Coastlines & Castles in Southern Portugal - September 25-October 5, 2026

Join us for an extraordinary 11-day journey through southern Portugal, where the Atlantic coastline's golden beaches meet medieval castles and centuries-old traditions. From the pristine shores of Comporta to the dramatic cliffs of the Algarve, through the historic heartland of Alentejo to magical Sintra, our all-women small group will discover Portugal's most captivating destinations. With its warm hospitality, world-class wines, and rich cultural heritage, southern Portugal offers the perfect blend of coastal serenity and authentic Portuguese life.

We've designed this trip to deliver equal parts adventure, culture, and luxury. Picture yourself horseback riding along untouched beaches where wild horses have galloped for centuries, navigating by private yacht to the famous Benagil Caves with their ethereal light, and trying your hand at the traditional art of azulejo tile-making. You'll journey through cork forests in 4x4 vehicles, taste exceptional wines at Portugal's oldest family-run winery, and experience the soul-stirring sounds of Fado—all with expert local guides who bring Portugal's stories to life.

Imagine exploring UNESCO World Heritage sites like medieval Évora, discovering Sintra's fantastical Pena Palace and exotic botanical gardens, and wandering through charming fishing villages along the dramatic Costa Vicentina. The itinerary balances cultural discoveries with indulgent leisure—from the world-class spa at Quinta da Comporta to the oceanfront elegance of Vilalara Grand Hotel Algarve, and the historic beauty of a restored convent in Évora. We'll conclude in Lisbon at the iconic Bairro Alto Hotel, perfectly positioned in the heart of this world-class city.

Every detail is expertly handled, leaving you free to immerse yourself in Portugal's enchanting blend of coastlines and castles. View the full trip description on our website, then get in touch if you want to learn more.