Special Edition: Partner Trip 2026

Benvenuti in Italia! Our first ride is an easy spin to shake off the cobwebs, but it’s also very pretty, heading south through the quiet Chianti countryside until San Giusto Alle Monache. There, we’ll loop back north, passing the stunning Castello di Brolio on the hill above San Regolo and finishing on our home climb up to Lecchi. This is the time to make sure everything with your bike is perfect – if something’s not quite right, let a mechanic or a guide know and we’ll be sure to fix it before the tough riding begins.

This morning we will climb toward the town of Radda before turning to Castellina. The earliest definition – in 1716 – of the wine area of Chianti, Lega del Chianti, is the region we explore on today’s ride. This will be a day of truly incredible views from the bike, especially after our left turn in the town of Colombaio at 35km, where the roads open up to provide plenty of quintessentially Tuscan views.

Although this region is always hilly, today’s ride includes more sustained climbing. After reaching the town of Panzano, we’ll start to really climb, rolling on some tiny roads with great views to the north towards Florence. After the summit, our Cima Coppi of the week, there’s a long, technical descent out of Albola that will test even the most-experienced riders. Don’t forget to enjoy the scenery.

This is a relaxed route inspired by the traditional coffee shop ride taken by inGamba’s founder, João Correia, when he was a professional racer. We’ll encounter gentle rolling hills and ample time for on-the-bike conversation as we ride to Volpaia, a small fortified village also known as Castello di Volpaia in Italian. Renowned for being the hometown of the della Volpaia family, clock and instrument makers, Volpaia is a place steeped in history. In the afternoon, we’ll embark on a captivating walking tour of Siena, a medieval city nestled in the heart of Tuscany. Siena, renowned for its timeless charm and rich history, beckons us to explore its narrow, winding streets that lead us to the magnificent Piazza del Campo, the shell-shaped central square that hosts the thrilling Palio horse race twice a year.

Expect gentle rolling hills and plenty of time for on-the-bike conversation as we make our way up to the castle of Monteluco di Lecchi. From this medieval fortress that dates back to 1176, you can see the whole Massellone Valley.

Today’s ride will take you south toward the town of Montalcino where the rolling Tuscan clay-colored views of postcards will be in full effect. This is the Crete Senesi, a region known for its production of white truffles. The highlight of our ride is the ridge south of Arbia.

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.