We might be biased, but Portugal is one of our favorite destinations here at Classic Journeys. Whether it’s a day spent traversing the seven hills of Lisbon, meeting the maker of hand-crafted olive oil in the Alentejo, or cruising through the grape-spangled slopes of the Douro Valley, we’re confident that this delightful country will fast become a favorite of yours too when you embark on our Portugal Cultural Walking Tour.

With this itinerary, you’ll explore enchanting cities, candy-colored palaces, castles, vineyards, and medieval villages in ways that can only be experienced with us. As ever, we veer far beyond the usual tourist trail, showing our intrepid guests a side of the destination that not all travelers are fortunate enough to see. These are just a few of the unique, experiential moments you can expect on your Portuguese adventure with Classic Journeys…

Visit Pena Palace, Before It Opens to the Public

Pena Palace in Sintra, Portugal

It’s an early start to our morning in Sintra, a UNESCO-inscribed town just northwest of Lisbon, but we know the luxury of an unimpeded visit to one of Portugal’s must-see attractions is worth it. Blending a mix of cultural influences and architectural styles that range from Moorish to Romanticism, Sintra was a long-time playground for the royal and rich, and today is the stuff of real-life fairytales.

Most striking of all is Pena Palace, a hilltop National Monument whose red, yellow, and lilac turrets draw millions of annual sightseers, making it the country’s most frequented site. This would usually mean jostling for space, clashing elbows, and competing for photographs but, with our exclusive access to the property, you’ll be able to beat the crowds and experience a visit here like no other. Before it opens to the public for the day, we’ll arrive at the colorful palace to leisurely stroll through the opulent halls, chambers, and gardens that were once the domain of kings and queens.

Sip a Glass of Portuguese Wine at a Douro Valley Vineyard

The scenic Douro Valley with its many lovely vineyards

There are several totems of Portuguese food culture that you should seek out during your time in the country; bacalhau (salt cod), pastéis de nata (custard tarts), Iberico pork, and francesinha (a multi-layered decadent sandwich hailing from the city of Porto) to name just a handful. But its crowning glory are the world-famous fortified port wines cultivated from the fruits of the verdant Douro Valley, a sprawl of beautiful UNESCO-recognized countryside rich with delicious possibilities. Port wine, or Porto, is characterized by its sweet flavor and aroma, often with notes of caramel, warm spices, and red berries. It is impossible to replicate anywhere outside of Portugal as port has a Protected Designation of Origin, meaning it can only be created right here in this country. You’ll have the chance to sample the iconic beverage for yourself on our cultural walking tour of Portugal.

The journey steers north and takes us through stunning Douro vineyards, where we will then be met by one of the region’s finest winemakers for an afternoon at their acclaimed quinta. Here, we learn how they craft their wines, plant the terraced vineyards with horse and plow, and trim and harvest the grapes by hand. Our exploration of the winery is topped off with a tasting of the house wines, accompanied by an indulgent picnic of local specialties – further proof that, in Portugal, too much is never enough.

Cruise Down the Douro River in a Portuguese Rabelo Boat

A classic rabelo boat in Portugal

Portugal’s Douro Valley is the second-oldest protected wine region in the world, after Chianti in Italy. Its historic scenery is marked by mountains and emerald, vine-covered slopes rising from the banks of the Douro River, which carves through the landscape from Porto into Spain.
One of the best ways to appreciate the full scale of this area’s beauty is by getting out on the water. As part of our trip itinerary, we include morning passage along the river in a traditional wooden Rabelo boat, which in its prime would have been used to convey port from the vineyards to the cellars of Vila Nova de Gaia (where we’ll also visit) before the time of roads and rail lines. These one-of-a-kind vessels are shallow and flat-bottomed to account for the Douro’s fast flow, and we think they’re the perfect mode of transport for this picturesque voyage.

Enjoy Having a Full-Time Portuguese Guide by Your Side

Our expert local guides can't wait to welcome you to Portugal

We’re big believers that the greatest tour guides are those with a personal, profound connection to the places and cultures they represent. That’s why we solicit the services of expert local guides wherever we go – to paint the most authentic and thorough picture of a destination through the eyes of the people who know it best.

On the Classic Journeys tour of Portugal, our insider guide becomes more like a trusted friend, whose valuable connections and knowledgable recommendations grant our guests opportunities to try the best Mediterranean-Asian fusion cuisine in Cascais, walk the ancient town walls of Marvão, and much more. They’ll warmly welcome you to their country and immerse you throughout the week in meaningful interactions, wonderful discussions, hidden highlights, and local encounters that will enrich your travel experience in unforgettable ways.

Ready to explore Portugal with Classic Journeys? Join us on foot and at eye level, to experience the best of this wonderful country. Contact us to reserve your space on an upcoming tour departure date.

A cliff in Portugal.