14 Day Portugal & Madeira Active Tour

• Day 1: 

  Arrival in Lisbon
  We arrive in Portugal's vibrant capital. Lisbon's story begins with Phoenician traders who called this natural harbour "Allis Ubbo" - safe haven - over 3,000 years ago. The city's seven hills stretch before us, each crowned with viewpoints that have witnessed everything from Roman legions to Moorish conquests to the Age of Discovery's bold departures.
  
  Overnight in Lisbon.

   

  Included Meal(s): Dinner
• Day 2: 

  Lisbon Exploration
  Morning finds us exploring Lisbon's soul on foot, beginning in Alfama, the city's oldest neighborhood where narrow medieval streets wind upward like a stone labyrinth. Built by the Moors in the 8th century, Alfama survived the devastating 1755 earthquake that leveled much of Lisbon, making it a living museum of medieval architecture. We climb past tiny tavernas where locals sip their morning coffee, our footsteps echoing on cobblestones worn smooth by eight centuries of daily life.
  
  Ascending through this vertical village, we pause at miradouros (viewpoints) that reveal the Tagus River spreading like molten silver toward the Atlantic. Laundry flutters from wrought-iron balconies while the haunting melodies of fado drift from hidden courtyards, creating an atmosphere unchanged since Moorish times.
  
  At São Jorge Castle, we walk the ancient ramparts where Moorish rulers once gazed across their western European stronghold. These weathered stones now offer us panoramic views over terracotta rooftops cascading toward the gleaming Tagus, where the iconic 25 de Abril Bridge spans the estuary like a crimson gateway to the sea.
  
  After a break for lunch in the grand Rossio Square - its distinctive wave-pattern cobblestones creating optical illusions beneath our feet - we explore Baixa district's elegant 18th-century grid. This rational urban design represents Europe's first earthquake-resistant city planning, where wide boulevards and reinforced buildings rose from earthquake rubble under the Marquis of Pombal's visionary reconstruction.
  
  We then ascend through the atmospheric Elevador de Santa Justa to fashionable Chiado, where writers like Fernando Pessoa penned poetry in iconic cafés that still serve bica coffee in tiny cups. The neighborhood's Belle Époque facades and literary heritage create an atmosphere of refined bohemian elegance.
  
  As afternoon light transforms the city to gold, we reach Miradouro de Santa Catarina, where locals gather to watch spectacular sunsets behind the bridge they affectionately call their "Golden Gate."
  
  Afternoon Options: Continue walking through Bairro Alto's steep streets lined with traditional shops and emerging galleries, or descend to Cais do Sodré for riverside strolls along the Tagus promenade where historic trams still clatter past waterfront cafés.
  
  Walk Summary: 4-5 hours covering 6-7 km through historic neighborhoods. Moderate to challenging terrain with significant uphill walking on cobblestone streets and stone staircases. Mix of narrow medieval alleys and wide boulevards with numerous scenic viewpoints.
  
  Overnight in Lisbon.

   

  Included Meal(s): Breakfast and Dinner
• Day 3: 

  Sintra Hike & Village Visit
  Today we travel to the charmingly historic town of Sintra, which seems plucked from a Brothers Grimm tale. Sintra's cobblestone streets wind between pastel-coloured mansions where 19th-century aristocrats built summer villas, creating Portugal's most romantic town centre.
  
  We bypass the challenging 2 km steep ascent by taking taxis directly to Pena Palace, our circular hike's start point. King Ferdinand II's 19th-century romantic masterpiece sprawls across the hilltop in a riot of colours - yellow towers, red battlements, and Moorish arches creating Portugal's most picturesque castle. We focus on exterior views and gardens, as the palace's vibrant architectural fantasy is actually its most spectacular feature.
  
  A highlight of our walk through ancient forest paths is the dramatically-perched 10th-century Moorish Castle, where weathered stones whisper of Christian reconquest battles. From these battlements, Moorish governors once controlled the strategic route between Lisbon and the Atlantic coast.
  
