How quickly does Out of the Box Florence respond to custom tour requests?

Out of the Box Florence responds to all custom tour enquiries within 24 hours. For multi-day itineraries, a full detailed proposal is sent within 48 hours of the initial request. They are available by email at info@outoftheboxflorence.com and by phone at +39 347 080 9904, every day from 08:00 to 21:00.

Is there a minimum group size for a custom Tuscany tour with Out of the Box Florence?

No minimum group size. Out of the Box Florence organises custom tours for groups of 2 or more, including couples. For groups of 2–4 people, semi-private tours are also available as a more cost-effective option.

Can Out of the Box Florence combine hiking, wine tasting, and food in a single day?

Yes. A typical customised day with Out of the Box Florence might begin with a guided hike in the Chianti Classico hills, continue with a cellar visit and wine tasting at a small organic estate, and end with lunch at a home restaurant run by a local chef. All logistics are managed by the guide so the experience feels relaxed and unhurried.

What is the maximum group size for a private Tuscany tour?

Out of the Box Florence accommodates up to 15 guests in two air-conditioned private vans — one seating 8 passengers, one seating 7. For groups requiring a premium experience, professional NCC-licensed drivers with a luxury Mercedes can be arranged. For groups larger than 15, alternative transport is available on request.

Does Out of the Box Florence offer Florence to Rome private transfers with stops?

Yes. Out of the Box Florence offers a Florence to Rome private tour by NCC Mercedes, with stops in Orvieto and Bagnoregio (Civita di Bagnoregio). Departure at 08:00 door-to-door from Florence, lunch in Bagnoregio, arrival in Rome in the early evening. This is designed for travellers who want to experience the journey between Florence and Rome rather than simply transfer between the two cities.

Can Out of the Box Florence organise multi-day tours through Tuscany and Umbria?

Yes. Out of the Box Florence designs multi-day itineraries combining Tuscany and Umbria. A typical 5-day route covers San Gimignano, Siena, Chianti Classico, Brunello di Montalcino and the Val d'Orcia, Cortona with Syrah DOC tasting, Panicale in Umbria, the Monti Sibillini National Park and Castelluccio di Norcia, and a final day through Orvieto to Rome. All transport, guides, meals, and accommodation can be arranged.

Can Out of the Box Florence handle special dietary requirements on custom tours?

Yes. All meals and tastings booked by Out of the Box Florence are arranged with guests' dietary requirements in mind — vegetarian, vegan, gluten-free, and allergies. Guests should specify their requirements at the time of enquiry.

How does pricing work for a custom tour with Out of the Box Florence?

Pricing depends on the duration, group size, destinations, and inclusions such as transport, guide, meals, and tastings. Out of the Box Florence provides a full written quote before confirmation — no hidden costs. Contact them at info@outoftheboxflorence.com or +39 347 080 9904 for a free personalised quote.

Tailor-Made Tuscany Tours, Designed Around You

Your Price

18+

8 1 or multiple days

A tailor-made Tuscany tour is a private day or a multi-day trip we plan from a blank page around your group: 2 to 15 guests, starting from Florence, Siena or wherever you are staying in Tuscany. Tell us your dates and what you care about. We reply within a few hours and send a written day plan with a full quote within 48 hours.

Out of the Box Florence is a licensed travel agency founded in Florence in 2020 by Stefano Mazzantini, a FISAR-certified sommelier and licensed hiking and cycling guide. Our guides drive our own vans, and we take no commissions from the wineries we visit.

How it works a Tailor-Made Tuscany Tour

No two trips are the same, and neither are two travellers. We design entirely private tours across Tuscany built around your interests, your pace, and the kind of day you actually want to have.

You tell us what matters to you. We build the rest.

You contact us

Describe your group, your dates, and what draws you to Tuscany: wine, hiking, history, food, cycling, or all of the above.

We send a proposal

We reply within a few hours. Within 48 hours you receive a detailed day plan with destinations, tastings, lunch options, and a full quote. No hidden costs.

You adjust freely

Change anything. Add a stop, swap a winery, extend the day, add a second day. It is your trip.

