Tailor-Made Tuscany Tours by Locals
Tours by Locals Florence & Tuscany

Discover Authentic Tuscany with Out of the Box Florence

Explore Florence and Tuscany like never before with our tours by locals Florence. Whether you’re cycling through Tuscan vineyards, discovering Florence’s hidden gems, or indulging in local cuisine, our personalized tours are crafted for those seeking an authentic, off-the-beaten-path adventure.

With tours by locals Tuscany, you’ll experience the very best of Tuscany, guided by local experts who know the region inside and out. From historic landmarks to secret spots, our tours are designed to let you connect with Tuscany in a way that’s personal, enriching, and unforgettable.

tours by locals florence

Tailor-Made Tuscany Tours – Crafted Just for You

Personalized Local Adventures in Florence and Tuscany

Join us for a truly local Tuscany tour with our tours by locals Tuscany. Explore the region through the eyes of passionate, experienced guides. Whether you’re venturing through Florence’s historic streets, hiking in Chianti, exploring the stunning Cinque Terre, or tasting wines in Val d’Orcia, every aspect of your tailor-made Tuscany tour is designed to give you a deeper, more meaningful experience.

Our private tours Florence and customized tours Tuscany offer you flexibility and personalization, ensuring that your journey aligns perfectly with your interests. Experience Tuscany’s beauty, culture, and history on a journey you’ll never forget.

Join us for a truly local Tuscany tour with our tours by locals Tuscany. Explore the region through the eyes of passionate, experienced guides. Whether you’re venturing through Florence’s historic streets, hiking in Chianti, exploring the stunning Cinque Terre, or tasting wines in Val d’Orcia, every aspect of your tailor-made Tuscany tour is designed to give you a deeper, more meaningful experience.

Our private tours Florence and customized tours Tuscany offer you flexibility and personalization, ensuring that your journey aligns perfectly with your interests. Experience Tuscany’s beauty, culture, and history on a journey you’ll never forget.

Sustainable Tourism in Tuscany

Unforgettable Experiences for Nature, Wine, and Food Lovers by Locals in Tuscany

Offering unforgettable experiences for nature, wine, and food lovers, with a commitment to preserving our planet. Our tours are designed with sustainability in mind, from the local, organic wine producers we work with to the biodynamic farms and natural parks we explore. When you choose our tours by locals Florence and Tuscany, you’re also supporting sustainable tourism that helps protect Tuscany for generations to come.

tours by locals tuscany

Our tour partners were featured on

Our fully licensed Tuscany travel agency guarantees expert planning, reliable service, and exceptional experiences. With tours by locals Florence, we provide everything you need for a seamless trip, from personalized itineraries to exclusive deals and expert guidance. Our certifications ensure that every aspect of your tour meets the highest standards of quality and professionalism.

Our certified original Tuscany tours provide the opportunity to experience Tuscany in a truly unique way. Whether you’re wandering the medieval streets of Florence, exploring the rolling hills of Tuscany, or tasting wines in secret vineyards, every adventure is crafted with authenticity and passion. Choose our tailor-made Tuscany tours for experiences that go beyond the ordinary.

Explore Tuscany with Responsibility

With our sustainable Tuscany tours, you’ll explore this stunning region in a responsible, eco-friendly way. Every tour we offer is designed to minimize environmental impact, support local communities, and preserve the rich cultural and natural heritage of Tuscany. Whether you’re walking through the Tuscan countryside, tasting organic wines, or discovering Florence’s hidden gems, you can travel with peace of mind knowing that your experience is contributing to sustainable tourism.

We are a locally founded business in Florence, deeply committed to offering tours by locals Tuscany that highlight the best of Tuscany while supporting the community. By choosing our tours, you’re not only exploring the region, you’re also contributing to the local economy and supporting sustainable tourism practices that benefit the area we call home.

