Sunday 7 November 2026 (day 1) - Arrival in Florence: First Light, First Frames

Your journey begins in Florence, where you’ll check in to your hotel and have time to settle in.

In the afternoon, we head out for a relaxed walking tour of Florence, ideal for easing into both the city and the trip. We’ll explore streets, viewpoints, and everyday corners that are perfect for observation and spontaneous photos — no pressure, just learning to notice light, details, and moments as they happen.

As evening approaches, Florence glows, offering beautiful views over rooftops and the river — the kind of light that makes even smartphone photos shine.

We end the day with a welcome aperitivo rinforzato at Formaggioteca Terroir, where artisanal cheeses, local products, and wine provide a delicious introduction to Tuscany and a convivial start to the journey.

Monday 8 November 2026 (day 2) - Chianti Classico: Villages, Vineyards & Wine

We leave the city behind and head into the rolling hills of Chianti Classico, where Tuscany opens up into vineyards, olive groves, and stone villages.

The day begins in Greve in Chianti, followed by time in Castellina in Chianti and Radda in Chianti — charming, human-scale towns that are easy to explore and naturally photogenic.

At a family-run winery, Poggerino, we enjoy a guided visit, wine tasting, and a relaxed lunch. This is a great moment to capture vineyard scenes, cellar details, and the rhythm of Tuscan food and wine culture.

In the afternoon, we visit the gardens of Castello di Brolio, where sweeping views and quiet paths invite slow wandering and easy photography.

We end the day in Siena, with a free evening to enjoy dinner, stroll the historic center, or simply rest.

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Tuesday 9 November 2026 (day 3) - Val d’Orcia: Postcard Tuscany, Slowly

Today we enter Val d'Orcia, one of Tuscany’s most beautiful and recognizable landscapes.

Our first stop is Montepulciano, where hilltop views, elegant streets, and cafés invite both wandering and casual photography.

Lunch is at Podere Il Casale, an organic cheese farm where pecorino, seasonal dishes, and the surrounding countryside come together — a wonderful mix of flavor and rural life.

The afternoon is dedicated to enjoying the Val d’Orcia scenery at a relaxed pace: cypress-lined roads, quiet chapels, and rolling hills. We also visit Pienza, a small Renaissance town perfect for gentle walks, people-watching, and light-filled streets.

Overnight in Pienza, where evenings are peaceful and unhurried.

Wednesday 10 November 2026 (day 4) - Sacred Places, Brunello & Slow Exploration

We begin the day in Bagno Vignoni, a unique village centered around an ancient thermal pool — a simple but striking setting that’s easy to photograph and deeply atmospheric.

We then visit the serene Abbey of Sant’Antimo, surrounded by olive groves and countryside. This is a place to slow down, enjoy the silence, and take in the beauty without rushing.

Lunch takes place at a local winery, with a tasting that introduces the wines of the area. Afterward, we stop in Montalcino, where you’ll have time to stroll, shop, or enjoy a glass of Brunello.

In the afternoon, we visit Monte Oliveto Maggiore, known for its frescoed cloisters and warm earth tones.

The evening back in Siena is free.

Thursday 11 November (day 5) - Monasteries, Medieval Towers & Etruscan Roots

Today blends dramatic landscapes with medieval towns.

We start at the iconic Abbey of San Galgano, where open sky and stone architecture create a striking, unforgettable setting.

Lunch is enjoyed at Castello di Spannocchia, a historic estate known for its hospitality and countryside cooking.

In the afternoon, we visit San Gimignano, where medieval towers rise above vineyards and olive groves. We then continue to Volterra, arriving as the town grows quieter and more intimate.

Free evening in Volterra.

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Friday 12 November (day 6) - Volterra, Salt, & Beer

The morning is dedicated to Volterra, including a visit to its Etruscan Museum, offering a deeper look into Tuscany’s ancient past.

Lunch takes us to the countryside near Mazzolla, where rustic dishes and a relaxed pace invite you to slow down and enjoy.

In the afternoon, we visit the Saline di Volterra, discovering a lesser-known side of Tuscany before enjoying a casual local beer tasting.

We continue to San Miniato, where the evening is dedicated to a group dinner featuring seasonal truffles — a warm, celebratory moment focused on flavor, conviviality, and the joy of eating together.

Saturday 13 November (day 7) - Truffles, Lucca & Renaissance Walls

Today begins with free time to explore the San Miniato truffle market, browsing stalls, meeting producers, and sampling truffle-based street food or enjoying a casual lunch.

In the afternoon, we head to Lucca for a relaxed bike ride along the city’s Renaissance walls, one of Italy’s most unique urban experiences.

After checking in to our hotel, you’ll have time to explore Lucca’s historic center, piazzas, and churches, and enjoy a free evening at one of Lucca's many lovely dining options.

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Sunday 14 November (day 8) - Medici Villas, New Olive Oil & Arrivederci

On our final day, we travel through the Tuscan countryside toward Florence.

We begin with a visit to the Medici Villa of Poggio a Caiano, a UNESCO-listed residence that offers insight into Renaissance life and Medici power.

We then continue to Capezzana, where fresh olive oil is being produced. Here we enjoy a guided wine and new-oil tasting, followed by a delicious farewell lunch at the countryside restaurant Da Delfina.

In the afternoon, we return to Florence for drop-off and departure — with memories, flavors, and a lot of photographs to take home.

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