Company retreats set in beautiful Tuscany.

We help founders and companies bring their remote or hybrid teams to Tuscany for offsites that actually matter. Instead of another video call, your team connects in person, surrounded by rolling hills, incredible food, and the kind of space where real conversations happen naturally.

Tuscany is more than just where we work; it’s our home. We know every winding backroad and hidden vineyard like the palm of our hand, and nothing brings us more joy than sharing those best-kept secrets.

Let us handle the details so you can focus on what matters: bringing your people together, sparking fresh ideas, and getting everyone aligned on what's next.

Board and training rooms help, but what if you never meet your team in person?

Think of a company retreat or an executive offsite as a deliberate hard reset for your team. It’s an opportunity for founders and team leaders to have the crew step away from the daily grind and immerse in an inspiring, fresh setting, whether that’s a quiet serviced villa in the countryside, an intimate small resort, or an elegant coastal boutique hotel.

Over a few focused days, you’ll move beyond the usual “office talk” to genuinely connect, brainstorm creatively, and recharge both personally and professionally. Whether you call it an offsite, a getaway, a hackathon or a retreat, the goal remains the same: to return to work with a clearer vision, renewed energy, and a noticeably stronger, more cohesive team.

Group of seven people sitting around a wooden table outdoors, working on laptops and taking notes, with a scenic countryside view in the background.

Meet your host

A smiling man in a blue suit and white shirt standing outdoors with green rolling hills and trees in the background.
Filippo Gargani

In the world of high-growth startups, plans change fast. My "above and beyond" approach means I anticipate logistical friction before it happens. Supported by my elite local network, I handle the complexities of Italian logistics, last-minute pivots, specialized tech needs, and bespoke culinary requirements, with total calm.

I help leadership teams step out of the "how" and stay focused on the "why," while I ensure the Tuscan backdrop performs flawlessly.

With a background serving royalty and Forbes billionaires and other discerning travelers with my other company, I bring a level of discretion, precision, and sophistication rarely found in the corporate travel space. I don't just book venues; I curate high-stakes environments where every detail, from the acoustic privacy of meeting spaces to the timing of an al fresco dinner, is engineered to support your team’s best work.

Your OnSite Team

We make sure everything works. While you run sessions, we coordinate with villa staff, monitor weather, and time meals. Sudden downpour, delayed flights, or Wi‑Fi failure, we handle it.

We ensure pickups, communicate dietary needs, and keep coffee flowing so nothing derails your day.

Essentially we turn a beautiful Tuscan villa into a functional workspace: you focus on the work, we handle the rest.

Above all we are all born and raised in Tuscany!

Our venues offer the perfect balance for work and play.

No sterile conference rooms or fluorescent lighting. We find places with character, restored villas, family-run hotels, spots where you can open the windows and actually want to be. You'll have the practical stuff (yes, the Wi-Fi works), but you're also looking out at olive groves instead of a parking lot.

After a few days of working together in a place like this,sharing meals that last hours, having conversations that go deeper than your usual standup, your team just feels different. Less like colleagues checking boxes, more like people who actually know each other.

A Selection of Venues

  • Aerial view of a countryside with a large house, swimming pool, and landscaped garden surrounded by rolling green hills, vineyards, and farmland under a blue sky.

    Villa Pesa - 24 Bedrooms

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    Villa Pesa, a manor house – hotel located in the heart of Tuscany near San Casciano in Val di Pesa and just 20 minutes away from Florence, is listed as a ‘Historical Residence’ of Italy. Guests feel right at home in this luxury Renaissance villa, tastefully restored by the owners.

    It has a total of 24 rooms, each with its own unique character and period furnishings and a great restaurant with a great chef.

    More rooms are available in the nearby annex.

  • An outdoor view of a rustic house with stone and stucco walls, surrounded by trees and shrubs, on a sunny day with a clear blue sky.

    Villa Mora - 46 Guests

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    A small medieval village, in the intimate, renovated houses that compose it and together in the theatre, in the dining room, in the living room and cinema rooms and, above all, in the courtyard and the swimming pool, surrounded by the unique Tuscany nature.

    Born as a pilgrimage retreat in the XV century, this hamlet has been restored by its owner having the outside as an integral part of its cultural and historical heritage. The estate comprises a central common area with the rooms spread in different homes around the main square, a structure that reproduces life in Tuscany as it was in the nineteenth century, a place where everyone has their privacy, but all social activities are shared, where endless walks are available for those who love nature walks. 