  We return to Sintra's charming village centre for lunch and independent exploration. Options include browsing artisan shops along Rua das Padarias or relaxing in traditional quintas (manor house gardens). Be sure to sample travesseiros - delicate almond pastries invented here in 1862 at Piriquita bakery.
  
  Before returning to Lisbon, we visit Quinta da Regaleira, revealing eccentric millionaire Carvalho Monteiro's obsessions, who spent 40 years creating an elaborate mystical landscape. We descend the famous Initiation Well - a 27-metre spiral staircase plunging into Earth's depths - and explore tunnels connecting mystical grottos adorned with Masonic and Templar symbols.
  
  Hike Summary: 4-5 hours of moderate hiking covering 5-6 km/3-4 mi through forested paths and palace grounds. Mostly undulating/downhill terrain with 300 metres/984 ft total descent on forest trails and stone paths.
  
  Overnight in Lisbon

   

  Included Meal(s): Breakfast and Dinner
• Day 4: 

  Lisbon - Alentejo: Castelo de Vide & Portalegre
  We leave Lisbon's urban energy for Alentejo's rolling plains, where cork oaks stretch toward horizons broken only by medieval towers. Castelo de Vide emerges from morning haze like a mirage, its white houses cascading down a hilltop crowned by a 13th-century castle. This remarkably preserved town harbours one of Iberia's most significant Jewish quarters, where Sephardic families flourished until the Inquisition's dark reach extended across Portugal.
  
  We explore narrow streets where Hebrew inscriptions still mark ancient doorways, visiting the medieval synagogue that served as a house of worship for over 200 years. The Gothic fountain at the town's heart has bubbled continuously since the 14th century, its waters believed to possess healing properties that drew pilgrims from across Europe. From the castle ramparts, we gaze across the Serra de São Mamede's granite peaks, understanding why this border fortress commanded strategic importance for centuries. You’ll have some time here to get some lunch and explore at your own pace.
  
  Our afternoon journey to Portalegre, the region's historic capital, positions us perfectly for tomorrow's mountain adventures. This textile town, famous for hand-woven tapestries that adorn palaces worldwide, offers authentic Alentejo cuisine featuring local wild herbs and local wines carry the essence of sun-baked earth. Tonight, we rest in anticipation of exploring one of Portugal's most pristine natural parks.
  
  Walk Summary: Approximately 2-3 hours of gentle exploration covering 5 km/3.1 mi through historic village streets and castle grounds. Moderate uphill walking on cobblestone streets with 150 metres/492 ft elevation gain to castle viewpoints. Terrain includes uneven medieval stonework and some steep narrow alleys.
  
  Overnight in Portalegre

   

  Included Meal(s): Breakfast and Dinner
• Day 5: 

  Mountain Fortress & Ancient Trails
  Morning finds us entering Serra de São Mamede Natural Park, where pristine cork oak forests harbour some of Iberia's rarest wildlife. Our hiking trail winds through landscapes unchanged since Roman times, revealing archaeological sites where Celtic tribes once gathered precious metals from mountain streams. The 6-8 km interpretive route with numbered discovery points showcases the park's incredible biodiversity - over 800 plant species thrive here, including endemic orchids that bloom nowhere else on Earth. Well-positioned viewpoints reveal dramatic transitions from ancient schist valleys to granite peaks.
  
  We then ascend to Marvão, often called Portugal's most spectacular village. This 13th-century fortress town balances impossibly on a granite crag 860 metres (2,822 feet) above sea level, its medieval walls following natural rock contours like a stone crown. From the castle's highest tower, Spain stretches eastward across the Alentejo plains, explaining why this strategic position controlled trade routes between kingdoms for 800 years. The village's 300 residents maintain traditions dating to the Middle Ages, from stone masonry techniques to recipes passed down through generations. Walking Marvão's narrow cobblestone streets feels like time travel - every archway frames views across battlements to distant horizons.
  