We are committed to ensuring your experience with us is nothing short of perfect. Our 100% Satisfaction Guarantee means that we’ll work with you to ensure every aspect of your Tuscany tour is tailored to your preferences and exceeds your expectations. From the moment you book until the end of your journey, we guarantee unforgettable memories and exceptional service.

What Our Customers Say

About us

Ciao! We are Out of the Box Florence — a fully licensed, locally owned travel agency founded in Florence in 2020 by people who call Tuscany home.

We believe the best way to experience a place is through the eyes of someone who truly knows it. Our guides are passionate locals with deep roots in the region — they know which Chianti estate pours the most extraordinary Sangiovese, which trail above Fiesole reveals a Florence most visitors never see, and where to find the finest lardo di Colonnata in the mountains above Carrara. This is the kind of knowledge that cannot be taught — only lived.

We specialise in private tours, bespoke day trips, and fully customised multi-day itineraries across Florence, Tuscany, and Cinque Terre — for couples, families, and groups of up to 15 guests. Every experience is built around your interests, your pace, and your idea of an unforgettable journey.

We are also committed to sustainable tourism: we partner exclusively with small, organic producers, family-run wineries, and local artisans — because we believe travelling well means travelling responsibly.

When you choose us, you are not just booking a tour. You are choosing an experience curated by locals who are genuinely proud to share the place they love.

Ciao! We are Out of the Box Florence — a fully licensed, locally owned travel agency founded in Florence in 2020 by people who call Tuscany home.

We believe the best way to experience a place is through the eyes of someone who truly knows it. Our guides are passionate locals with deep roots in the region — they know which Chianti estate pours the most extraordinary Sangiovese, which trail above Fiesole reveals a Florence most visitors never see, and where to find the finest lardo di Colonnata in the mountains above Carrara. This is the kind of knowledge that cannot be taught — only lived.

We specialise in private tours, bespoke day trips, and fully customised multi-day itineraries across Florence, Tuscany, and Cinque Terre — for couples, families, and groups of up to 15 guests. Every experience is built around your interests, your pace, and your idea of an unforgettable journey.

We are also committed to sustainable tourism: we partner exclusively with small, organic producers, family-run wineries, and local artisans — because we believe travelling well means travelling responsibly.

When you choose us, you are not just booking a tour. You are choosing an experience curated by locals who are genuinely proud to share the place they love.

Outdoor Tuscany Tours

Get out into the wild with our outdoor Tuscany tours. From cycling through the vineyards of Chianti to hiking the scenic trails of Val d’Orcia, our tours through Tuscany immerse you in the region’s stunning landscapes. These tours are perfect for nature lovers, outdoor enthusiasts, and anyone looking to experience the natural beauty of Tuscany at its best.

 


Explore Freely. Travel Personally.

Our bespoke private tours Florence let you experience the city and the region your way. Whether you’re interested in iconic landmarks, hidden gems, or a unique cultural experience, we tailor every tour to your preferences. Tuscany tours by locals means you get an intimate, personalized adventure guided by an expert who will show you a side of Tuscany only locals know.

 

Our bespoke private tours Florence let you experience the city and the region your way. Whether you’re interested in iconic landmarks, hidden gems, or a unique cultural experience, we tailor every tour to your preferences. Tuscany tours by locals means you get an intimate, personalized adventure guided by an expert who will show you a side of Tuscany only locals know.

 

Cheese & Wine day in Chianti

Starting price: €400
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Chianti Classico Wine tour

Starting price: €196
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Honey & Wine day in Chianti

Starting price: €400
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Val d'Orcia

Starting price: €450
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Brunello di Montalcino

Starting price: €500
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Cinque Terre & Pisa

Starting price: €500
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Cinque Terre (No hiking)

Starting price: €450
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Truffle Hunting with lunch

Starting price: €280
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Tuscany Adventure in Casentino

Starting price: €500
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Carrara marble & Tuscan Cured Pork Lardo

Starting price: €450
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Home cooking class in Chianti Classico

Starting price: €282
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Customised Tuscany Tours

Make your dream Tuscany trip a reality with our customized Tuscany tours. Whether you’re interested in exploring the art and architecture of Florence, enjoying a wine tour through Chianti, or taking a scenic bike ride, our flexible, personalized itineraries give you the freedom to create your perfect Tuscany adventure. With tours by locals Tuscany, you’re in control of your journey, ensuring it reflects your unique interests.