    New-fashioned, yet very comfortable, this is a contemporary retreat with an elegant aura and a welcoming vibe, blending traditional and modern Italian architecture, with a powerful eco-friendly accent.

  • A scenic view of a luxurious mansion with a pool, surrounded by greenery, vineyards, and a lake, with rolling hills in the background under a partly cloudy sky.

    Dimora - 44 guests

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    Dimora sits in the countryside near Firenze. The exclusive resort features private villas, a refined spa and a beautiful pool, offering top‑level luxury and thoughtful comforts in Tuscany.

    The small historic village mixes natural beauty with Renaissance heritage. It once housed famous Florentine artists, including Domenico Ghirlandaio’s family, favored by Lorenzo de’ Medici, where many masterpieces began.

    Excellent five‑star service completes the stay.

  • Aerial view of a rustic estate with castle-like stone towers, a swimming pool, and surrounding greenery in a rural landscape under cloudy sky.

    Casa Maremma - 22 guests

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    Perched on a Maremma ridge, Villa Argentaia blends medieval ruins with modern luxury. Built from weathered stone on a former monastery and fortress, it overlooks the Tyrrhenian Sea and Argentario. Surrounded by olive groves and Mediterranean macchia, the estate offers quiet, rustling Holm oaks and distant church bells.

    Inside, noble rustic details, beamed ceilings and reclaimed terracotta, meet contemporary art and bespoke furnishings. Arched windows flood expansive yet intimate rooms with light. Outside, an infinity pool seems to spill into the vineyards; courtyard gardens bloom with lavender and rosemary. Dining under a vine-covered pergola or watching sunsets from the watchtower, the villa delivers secluded, romantic Tuscan belonging.

  • A group of friends enjoying a hot spring with waterfalls and natural surroundings, some sitting and others socializing in the water.

    Buonconvento - 32 guests

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    Discover the allure of Casali di Bibbiano, a luxurious 75-acre Tuscan estate a short drive from Montalcino. This opulent 18th Century country estate operates as two luxury villas and a charming cottage, offering exclusive full-property use or non-exclusive single villa use options for discerning travelers. Casali di Bibbiano’s unique atmosphere and inherent beauty allow guests to immerse themselves in the rich heritage and traditions of the region. Every detail of the Casali experience is curated with an eye towards sophistication and simplicity, promising an unforgettable experience.

    The estate offers a stunning swimming pool, gym, tennis and basketball courts, soccer field, and even a relaxing sauna. As an added treat, golf enthusiasts can enjoy exclusive access to the world-renowned Castiglion del Bosco golf course, where breathtaking fairways blend seamlessly with the beauty of the Tuscan countryside.

  • Aerial view of a rural estate with stone buildings, a swimming pool, and surrounding green fields and hills.

    Tessaroni

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    Nestled in Val d’Elsa (Siena), Villa Tessaroni is a restored 16th‑century farmhouse revitalized by the Eriksen Tellier family. It blends historic charm with modern comforts amid classic Tuscan landscapes.

    A testament to Val d’Elsa heritage, the main casale and annex harmonize old‑world elegance with contemporary living for an authentic stay.

    Capacity & rooms

    Up to 22 guests

    Main casale + annex

    Eight ensuite rooms

Itineraries.

We're not going to tell you how to run your offsite, that's your call. But we've done this enough times to know what works and what doesn't. So if you want to run something by us, we're here.

Need help thinking through the agenda? Wondering if an idea will actually land with your team? Just ask. We're happy to share what we've learned.

Millennials having a business meeting in Tuscany
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Activities

Its not all work, work, work. Experience the pleasures that Tuscany has to offer.

All work and no play? Absolutely not.

A successful offsite should include moments when bonding and shared activities are paramount. We will suggest carefully chosen experiences that relax, motivate, and help the team genuinely enjoy their time together.

  • Group of people gathered around a table in a home, smiling for a photo, with some holding drinks and desserts on the table, in a cozy room with wooden ceiling beams and decor.

    Cooking Classes

    Our dear friend Federica is a fantastic chef and a dedicated, knowledgeable cooking-classes master. With her warm guidance and patient instruction you’ll discover the true secrets of pasta and pizza making, plus a rich collection of authentic, tasty Tuscan recipes that you can recreate at home. And she is also a certified sommelier for a wine tasting and pairing class.

