Cross the 25th of April Bridge out of Lisbon and the air shifts immediately—warmer, drier, scented with cork and wild lavender—as your first ride carries you through olive groves to the foot of Alter do Chao's medieval castle for lunch. Tonight's home is Torre de Palma, a 14th-century landmark tower reimagined as a wine hotel, where a cellar tour, sky bar cocktails with 360° views and a welcome dinner under the stars await.

Today's loop winds through whitewashed hilltop villages and into the Serra de S. Mamede Natural Park, with a wine tasting and gourmet picnic at Quinta da Fonte Souto — a converted estate winery on private grounds. The afternoon is yours (pool, spa, horseback ride, or the optional Century route), before chef Ruben hosts the group for a rooftop dinner, followed by a stargazing lesson.  

This morning’s ride takes us west toward Evora, where we’ll dive into Portugal’s famous cork industry. We'll arrive at our friend Nuno's family estate for a tour and homemade lunch with his own wines, before arriving in Evora — a UNESCO World Heritage city with a Roman temple, one of Europe's oldest universities and streets narrow enough to get pleasantly lost in. The evening ends with a magical event over cocktails and petiscos, then the night is yours to explore.

Joined by our local guide, we'll spend the morning learning about Evora's layered history, wandering its narrow streets and stopping to see some of its most important monuments. Then, pedal along Alentejo's Atlantic coast, stopping for a fresh seafood lunch at Praia da Comporta, right on the beach. A short ride and a ferry crossing bring you to Casa Palmela, a former manor farm turned boutique hotel among the Arrabida vineyards, for an evening of cocktails on the terrace and dinner.

The morning starts at a traditional azulejo workshop before the day's ride climbs into the Arrabida Natural Park, finishing at the Setubal piers where a catamaran is waiting to sail you along the limestone cliffs — picnic on deck, dolphins if you're lucky! Back at Casa Palmela, the final evening brings golden hour cocktails on the terrace, local delicacies and a final night celebration to remember.