The Tuscany Experience

From the rolling hills of the Val d’Orcia to the Renaissance streets of Montepulciano, this corner of Tuscany is as rich in culture as it is in scenery.

A UNESCO World Heritage landscape, the Val d’Orcia is shaped by its vineyards, olive groves, and iconic cypress-lined roads. At its heart lies Montepulciano, a medieval hilltop town famed for Vino Nobile, grand piazzas, and winding cobbled streets. Nearby Pienza, Montalcino, and Bagno Vignoni each bring their own charm — from pecorino and truffles to Brunello wine and thermal hot springs.

Just over an hour from Florence Airport, you’ll quickly swap city bustle for Tuscan calm. Routes here roll between vineyard climbs, sweeping white gravel lanes, and espresso stops in sunlit squares. Evenings are for long tables, local wines, and sunsets that feel like they belong on a postcard.

Two mountain bikes lying on a dirt road in a rural area, with an old brick building on the left and a light-colored building in the distance, surrounded by trees and shrubs under a blue sky.
Two people riding bicycles on a gravel path lined with tall green cypress trees.

Why Tuscany?

Cycling in Tuscany puts you at the heart of Italy’s rich cycling culture. The white gravel “strade bianche” have become legendary thanks to the Strade Bianche race, where pros battle over the same roads you’ll ride. The rolling climbs and vineyard landscapes are iconic in their own right, blending challenge with beauty at every turn.

Riding here feels cinematic, it’s the landscape of Gladiator, of sweeping golden fields and sunlit gravel roads lined with cypress tress that seem made for epic journeys. Here you can test yourself on routes that inspire the pros, then reward yourself with world-class food, wine, and the timeless charm of Italy’s hilltop towns.

Accommodation

Outdoor dining table set for a meal with wine glasses, bottles, bowls, and a flower, overlooking a vineyard at sunset under a covered patio with string lights.

A catered villa stay in the heart of Tuscany.

We know that recovery and comfort are just as important as the ride. That’s why our Tuscan cycling retreats are based in one beautiful villa for the entire week - no moving, no repacking, just a perfect base surrounded by vineyards and white roads.

Each villa is carefully chosen to blend rustic charm with refined comfort. Expect elegant en-suite bedrooms, spacious living areas with exposed beams and stone walls, and sweeping views across the Val d’Orcia countryside.

After a day on the gravel roads of the strade bianche or exploring medieval towns, relax by the pool, unwind in landscaped gardens, or share long dinners under a shaded pergola with local wine as the sun sets over the hills. Your Tuscan retreat is more than just a place to stay - it’s part of the adventure.

Among Vineyards and Hilltops

Our villas are set among the rolling hills of Tuscany, surrounded by vineyards, olive groves, and quiet roads. While towns like Montepulciano and Pienza are a short ride or drive away, the setting offers tranquillity, sweeping views, and the perfect base for exploring Tuscany’s culture, food, and wine at your own pace.

En-suite Rooms

Our riders deserve a private retreat after a day in the saddle. Our selection of beautiful accommodations ensures you have that personal space with spacious en-suite rooms.

A True Tuscan Stay

Each of our villas is chosen with cyclists in mind - peaceful settings among vineyards, pools for post-ride recovery, shaded terraces for al fresco dining, and authentic Tuscan character throughout. It’s the perfect base whether you’re chasing epic rides or simply soaking up the rhythm of la dolce vita.

Aerial view of a countryside estate with stone house, swimming pool, cypress trees, and green rolling hills.
Kitchen with a wooden island, fresh vegetables, fruits, and a basket of tomatoes, cream-colored cabinets, open shelves with decorative items, and a window with natural light.
View of a cozy kitchen made of wood with a small center island and a window overlooking greenery, seen through a doorway in a home interior.
Dining room with a long wooden table set with dishes and glasses, surrounded by wooden chairs, beige tiled floor, white walls, wooden ceiling beams, and a beige sofa with pillows in the background.
A scenic view of a stone house with a tiled roof, surrounded by greenery, cypress trees, and rolling vineyard hills in the background. In the foreground, there is a swimming pool with lounge chairs and umbrellas on a paved patio.
A rustic stone house with tiled roof, surrounded by green lawns and trees, and overlooking rolling hills under a blue sky with clouds.
An outdoor dining table set for a meal at sunset, with wine glasses, bottles, and food, overlooking a vineyard landscape.
An outdoor dining area with a long wooden table set for a dinner, featuring candles, wine, and candles, under a wooden pergola with string lights, against a stone and brick wall, with tall cypress trees visible in the background at dusk.
Bathroom with open window overlooking green fields and rolling hills, featuring a sink with a flower arrangement, folded towels, and a toilet.
Bathroom with a walk-in shower featuring patterned tiles, a bidet, a toilet, a sink with a marble countertop, a mirror, a towel rack with a towel, and a small potted pink flower.
A bedroom with a bed featuring a floral bedspread, a gray headboard, and white pillows. There are two nightstands with bedside lamps, an open window with a view of green hills, and a gray dresser with a mirror. The room has tiled floors, exposed wood
An outdoor swimming pool illuminated at night, with lounge chairs and umbrellas nearby, in front of a stone house with lit windows, surrounded by trees and tall cypress trees, with a hilly landscape in the background.
Sunset view of a swimming pool with lounge chairs and umbrellas, stone house, tall cypress trees, and rolling hills in the background.