    Watch the video clip

  • Exhibition of Ferrari Formula 1 cars at Museo Ferrari Maranello, with red race cars on display and visitors viewing and taking photos, illuminated by indoor lighting.

    Ferrari at Mugello Racetrack

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    An incredible super car experience that includes:

    -Welcome with refreshments
    -30-minute theory course with instructor
    -driver Circuit reconnaissance aboard a van with a professional driver
    -Consecutive laps in a Supercar with our professional co-driver
    -Personalized certificate of participation with company logo & Gadget RC and FULL KASKO insurance with track extension

  • Group of friends in a natural hot spring with waterfalls and scenic landscape in the background, enjoying conversation and beverages.

    Hot Springs Party

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    Tuscany is the land of hot springs, with dedicated resorts scattered throughout the region. Planning a hot spring party or an aperitivo by the thermal pools is a delightful, relaxed way to bond with your colleagues.

  • The historic Palazzo Vecchio in Florence, Italy, with statues in front, illuminated at dusk, and the moon visible in the sky.

    Tours

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    Tuscany boast 7 UNESCO World Heritage Sites, plenty to visit.

    Historic Centre of Florence (1982): Known as the cradle of the Renaissance, containing masterpieces like the Duomo and Uffizi.

    Piazza del Duomo, Pisa (1987): Renowned for the Leaning Tower, Cathedral, Baptistery, and Campo Santo.

    Historic Centre of San Gimignano (1990): Famous for its well-preserved medieval architecture and, specifically, its fourteen surviving tower houses.

    Historic Centre of Siena (1995): A prime example of a medieval city, famed for the Piazza del Campo.

    Historic Centre of Pienza (1996): Known as the "ideal city" of the Renaissance, designed by Pope Pius II.

    Val d'Orcia (2004): A rural cultural landscape, reflecting Renaissance aesthetic ideals.

    Medici Villas and Gardens (2013): A group of 12 villas and 2 gardens (Boboli and Pratolino) representing the Medici family's patronage.

  • A group of people with bicycles on a dirt trail in a rural area, wearing helmets and outdoor clothing, with green rolling hills and a mountain in the background under cloudy skies.

    Biking

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    Whether you choose e-bikes to level the playing field or classic bikes to find a shared rhythm, the experience is all about the journey. You’ll wind through vineyards and olive groves, stopping whenever the mood strikes, maybe for a shaded picnic debrief or a quick mindfulness break at a hilltop vista.

    Why your team will love it:

    Inclusive: E-bikes ensure everyone stays together, regardless of fitness.

    Organic Connection: Miles of quiet dirt roads naturally spark better conversations than a conference table ever could.

    Active Recovery: A perfect mix of fresh air, movement, and Tuscan scenery to reset the mind.

    It’s team building that feels less like "work" and more like a shared breath of fresh air.

  • Two sailboats racing on the water with crews onboard and mountains in the background

    Competitive Regattas

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    Corporate sailing events work well because a sailboat naturally supports corporate goals. Away from comfort zones, people develop cross-functional skills, enjoy a fresh experience, and build resilient teams that respond effectively in crises. Meetings, incentive events, or training become chances to showcase and reward each person’s contribution to the team.

Hiking in Tuscany during a retreat

FAQs.

Got another question?

Bridging the Gap:
Heritage Luxury meets Modern Corporate Strategy

TuscanyOffsite.com is a dedicated venture designed to redefine the corporate retreat. While the name is new, the foundation is decades deep.

TuscanyOffsite.com is powered exclusively by the infrastructure, expertise, and elite reputation of ItalysFinest.com.

Over the Years They Have Said About Us

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Find out more about our luxury corporate retreats in Tuscany.


A smiling man with gray hair and a white shirt standing with arms crossed outdoors, with a view of a large body of water, boats, and steep cliffs or mountains in the background.

Ready to turn the "Dream" into a Departure Date? Planning the perfect Tuscan offsite shouldn't feel like work.

Book a free discovery call today, and let’s map out your vision. In just 15 minutes, we’ll provide all the logistics, creative inspiration, and local secrets you need to start planning the retreat your team will talk about for years.

CALL OR WHATSAPP: +39 335 8352882

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If you want to book a private vacation or arrange a formal corporate event in Italy, choose our mother company, Italy’s Finest.

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