Day Trips & Tours from Siena | Private, Tailor-made Experience

Name: Day Trips & Tours from Siena
Brand: Day Trips & Tours from Siena
SKU: 29235
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Depends on the trip

5+

8 1 or multiple days

Day Trips & Tours from Siena | Out of the Box Florence

Out of the Box Florence

Day Trips & Tours
from Siena

Explore Florence and Tuscany like never before with our private tours by locals. Whether you're tasting Brunello in Montalcino, hiking through Chianti vineyards, or cycling the iconic Strade Bianche, our tailor-made experiences are crafted for those seeking an authentic, off-the-beaten-path adventure — departing directly from Siena.

Plan a Custom Trip Browse All Tours

Chianti Classico Val d'Orcia Brunello Gravel Biking Cooking Classes Truffle Hunting

Why depart from Siena

Tuscany starts at your doorstep

Siena sits at the gateway to the finest landscapes in Italy. Chianti Classico, Val d'Orcia, and Montalcino are all within an hour — meaning more time exploring, less time in transit.

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Wine Country, Right There

The Chianti Classico DOCG begins just north of Siena. World-class estates and organic producers are closer here than from anywhere else in Tuscany.

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No Long Transfers

We meet you just outside Siena's restricted traffic and pedestrian zones for a fast, smooth departure. Your private vehicle and local expert are ready the moment you step in.

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Fully Private & Tailor-Made

Every tour departs exclusively for your group. We adapt timings, stops, and pace around you — not a fixed schedule shared with strangers.

Private Tours from Siena

Choose your experience

All tours below are fully private and depart from just outside the historic centre of Siena. Prices shown are per person unless otherwise noted.

Wine & Hiking 📍 Siena or Florence

Chianti Classico Wine Hiking Tour

Walk the trails connecting three of Chianti's finest estates. Tastings, cold cuts, and a full lunch included in the heart of the DOCG.

⚠ Siena departure: +€150 supplement applies

Full day · 9 hrs Max 8 guests 3 wineries

Wine Tour · Private 📍 Siena or Florence

Chianti Classico Wine Tour

A private half or full-day journey visiting family-run organic estates inaccessible to the general public. For wine lovers seeking depth over breadth.

⚠ Siena departure: +€150 supplement applies

Half or full day Private group Max 8 guests

Food & Wine 📍 Siena or Florence

Cheese & Wine Day in Chianti

Pair Chianti Classico with artisan Pecorino, aged cheese from small producers, and the finest local olive oil. A full sensory experience in the countryside.

Full day Private Max 8 guests

Food & Wine 📍 Siena or Florence

Honey & Wine Day in Chianti

A unique tasting itinerary combining an artisan apiary and a Chianti Classico winery. Discover the harmony between Tuscan honey varietals and local wine.

Full day Private Max 8 guests

UNESCO Landscape 📍 Siena · Gateway Tour

Val d'Orcia Day Trip

Cypress-lined roads, rolling clay hills, and medieval villages at their most accessible from Siena. A photographic, cultural, and gastronomic journey in one.

Full day · 10 hrs Private vehicle Max 8 guests

Fine Wine 📍 Siena · only 40 km

Brunello di Montalcino

Montalcino is a short drive south of Siena — the perfect base for the world's most celebrated Sangiovese. Taste the "King of Italian wines" at iconic estates.

Full day Private Max 8 guests

Foraging & Lunch 📍 Siena or Florence

Truffle Hunting with Lunch

Join a real truffle hunter and his dog through the Tuscan woods. After the hunt, sit down to a lunch built around your finds — deeply authentic.

Half day + lunch All ages Max 8 guests

Cooking Class 📍 Chianti Classico

Home Cooking Class in Chianti

Cook traditional Tuscan dishes in a private Chianti farmhouse. Hands-on, intimate, with lunch and wine pairings. Nothing like a commercial cooking school.

Half day + lunch Max 8 guests All levels

Gravel Cycling 📍 Siena · Strade Bianche · Eroica · Via Francigena

Tuscany Gravel Bike Tours

Ride the legendary strade bianche — the white gravel roads of the famous pro cycling race — departing directly from Siena. Choose between a self-guided adventure or a fully guided experience with a local expert. Routes include the iconic Eroica roads and stretches of the historic Via Francigena. Single or multi-day.

1 or multiple days Self-guided or Guided

20+

Years of experience

Max guests (2 vans)

100%

Private departures

5★

Google & TripAdvisor

Tuscany from Siena

The best private day trips from Siena — guided by locals

Siena is one of Tuscany's most beautiful medieval cities, and one of the best bases for exploring the surrounding countryside. Out of the Box Florence offers private, fully licensed day tours departing from just outside the historic centre of Siena — so you never waste time navigating the city.

Whether you're staying in Siena for a few days or simply passing through, we can build your perfect Tuscan day around your schedule and interests. Our English-speaking guides — Stefano, Manuel, and Alessandro — have years of experience guiding international travellers through the region's wineries, farms, hiking trails, and hidden villages.