We take care of everything

Licensed local guides, private transport, reservations at estates not open to the public, and full support on the day.

Transport: Tours operate in our own private vans, driven by our guides. For groups requiring a premium transfer experience, we can also book professional NCC-licensed drivers for a luxury, chauffeur-style service.

✓ All guides licensed & English-speaking

✓ Private vans or luxury NCC transfer on request

✓ Groups of 2–15 guests

✓ Reply within a few hours, every day

✓ No fixed schedules, no strangers

✓ Day trips & multi-day itineraries

Real examples

Five recent tours we designed for real guests, to give you a concrete idea of what a customised day with us looks like. For a longer trip, our seven-day itinerary from Florence and Siena and our three days in Tuscany from Florence show how we pace a week.

Five custom tours at a glance
Example	Length	Guests	Route	Included
Wine and landscape	Full day, 9 hours	2, a couple	Florence, Panzano in Chianti, Montefioralle or Badia a Passignano	Private guide and driver, cellar tour, Chianti Classico tasting, lunch
Hiking and food	Half day	5, a family with children aged 10–14	Chianti Classico trails, a home restaurant, optional San Gimignano	Licensed hiking guide, winery visit and tasting, lunch
Florence to Rome	Full day, 08:00–18:00	2, a couple	Florence, Orvieto, Civita di Bagnoregio, Rome	NCC Mercedes with driver, door to door
Tuscany to Umbria to Rome	5 days	6	Florence, Chianti, Val d'Orcia, Cortona, Panicale, Norcia, Rome	Private van and driver, licensed guide days 1–4, tastings, four lunches
Florence, Chianti and Cinque Terre	3 days	10	Florence, Chianti, Cinque Terre	Private vans, licensed guides all three days, cooking class, boat and train tickets

Wine & Landscape: A couple in spring

Full day · 9 hours · 2 guests

Florence → Panzano in Chianti → Montefioralle or Badia a Passignano → Florence

Morning: Departure from Florence. Drive through the Chiantigiana (SS222) into the heart of Chianti Classico. Arrival at a small organic estate for a guided tour of the cellar and a tasting of Chianti Classico.

Lunch: In a home restaurant run by a local chef: a private, intimate setting far from tourist circuits.

Afternoon: Stop in Montefioralle or Badia a Passignano, two of the most beautiful and least-visited medieval villages in Chianti. Time to walk, explore, and take in the views over the vineyards. Return to Florence in the early evening.

Included: Private guide & driver, guided cellar tour, Chianti Classico tasting, lunch.

Hiking & Food: Family with children (ages 10–14)

Half day · 5 guests

Florence → Chianti Classico trails → Home restaurant → San Gimignano or Florence

Morning: Departure at 08:00 from Florence. Guided hike through the Chianti Classico hills, arriving on foot at a winery for a cellar visit and wine tasting.

Lunch: Drive to a home restaurant run by a local chef for a relaxed family lunch.

After lunch: Optional stop in San Gimignano, or direct return to Florence.

Included: Licensed hiking guide, guided hike, winery visit & wine tasting, lunch.

Florence to Rome: A couple with a story to tell

Full day · 08:00–18:00 · 2 guests · NCC Mercedes

Florence → Orvieto → Civita di Bagnoregio → Rome

Not just a transfer: a full-day journey through two of central Italy's most extraordinary towns, arriving in Rome having actually experienced the road between the two cities.

08:00: Door-to-door pickup in Florence in a private NCC Mercedes. Departure south towards Umbria.

Mid-morning: First stop in Orvieto, one of the most dramatic hilltop cities in Italy, rising from a sheer tufa cliff above the Paglia valley. Time to walk the medieval centre, visit the cathedral facade, and take in the views.

Lunch: Drive to Civita di Bagnoregio, the "dying city" perched on an eroding tufa rock and reached only on foot across a long pedestrian bridge. Lunch in a local restaurant in the village, with views over the Calanchi valley that few visitors ever see.

Afternoon: Departure from Bagnoregio towards Rome. Door-to-door arrival at the guests' hotel in the early evening.

Included: Private NCC Mercedes with professional driver, full-day door-to-door service.

