Leave Lisbon behind and pedal into the sun-drenched plains of Alentejo, pausing at a cork producer to learn about one of Portugal's iconic natural resources. Continue to a family-run estate for a welcoming lunch, then explore the UNESCO-listed streets of Évora with a local guide. Settle into Octant Évora, your home for two nights, with cocktails overlooking the plains and dinner at the hotel.

Spend a second day exploring Alentejo's vast, quiet landscapes by bike, winding past cork oaks, vineyards, and olive groves to a traditional village café. Pause for a picnic lunch on a private property before returning to the hotel to unwind by the pool. This evening, enjoy a traditional singing performance in Évora, then choose your own restaurant for dinner in the city's vibrant gastronomic scene.

Leave the plains of Alentejo behind as the landscape shifts toward the coast, riding through cork and pine forests with a growing hint of Atlantic air. Pause in Grândola for a relaxed lunch before continuing through the gentle hills of the serra to Melides. Settle in for the night at Vermelho, a boutique hotel blending bold design with Alentejo's traditional craftsmanship.

Ride through rice fields and wetlands alive with storks, herons, and migrating birds on the way to the coast. Stop for a fresh seafood lunch by the ocean, with time for a swim in the Atlantic, before crossing Setúbal Bay by ferry. Arrive at Casa Palmela, a boutique retreat among the vineyards of Arrábida Natural Park, for cocktails, live music, and a barbecue dinner under the stars.

Begin the day with a visit to a traditional azulejo workshop before biking through the dramatic landscapes of Arrábida Natural Park, where sea cliffs, forests and hidden coves overlook the Atlantic. Board a private catamaran cruise along the coast and enjoy a picnic lunch onboard. Tonight, celebrate your final evening in Portugal with a winery visit,, regional cuisine and a soulful live fado performance in a historic setting.