The most popular private departures from Siena include:

Wine tasting tours in Chianti Classico — the DOCG begins just north of Siena
Val d'Orcia day trips — UNESCO landscape and medieval villages
Brunello di Montalcino — just 40 km south, an easy and memorable visit
Truffle hunting in the Crete Senesi — the ideal local terrain
Gravel cycling on the iconic Strade Bianche — departing from Siena's centre
Home cooking classes in a Chianti farmhouse — authentic, hands-on, delicious

Please note: some tours departing from Siena carry a supplement of approximately €150 to cover the additional transfer distance. We will always be transparent about this when you request a quote.

Meeting point

🏛️ Outside Siena's historic centre (ZTL)
🏨 Agriturismo & hotels in the Siena area
🏙️ Florence city centre
📍 Anywhere in Tuscany on request

FAQ

Frequently asked questions

We meet you just outside the ZTL (Zona a Traffico Limitato) — the restricted traffic and pedestrian areas of Siena's historic centre. We are not authorised to enter the ZTL, so we will confirm a convenient meeting point nearby when you book, ensuring a fast and easy departure from the city. Hotels and agriturismi outside the centre can be reached directly.

From Siena, the most natural choices are the Brunello di Montalcino tour (only 40 km away), any Chianti Classico wine experience (the DOCG starts just north of Siena), the Val d'Orcia day trip, and truffle hunting in the Crete Senesi. Gravel biking on the Strade Bianche roads is also iconic and departs directly from the city. All tours are available year-round.

Yes, some tours departing from Siena carry a supplement of approximately €150 to cover the additional transfer distance compared to a Florence departure. This applies in particular to the Chianti Classico Wine Hiking Tour and the Chianti Classico Wine Tour. We will always confirm the exact cost when you contact us for a quote — there are no hidden charges.

Absolutely. We specialise in bespoke itineraries that combine, for example, a morning wine tasting in Chianti with a truffle lunch, or a Val d'Orcia scenic drive with a stop at a Brunello estate. Contact us with your dates and interests and we will design the perfect full-day programme for your group.

We recommend booking at least 2–3 weeks in advance, especially during spring and autumn (April–October). For tours involving wineries, truffle hunters, or cooking classes, earlier booking ensures availability. That said, we always try to accommodate last-minute requests — contact us and we will see what we can arrange.

What's included varies depending on the tour you choose — each experience is designed around a specific destination and activity, and all are fully customisable to match your interests, pace, and group. As a general rule, prices cover private transport, a licensed local guide for the full duration, and any wine tastings or meals listed in the tour description. There are no hidden costs. Any optional extras will be communicated clearly when you contact us. We encourage you to reach out so we can tailor the perfect experience for you.

Ready to explore Tuscany from Siena?

Tell us your dates, group size, and passions. We'll craft the perfect private day — wine, food, cycling, or all three.

Please note: some tours departing from Siena carry a supplement of approx. €150 — we'll confirm the exact cost in your personalised quote.

Hike through Chianti Classico vineyards with guide, Panzano in Chianti, Tuscany

Last Trip Customised for Clients:

Tuscany Wine Tours

Chianti classico, Bolgheri, Brunello di Montalcino e Carmignano

Val d'Orcia

Explore the stunning Val d’Orcia, a UNESCO site in Tuscany, with its rolling hills, charming villages, and renowned wines for an unforgettable experience.

Casentino

Discover the serene beauty of Casentino, a hidden gem in Tuscany. Explore ancient forests, medieval castles, and charming villages while immersing yourself in its rich history and natural splendor.

Garfagnana

Experience the untouched charm of Garfagnana, a lush Tuscan region of rolling hills, quaint villages, and scenic landscapes. Perfect for nature and history enthusiasts alike.

Val di Cecina

Explore the picturesque Val di Cecina, a Tuscan gem with rolling hills, historic villages, and geothermal wonders. Perfect for history, nature, and wine lovers.

Tuscany Sea Towns

Embark on an unforgettable hiking adventure through Tuscany’s scenic sea towns. Explore coastal trails, breathtaking cliffs, and hidden beaches while immersing yourself in nature’s beauty.

Start your journey adventure voyage experience

Are you ready for a one-of-a-kind adventure through the timeless beauty of Florence and Tuscany? Our team of seasoned local experts, with over 15 years of immersive experience, is here to take you on an unforgettable voyage that is as unique as you are.

Our custom-tailored itineraries are more than just trips; they are journeys that reflect your passions and interests. Whether you’re an art enthusiast, a nature lover, a foodie, or a wine connoisseur, we craft experiences that cater to your desires.

Immerse yourself in the captivating aura of Florence, a city steeped in art, culture, and history. With our local experts as your guides, explore hidden gems and iconic landmarks, ensuring that every moment is a revelation.

Our itineraries are not just cookie-cutter tours but personalized journeys that reflect your unique tastes and preferences. With our local expertise and exclusive access to hidden gems, your adventure will be one that you cherish forever.

Ready to embark on your dream journey through Florence and Tuscany? Contact us for a free consultation, and let’s begin crafting your perfect escape. Welcome to the extraordinary world of Florence and Tuscany, where every moment is an opportunity to make memories that last a lifetime.

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Day Trips & Tours from Siena | Private, Tailor-made Experience

Depends on the trip

5+

8

1 or multiple days

Day Trips & Tours
from Siena