The Gravel Rides

Our guided cycling holidays in Tuscany are designed to balance effort and indulgence, with each day shaped by vineyard climbs, sun-dappled gravel tracks, and rides through medieval hilltop towns. Here’s a sample itinerary of how your week could unfold:

Day 1 – Buongiorno

Arrive in Florence where your driver will meet you for the transfer to our villa in Val d’Orcia. Once settled, we’ll help set up your bike, enjoy a gentle spin through the countryside, and finish the day with a glass of local wine overlooking the hills.

Day 2 - La Dolce Vita

A perfect introduction to Tuscany. Gentle climbs, vineyard roads, and sweeping descents through cypress-lined lanes. A day straight out of a postcard to get your legs turning and your heart tuned to “la dolce vita.”

Day 3 - “Are you not entertained?”

We ride into the heart of the Val d’Orcia, passing Maximus’s house, medieval towns and sunlit piazzas. Expect espresso stops, golden fields, and unforgettable views - this is Tuscan cycling at its finest.

Day 4 - Hot Springs

Drop into the valley and ride to the historic spa village where you can dip in the thermal rivers. Take in the natural hot springs before the climb back to the villa - a challenge rewarded with both scenery and satisfaction.

Day 5 - Rest Day Your Way

Recharge as you wish: start your morning with a yoga session (included), then relax by the pool, indulge in a spa treatment, or take a taxi to explore the nearby towns. We can also arrange wine tours, Vespa rides, or visits to Tuscany’s famous hot springs.

Day 6 - Strade Bianche

Ride the legendary strade bianche - Tuscany’s iconic white gravel roads. A mix of rolling climbs and fast descents, this is a ride that captures the essence of cycling in the region: raw, beautiful, and unforgettable.

Day 7 - Il Crescendo

Your final day in the saddle takes you through vineyards and olive groves, ending in the Renaissance town of Montepulciano. One last climb, one last view, and one last dinner together to toast the week.

Day 8 - Arrivederci

Enjoy a private transfer to Florence Airport, bidding farewell to an unforgettable week living the Italian dream.

Food. Indulge in our catered dining experience

Exceptional food is at the heart of every Slipstream Adventures trip. Our catered cycling holidays include a dining experience crafted by a professional private chef – with menus designed to nourish, delight, and restore. Whether you’re vegan, vegetarian, gluten-free, or have other dietary needs, we’ve got you covered.

You’ll enjoy nutritionally balanced meals tailored for performance on the bike - from hearty breakfasts and protein-rich afternoon tea to elegant three-course dinners with wine, all from the comfort of your chalet.

Breakfast and coffee to start the day before road cycling in Morzine

Breakfast

This is the most important meal of the day, a chance to give the body all the fuel needed to kick off the ride in the right gear.

Vegan and gluten-free friendly meals prepared by a private chef for cyclists in Morzine

Afternoon Tea

Waiting for our riders when back to the villa at the end of each ride.

Relax with a cup of coffee & cake, this is how we like to finish the day!

Cyclists enjoying post-ride afternoon tea in a private chalet on a catered Alps cycling retreat

Dinner

A delicious 3-course meal (6 nights out of the 7) prepared by a Private Chef.

We serve restaurant-quality food from the comfort of your chalet, wine included.

Luxury Cycling Holidays in Tuscany, Italy

Highlights. What’s Included:

Logistics

  • Group Florence airport transfers including bike luggage

  • Hosted by English-speaking guides both in the villa and while out cycling

Cycling

  • 5 led group rides with extra self-guided options

  • Route maps and GPX files, tailored around your group

  • Mechanical expertise for minor repairs

  • In-depth rider briefings the day before each stage.

  • Private yoga session by the pool on the rest day

Food & Nutrition

  • Breakfast, afternoon tea and 3-course evening dinner 6 days

  • Continental self-service breakfast on the chef’s days off

  • Sports nutrition welcome pack and an Elite Slipstream water bottle to fuel your rides

  • Dietary needs covered vegan, vegetarian, gluten-free friendly

Accommodation

  • 7 nights luxury accommodation in Tuscany

  • Our accommodation is based on 2 people sharing a room, however, if you would like a private room, feel free to get in touch.

  • Swimming pool, bike storage and laundry

What’s Not Included

  • Flights are organised directly by the riders

  • Bike Hire (see FAQ for recommendations)

  • Travel Insurance (see FAQ for details)

  • Lunch (see FAQ for suggestions)

  • Dinner on 2 nights (we can facilitate restaurant reservations)

Optionally, you can add:

  • Sport Massage (mobile service)

  • Slipstream Adventures Jersey

  • Bike Hire from €35.00/day

  • There are loads of activities to do for non-riders and on your rest day. More information will be sent to you in our booking guide

A step closer to your next adventure