Our journey begins in Lisbon, where the group gathers before setting out for the fairytale village of Sintra, tucked into the forested hills of the Sintra-Cascais Natural Park, a UNESCO World Heritage site. A place of legends and poetry, Sintra has long enchanted artists, dreamers, and royalty alike.
Our first stop is the Quinta da Regaleira, a mysterious 20th-century estate wrapped in romantic gardens, secret passageways, and arcane symbolism—where every path seems to whisper a forgotten story. From there, we ascend to the Peninha Sanctuary, perched high above the sea. With its windswept cliffs, crumbling hermitage, and panoramic views of the Atlantic, this serene outpost feels like a place suspended between earth and sky.
Our hike begins here, winding down through pine forests and open heathland toward the vast shoreline of Guincho Beach. We cross the rolling sands of the Cresmina Dunes, shaped by time and tide, and pause at the local nature center for a late lunch.
The landscapes here are a symphony of contrasts—rugged coastlines, hidden chapels, wild hills, and grand estates—where the natural and the manmade exist in quiet harmony. In the evening, we arrive in Cascais, a charming seaside town once beloved by kings, where a delicious dinner of regional flavors awaits.
Overnight in Cascais, Pestana Cidadela
Breakfast, lunch and dinner included
Hiking distance: 10.5 km / Hiking duration: 4 hr
Driving distance:
Lisboa to Regaleira Palace 30 km / 40 min
Regaleira to Peninha Sanctuary 15 km/ 30 min
We begin the day at Praia Grande, where the Atlantic meets towering cliffs in a scene of raw, untamed beauty. From here, our coastal path stretches toward Cabo da Roca, the westernmost point of continental Europe—a place where the world seems to fall away into the sea.
Along the trail, ocean breezes carry the scent of salt and wild herbs as we pass windswept bluffs and lonely fishing coves. Reaching Cabo da Roca, we pause to take in the vastness of the horizon and watch local fishermen practicing age-old traditions on the rocks below.
In the afternoon, we step into a different kind of quiet at the Convento dos Capuchos. Tucked deep in the forest, this humble 16th-century monastery was carved into stone and shaded by ancient trees. Built by Franciscan monks, it remains a powerful tribute to simplicity, solitude, and spiritual connection with nature.
Later, we return to Cascais, where cobbled streets, seaside views, and a gentle pace of life invite you to explore at your leisure. Tonight, dinner is on your own—perhaps a café by the sea, or a quiet table tucked away in the historic center.
Overnight in Cascais, Pestana Cidadela
Breakfast and lunch included
Hiking distance: 8 km / Hiking duration: 3,5 hr
Driving distance:
Hotel to Praia Grande 20 km / 35 min
End of the hike in Azoia to Capuchos 8,5km / 15mCapuchos to hotel in Cascais 13 km / 30 min
The day begins with a gentle seaside stroll from Cascais to Estoril, where the morning light dances on the waves. Soon, we leave the coast behind and cross the wide, glistening Tejo River, venturing south into a quieter, more pastoral side of Portugal.
Our first stop is Azeitão, a graceful town of tiled mansions and leafy streets. Here, we visit a traditional workshop and learn the art of azulejos—Portugal’s signature hand-painted tiles, each one a fragment of the country’s soul.
After time to explore and enjoy lunch on your own, we head into the Arrábida Natural Park, where limestone hills rise above vineyards and olive groves. Our afternoon hike follows the Rota dos Moinhos, or Windmills Path, past ancient stone mills and the haunting remains of a Copper Age settlement. The views stretch far over the Tejo Estuary, the Palmela Castle, and rolling hills that seem to fold into the sky.
By early evening, we arrive in Vila Nova de Milfontes, a whitewashed village nestled at the mouth of the Mira River. With its riverside charm, slow rhythms, and excellent seafood, it’s the perfect place to rest. Tonight, we gather for a cozy dinner in one of its most beloved local restaurants.
Overnight in Vila Nova de Milfontes, HS Milfontes Beach
Breakfast and dinner included
Hiking distance: 7,3 km / Hiking duration: 2 hr
Driving distance:
Estoril to Azeitão 57 km / 1 hr
Palmela to V.N. de Milfontes 149 km / 1 hr 40 min
Today we enter one of the wildest and most soul-stirring stretches of the Portuguese coast. A short ferry carries us across the pristine Mira River, where our path reconnects with the Rota Vicentina, a centuries-old fisherman’s trail that clings to the edge of the Atlantic.
As we hike south, the landscape shifts from gentle farmland to wild dunes and windswept bluffs. Hidden coves and sleepy fishing ports dot the shoreline, while the sound of waves and seabirds surrounds us. Towering cliffs lead us to Cabo Sardão, where white storks nest impossibly on the edge of the sea—the only place in the world where they do.
After taking in the drama of this place, we return to Milfontes, where the quiet flow of the Mira and a warm, familiar hotel welcome us back.
Overnight in Vila Nova de Milfontes, HS Milfontes Beach
Breakfast included
Hiking distance: 10 km / Hiking duration: 4h
Optional hike: 8 km / Hiking duration: 3h
Driving distance:
Almograve to V.N. de Milfontes 17 km / 15 min
This morning, we travel to Zambujeira do Mar, a picturesque village perched above the Atlantic. From here, we begin a breathtaking walk along one of the most geologically striking stretches of the coast. The path leads us over twisted rock formations, wildflower fields, and soft cliffs, with the ocean a constant companion.
Our destination is Ponta em Branco, or White Summit—a windswept promontory offering a stunning view of Odeceixe Beach, where the Seixe River meets the sea and the Alentejo yields to the Algarve.
We descend to the golden sands below and let the ocean air carry away the fatigue of the day. From here, we transfer to Sagres, a remote and storied town at the edge of Europe, where explorers once looked westward toward the unknown.
Overnight in Sagres, Memmobaleeira or similar
Breakfast, lunch and dinner included
Hiking distance: 13.7 km / Hiking duration: 6h
Driving distance:
V.N. Milfontes to Zambujeira do Mar 29 km / 30min
Odeceixe Beach to Sagres 57 km/ 1 hr
This morning you can choose to take it slow, enjoy a relaxed start to the day at the hotel before transferring to lunch in the coastal village of Zavial around 12:15, or join your guide for one final hike along the southern Algarve coast.
If you choose to hike, our trail begins right from the hotel in Sagres and follows the dramatic shale cliffs eastward. In spring, the path comes alive with wildflowers, while the views stretch across untouched bays, hidden coves, and a coastline that feels worlds away from the busy resorts farther east.
Along the way, you’ll pass small farms and fishing outposts where locals continue to live in harmony with the land and sea, producing the fresh ingredients that define the region’s rich and flavorful cuisine. Sagres remains one of the last bastions of wild beauty in the Algarve—a place where history, culture, and nature still thrive together.
We finish our walk at the golden sands of Zavial beach, where we’ll gather for a seaside lunch before continuing on with our journey back to Lisbon.
Breakfast and lunch included
Hiking distance 9.6 km / Hiking duration 3h
Driving distance:
Sagres to Plaza hotel in Lisbon or at the airport of Lisbon 320 km / 3 hrs
We are constantly updating our unique itineraries based on new information and experiences available. The walks, accommodations, and visits listed may be adjusted. The itineraries presented are subject to modification and change by Tripin Adventures. We reserve the right, without penalty, to make changes in the published itinerary whenever, in our judgment, conditions warrant, or if we deem it necessary for the comfort, convenience, or safety of participants, anything not mentioned in above program.
