tuscany

THE "GETTING AROUND" SOLUTION

Traveling across Tuscany involves narrow country roads, restricted traffic zones (ZTL) in Florence and Siena with heavy fines, and limited parking in the hill towns, not to mention wine tastings that make driving a bad idea.

We manage all local transport and logistics with a clear, reliable plan built around your schedule. From private drivers and airport transfers to high-speed train connections with Rome, Milan or Venice, we organize every leg of your trip so you can travel comfortably between destinations.

Private Driver Service: Door-to-door transport with professional English-speaking drivers between Florence, Siena, San Gimignano, Chianti, Val d'Orcia, Lucca and Pisa.
Wine & Food Experiences: Private tastings at family-run wineries in Chianti and Montalcino, truffle hunting with expert hunters and their dogs, and hands-on cooking classes in a Tuscan family kitchen.
Guided Tours & Excursions: Licensed private guides for Florence's Uffizi and Accademia galleries, Siena's medieval center and the hill towns of Val d'Orcia.
Seamless Logistics: Full coordination of airport transfers, train connections, guide meetings, museum entries and restaurant reservations, so every day runs smoothly.

Sant'Antimo Abbey near Montalcino in the Tuscan countryside

Your Tuscany & Florence experience includes:

✓ 24/7 Concierge Assistance for any need or emergency
✓ Curated Recommendations, from hidden trattorias to exclusive reservations
✓ Last-Minute Adjustments, whenever possible

10-Day Tuscany & Florence Itinerary

A sample private itinerary across Florence, Chianti, Siena and Val d'Orcia, with two experiences particularly loved by families with kids.

Florence Cathedral dome and Giotto's bell tower above the city rooftops

DAY 1 | ARRIVAL IN FLORENCE
Your private driver meets you at Florence or Pisa airport, or at Florence Santa Maria Novella station, for the transfer to your hotel. Enjoy the rest of the day at leisure with a first evening stroll along the Arno.

DAY 2 | FLORENCE, CRADLE OF THE RENAISSANCE
A private guide leads you through the historic center, from the Duomo and Piazza della Signoria to the Uffizi Gallery with reserved entry, avoiding the longest queues. The evening is free, with dinner reservations handpicked for you.

DAY 3 | ACCADEMIA & THE OLTRARNO ARTISANS
Meet Michelangelo's David at the Accademia Gallery, then cross the Ponte Vecchio to the Oltrarno, Florence's artisan quarter, to visit traditional leather, paper and goldsmith workshops. End the day at Piazzale Michelangelo for sunset views over the city.

DAY 4 | CHIANTI COOKING CLASS & WINE TASTING (FAMILY FAVORITE)
Today you move to the Tuscan countryside with a full day dedicated to Tuscany's culinary traditions, an experience particularly loved by families with kids. After a scenic drive through the Chianti hills, you are welcomed into a family kitchen for a hands-on cooking lesson: make handmade pasta from ancient recipes, bruschetta with genuine extra virgin olive oil, and a classic Tuscan dessert. Children love rolling and cutting their own pasta! Then enjoy a tasting of the best Chianti wines paired with local extra virgin olive oils, before sitting down to lunch with the dishes you have prepared, accompanied by 5 Chianti wine tastings.
Included: air-conditioned vehicle, English-speaking driver, hands-on cooking lesson, lunch and 5 wine tastings. Duration: 8 hours.

Ponte Vecchio bridge over the Arno river in Florence

Tuscan vineyard at sunrise with morning mist over the hills

DAY 5 | TRUFFLE HUNTING IN THE TUSCAN WOODS (FAMILY FAVORITE)
One of our most loved experiences, and a true highlight for families with kids. A friendly driver picks you up from your hotel or villa and takes you through the Tuscan countryside to meet an expert truffle hunter. Learn about the different varieties of truffles, the rules of truffle hunting and how the dogs are trained, then head into the forest to join the hunt alongside the hunter and his four-legged companion. Children are fascinated by the dogs at work! Afterwards, enjoy lunch at a charming local restaurant: a truffle-based menu when the season allows, and always a generous Tuscan lunch with delicious first courses, paired with five Tuscan wines including Chianti Classico and a Super Tuscan.
Good to know: the hunt involves some walking in wooded areas, so wear comfortable clothing and sturdy shoes. Children are welcome, with supervision during the hunt. Let us know about any dietary needs in advance. Timing may vary slightly with the season and truffle findings.
Included: truffle hunt, English-speaking driver, lunch and local wine. Duration: 6 hours.

