We don’t offer pre-packaged itineraries. Instead, we craft bespoke Tuscany journeys that align with your interests, whether it’s private wine tastings in Chianti, artisan workshops in Florence, or an immersive truffle hunt in San Miniato. Every experience is hand-selected to bring you closer to the heart of Tuscany’s culture, cuisine, and landscapes.

Tuscany is more than a destination—it’s an experience woven from medieval hilltop towns, vineyard-covered valleys, and Renaissance cities brimming with art and history. Whether you dream of sipping Brunello in Montalcino, strolling through the Piazza del Campo in Siena, or uncovering the secrets of hidden villages untouched by time, our custom Tuscany tours ensure every detail is tailored to your tastes.

Below, you’ll find a curated selection of some of the most captivating places in Tuscany—all of which can be included in your itinerary. But this is just the beginning. With our deep local knowledge and connections, we can guide you beyond the well-trodden paths to hidden gems and exclusive experiences known only to insiders.

Let’s design a journey that speaks to your passions. Contact us to start planning your private Tuscan adventure.

Tuscany Escorted Touring: Your Favorite Spots

These places are some of our travelers’ favorites. If you have other places you would like to visit on a Tuscany tour, just say so and we will make it happen!

Florence: The City That Defined Beauty

Florence is more than a city—it’s a statement. The birthplace of the Renaissance, where art, architecture, and ambition converged to redefine the world. Every street, every piazza, holds echoes of genius, from Michelangelo’s David standing in quiet defiance to Brunelleschi’s dome, an impossible feat made real. But Florence is not a museum; it breathes. It’s in the goldsmiths of the Ponte Vecchio, in the scent of leather from ancient workshops, in the ritual of an espresso standing at the counter. To walk here is to move through history, but to truly see it is to feel the pulse of something timeless.

Chianti: The Landscape That Tastes Like Wine

Chianti is Tuscany distilled—rolling hills striped with vineyards, medieval hamlets frozen in time, cypress trees lining roads that seem to lead nowhere and everywhere at once. This is where the Sangiovese grape finds its finest expression, where the land itself shapes the wine, and the wine, in turn, shapes the people. Between the hilltop towns of Radda, Greve, and Castellina, life follows an unhurried rhythm—lunches stretch long, cellars echo with stories, and the line between past and present dissolves in a glass of ruby-red perfection.

Lucca: The City of Stillness and Song

Lucca keeps its secrets behind thick Renaissance walls, standing as both a fortress and a refuge. Within, a perfect medieval city unfolds—cobbled streets, quiet churches, and a rhythm dictated not by tourists, but by those who live here. The walls, once built for defense, now cradle a way of life: cycling in the golden light, an unhurried aperitivo in Piazza dell’Anfiteatro, the distant notes of Puccini—Lucca’s native son—drifting through the evening air. Unlike its louder Tuscan sisters, Lucca does not demand attention. It rewards those who linger.

Montalcino: A Hilltop Kingdom of Wine

Montalcino rises above the Val d’Orcia like a medieval dream, a town of stone towers and sloping vineyards where Brunello reigns supreme. Time moves differently here—longer, slower, richer. The wine, aged for years in oak, is a reflection of the place itself: deep, complex, with a patience that only the best things possess. Beneath the fortress walls, winemakers tend vines as they have for centuries, knowing that perfection cannot be rushed. This is not a place for haste. It is a place to savor.

Montepulciano: Where Wine Meets Wonder

A town built on ridges, reaching for the sky, Montepulciano is a place of grandeur—of noble palaces, hidden courtyards, and cellars carved deep into the rock. Vino Nobile di Montepulciano, its signature red, carries the weight of history in every glass. But Montepulciano is more than its wine. It is the morning fog rolling through the valley, the quiet dignity of its Renaissance streets, the moment the sunset turns the stone walls to gold. A town that looks as if it was created to be painted.

Pienza: The Renaissance Dream Made Real

Pienza is an idea made tangible. In the 15th century, Pope Pius II envisioned the perfect Renaissance town, a place where beauty and proportion ruled, where architecture and landscape lived in harmony. Today, it remains just that—a masterpiece in miniature, perched above the rolling expanse of the Val d’Orcia. The air is thick with the scent of pecorino, aged in caves beneath the town, while the view stretches endlessly, a canvas of cypress-lined roads and golden fields. Pienza is not just seen. It is felt.

San Gimignano: The Skyline That Time Forgot

San Gimignano rises from the Tuscan hills like a mirage, its medieval towers defying both gravity and time. In the 14th century, there were 72 of them, each built in competition, a city of stone skyscrapers before the modern world even conceived of the idea. Today, only a handful remain, but their presence is enough to transport you. Climb Torre Grossa and look out—over vineyards, olive groves, and landscapes unchanged for centuries. In the shadow of these towers, time is not lost. It is suspended.

Siena: The City That Runs on Tradition

Siena is a city built on rivalries. The Palio, its fiercely contested horse race, is not a spectacle for tourists—it is a battle, waged in the heart of the Piazza del Campo, where the city’s contrade fight for honor as they have for centuries. But beyond the race, Siena is a place of quiet majesty. The striped marble of its cathedral, the sunlit alleys where the past is never far away, the devotion—religious, civic, personal—that seeps into every brick. Siena does not change for anyone. That is its power.

Val d’Orcia: Tuscany at Its Most Poetic

If Tuscany has a soul, it is the Val d’Orcia. A land of rolling hills and Renaissance ideals, where cypress trees stand like sentinels along empty roads, where every curve in the landscape feels deliberate, as if composed by a painter’s hand. Towns like Bagno Vignoni, with its steaming thermal pools, and Monticchiello, where the same families have performed their own plays for generations, remind you that life here is both simple and profound. The Val d’Orcia is not just a place to see. It is a place to dream.

Want to see what touring with us looks and feels like? We take photos during the trips, and you can see some of them in the galleries dedicated to them:

Tuscany, Amalfi & Rome 14-day Escorted Tour | Tuscany, Rome, Puglia & Capri 14-day Trip | Scot’s Tuscany photography