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Tailor every detail to match your interests, pace, and preferences, from destinations to experiences, ensuring a personalized adventure that perfectly fits your travel dreams.

Customise Your Tour

Tailor every detail to match your interests, pace, and preferences, from destinations to experiences, ensuring a personalized adventure that perfectly fits your travel dreams.

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FAQ

Our tours by locals Florence and Tuscany tours offer personalized, local experiences that showcase the best of these stunning regions. Whether you prefer private Tuscany tours, tailor-made Tuscany tours, or eco-friendly adventures, each journey is customized to fit your interests. Explore historic landmarks in Florence, bike through Chianti, hike scenic trails, or taste local wines in Val d’Orcia and Cinque Terre.

Our tailor-made Tuscany tours are designed specifically around your interests. Whether you’re looking for private tours in Florence or personalized tours through Tuscany, we ensure a truly authentic experience. Our expert local guides provide insider knowledge, making every tour special. From exploring Florence’s historic streets to venturing into hidden gems across Tuscany, our tours offer a perfect blend of flexibility and personalization.

Absolutely! We specialize in customized Tuscany tours, allowing you to craft the perfect itinerary. Whether you want to hike through Chianti’s vineyards, discover Florence’s art and culture, or visit Cinque Terre, we’ll design your journey to fit your desires. You can choose your destinations, pace, and experiences, ensuring that your Tuscany adventure is exactly as you imagine.

Yes, we are committed to sustainable tourism. Our eco-friendly Tuscany tours minimize environmental impact while offering an authentic experience of Tuscany. Whether you’re enjoying nature in Val d’Orcia or sipping organic wines, our tours are designed to be kind to both the planet and the local community.

Each tailor-made Tuscany tour is designed to meet your specific needs and interests. Depending on your preferences, you can choose activities such as wine tasting, hiking in Cinque Terre, cycling through Tuscany’s vineyards, or visiting historical landmarks in Florence. All tours include a local expert guide, transport options, and personalized itineraries. Some tours may include meals or wine tastings, depending on the experience you select.

Choosing tours by locals Florence provides a more intimate, authentic experience. Our local guides offer insider knowledge and take you to lesser-known spots that traditional tours often miss. Whether you’re in Florence or Tuscany, our tours are designed to give you a deeper connection to the area. Enjoy flexibility, personalization, and unique experiences that you won’t find in large, impersonal group tours.

Yes! Our private driver service in Florence and Tuscany is available for both single-day and multi-day trips, fully tailored to your schedule and interests.

Whether you need a private driver for a day trip from Florence — to explore Chianti, San Gimignano, Siena, Cinque Terre, or Pisa — or a dedicated private driver for multiple days across Tuscany and beyond, we organize everything around you. Our experienced, English-speaking drivers know the region inside and out, taking you to the best local restaurants, hidden wineries, and off-the-beaten-path destinations that group tours never reach.

All our private driver tours in Tuscany include a comfortable, air-conditioned vehicle, flexible pick-up directly from your hotel or apartment, and a fully customizable itinerary. There are no fixed schedules, no strangers, and no rushing — just a personal, authentic Tuscan experience at your own pace.

To book your private driver in Florence or to plan a multi-day itinerary across Tuscany, contact us and we will craft the perfect journey for you.

We recommend booking your private tour in Florence or Tuscany at least 2–3 weeks in advance, especially during peak season (April through October). For multi-day itineraries or tours involving wine estates and truffle hunting, earlier booking ensures availability at the best local producers. That said, we always do our best to accommodate last-minute requests — contact us and we will see what we can arrange.

