Step into Portugal’s storybook landscapes on this 12-day hiking and e-biking adventure, where cobbled medieval villages, forest trails, vineyard-clad hills, and megalithic mysteries await at every turn. From the golden plains of the Alentejo to the granite peaks of the Beira Mountains and the terraced beauty of the Douro Valley, this journey weaves together the best of Portugal’s countryside, culture, and cuisine.
We begin in the Alentejo, where ancient traditions echo through the oak and cork forests, stone circles dot the hills, and locals welcome you with a warm smile and a glass of robust red. Hike through rolling fields and past timeworn castles as you discover the peaceful rhythm of village life.
Then it’s time to cycle on our hybrid e-bikes through the mountain air as we pedal past the dramatic fortress walls of Trancoso, the granite homes of Linhares da Beira, and the hidden corners of Sortelha. Stop to admire Roman ruins, medieval towers, and panoramic views that make the climbs worthwhile. In the Douro Valley, the scenery softens to sweeping vineyards, historic estates, and postcard-perfect towns like Peso de Régua and Lamego.
Our trip ends with three nights in vibrant Porto, where the pace is yours to choose. Wander riverside lanes, explore baroque churches, sample port wine in atmospheric cellars—or simply soak it all in from a scenic café.
Walking, cycling, or unwinding – connect with Portugal’s past and present while sharing good company and exhiliarating adventures.
Lisbon, Portugal
Porto, Portugal
27 May – 7 June 2026
Our starting point is Lisbon. If you’re arriving with the group today, we’ll transfer together to our hotel. The rest of the day is yours to soak up the sights, sounds, and charm of this lively capital before we come together this evening for a welcome dinner – a chance to meet our fellow travellers and set the tone for the hiking and e-biking adventure ahead.
O/N 1 nt 3-4 star hotel
Our adventure begins today as we are whisked away to the charming hilltop village of Castelo de Vide. Settle in, get comfy, and enjoy the drive—this is our first taste of the tranquil beauty that defines Portugal’s Alentejo region. There will be time to take a stroll through the cobbled streets and enjoy a delicious dinner. The castle, perched above whitewashed houses, offers sweeping views of the Alentejo countryside—a first glimpse of the magic to come.
O/N 2nts Casa Amarela (or similar)
Today our hiking adventure begins. We start at the Meada Menhir, the tallest standing stone in the Iberian Peninsula and walk toward Monte Marôco, where sweeping countryside views greet us from its scenic hilltop. The trail winds through olive groves and cork oak trees, revealing the rustic charm of Alentejo. Passing scenic viewpoints and prehistoric standing stones our path leads back into Castelo de Vide, and it’s medieval castle with panoramic views. If we have energy left, we can explore the Synagogue Museum in the old Jewish Quarter before strolling the cobbled lanes back to our accommodation—a day steeped in history, nature and soul-soothing scenery.
Today our hike is from the charming village of Castelo de Vide to the hilltop haven of Marvão through the serene Serra de São Mamede Natural Park. We pass by red-roofed houses and lush green hills as our trail takes us through oak and chestnut forests. The path gently climbs to Marvão, known as the ‘Eagle’s Nest’ because of its lofty position, where cobbled streets, whitewashed houses, and (another) medieval castle await. Spend the rest of the day exploring the village, and taking in the breathtaking views.
O/N 2 nts Pousada de Marvão (or similar)
A downhill descent from Marvão and more spectacular views are in order for today. The first stop is a peaceful convent tucked just outside the village—an ideal place for a pause. Continue to the valley below, where the riverside village of Portagem awaits. Wander its leafy lanes and follow the gentle Rio Sever, a tranquil stretch rich in birdlife and natural beauty. We cross the stone bridge near a charming chapel before beginning the steady climb back to Marvão, rewarded by ever-expanding views and the silhouette of the hilltop village guiding us home.
Today is a well-earned rest day as we farewell the trails of Marvão and transfer north to the historic village of Trancoso. On arrival, we’ll get set for the next stage with a personalised bike fitting, ready to roll into the cycling chapter of our journey.
O/N 1 nt Solar Sampaio e Melo (or similar)
After a hearty breakfast, we start our cycle adventure. E-bikes are the way to go, crushing the inclines and declines with ease. We pass one of the more curious landmarks of the trip—a replica of the FIAT G-91 aircraft, honouring Portugal’s aviation history. From there, it’s a ride through postcard-worthy villages, their cobbled laneways and ancient stone buildings whispering stories of centuries past. The scenery keeps impressing, with panoramic viewpoints that practically beg us to stop, catch our breath, and take it all in. Ride through Vila da Ponte, steeped in Roman heritage, and the chestnut-rich region of Sernancelhe. We wrap up the day in the charming village of Freixinho. This is the perfect spot to treat yourself to something sweet—the Cavacas pastries are a local favourite.