DAY 6 | SIENA & SAN GIMIGNANO
Explore Siena's medieval center and Piazza del Campo with a licensed guide, then continue to San Gimignano, famous for its towers, its views over the countryside and some of Italy's best gelato.

DAY 7 | VAL D'ORCIA, PIENZA & MONTALCINO
Drive through the UNESCO-listed Val d'Orcia, Tuscany's iconic landscape of cypress-lined roads and rolling hills. Taste pecorino cheese in Pienza and enjoy a private Brunello tasting in Montalcino.

DAY 8 | MONTEPULCIANO & THERMAL SPRINGS
Visit the Renaissance hill town of Montepulciano and its historic wine cellars, then relax in the natural thermal waters of Bagno Vignoni or Bagni San Filippo, a favorite with all ages.

Stone farmhouse and cypress trees in the Val d'Orcia near Pienza

Church of San Michele in Foro in Lucca, Tuscany

DAY 9 | LUCCA & PISA
Cycle along Lucca's Renaissance walls and explore its charming squares, then stop in Pisa for the Leaning Tower and the Field of Miracles on your way back.

DAY 10 | DEPARTURE
Enjoy a final relaxed morning before your private transfer to the airport or station, or continue your journey to Rome, Cinque Terre or Lake Como.

We are not satisfied until you are.
Our philosophy is simple: your happiness comes first.

Unrivaled Support & the “Happiness Guarantee”

Our service doesn’t end once your trip is booked: it’s only the beginning.

While you are in Italy, we remain at your side as a discreet yet constant point of support, available 24/7 (phone, email, or WhatsApp) to handle last-minute changes, secure exceptional experiences, or resolve any unexpected issues.

Our philosophy is simple: your happiness comes first.

Marble facade of Florence Cathedral and Giotto's bell tower

SEASONALITY & PLANNING TIMELINE

Understanding seasonal differences helps you choose the right time to visit Florence and Tuscany and secure your preferred hotels, countryside villas, wine experiences and guided museum visits.

We help you choose the best time to travel based on your schedule and handle all reservations well in advance.

Spring (April – June): Mild weather, green hills and blooming countryside with fewer crowds than peak summer. Ideal for Florence's museums, Chianti wineries and walks through the hill towns of Val d'Orcia.
Summer (July – August): Hot and busy in Florence and Siena, but lovely in the countryside with a pool villa. Book early for villas, private drivers and the most popular restaurants.
Autumn (September – October): Warm days, golden light and the grape and olive harvests across Chianti and Montalcino, plus the start of the white truffle season.

Arno river and Ponte Santa Trinita bridge in Florence

Planning Timeline: Top boutique hotels, countryside villas, private drivers and the best wine experiences in Florence and Tuscany often book up 6 to 12 months in advance. Contacting us early helps us secure your preferred accommodations and private transport before options become limited.

Call Now — Speak With a LOCAL SPECIALIST for Your Tailor Made Italian Holidays

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MULTI-DESTINATION SEAMLESS SUPPORT

Many travelers combine Tuscany with Rome, Cinque Terre, Lake Como or Venice in a single trip.

Moving between cities, countryside villas and the coast requires clear planning and reliable transport.

We act as your single point of contact, managing your multi-destination itinerary so every connection is simple and well-coordinated.

Connections Between Destinations: Private drivers, high-speed train tickets and transfers connecting Florence and the Tuscan countryside with Rome, Cinque Terre, Lake Como, Venice and Milan.
Single Point of Contact: One local travel designer manages your entire itinerary across every region, handling schedule adjustments and providing direct ground support throughout your stay.
Luggage & Station Logistics: Door-to-door luggage transport, driver meetings at airports and train stations, and hotel check-in coordination built around your preferred schedule.

