Black pork from the Alentejo plains, slow-cooked lamb with migas, açorda de coentros — a silky bread soup fragrant with coriander and garlic — fresh sheep’s milk cheese drizzled with local honey, wild mushroom rice, chouriço roasted over an open flame, and pastel de Tentúgal straight.
Alentejo reds from some of Portugal’s most celebrated estates, Vinho Verde to start the evening, Medronho brandy after dinner, fresh-pressed orange juice from the orchards we ride past, espresso from our La Marzocco, and a cold Sagres at the end of a long day in the saddle.
Vast cork forests, sun-bleached plains, ancient hilltop villages, and some of the most rewarding riding in all of Europe. Alentejo is the Portugal that most visitors never find — and that’s exactly what makes it so special.
This is the region that feeds the country: black pork, wild mushrooms, sheep’s milk cheese, hand-harvested olive oil, and wine from estates that have been producing for centuries. It’s also where much of the inGamba team grew up, which means this trip comes with something no guidebook can offer — genuine insider knowledge, passed on over long dinners and longer rides.
Over six days, you’ll move point-to-point through the heart of the region, staying in three of its most extraordinary properties. The riding is varied and endlessly scenic: quiet roads through olive orchards, climbs through Serra de São Mamede, and a final loop around Alqueva, Europe’s largest artificial lake. No transfers, no doubling back — just forward momentum through one of the world’s most quietly magnificent landscapes.
Borgolecchi is a destination in itself. Non-riding companions can enjoy a full programme of cultural experiences, relaxation, and Tuscan exploration while you’re on the bike.
For cyclists who like to keep the legs turning without too much time out of the saddle. Expect gentle undulations, flowing roads, and a rhythm that lets you soak in the scenery as much as the ride.
Stay in the stunning locations that we know and love, and spent years finding.
The latest DOGMA F engineered for any road, equipped with the lightest electronic groupset available. E-bike option also available.
Every breakfast, lunch and dinner — from handmade pasta to Fiorentina steak grilled while you watch. Wine, espresso and aperitivi included.
Seamless transfers to and from major airports in our inGamba fleet of vehicles.
High-tech performance meets luxury for the optimal riding experience with our Custom 36.5 kit.
Professional soigneurs with peloton experience ease sore muscles and prepare you for the next day.
Five mechanics work meticulously to ensure your Pinarello is race-ready every single morning of your trip.
Don't worry about chores whilst you're away, all cycling kit is cleaned overnight, so it’s fresh, dry and ready to go each morning.
Make use a beautiful day bag from Ideal & Co. Yours to keep after the trip.
Fill your pockets with fresh snacks, or make use of an entire Enervit collection.
Our trip begins in Monforte, a historic Alentejo region known for its tranquil countryside. The landscape is classic Alentejo: gently rolling plains dotted with cork oaks, olive groves, and vineyards, all under a vast, open sky. This area is rich in history, with roots stretching back to Roman times, and its quiet villages and whitewashed houses offer a glimpse into authentic rural Portuguese life. This is an easy ride to shake off the cobwebs and make sure everything on your Pinarello is to your liking. If something isn’t quite right, now is the time to speak to the mechanic.
On our second day, we will ride around Alegrete. It’ll be a scenic ride through rolling countryside, with just a teasing brush against the slopes of Serra de São Mamede—enough to keep things interesting, but not enough to make your legs regret it.
This point-to-point takes us south, from Torre de Palma to the wonderful the Convento do Espinheiro. While there are no major climbs to speak of, the terrain will be undulating throughout the day so be sure to conserve some energy for the home straight.
Riding around Évora is like stepping back in time, into a land of little villages and farms stretching out in every direction, criss-crossed by empty, undulating roads. Aside from the occasional tractor, we can expect to have the road to ourselves all day.
Today’s ride connects two gems of Alentejo: we’ll roll out from the historic Convento do Espinheiro, a former 15th-century monastery that’s hosted everyone from monks to monarchs, and make our way to the tranquil vineyards of Herdade do Sobroso. Along the way, you’ll pass through classic Alentejo scenery—think endless cork oak forests, sleepy whitewashed villages, and maybe even a stork or two perched on a chimney. By the time we reach Herdade do Sobroso, you’ll have earned a glass of their excellent local wine and a well-deserved rest amid the vines.