O/N 1 nt Hotel Convento Nossa Senhora do Carmo (or similar)
Get those cycling legs geared up for a big day on the trails (thank goodness for e-bikes). As our journey continues through postcard-worthy scenery, we pass along the glimmering Vilar Dam. The Senhora da Saúde viewpoint offers sweeping views that are well worth a photo stop. We climb gently toward Alvite, passing through Moimenta da Beira—a lovely town cradled by rivers, vineyards and mountains. Explore its historical treasures, including the Mother Church and the Convent of Nossa Senhora da Purificação. The terrain starts to rise as we near Tarouca, where the magnificent Monastery of São João de Tarouca awaits—Portugal’s first Cistercian monastery, and a sight to behold. But the real showstopper? The medieval bridge in Ucanha. We’ll cross its ancient stones before riding through the peaceful Varosa Valley. A well-earned glass of local wine and a generous helping of regional flavours sounds like a perfect way to end the day.
O/N 1 nt Hotel Rural Casa dos Viscondes da Várzea (or similar)
Today we cycle deep into the heart of the Douro Valley—Portugal’s legendary wine region and a UNESCO World Heritage site. The landscapes are pure magic: steep vineyard terraces, grand old Quintas, and river views that seem to go on forever. We make our way through sleepy villages and sun-washed countryside, with a stop in Lamego to admire the impressive Baroque stairway leading to the iconic Nossa Senhora dos Remédios church. Follow the river all the way to Peso de Régua, a town synonymous with port wine and relaxed riverside charm. A tasting here is the perfect way to toast another unforgettable ride.
O/N 1 nt Orignal Duoro Hotel (or similar)
This morning we bid farewell to the peaceful pace of the countryside and turn our attention to the vibrant city of Porto.
After a short transfer to the city (1.5hrs) we check into our hotel and chill out with free time to time to discover the vibrant energy of this beguiling city. Get lost in the city’s winding streets, gaze at the tiled facades or enjoy an aperitif at a street-side cafe and simply watch the world go by. Later, we’ll gather for a relaxing sunset cruise along the Douro River—a picture-perfect way to toast our arrival and enjoy the city’s magic from the water.
O/N 2 nts 3-4 star hotel
This morning, we’ll set off on a walking tour of Porto, guided by a local who’ll share the city’s rich history, striking architecture, and some of the lesser-known stories that bring its past to life. The afternoon is yours to shape. Take it slow with a leisurely wander or simply enjoy a well-earned break. For those keen to dive deeper, you might opt to join a hands-on tile-making workshop (€30pp), where you’ll create your own Portuguese-inspired tile—compact, colourful, and easy to slip into your bag as a one-of-a-kind keepsake. Or, if you’re more of a hop enthusiast, a guided tasting tour of Porto’s emerging craft beer scene (€50pp) might be just the thing. This evening we will gather for a farewell dinner one last chance to raise a glass, relive favourite moments, and celebrate the new friendships and unforgettable adventures we’ve shared over the last 12 days.
All good things must come to an end. After a truly wonderful tour discovering the rich charms of Portugal we say goodbye to this beautiful country and the new friends we’ve made along the way. If you’re not quite ready to jump on that long-haul flight home just yet, don’t worry, we’re here to help you extend your adventure. Whether it’s a leisurely extra few days soaking up Porto’s magic, exploring the Algarve’s stunning coastline, or venturing onwards to another captivating destination, we can arrange the perfect next chapter to your journey.
Fearlessly taking on any challenge, Kerri works closely with Suzanne to curate unforgettable travel experiences for ICON Adventure clients. This dynamic duo can handle any situation, including the odd tricky one, to ensure your travel experience is seamless and worry-free.
Starting with Flight Centre in the 90s, Kerri has worked with various retail and wholesale travel companies. She has spent the last 20 years in local tourism and event management but is enthusiastically back working as a travel consultant (or Adventure Wizz as we like to call her).
Kerri’s contagious passion for exploration shines. From hiking the parks and forests of her local area, to sharing insider tips and planning international adventures, her enthusiasm for travel is evident in all she does.