Ponte Vecchio and the Arno river at sunset in Florence

Accredited Travel Agent IATA - International Air Transport Association

How Many Days Do You Need in Tuscany?

Four to five days is the realistic minimum if you want to see both Florence and the Tuscan countryside, and a full week lets you slow down and truly enjoy it. Most travelers spend between five and nine days in Tuscany.

With only three days, you can see Florence plus one day trip, but the pace will feel rushed. Florence alone deserves two to three days for its museums, churches and neighborhoods.

Our sample 10-day itinerary combines three days in Florence with a week in Chianti, Siena, Val d'Orcia and Lucca, at a relaxed pace that works for couples and families alike.

Baptistery of San Giovanni and Florence Cathedral in Piazza del Duomo

Is 2 Days Enough for Florence?

View of Florence and the Duomo from the hills through cypress trees

Two full days is enough to cover Florence's essentials: the Duomo complex, the Uffizi Gallery, Michelangelo's David at the Accademia, the Oltrarno district across the Ponte Vecchio, and sunset at Piazzale Michelangelo.

Three days gives you breathing room for smaller museums, artisan workshops and long lunches, while four or five days let you use Florence as a base for day trips to Siena, Pisa, Lucca or Chianti.

A useful tip: the Uffizi and the Accademia are closed on Mondays, so plan your museum days around that and book timed entries well in advance, especially from spring to autumn. We arrange reserved entries and private guides as part of every Florence itinerary.

Can Tourists Drive in Florence?

Not freely. The historic center of Florence is a ZTL (Zona a Traffico Limitato), a restricted traffic zone monitored by cameras, and only residents and authorized vehicles can enter.

Driving in without a permit triggers a fine, usually between about 80 and 335 euros per entry, often mailed months later through your car rental company, which adds its own administrative fee. Many other Tuscan towns, including Siena, Pisa and Lucca, have similar zones.

Hotels inside the zone can sometimes register your license plate, but the simplest solution is not to drive in Florence at all. Our clients arrive and move around with private transfers and drivers, so there is no risk of fines and no stress about parking.

Copy of Michelangelo's David in Piazza della Signoria, Florence

Is Tuscany Good for Families with Kids?

Street artist drawing a portrait in the historic center of Florence

Yes, Tuscany is a wonderful destination for families, as long as the trip is planned at the right pace.

Children love hands-on experiences, and two of the most popular with our families are included in our 10-day itinerary: truffle hunting in the woods alongside an expert hunter and his trained dogs, and a cooking class in a Tuscan family kitchen where kids make their own fresh pasta.

Countryside villas and agriturismi with pools give children space to play after a day of sightseeing, and walled towns like Lucca, where families can cycle along the Renaissance walls, are easy to explore at a child's pace.

For families, we plan shorter driving days, flexible schedules and family-friendly restaurants, so the trip works for every age.

Should You Stay in Florence or the Tuscan Countryside?

This is one of the most common questions travelers ask, and for most trips the best answer is both.

Florence is ideal for art, architecture, shopping and restaurants, and it is easy to explore on foot. Two to three nights in the city lets you enjoy its museums and evening atmosphere without rushing.

The countryside is where Tuscany slows down. A villa or agriturismo in Chianti or Val d'Orcia makes a perfect base for wine tastings, cooking classes, truffle hunting and day trips to Siena, San Gimignano, Pienza and Montalcino.

Splitting your stay avoids long daily drives back and forth from Florence and gives you the best of both worlds. That is exactly how our 10-day itinerary is designed.

Rooftops of Lucca and the Guinigi Tower with the Tuscan hills beyond

What Is the Best Time to Visit Tuscany?

Palazzo Pfanner gardens and San Frediano bell tower in Lucca

The best times to visit Tuscany are generally from April to June and from September to October.