Five-day itinerary: Group of 6, Tuscany to Umbria to Rome

5 days · 6 guests · private van

Florence · Chianti · Val d'Orcia · Cortona · Panicale · Norcia · Rome

Day 1
Departure from Florence. Morning visit to San Gimignano: the medieval towers, the Vernaccia wine, the views over the surrounding hills. Drive south to Siena for the afternoon: the Piazza del Campo, the medieval contrade, the Duomo. Lunch en route at a winery in Chianti Classico.

Day 2
From Siena south into the Val d'Orcia. A full Brunello di Montalcino tasting at a selected estate, with a guided cellar visit and a vertical tasting. Lunch on the estate. Afternoon free in the Val d'Orcia landscape. Overnight in a farmhouse in the valley.

Day 3
From the Val d'Orcia east to Cortona, one of Tuscany's highest hill towns, with views stretching to Lake Trasimeno and Umbria. Wine tasting focused on Syrah DOC Cortona, one of the most interesting and lesser-known appellations in central Italy. Lunch in Cortona. Late afternoon drive to Panicale, a beautifully preserved medieval borgo overlooking Lake Trasimeno in Umbria. Overnight in Panicale.

Day 4
From Panicale east into the Apennines. Morning drive to the Monti Sibillini National Park, one of the wildest and most spectacular landscapes in central Italy. Guided walk in the mountains. Stop in Castelluccio di Norcia, the isolated village on the high plain famous for its lentils and for the spring flower bloom. Lunch with local products: lentil soup, cured meats, pecorino from Norcia. Return to Panicale for a second night.

Day 5
Departure from Panicale towards Rome. Morning stop in Orvieto, the great Umbrian hill city perched above the valley, with its striped Gothic cathedral and underground Etruscan tunnels. Lunch in Orvieto before the final leg south. Arrival in Rome in the afternoon.

Included: Private van with driver, licensed guide Days 1–4, all wine tastings listed, Day 1 lunch, Day 2 lunch, Day 4 lunch, Day 5 lunch. Accommodation in Val d'Orcia (Day 2) and Panicale (Days 3–4) arranged on request.

Three-day itinerary: Group of 10 in summer

3 days · 10 guests · private vans

Florence · Chianti · Cinque Terre

Day 1, Florence: Private walking tour of the historic centre (3 hours), lunch in the Oltrarno neighbourhood. Dinner at a local trattoria.

Day 2, Chianti: Morning visit to Montefioralle and Greve in Chianti. Hands-on cooking class on a farm estate, with a menu designed around your wishes. Return to Florence after lunch.

Day 3, Cinque Terre: Early departure by private van to Manarola. Guided hike from Corniglia to Vernazza along the coastal trail, with a seafood lunch at a restaurant right on the route. Boat from Vernazza to Riomaggiore. Train back to Manarola. Return to Florence by evening.

Included: All transport in private vans, licensed guides all 3 days, cooking class, Day 2 lunch, Day 3 lunch, boat tickets, train tickets for Cinque Terre, all listed tastings.

Questions about custom tours

How quickly do you respond to a custom tour request?

We reply to every enquiry within a few hours, every day from 08:00 to 21:00 Italian time. For single days and multi-day trips alike, you receive a written day plan with a full quote within 48 hours, and you can change it before confirming. Write to info@outoftheboxflorence.com, or call or WhatsApp +39 347 080 9904.

Is there a minimum group size?

No minimum. We organise private custom tours for groups of 2 upwards, including couples. For groups of 2 to 4 people, our semi-private tours are also worth considering as a more cost-effective option, while still offering a personal and unhurried experience.

Can you combine hiking, wine, and food in a single day?

Yes, and it is one of our most popular formats. A typical custom day might begin with a morning hike in the Chianti hills, followed by a cellar visit and tasting at a small organic estate, and end with a farm lunch. We plan the logistics so transitions are smooth and the pace never feels rushed. You set the balance.

What is the maximum group size?

