Start off your adventure with a farm-to-table lunch surrounded by groves of silvery-green olive trees and wide plains • Cycle on tranquil back roads past rolling vineyards and ancient cork oak fields • Settle into a converted 16th-century estate in historic Évora, the region's capital city • Learn how the Alentejo—the world's leading cork exporter—harvests and produces this useful good • Savor homemade wines and rustic Portuguese fare at a local lunch • Stroll through Évora's well-preserved commercial center (ideal for souvenir shopping!) on a guided tour.

Spin through quintessential Algarve countryside passing green hillsides dotted with whitewashed homes and scented by fragrant citrus groves • Pause in the quiet town of Salir for a family-style Portuguese lunch • Wander through the covered market in the laid-back town of Loulé, where locals shop for fresh produce and regional specialties.

Take in majestic coastal vistas from the Monchique Mountains • Sample Medronho, a traditional wild berry liqueur, at a midmorning rest stop • Enjoy freshly caught seafood in Sagres, a breathtaking coastal town on the southern tip of Portugal • Ride along the wild and protected Costa Vicentina to the bustling town of Lagos, with views of unspoiled beaches, crashing Atlantic waves and windswept bluffs • Explore Lagos, and the dramatic cliff formations near it • On your last morning in Portugal, an out-and-back ride to Cape São Vicente leads to an iconic lighthouse and panoramic ocean views.