Spring brings mild temperatures, green rolling hills and wildflowers, with fewer crowds than summer. It is a lovely season for museums in Florence, countryside walks and wine tastings.

Summer, particularly July and August, is hot and busy in Florence and Siena. It is still a great time to enjoy a countryside villa with a pool, long dinners outdoors and Siena's famous Palio horse race, held on July 2 and August 16.

September and October are many travelers' favorite months: warm days, golden light, the grape harvest across Chianti and Montalcino, and the start of the white truffle season.

November to March is quieter and cooler, with lower prices and a more local feel, plus the olive oil harvest and November's white truffle fairs.

Whatever the season, we recommend booking 6 to 12 months ahead for the best villas, drivers and experiences.

Do You Need a Car in Tuscany?

It depends on your trip, but a rental car is not always the best choice.

Tuscany's hill towns, wineries and countryside villas are hard to reach by public transport, which is why many travelers consider renting a car. Trains and buses work well between cities such as Florence, Pisa, Lucca and Siena, but not for Chianti, Val d'Orcia or most wine estates.

Driving also comes with real drawbacks: camera-controlled restricted traffic zones (ZTL) in Florence and many other towns, limited parking in hill towns, narrow and winding country roads, and wine tastings that make driving a bad idea.

That is why we organize most countryside days with a private driver. You get all the freedom of a car, with door-to-door service, no navigation stress and no worries about parking, fines or how much Chianti you taste.

Lucca Cathedral of San Martino with its arcaded facade and bell tower

If you prefer to drive, we recommend picking up a rental car only when you leave Florence for the countryside, ideally outside the city center or at the airport, and returning it before you head back into town.

In our experience, the most relaxing way to discover Tuscany is to focus on the art, food, wine and landscapes while leaving transport to local professionals. This lets you make the most of your time and fully enjoy every day of your trip.

What Are the Must-See Places in Tuscany?

Medieval towers and terracotta rooftops of Lucca below the Apuan Alps

Tuscany combines world-class art cities with some of Italy's most beautiful countryside, vineyards and medieval hill towns.

Some of the places we most often include in our itineraries:

Florence – The cradle of the Renaissance, home to the Duomo, the Uffizi, Michelangelo's David and the Ponte Vecchio.
Siena – A beautifully preserved medieval city, famous for Piazza del Campo and its striking Gothic cathedral.
San Gimignano – The hilltop town known for its medieval towers and sweeping countryside views.
Chianti – Rolling vineyards and villages between Florence and Siena, home of Chianti Classico wine.
Val d'Orcia – A UNESCO-listed landscape of cypress-lined roads, golden hills and iconic farmhouses.
Pienza – A small Renaissance town overlooking the Val d'Orcia, famous for its pecorino cheese.
Montalcino and Montepulciano – Hill towns renowned for Brunello di Montalcino and Vino Nobile wines.
Lucca – An elegant walled city where you can walk or cycle along the Renaissance walls.
Pisa – The Leaning Tower and the Piazza dei Miracoli, easily combined with Lucca in one day.

Together, these places show the incredible variety that makes Tuscany such a rewarding destination, and we tailor the mix to your interests and pace.

When Is Truffle Season in Tuscany?

Tuscany is one of Italy's great truffle regions, and truffles can be found here all year round, with different varieties depending on the season.

The main truffle seasons are:

White truffle (October to December) – The most prized and aromatic truffle, at its best in November. San Miniato, between Florence and Pisa, is the white truffle capital of Tuscany and hosts its famous truffle market on the last three weekends of November.
Winter black truffle (about December to March) – A rich, earthy truffle, perfect for winter pasta dishes and found in areas such as the Crete Senesi south of Siena.
Summer black truffle (late spring to summer) – Milder and more affordable, which makes summer a lovely time for a family truffle hunt in the woods.

Rolling hills, vineyards and woodland in the Tuscan countryside, truffle country

Thanks to these different seasons, our truffle hunting experience can be enjoyed for much of the year, with the lunch menu adapting to the truffles in season. If tasting fresh white truffle is a priority, plan your trip for October or November.