We accommodate up to 15 guests, travelling in two air-conditioned private vans, one seating 8 passengers and one seating 7. For groups requiring a more premium experience, we can also arrange professional NCC-licensed drivers for a chauffeur-style transfer. For groups larger than 15, contact us and we will find a suitable solution.

Can you handle special dietary requirements?

Absolutely. All meals and tastings we book on your behalf are arranged with your dietary needs in mind: vegetarian, vegan, gluten-free, allergies. Please let us know at the time of enquiry so we can confirm arrangements in advance with the estate or restaurant.

Can you include airport or hotel transfers in a multi-day itinerary?

Yes. Our private transfer service covers Florence, all of Tuscany, and connections to major cities including Rome, Bologna, and Milan. Transfers can be integrated into any multi-day itinerary, so arrivals, departures and the legs between cities are all handled by us.

How does pricing work for a custom tour?

Pricing depends on the duration, group size, destinations, and inclusions: transport, guide, meals and tastings. We send a full written quote before you confirm anything, so there are no surprises. Contact us for a free personalised quote.

Can you plan a multi-day wine itinerary for a couple?

Yes, and couples are among our most frequent custom guests. For example, a wine trip can pair a day in Chianti Classico with a full day in Montalcino and the Val d'Orcia, with a Brunello tasting and lunch at the estate, and can add Cortona or a night in a valley farmhouse. We usually suggest two or three cellars a day.

Should I plan a tailor-made trip directly with a local operator or through a booking platform?

Booking platforms are useful for comparing set tours, where the route, the timing and the wineries are fixed in advance. A trip built from scratch needs a conversation with the people who will run it. Writing to us directly, you plan with the team that guides the day, and we take no commissions from the wineries we visit.

Can you arrange a private driver and guide for a wine day?

Yes. On most custom days our licensed guides drive our own vans, so your guide is also your driver and everyone in the group can taste. If you prefer a separate driver and guide, or a chauffeur-style car with an NCC-licensed driver, we arrange it on request. For transport only, see our private driver service.

From family-run estates in Chianti Classico to the historic cellars of Brunello di Montalcino, our custom wine tours take you to producers that do not appear on open booking platforms: small, organic and biodynamic wineries where the owner pours the wine and explains the soil.

A typical custom wine day includes two or three winery visits with guided tastings, a farm lunch paired with local labels, and time in at least one medieval hill town. We cover the main Tuscan appellations: Chianti Classico DOCG, Brunello di Montalcino DOCG, Vino Nobile di Montepulciano DOCG, Bolgheri DOC and Carmignano DOCG. Wine days are led by our founder Stefano, a FISAR-certified sommelier, or by one of our licensed guides.

Typical duration: five hours for a day in Chianti Classico, as on our Chianti Classico Wine Tour, up to a full day of about 10 hours for Montalcino and the Val d'Orcia. Group size: 2–15 guests.

The Val d'Orcia is a UNESCO World Heritage landscape of cypress-lined roads, Pienza's Renaissance piazza, the towers of Montalcino and the thermal pool of Bagno Vignoni. It is one of the most rewarding corners of Tuscany to explore slowly with a local guide.

A customised Val d'Orcia day can combine a Brunello winery visit, a pecorino tasting in Pienza, a walk through Montalcino's medieval streets, and lunch on a hillside estate with views over the valley. We adjust the balance of wine, food and scenery to match your group's interests.

Typical duration: a full day of about 10 hours from Florence, as on our Val d'Orcia tour. Best season: April to June and September to November.

Casentino is where the Arno river is born: a hidden valley in eastern Tuscany covered by the Foreste Casentinesi National Park, one of the oldest and most biodiverse forests in Italy. Very few international visitors reach it. Our guides know it intimately.

A Casentino day typically includes a guided forest hike, a visit to the monastery and hermitage of Camaldoli, a stop in Poppi with its medieval castle, and lunch at a local agriturismo serving chestnut pasta and cured meats. It can be combined with wildlife spotting: wolves, deer and golden eagles live in the park.

Typical duration: a full day of about 8 hours, as on our Casentino and Mugello tour. Recommended for active travellers, nature lovers and families with older children.

