Tuscany: Chianti Classico


This is our classic Tuscany trip, the culmination of all our local knowledge and a perfect expression of the Mangia, Beve, Bici experience. Back when he was still a professional cyclist, our founder, João Correia, sat outside the cafe that now faces our pristine service course, dreaming of sharing this incredible place with like-minded travelers. He knew that Tuscany’s unique blend of cuisine, culture and beautiful landscapes would resonate with other cyclists, and so inGamba was born.

Riding in Chianti is characterized by sweeping panoramas, winding ribbons of perfect tarmac, challenging climbs and thrilling descents. You can spend hours here without coming across other road users, and when you do, the locals are always friendly. In fact, it’s the people who give the place a lot of its charm, and over the course of your stay with us you’ll see why as you get to meet local artisans and culinary masters, all eager to give you a taste. We know every inch of the place like the back of our hands and we promise that if you join us there, you’re in for an unforgettable adventure.

Included With Trip:

  • All lodging*
  • All food and beverages**
  • Pinarello Dogma F12 Disk with SRAM RED eTap 11-speed WiFLi components and daily bike wash
  • One Giordana FRc custom inGamba cycling kit
  • Daily post-ride massage from a professional soigneur
  • Laundry service for cycling clothing

*Pre/post-trip lodging is not included

**Beverages ordered by guests beyond normal amounts and away from group activities will incur additional charges

Trip at a Glance

Start Location:


Finish Location:


Days Riding:


Group Size:

8 – 12

Total Distance:


Total Elevation:


Longest Day:

Day 4. Gargonza. 87km

Biggest Climbing Day:

Day 3. Dudda. 1,846m


Day by Day Breakdown


Il Giro del Barone

Benvenuti in Italia! Our first ride is an easy spin to shake off the cobwebs, but it’s also very pretty, rolling out of Lecchi and heading towards the stunning Castello di Brolio. After that, it’s south through the quiet Chianti countryside until San Giusto Alle Monache, where we’ll loop back towards home, eventually climbing through the neighboring town of San Sano before reaching the service course. 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 Colombiao at 55km.


It’s time for you and your bike to explore the beauty and brutality of Chianti’s hard climbs. Although the region is built on undulating terrain, today’s ride will include more sustained climbing, particularly in the second half of the loop. Starting out, we'll warm up on the way to Radda, climbing through Panzano and north to Le Quattro Strade. From there, it's east to Greve in Chianti, where the real challenge begins. The climb to Dudda is well-known as one of the toughest in the area, but don't overdo it, because right after we'll be going uphill again to Badiaccia A Montemuro on a climb that's around 9km long with sections that go above 11% in gradient.


Today’s ride takes us south towards Rapolano, an area just beside Crete Senesi that’s famous for its natural thermal spas and for the beauty of its rolling landscape. You can expect plenty of picturesque medieval towns and some stunning panoramic views along the way, but there’ll be some testing terrain too so this is much more than just a sightseeing loop. The day’s biggest climb comes just after the midway point, but it’s undulating throughout so you’ll need to manage the efforts carefully.


This relaxed route starts out heading north as far as Radda before turning around through Castellina in Chianti and heading south to Siena, one of Italy’s most beautiful cities. A UNESCO World Heritage Site, it dates back to Etruscan times and is famous for the annual Palio horse race — which is run around the Piazza del Campo, right in the heart of downtown.

Crete Senesi

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.

Badia a Coltibuono

The Badia a Coltibuono ride always reminds us how lucky we are to be able to ride here. Named after an abbey founded in 1051 by the patron saint San Giovanni Gualberto, there’s an enjoyable 7km climb followed by a rhythmic descent to Radda as a reward for your efforts. It’s a short but fun loop that involves just enough hard work to develop an appetite for dinner.




Pinarello Dogma F12 Disk


ZIPP Service Course SL




Speedplay (or your own)


Selle Italia


Zipp 302 Carbon Clinchers


Vittoria Corsa CX


Elite Custom Race


Elite Corsa Team


Garmin Edge 820