Our grand finale is the Alqueva Loop—a ride that circles Europe’s largest artificial lake, where the Alentejo sun glimmers on endless water and the sky seems even bigger than usual. This region is famous for its stargazing thanks to some of the clearest night skies in the world, but by day, you’ll pedal past olive groves, cork forests, and sleepy villages that haven’t changed much in centuries.
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.
After an impressive pro career that started back in 2003, Sérgio Paulinho joined the inGamba team at the start of 2022 after his retirement. But we’ve known him for a long time, as not only did he race against our founder João Correia, but he was also a teammate of our star guide Manuel Cardoso back in the day. A two-time national champion in Portugal, Sérgio has also won stages at the Tour de France and Vuelta a España, and in 2004, he won a silver medal in the road race at the Athens Olympics. So it’s fair to say the man has pedigree! It isn’t the racing victories that impress us most about Sérgio though, it’s his personality, his friendly nature on and off the bike, and the fact that he’s always ready with a smile. That said, if you find yourself running out of gas on a big climb, it certainly helps to have someone like him beside you!
”"We're specifically trying to give our guests the closest experience of what it means to be in a pro team, at any speed."
With years of experience in the professional peloton, our mechanics and soigneurs bring WorldTour-level care to every detail of your ride. Up to five mechanics work meticulously each day to ensure your Pinarello is perfectly tuned and adjusted for you alone—not just race-ready, but dialed to your precise preferences. Meanwhile, our soigneurs draw on their own experience as professional riders to anticipate your needs before you voice them: bottles filled and positioned exactly right, ride food prepared and timed to fuel you through the hardest climbs, post-ride massages that ease tired muscles, and the kind of quiet, confident support that prepares you mentally and physically for whatever the road brings next. This is the care that once belonged only to the pros. With inGamba, it’s yours.
Your week moves through three of Alentejo’s most extraordinary properties, each one a different expression of the region’s character.
Torre de Palma Wine Hotel is where the trip begins: a historic estate in the hills above Monforte, surrounded by vineyards and cork oaks that have been here for centuries. The wine is estate-grown, the pool is built for long afternoons, and the chapel in the courtyard has been standing since the 14th century. It’s the kind of place that makes you want to arrive early and leave late.
By mid-week you move to Convento do Espinheiro, a restored 15th-century monastery on the outskirts of Évora, a UNESCO World Heritage city. Monks, queens, and cardinals have all passed through here. You get frescoed corridors, soaring ceilings, a serious spa, and a bathroom with a freestanding tub and views across the Alentejo plain. History has never been so comfortable.
The week closes at Herdade do Sobroso, a working wine estate deep in the cork forests south of Évora. Dinner here is served under ancient stone arches, the wine comes straight from the cellar, and the silence after dark is the kind you only find this far from anywhere. A fitting end.
”"An amazing travel experience. They make you feel like a star. I was blown away by the treatment that can only be likened to a professional athlete — just without the race."
Daniel B.Guest in 2024
”"The whole experience is magical. The rides are stunning. The care and attention to detail is first class. The massages are a lifesaver."
Lyn K.Guest in 2018, 2019 & 2023
”"The best in the industry. A once in a lifetime experience every time! The people that make inGamba are the reason you will want to travel with them again and again."
Victoria P.Guest in 2024
Single Supplement: $1,200 per person · Private Trips: Available on request for groups of 6+
Guests of inGamba are passionate cyclists who love the sport and the lifestyle that surrounds it. Most of our community are experienced riders of all ages and various abilities, who appreciate great roads, fine food, and unforgettable company.
While everyone enjoys a challenge, no one’s chasing a pro contract here. Instead, the focus is on sharing incredible rides at a comfortable pace, soaking in the scenery, and enjoying the journey. You’ll find more “middle of the pack” and “social” riders than hard chargers at the front, and with our exceptional staff-to-guest ratio, every rider is fully supported, no matter their speed or style.
Fly to: Lisbon Airport (LIS)
Pick-up: Lisbon Airport 11:00
Drop-off: Lisbon Airport, departure from hotel at 8:30am
We recommend arriving the night before. Our concierge can help with hotel recommendations.
Gratuities are customary if you feel the staff delivered an exceptional experience. Most guests find 10-20% of the trip cost appropriate. All tips are split evenly among the entire team.
We recommend purchasing travel insurance to protect your booking. View our cancellation policy →
Need to change dates? Contact us as early as possible and we’ll do our best to accommodate.
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