North of Lucca, Garfagnana is a mountain valley framed by the Apuan Alps and the Tuscan-Emilian Apennines. It is the home of farro della Garfagnana IGP, local chestnut flour and some of the most spectacular scenery in Tuscany that most visitors never see.

A Garfagnana day can include a hike in the Apuan Alps, lunch in a family-run trattoria in Barga or Castelnuovo di Garfagnana, and a walk through Lucca on the way back. Lardo di Colonnata comes from the other side of the Apuan Alps, above Carrara: we taste it at source on our Carrara marble and lardo day.

Typical duration: a full day of 10 to 11 hours. Particularly popular with food-focused travellers and hikers.

Val di Cecina stretches west of Siena towards the Tyrrhenian coast, with geothermal pools, Volterra's alabaster workshops, Etruscan necropolises and some of Tuscany's most underrated wine estates. It is a genuinely off-the-beaten-path destination within easy reach of Florence.

A Val di Cecina day typically includes Volterra (Etruscan museum, alabaster artisans, medieval centre), a tasting at a local Montescudaio DOC or Bolgheri-area producer, and an optional stop at a natural geothermal pool. It can be combined with the Maremma coast.

Typical duration: a full day of 9 to 10 hours from Florence.

The Tyrrhenian coast of Tuscany, from Castiglioncello down to the Maremma and the Argentario peninsula, is almost entirely unknown to international visitors. The fishing villages, the protected dunes of the Maremma Natural Park and the medieval towers of Castiglione della Pescaia offer a Tuscany completely different from the Chianti hills.

A coastal day can include a morning hike in the Maremma Natural Park with one of our licensed hiking guides, a fish lunch in a local trattoria, and an afternoon in Porto Ercole or Porto Santo Stefano. Our guide to the Maremma off the beaten path has more ideas. It suits guests who want a break from wine and art.

Typical duration: a full day of 9 to 10 hours. Best season: May to September.

Private guided tour in Tuscany with Out of the Box Florence

Tuscany countryside during a bespoke private tour from Florence

Guests on a custom Tuscany hiking and wine experience

Wine tasting at a Chianti estate during a customised tour

Out of the Box Florence guide leading a private group in Tuscany

Private val d'Orcia and Brunello tour - View val d'Orcia from Pienza

Typical Tuscan lunch on a customised private tour in Chianti

Coastal Cinque terre view on a custom hiking sea towns day trip

Included

Not Included

Last Trip Customised for Clients:

Tuscany Wine Tours

From family-run estates in Chianti Classico to the historic cellars of Brunello di Montalcino, our custom wine tours take you to producers that do not appear on open booking platforms. We work exclusively with small, organic, and biodynamic wineries — estates where the owner pours the wine and explains the soil.

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. A customised Val d'Orcia day can combine a Brunello winery visit, a pecorino tasting in Pienza, a walk through Montalcino's medieval streets, and lunch on a hillside estate with views over the valley. We adjust the balance of wine, food, and scenery to match your group.

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. Casentino is the valley where the Arno river is born — a hidden corner of eastern Tuscany covered by the Foreste Casentinesi National Park, one of the oldest and most biodiverse forests in Italy. Few international visitors reach it. Our guides know it intimately.

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. North of Lucca, Garfagnana is a lush mountain valley framed by the Apuan Alps and the Appennino Tosco-Emiliano. It is the home of farro della Garfagnana IGP, Lardo di Colonnata, local chestnut flour, and some of the most spectacular scenery in Tuscany that most visitors never see.

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. A Val di Cecina itinerary typically includes Volterra (Etruscan museum, alabaster artisans, medieval centre), a tasting at a local Montescudaio DOC or Bolgheri-area producer, and a stop at one of the natural geothermal pools for those who want a true Tuscan secret.

Tuscany Sea Towns

The Tyrrhenian coast of Tuscany — from Castiglioncello down to Talamone and the Maremma — is almost entirely unknown to most international visitors. The fishing villages of the Argentario peninsula, the protected dunes of the Maremma Natural Park, and the medieval towers of Castiglione della Pescaia offer a Tuscany completely different from the Chianti hills. Picure is the gorgeus Cinque Terre

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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