Acorn-fed black pork grilled over coals, carne de porco à alentejana with clams, migas fried golden in olive oil, açorda alentejana, a fragrant bread soup with coriander, garlic and a poached egg, creamy Serpa sheep’s cheese with warm Alentejo bread, wild mushrooms in season, and sericaia, a cinnamon custard served with Elvas plums.
Bold Alentejo reds from Borba, Redondo and Évora, crisp whites of Antão Vaz and Arinto to start the evening, vinho de talha made in clay amphorae the way the Romans did, a glass of medronho after dinner, espresso from our La Marzocco, and a cold Sagres at the end of a long day in the saddle.
Much of the inGamba team of soigneurs and mechanics call Portugal home. This special trip is an opportunity to share their intimate knowledge and discover Alentejo, the sparsely populated, agrarian region known as Portugal’s breadbasket, that is also one of the world’s most charming and unique destinations.
Alentejo is famous for rich, uncomplicated cooking and for its salt cod, sheep’s cheese, black pork, olive oils, mushrooms – and its wine. The region makes almost half of Portugal’s total, and in some neat synergy, it’s also the largest producer of cork in the world.
On this week-long odyssey through the Alentejo, you’ll get to know it intimately from the vantage point of your saddle. We’ll be based in Estremoz at Casa do Gadanha, an elegant boutique hotel in the heart of town, so each morning begins with a quiet roll past marble squares and castle walls. Nestled among miles of cork oak, olive groves, and vineyards, this ancient region is regarded as one of the most beautiful in Portugal and is steeped in the history and culinary culture that make the Alentejo so irresistible—think long lunches, local talha wines, and whitewashed villages linked by serene, undulating roads.
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.
*Note that this itinerary may be subject to change.
We begin with a gentle loop around Estremoz, a historic hilltown famed for its marble quarries – the “white gold of Alentejo”. Flat roads and easy miles let you spin the legs and take in the scenery of vineyards and olive groves. Overlooking our route is Estremoz’s medieval castle, where Queen Isabel of Portugal spent her final days. It’s a relaxed warm-up ride that blends natural beauty with the town’s rich cultural heritage, setting the stage for the adventures to come.
Today’s ride leads to Vila Viçosa, known as the “Princess of Alentejo” and set in the heart of marble country. The approach is mostly rolling terrain, surrounded by olive orchards and marble outcrops. In town, we’re greeted by the imposing Ducal Palace with its 110-meter marble façade, a legacy of the Braganza dynasty that called this royal town home for 500 years. With over 150 marble quarries in the area, nearly every building here gleams with local stone. Cycling through ornate plazas and tree-lined boulevards, you can sense the opulence of a bygone era while enjoying the village’s laid-back charm.
We pedal through golden plains and cork oak forests towards Redondo, a quaint Alentejo town celebrated for its artisanal pottery and robust wines. Nestled at the foot of the Serra d’Ossa hills, Redondo charms us with whitewashed houses, a tiny medieval castle, and family-run pottery studios where centuries-old ceramic traditions live on. This region’s winemakers still honor ancient methods – some ferment their rich reds in huge clay talha (amphora) jars, just as the Romans did. After cruising past vineyards, we might pause to savor a sip of local talha wine or admire earthenware handiwork, experiencing Redondo’s rustic blend of history and homegrown hospitality.
A scenic loop carries us north on quiet backroads to the sleepy village of Veiros. We spin by pastoral fields – where the only sounds are distant sheep bells – before reaching this whitewashed hamlet with its modest 14th-century castle. Though Veiros is tranquil today, it holds a noble secret: it once belonged to the House of Bragança and was the birthplace of the family’s first duke, who would found Portugal’s last royal dynasty. Standing by the old castle walls and pillory, you can imagine medieval knights guarding these lands. This ride feels like a journey back in time, as we cycle through living history and return enriched by the village’s stories.
We cruise across open plains until the road ramps upward toward Évora Monte, a fortified village perched on a solitary hill. The climb is steady, leading to the ancient gates of Évora Monte and its striking Renaissance castle, distinguished by thick knot-like bands encircling its round bastions. From the hilltop, breathtaking views sweep across the Alentejo, an ocean of rolling wheat fields, cork forests, and distant villages. After absorbing the panorama, we enjoy a thrilling descent from the castle walls back to the tranquil countryside.
Our final loop explores the rural charms around Sousel, a land of ancient olive groves and gentle hills. We ride through quiet lanes flanked by gnarled olive trees, passing manor houses and farmland that reflect Alentejo’s slow pace of life. The normally flat plains are briefly interrupted by the limestone heights of Serra de São Miguel. A short detour up there rewards us with a 360º vista over the endless plains: to one side, patches of cork oak forest; to the other, mosaic fields and the village of Sousel itself, known for its fine olive oil and hunting heritage. It’s a fitting end to our journey, blending panoramic natural beauty with a touch of local tradition.
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!
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.
Tucked along one of the most central streets in Estremoz, Casa do Gadanha is a lovingly restored manor house turned twelve-room boutique hotel, a few minutes’ walk from the castle and the town’s marble squares. It’s the work of Michele Marques and Mário Vieira, the duo behind Mercearia do Gadanha, one of the Alentejo’s most beloved restaurants, and that same devotion to good food runs through the house. Rooms are calm and minimalist, finished with local touches and Alentejo sayings on the walls. Breakfast is a spread of regional specialties and fresh pastries, the restaurant downstairs celebrates the region’s ingredients, and up on the roof, a plunge pool and sun deck look out over the whitewashed rooftops of the “White City” to the plains beyond. After a day in the saddle, there’s no better place to watch the sun go down with a glass of local red.
* Please note that hotels may be subject to change.
”"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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