Day 1- Giro del Barone

26KM/440M

Arriving mid-day Sunday, the Giro del Barone ride is just a short loop to stretch our legs and dial in our bikes. But already there will be plenty to see, for while this ride is only 27 kilometers in distance, it is clearly “Made in Chianti.” After all, we are in the heart of one of Italy’s most famous wine regions. Fittingly, we roll past Castello di Brolio early in the ride, just one of the many expansive domains tucked away in these rolling hills that will be on non-stop display throughout the week.

Day 2: Off Bike

Rather than a ride on day 2, this is a day dedicated to meditation, ice baths, a yoga flow, and a chance to talk with Patrick Sweeney about your mental game.

Day 3: Castelnuovo Berardenga

42KM / 721m

Again, we pass by the Castello di Brolio early in the ride, before rolling down to Castelnuovo Beradenga, another one of the historic wineries in this region, not to mention a great place for a coffee stop in Café Agribar Brolio, which sponsors its own Eroica team and covers its walls with its rich collection of cycling memorabilia. 

This loop was first designed as the coffee ride by inGamba founder João Correia when he was a professional cyclist living in Lecchi. João loved to ride down to Pianello, where he would sit down for coffee and read Gazzetta dello Sport, and as the inGamba crew unanimously agrees, it makes for an ideal relaxed ride.  

Day 4: Monteluco Radda via Vila

40KM / 932m

Our destination today is Volpaia, one of Chianti’s most enchanting fortified hamlets. The ride builds steadily, offering long, flowing climbs that reward patience with panoramic views over vine-covered valleys. Volpaia feels suspended in time, its stone towers and narrow alleys echoing centuries of winemaking tradition. We stop here for an espresso or aperitivo before descending back through forests and vineyards that glow in the afternoon sun.

Day 5: Castellina

61KM / 1100m

Today’s route explores the classic heart of Chianti. We ride deeper into the region, weaving between historic estates and ancient farmhouses en route to Castellina in Chianti. The terrain is quintessential Tuscany: rolling climbs, graceful descents, and postcard-perfect vistas in every direction. Castellina’s charming old town invites a relaxed pause, and from here the return ride offers some of the most scenic roads of the week.

Day 6: Monteluco via La Villa

57KM / 1242m

Our final ride is also our most rewarding. The climb to Monteluco is a true Tuscan classic, rising steadily through oak forests and open ridgelines. The effort is met with sweeping views across the Crete Senesi and the distant silhouettes of medieval hill towns. We linger at the summit to take in the panorama before a flowing descent carries us home—an unforgettable finale to a week of extraordinary riding, culture, and cuisine.

DEPARTURE

Monday
This is our final morning together and after a leisurely breakfast, it will be time to say goodbye, or at least arrivederci, until we meet again. Transfers to the airport will be arranged by our hard-working crew but if you’re planning on staying a few extra days, let us know if we can help with reservations or a few recommendations.

The Daily Schedule

This is something different than a normal inGamba week in Tuscany. While each day’s ride plan looks different, the general itinerary will include multiple opportunities to practice breathwork, meditation, yoga and more with Patrick, as well as the typical riding, massage and mealtimes. Each day will begin with an ice bath and meditation session before breakfast, a pre-ride breathwork practice, post-ride massage, and meditations and discussions throughout the afternoon and evening.

Why Cold Plunge?

Breathwork and purposeful discomfort like cold plunging are a key part of Sweeney’s process, and will be a daily ritual on this trip. The cold plunges are set up on the terrace at Borgolecchi, so as you plunge in the morning to kickstart your brain and prepare for the day ahead, you’ll be treated to a beautiful vineyard view. As Sweeney says, it’s not about gritting your teeth and getting through these moments. Instead, it’s about accepting the challenges and surrendering to the challenges. Sweeny explains that “Many people, when they do it, immediately say that they've never felt this alive and completely present, just as a result of working with on the breath while being immersed in this cold water.” And that focus will translate to your ride later.