23 nov - 30 nov
PUGLIA FROM THE INSIDE
More Than a Cycling Tour
A Week Through Italy's Deep South
Stone towns carved into cliffsides. Cave churches from the 9th century. Whitewashed villages surrounded by olive groves that have been here for a thousand years. Puglia is the part of Italy that most visitors never reach, and the part that Italians keep for themselves.
This trip takes you through all of it at a comfortable pace - from the ancient streets of Bari to the Sassi of Matera, through the trulli of Alberobello, past wineries and mozzarella farms, and down to the Adriatic coast at Polignano a Mare. Short days on the bike, long lunches, pool time in the afternoon, and dinners that make the whole day worth it.
Eight Days from Bari to the Adriatic Coast
DAY 1
Bari and the Drive to Ruvo
You land in Bari. Before leaving the city, we walk through Bari Vecchia - the old quarter where women still make orecchiette by hand in the doorways - and visit the Basilica di San Nicola. From there, a private transfer takes you to Ruvo di Puglia, where we check into Hotel Pineta. Bike fitting if time allows, then dinner together to open the week.
DAY 2
Ruvo to Matera via Altamura
The first real day on the bike. We ride south through the Puglian countryside to Altamura, a hilltop town famous for one thing: bread. Pane di Altamura has its own DOP designation, and lunch revolves around it. After eating, another 20 kilometers brings us to Matera - the city built into a limestone gorge, inhabited for 9,000 years. Dinner tonight is in the Sassi, the ancient cave district. We stay two nights here.
DAY 3
Matera Loop and Evening in the Sassi
A morning ride through the Murgia plateau, past cave churches carved into the rock by monks a millennium ago. Coffee stop in Ginosa, then back to Matera by early afternoon with time for the pool or spa. In the evening, a guided walk through the Sassi as the sun goes down. Dinner in a restaurant carved directly into the rock.
DAY 4
Matera to Alberobello
The longest ride of the week, and the one where Puglia starts to change around you. The dry, rocky landscape softens into green rolling hills, stone walls, and red soil. We stop for coffee along the way, lunch near Noci, and arrive in Alberobello by late afternoon. Pool first, then a walk through the trulli district - hundreds of cone-roofed stone houses clustered together in a way that exists nowhere else on earth. You turn a corner and it feels like you've walked into a fairy tale someone forgot to write down.
DAY 5
Ostuni via Martina Franca and the Wineries
A shorter day with more stops. We ride to Martina Franca, a baroque town with wide piazzas and the kind of coffee you'll think about for months. Then through Cisternino and on to Cantine Semeraro for a winery tour, tasting, and light lunch among the vines. We arrive in Ostuni by mid-afternoon - the "White City" perched on a hilltop, every building painted the same blinding white against blue sky. Check into Hotel Monte Sarago. Spa, pool, dinner. Two nights here.
DAY 6
Ostuni Loop: Carovigno, San Vito, Masseria
An easy loop through the countryside around Ostuni. Coffee in Carovigno, a quick stop in San Vito dei Normanni, then the highlight of the day and possibly the week: Masseria Fragnite, where you walk into the caseificio and watch burrata being made by hand, then eat it still warm, minutes old, with bread and olive oil. Nothing in a restaurant will ever taste like this. Back to Ostuni for the pool, spa, and dinner in the old town.
DAY 7
Ostuni to Polignano a Mare
The flattest and most relaxed day of the trip. We ride toward the coast with a coffee stop by the sea, then lunch in the port town of Monopoli where the fishing boats are still tied up at the harbour wall. A short transfer brings us to Polignano a Mare - the town built on cliffs above the Adriatic, with the famous Lama Monachile cove carved between the rocks below. Check into Pietrablu Resort. Afternoon by the pool or the sea. Farewell dinner with the sound of waves underneath you.
DAY 8
Departure
Sleep in. One last breakfast at the resort with the Adriatic in front of you. There is no rush, no packing chaos. You leave your bike with the team, and a private transfer takes you to Bari airport at whatever time your flight requires. A week of Puglia in your legs and in your stomach - and the taste of that burrata still fresh in your mind.
The Man Behind the Roads
Rodolfo Massi won a stage at the Tour de France in the Pyrenees. He won a stage at the Giro d'Italia. He wore the King of the Mountains jersey - the polka dots - through the same cols you'll ride on this trip.
He's not a tour operator who studied a map. He's a former professional who spent his career on these exact roads. He knows where the gradient kicks, where the wind hits, where to stop for the view that nobody else knows about. And he knows something most guides don't: how to make a climb feel like a gift instead of a punishment.
Today, Rodolfo takes a handful of people each year through the mountains that shaped his life. Not to race. Not to suffer. To feel what it's like to ride roads that were built for something extraordinary - with someone who lived it.
Massi's "Service Course" Treatment
We handle every logistical detail so your mind remains completely free.
Note: flights, medical insurance, room upgrades and personal expenses are not covered.
Worried You're Not Fast Enough?
Read This
Every single person who books this trip asks some version of the same question:
"Can I actually do this?"
Yes. Here's why.
This is not a race. There is no pace to hold and no group to keep up with. Rodolfo has guided riders of every level through these cols - from people who train five days a week to people who ride on weekends when the weather is nice.
The support van follows the group every day. If you hit a wall, you can still enjoy the view in the van without judgment. If you want an e-bike for the bigger days, several guests choose exactly that every trip.
The only thing that matters is that you enjoy riding. If you're worried about being a burden, that worry itself is proof that you're the kind of person this trip was made for: someone who cares about the experience and the people around them.
the investment
8 days across the French Alps with Rodolfo Massi. Luxury accommodation, all dinners, airport transfers, full ride support, and mechanical service included.
puglia
23 nov - 30 nov
$3,800
8 days
7 nights
Bari to Polignano
Limited to 12 spots
your piece of mind
Will I slow the group down?
What about my luggage and transfers?
How do I add videos?