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A stone farmhouse on a grassy hill with tall cypress trees and a dirt path, ideal for luxury Tuscany tours.

Luxury Tuscany Tours made for you

Discover the wonders of Tuscany with our private, tailor-made tours

Rich heritage and a richer soul

Few scenes are more evocative of Italy than that of rural Tuscany: undulating hills dotted with stoic stone farm houses, dark green cypress trees and ranked vines, all under a shawl of a dawn’s mist. Embark on a journey that effortlessly blends culture, history and food and wine with a luxury tour of Tuscany designed just for you.

Laying claim to some of Italy’s finest wines, the region’s hills are ripe with tasting opportunities for curious oenophiles. Cycle between the vineyards with your private guide, stopping at a variety of carefully chosen vineyards to learn the secrets of production, and of course, tasting your way through a fruity Chianti or ruby-red Brunello di Montalcino. Find the perfect pairing for the most coveted of Tuscan foods, the truffle. Head out into the woods with an experienced truffle hunter and their highly trained dogs in search of these buried treasures, before preparing a fresh truffle pasta dish with your spoils.

Just as enchanting as its countryside, Tuscany’s cities are each destinations in their own right. The home of the Renaissance, Florence has captivated creative minds across the centuries, and now proudly displays some of the world’s most remarkable works of art. Private guided tours of the Uffizi Gallery and Galleria dell’Accademia will introduce you to the geniuses behind each masterpiece, giving an insight into the lives of Da Vinci, Michelangelo, Galileo and others.

In addition to its eponymous leaning tower, Pisa’s Duomo, Baptistery and Camposanto complete a stunning quartet of medieval triumphs. Siena’s scallop-shaped Piazza del Campo, flanked by soft orange townhouses and Torre del Mangia, is one of Europe’s greatest Medieval town squares. Towns seeming untouched by time, such as Montalcino, Pienza and San Gimignano, sit scattered across the region amidst golden wheat fields, silver olive groves and ancient vineyards, with the charms of each ready to be discovered on personalised excursions.

Get in touch with our Europe team to start planning your luxury Tuscany tour and unlock each marvellous facet of this intoxicating region.

  • View over terracotta rooftops of a hillside town toward a green valley and mountains, featuring luxury Tuscany trips.
  • Close-up of red wine being poured into a crystal glass at a vineyard during luxury Tuscany holidays.
  • Sunset view of a medieval Italian village with stone towers and surrounding olive groves for luxury Tuscany vacations.
  • nterior of an ornate museum gallery with a central marble sculpture and large windows for luxury Tuscany tours.
  • A worker pouring a bucket of dark grapes into a large container on luxury Tuscany trips.
  • A man kneeling in a forest with two dogs searching through leaves during luxury Tuscany holidays.
  • A stone archway framing a scenic view of the Tuscan landscape, perfect for luxury Tuscany vacations.
  • The interior of a grand cathedral with colorful frescoes and a large crucifix for luxury Tuscany tours.
  • A sun-drenched vineyard with rows of grapevines leading toward rolling hills on luxury Tuscany trips.
  • Ornate domed ceiling fresco with numerous figures and an octagonal lantern for luxury Tuscany vacations.

From our experts

Experiences picked by our Tuscany specialists

Hunt for truffles and cook them at Borgo Pignano

Go truffle hunting with skilled guides at Borgo Pignano Volterra before enjoying a cooking class to prepare a delicious meal with your findings

Tour the Uffizi Gallery with an art expert

Gain an insight into the great minds of the Renaissance on a guided art tour of Florence’s Uffizi Gallery

Cycle the Chianti vineyards

Taste your way through the finest Chiantis on a cycling tour of the region’s scenic vineyards

Drive Tuscany's hills in an Italian sports car

Take in Tuscany’s rolling hills and ordered vineyards from the elegant comfort of an Italian sports car

Walk medieval Montepulciano and Pienza

Explore the region’s Medieval towns, such as Montepulciano and Pienza, with a local guide

A word from one of our experts

With a great balance of both fascinating cities and alluring countryside, Tuscany allows for an in-depth experience of some of the very best that Italy has to offer. Pair some of the world’s most exceptional red wines with hearty Tuscan dinners of ribollita and pappa al pomodoro before exploring the artworks and innovations of the Renaissance.

Dan Rhodes Travel Designer

Luxury accommodation in Tuscany

There are many incredible places to stay in Tuscany. Here are some of our favourites, handpicked by our travel designers:

Why book with Jacada?

  • Personalised design

    We’ll plan your trip around your specific interests, tastes and preferences, providing helpful tips and honest advice based on first-hand knowledge of the destination.

  • Authentic experiences

    Our expert guides and brilliant travel concierges are hand-picked to provide a genuine experience, bringing your destination to life with care and passion.

  • Responsible travel

    Our luxury trips are designed with responsible travel principles that prioritise travel experiences that are both good for you and good for the planet.

Tuscany trip inspiration

Get inspired with our Tuscany example trips and then get in touch to plan your own adventure

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Ready to plan your adventure to Tuscany?

Whatever you want from your Tuscany tour, our team of expert travel designers are ready to help.

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Explore more of Italy

Meet your Europe team

When to visit Tuscany

While Tuscany can be a year-round destination, the shoulder seasons of spring (March to May) and autumn (September to November) are great times to visit to avoid the busier summer months and sometimes intense summer heat. During September and October, the landscapes come alive with the colours of autumn foliage, while temperatures are comfortable for exploring, often hovering around 17°C (63°F). This is also the best time to go if you want to witness the wine harvest in September, or the olive harvest in October. If you want to go truffle hunting, truffle season runs from October to December for the coveted white truffle.

Grape harvest

September–October

Truffle hunting

October–December

When Is the Best Time to Go to Italy?

Tuscany travel guides

Plan your trip to Tuscany

Whatever you want from your adventure in Tuscany, our team of expert travel designers are ready to help.

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“We enjoyed our first trip with Jacada…”

We enjoyed our first trip with Jacada and it surely won't be our last! Every detail and moment of our trip was perfectly planned. We were met every step of the way with courteous and knowledgeable drivers and guides. We really appreciated the local guides and the commitment they had to make every day special. Thank you Jacada for the…

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My wife and I used Jacada to plan our honeymoon to French Polynesia. Working with the Jacada team was fantastic and effortless. Every question was quickly answered. Every hiccup was quickly addressed. We felt like we were in the hands of experts who are equally passionate about travel, and who were committed to helping us have the trip of a…

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We enjoy traveling and we have used Jacada Travel for some wonderful trips over several years. We have never been disappointed. In 2024 we took a Safari in Botswana Africa and walked with the gorillas in Rwanda planned by Jacada and the itinerary was amazing. In 2025 we had planned a trip to Antartica ( with another company ) but…

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Communication and organization were excellent. The Jacada team was helpful and genuinely interested in our experience. The guides were personable, knowledgeable, and clearly enjoy their work. Vehicles were spotless, timely, and coordinators managed our every need brilliantly. I will recommend Jacada to friends and family. The only way to travel!

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We had a wonderful trip planned through Jacada. We enjoyed the venues and the excursions. This is a beautiful place we'd recommend to anyone who wants to go on a new adventure.

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Your trip, your story

We craft trips deeply personal, delightfully surprising and entirely one of a kind. Every Jacada journey begins in conversation with a travel designer, a specialist in their destination of expertise. Behind each journey is a wealth of insight, gathered over years of on-the-ground exploration.

Once you’re booked, you’ll meet your concierge. Based in the region you’re visiting, they’ll take care of all the details so your mind is at rest. They make the trip truly special – and truly yours.

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