Arrive at any time. This evening, savour a traditional Portuguese dinner and performance of fado, a local folk singing tradition, in one of Lisbon's oldest neighbourhoods.

Travel back in time to the fairytale castles and hills of Sintra, a 19th-century resort town and UNESCO World Heritage site. Explore the colourful manors, medieval palaces, and lush gardens that enchanted English Romantic poet Lord Byron as well as Portuguese royalty. Enjoy a short orientation walk followed be a free afternoon to discover Lisbon’s pastel-hued architecture and lively plazas. Opt to soar over Lisbon on the historic Santa Justa lift, an engineering marvel that ascends 147 feet to an epic viewing platform.

Head to medieval Évora, in the heart of the bucolic Alentejo region, for a fascinating foray into the past. Be mesmerized by the haunting Chapel of Bones, erected by 16th-century Franciscan monks. Then pay a visit to one of the best preserved Roman temples on the Iberian Peninsula, known as Diana’s Temple.

Venture into the Alentejo countryside, home to centuries-old cork forests. Join a local expert at a traditional farm, and learn about cork harvesting and production. Then sit down to a traditional cork stripper’s lunch at the cork farm. This afternoon, return to Évora and explore its UNESCO World Heritage–designated city centre on your own, walking past whitewashed houses decorated with azulejos and wrought-iron balconies.

Spend the day in Tomar and delve into the Crusades era in Portugal. Go on a guided walk with a local expert around the vast medieval complex of the Convent of Christ, a UNESCO World Heritage site, and the Templar Castle, founded in 1160 by Gualdim Pais—grand master of the Knights Templar. Continue on to Coimbra for the evening.

This morning, enjoy a tour around the centuries-old University of Coimbra, Portugal's most prestigious university and a UNESCO World Heritage site. Enter through the 10th-century Porta Férra, the old entrance to the citadel of Coimbra. Following mosaic cobblestone paths around campus, stopping to see the baroque stylings of the Joanina Library, elaborate azulejo wall tiles adorning the Chapel of São Miguel, and the 18th-century Botanical Garden. Later, catch the train to Porto on the coast.

Board a boat down Portugal's Douro River, or "river of gold". Float on the typical Rabelo Boat along the riverbanks of Porto and Vila Nova de Gaia and marvel at the historical bridges connecting the two cities. Famous for centuries as a port wine shipper's centre, discover the rich tradition of port making at a local wine cellar, then cap off the day with a tasting of this distinct regional specialty. In your free time, explore the cobblestone streets of Porto’s medieval Ribeira district, marvel at the baroque São Francisco Church, and admire the palatial Palácio de Bolsa, a one time stock market.

Depart at any time.