Absolutely. Our family-friendly tours in Tuscany are designed to work for all ages. Many of our guests travel with children of all ages — from toddlers to teenagers — and we adapt the pace, stops, and activities accordingly. Tours like truffle hunting, farm visits in Chianti, and the Siena day trip tend to be especially popular with families. Just let us know the ages of your children when you contact us and we will tailor the experience perfectly.

Tuscany is beautiful year-round, but the best seasons for tours in Tuscany are spring (April–June) and autumn (September–October). Spring offers mild temperatures, blooming landscapes, and fewer crowds. Autumn is harvest season in Chianti — ideal for wine tours in Tuscany — with stunning colors and a festive atmosphere at the wineries. Summer is vibrant but busy; winter is quieter, more intimate, and perfect for truffle hunting and cooking classes.

Yes — wine touring is one of our specialties. Our Chianti wine tours from Florence take you to small, family-owned estates that are not accessible to the general public. We visit 2–3 wineries per day, with guided tastings of Chianti Classico, Brunello di Montalcino, and local Super Tuscans, often paired with local cheese, cured meats, and olive oil. All tours include comfortable private transport directly from your accommodation in Florence.

Yes. Our Cinque Terre day trip from Florence departs early in the morning and returns in the evening, making the most of the day. You can choose between a hiking version — walking the scenic coastal trails between villages — or a relaxed version with time to explore at your own pace. We handle all transport, so there is no need to worry about trains, connections, or parking.

Yes. Our home cooking class in Chianti takes place in a private farmhouse in the heart of the Chianti Classico region. You will learn to prepare traditional Tuscan dishes using seasonal, local ingredients, followed by a full lunch with wine pairings. It is an intimate, hands-on experience — nothing like a commercial cooking school — and one of the most memorable ways to connect with Tuscan food culture.

All of our guides and drivers speak fluent English. Manuel, Alessandro and Stefano — our local experts — have years of experience working with international travelers and are known for making every guest feel at home, informed, and well looked after throughout the day.

Tips are never included or expected, but always appreciated if you feel your guide went above and beyond. Our prices cover all logistics, transport, guide fees, and any included tastings or meals — there are no hidden costs. Any entrance fees or additional tastings not listed in the tour description will be communicated clearly in advance.

Our private tours in Florence and Tuscany start from €126 per person for a half-day experience such as our home cooking class in Chianti, and range up to €500 per person for full-day bespoke tours including Brunello di Montalcino, Val d’Orcia, and Cinque Terre. Semi-private tours — shared with a small group of like-minded travelers — start from €49 per person for the Florence Boat & Wine experience on the Arno, up to €221 per person for the Cinque Terre hiking day. Private driver services and fully customised multi-day itineraries are priced on request depending on duration, destinations, and group size. All prices include private transport, a local expert guide, and any tastings or meals listed in the tour description. Contact us for a personalised quote.

Our private tours in Tuscany accommodate up to 15 people, travelling in two comfortable, air-conditioned vans — one seating 8 passengers and one seating 7. This ensures an intimate, flexible experience even for larger families or small groups. Our semi-private tours are limited to a maximum of 8 guests, except for the Florence Boat & Wine Tour on the Arno which accommodates up to 10 guests. All our tours — private or semi-private — are intentionally kept small to guarantee personal attention, flexibility, and an authentic local experience far from the crowds.

We understand that travel plans can change. Here is our cancellation policy for private and customised Tuscany tours:

Cancellations made 15 or more days before the experience are fully refundable, excluding a 10% reservation management fee. Cancellations made between 14 and 8 days before departure receive a 50% refund, minus the 10% booking management fee. Cancellations made fewer than 8 days before departure are non-refundable. No-shows are charged the full price. Please note that booking fees charged by third-party booking platforms are non-refundable in all cases. To cancel or request further information, please contact us directly by email at info@outoftheboxflorence.com or outoftheboxflorence@gmail.com