Escape to a Luxury Italian Villa

Create your own Luxury Italian Escape

Our luxury villas and chalets are tailor-made for groups seeking the very best of Italy

Discover the essence of Italy through our luxury villa rentals and curated experiences. Create your own exclusive private trip centred around the very best villas, tailored advice and unforgettable experiences.

Whether you are a club, group of cyclists or even a cyclist travelling with a group of non-cyclists, we can help you to live out your Italian dreams
Luxury villas with private pools offering chef and housekeeping services. We can pre-stock groceries and fine wines and host special events
Ride for 50km or 200km on road, gravel or both with a full support crew or simply enjoy our carefully curated GPX routes at your leisure
We will help you craft all the details; groceries and housekeeping, off-bike itinerary, ride logistics. Everything

How does it work?


Choose your Villa

We have carefully selected each villa and chalet to offer beautiful, well maintained rental properties in the finest locations, showcasing the best of Italy. Choose from our selection of Villas, situated in the cycling heartlands of this storied country. 

During your stay our community of expert chefs, sommeliers, personal trainers and house managers will be available alongside our professional cycling guides and mechanics to provide assistance and insight. We will be delighted to offer tips on places to eat and we can arrange as little or as much of your itinerary as you require.

Build your Italian Adventure

Build your Italian Adventure

Whether you’re a group of a cyclists or a family or group with just one or two cyclists, your Italian adventure can be whatever you want it to be.

Perhaps your group are particular fans of food and wine, you have certain desires for location or you want to coincide with another event — all these are great reasons to make the trip your own.

The cycling element of your trip can be literally anything; any length, feature road, gravel or both and be as hard or easy as you want. Our expert team are on hand to plan your bespoke trip in as much detail as you require.

Choose Cycling Support

Choose Cycling Support

Any kind of challenge is made so much more achievable with the support from our expert guides, support staff and mechanics. There's no greater sight at the top of a tough climb, than the van parked ahead ready to fill your bottles and offer some well earned nutrition.

We can offer as much support as you like on your. From just a van to a full team of guides and mechanics, we offer a totally flexible and bespoke support package to suit you. Maybe you want no support at all, in that instance we will provide you with turn by turn GPX routes, tips and helpful insights. The choice is entirely yours!

Discover the Villas & Chalets

Discover the Villas & Chalets

Villa Le Pratola, Tuscany


Gaiole in Chianti, Tuscany

Close to Siena, Florence and Cortona


5 bedrooms, 6 bathrooms. Sleeps 10, plus 3 infants


Perfectly positioned on a hill with 360-degree views of the verdant Chianti countryside, Le Pratola is the perfect luxury villa in Tuscany to enjoy a family holiday, refurbished to the highest standard and offering expansive interiors and plenty of outdoor spaces to relax and admire the gorgeous surroundings.

With wineries and medieval villages on your doorstep, there are endless opportunities for daily excursions and activities. Back at the villa, the barbeque and wood burning oven call for al fresco dinners watching the sun set behind the vineyards. Designed with all family members in mind, the heated infinity pool has a remote-controlled electronic safety cover – perfect for families with children – while the game room with pool table and table football will entertain kids and adults alike.

This large family villa in Chianti is set around a large central courtyard and offers three spacious terraces. One double bedroom is located at ground level and has its own terrace, while the other four bedrooms (3 doubles and one twin) are located on the second floor. Each bedroom has air conditioning, en-suite bathrooms and guests are supplied with Ferragamo Salvatore toiletries and slippers.

A beautifully restored 400-year-old private villa – perfectly located to explore the region and impeccably renovated with all the comforts and ultimate facilities


Alba Estate, Piedmont


Verduno, Piedmont

Close to Barolo, Alba and Asti


4 bedrooms, 3 bathrooms. Sleeps 7 plus 2 children in sofa beds


Among Italy’s Unesco World Heritage Sites aren’t just artworks, castles and monuments; there are also entire areas, such as the vineyard landscape of Nizza-Monferrato in Piedmont. In this area, where one of the world’s greatest wines originates, lies Alba Estate – Villa D. Owned by a local winery, guests can visit the vineyards and widen their wine knowledge with older vintages, verticals and lesser-known indigenous varieties. This family villa for rent in Piedmont has all you need for a comfortable holiday in Northern Italy.

A timeless wine culture pervades the area, although truffle hunting is also a must-try activity during your stay. The noble white truffle, coined Tartufo bianca di Alba comes from this region and, in spring and summer, you can experience black truffles too. Alba Estates work alongside the Truffle Dog University, where the dogs and hunters will use the grounds to forage delicacies.

Villa D captures the essence of noble life in the Northern Italian countryside. Elegant, cosy furnishings framed by wooden beams, spacious bedrooms, private balconies and endless vineyard views are some of the elements that make this villa so special. With three double bedrooms and one single, the villa can accommodate up to 7 guests plus two additional children or teenagers in sofa beds.

Immersed in a fairy tale scenario with vineyards and hazelnut groves, a quintessential Italian villa with elegant interiors, spacious grounds and impeccable services


Villa Monticchiello, Tuscany


Pienza, Tuscany

Close to Monticchiello, Montepulciano and Montalcino


6 bedrooms, 6 bathrooms. Sleeps 12


The atmosphere typical of a Tuscan farmhouse and the spectacular views over Pienza and Monticchiello are the backdrop for this beautifully renovated villa for rent in Val d’Orcia, a property born from the dream of the owners that have spent six years refurbishing what once was just a bunch of old stones.

Wrapped in scents of aromatic herbs and wild flowers, this comfortable villa rental in Pienza is immersed in nature and surrounded by the most picturesque villages of southern Tuscany. Pick your own veggie from the kitchen garden and prepare delightful meals to share with the family; challenge your friends with a game of billiard or ping pong, paint, read, swim or just relax enjoying the gentle rhythms of nature.

The spacious interiors of Villa Monticchiello can accommodate up to 12 guests in six double bedrooms, five of which have en suite bathrooms. Sustainability is a top priority for the owners that have created a modern and comfortable home reusing and recycling fabrics, vintage objects and furnishings to surround guests with an authentic Tuscan lifestyle.

A sublime country house, superbly restored by the owners with all the comforts of a modern home and the backdrop of charming Pienza


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Incredible scenery, riding, safety, food, hotel, town. The staff at the hotel fantastic. The routes amazing. I would love to see a social afternoon/cultural event to add a little local flavor to the week. You could do a cooking class (optional), visit to a winery, castle or olive oil. Lots of cool options in Tuscany.

Emily Evans, USA — 2018

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Fantastic trip from routes through Piedmont vineyards to the Italian Maritime Alps. We enjoyed parts of Italy not usually seen by tourists; hazelnuts being harvested on narrow farm roads, grapes in Barolo being thinned, the smell of freshly mown hay through farmland, then on to the mountain Colle's with little towns interspersed high up on unlikely ledges of the Maritime Alps. While riding through these small villages, I could imagine where Collodi got some inspiration for Pinocchio. My favorite day was Colle delle Finestre with 9K of gravel at the end. In keeping with a typical rigorous 'Thomson' tour, there ...

susan moerer, USA — 2016

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I have been a repeat Thomson client for 15 years and I keep coming back because of the great riding and outstanding staff. My latest trip was the Trans Piedmont and it was fantastic. That part of Italy is so beautiful and the roads have little traffic. Peter consistently puts together amazing routes which are so well thought out. But what sets the trips apart is the staff, they took such good care of us and were flexible and accommodating. Amazing trip!

Jim Cracraft, USA — 2019

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Build your tailor-made, luxury trip to Italy with Thomson Bike Tours