Medieval Towns & Traditional Wineries: A Journey Through Rural Portugal

Enjoy a morning of R&R in your beautiful hotel before getting ready for a day of exploring your medieval surroundings with a private guide. Boasting a cathedral without a bishop, a palace without a king and a bridge without a river, Guimarães is a city of many paradoxes. It dazzled as the nation’s first capital of Portugal during the 12th century and continues to delight visitors today with its wildly picturesque UNESCO-listed historic centre. This walking tour is a great opportunity to gain an insight into the fascinating history that swirls around the city’s many medieval sites, including the towering Castle of Guimarães, the Saint Michel Chapel and the Palace of the Dukes of Braganza, a medieval estate dating back to the 15th century.

Wave goodbye to the medieval treasures of Guimarães as you journey an hour and a half to Pinhão, a beautiful town nestled deep in the Portuguese hinterland. Your home for the next two nights here is a charming vineyard perched on the vertiginous banks of the Douro River. After settling in and freshening up, hop onto a private rabelo (traditional wooden cargo boat) and enjoy a gentle cruise down the beautiful Douro. The banks of the river are seriously picturesque, featuring a delightful collection of vineyards, farmhouses and tiny hilltop hamlets.

Continue savouring the delights of the Douro Valley today with a guided adventure to some of the region’s top sites. Born in the mountains of old Spanish Castile, the Douro crosses Portugal from east to west for nearly 150 miles, finally flowing into the Portuguese waters in the Atlantic Ocean in Porto. Your guide for the day is a clued-up local who knows these landscapes like the back of their hand. The focus of today naturally centres around the Douro’s prestigious wine production, with scheduled stops at a wine museum in São João da Pesqueira and a tasting with a view at Miradouro de São Salvado do Mundo. Round off your adventure with a cruise down the enchanting river aboard a rabelo. The rest of today is then yours to spend further soaking in the delights of the Douro Valley at your own pace. You can tour the many wineries that surround Pinhão, admire the period residences of Sabrosa, stroll along the medieval São Gonçalo bridge in Amarante or even enjoy a sunset aperitif on one of Porto’s many rooftop bars.

Soak in your final vistas of the Douro Valley as you travel two-and-a-half hours to Coimbra, a scenic riverside city steeped in medieval history. Break up the journey with a stop along the way at the charming town of Viseu. The town harbours a beautiful historic centre filled with traditional restaurants perfect for a lunchtime feast. Walk off your meal with a stroll through the enchanting walled arboretum of the nearby Buçaco Forest. On arrival in Coimbra, check in for two nights in a warm and welcoming guesthouse in the heart of the city and spend the rest of today settling into your new surroundings with a gentle stroll through town.

On today’s agenda: a private tour of Coimbra with a local guide who’s passionate about the city’s medieval roots. Coimbra is perhaps most famous for its historic university, which lays claim as the nation’s first university, as well as being one of the oldest higher-education institutions in Europe. As you get lost in the picturesque streets of the medieval centre, you’ll learn all about the city’s regal character (Coimbra was the birthplace of the first six kings of Portugal), as well as its historic connection to the university. During the Salazar dictatorship, the students at the university embodied a powerful fervour of resistance. Round off your walking tour with a visit to the Sé Velha Cathedral, which features a grand display of Romanesque art. The rest of today is then yours to spend further soaking in the cultural offering of Coimbra at your own pace. We recommend dining to the sound of fado (Portuguese melancholic music) at a traditional restaurant. Curiously, fado here is exclusively performed by men draped in black capes.

Hop back into your hire car this morning and hit the road three hours south to Evora, a beautiful city steeped in artistic and historic heritage. Along the way, make a stop at Arraialos, a delightful town famous for its oriental-patterned carpets and its pretty white-washed houses. There is also the medieval Castle of Arraiolos, which offers beautiful views across the ramparts and the olive groves beyond. Your home for the next two nights in Evora is a warm and welcoming guesthouse nestled inside an old convent. Spend the rest of today relaxing and enjoying the facilities at your new hotel ready for a day of exploring tomorrow.

Rise and shine, you only have one full day in Evora and there’s not a moment to waste. Today you’ll be exploring the ‘white city’ of Evora in the company of a knowledgeable local guide. Previously a second home of Portuguese sovereigns, the hilltop capital of the Alentejo region is nothing short of a living museum. In addition to its exceptional density of churches, which includes the Notre-Dame de l’Assomption basilica and the Chapel of Bones, Evora also houses the famous temple of Diana, a formidable example of the Roman presence in the region. Spend a few hours soaking in these impressive sights with your clued-up guide before spending the afternoon getting lost in the historic centre, which protects an incredible wealth of art, history and culture within its 17th-century ramparts. We could also arrange for you to head onto the gentle waters of Lake Alqueva for a private cruise.

Your epic road trip across Portugal continues today with a one-hour drive to Alcacer do Sal, an enchanting medieval town nestled along the banks of the Sado River. Settle in for your final two nights here in a stylish hotel fit with indulgent facilities before spending the rest of today soaking in your new environment with an evening of wining and dining in the historic centre.

Stretching from Cape Espichel to Palmela, the Setubal peninsula is a seriously scenic sliver of Portugal filled with vineyards, orchards and olive groves. Head out into these enchanting lands today to reach a beautiful family-run vineyard. After touring the vineyards and cellars, settle in for a tasting of indulgent wines made from local grape varieties, such as Trincadeira, Touriga Nacional, Aragonês, Syrah and Alicante Bouschet, alongside a selection of regional specialities.