  As afternoon shadows lengthen, we journey to Castelo Branco, positioning ourselves for tomorrow's encounter with one of Europe's most extraordinary villages. This episcopal city, known for its exquisite baroque gardens and distinctive embroidered bedspreads (colchas), offers the perfect blend of urban comfort and traditional Portuguese charm for our evening's rest.
  
  Hike Summary: 3-4 hours of moderate hiking covering 6-8 km/4-5 mi through cork oak forests on marked interpretive trails with educational stops. Well-marked trails with gentle to moderate inclines and 200 metres/656 ft total elevation gain. Natural paths with some rocky sections and root obstacles. Distance can be shortened to 4-5 km if group prefers more time exploring Marvão village and castle.
  
  Overnight in Castelo Branco

   

  Included Meal(s): Breakfast and Dinner
• Day 6: 

  Granite Giants & Ancient Rome
  Monsanto appears like a geological impossibility - houses sprouting between granite boulders the size of buildings, creating architecture that defies conventional logic. This "most Portuguese village" earned its title not through tourism marketing, but by preserving building techniques unchanged since Celtic times.
  
  We begin with a mountain loop hike above the village, where 4-5 km (2.5-3 miles) of ancient paths lead to panoramic viewpoints revealing how glacial action scattered these massive stones across the landscape millions of years ago. The village itself becomes our outdoor museum as we wind between houses where granite boulders serve as walls, roofs, and even dining room tables. Medieval castle ruins crown the highest outcrop, where Christian forces once maintained vigilance against Moorish raids.
  
  After a break for lunch, we embark on a section of the GR22 trail toward Idanha-a-Velha, following Roman roads through countryside dotted with abandoned windmills and cork groves. Idanha-a-Velha reveals layers of Portuguese history in its archaeological treasures - Roman temples, Visigothic churches, and medieval fortifications occupy the same sacred ground. This UNESCO-recognized site served as a Roman municipal capital, then a Templar stronghold, before plague and war reduced it to today's hamlet of 50 residents. Cathedral ruins and Roman inscriptions tell stories of prosperity and decline, while ancient olive trees continue producing fruit as they have for a millennium.
  
  We end our day in mountain town Guarda, ready for tomorrow's ascent into mainland Portugal's highest peaks. At 1,056 metres elevation, Guarda stands as Portugal's highest city, its granite cathedral and medieval walls earning it the nickname "City of Four F's" - Fria, Farta, Forte e Feia (Cold, Abundant, Strong, and Ugly).
  
  Hike Summary (Monsanto Loop): 2-3 hours covering 4-5 km/2.5-3 mi on ancient mountain paths. Moderate terrain with 200 metres/656 ft elevation gain to summit viewpoints. Rocky granite paths with some scrambling sections. Can be shortened to village exploration only.
  
  Hike Summary (GR22 Trail): 1-2 hours covering 3-6 km/1.9-3.7 mi on gentle countryside paths with minimal elevation change. Dirt tracks and Roman stone sections. Distance flexible based on time and group energy levels.
  
  Overnight in Guarda

   

  Included Meal(s): Breakfast and Dinner
• Day 7: 

  Walking Serra da Estrela - Douro Valley
  We ascend into Serra da Estrela, where glaciers carved Portugal's most dramatic mountain landscapes during the last ice age 30,000 years ago. Starting above 1000 metres (3,280 feet) elevation, our 4-5 km (2.5-3 mile) granite plateau loop reveals why this UNESCO Geopark captivates geologists worldwide. Ancient glacial valleys stretch below us like stone amphitheatres, while granite tors - weathered rock pillars - stand sentinel across the landscape like petrified giants.
  
  The trail leads us to spectacular "balcony" viewpoints where the Atlantic's influence meets continental climate, creating unique ecosystems found nowhere else in Portugal. Endemic plants cling to granite crevices, including the rare Serra da Estrela violet that blooms only at these altitudes. From our highest point at 1020+ metres (3,347+ feet), the view encompasses half of Portugal - from Spanish peaks eastward to Atlantic coastal plains westward.
  
  Our afternoon descent toward the Douro Valley reveals one of Europe's most dramatic landscape transitions - from granite peaks to river-carved gorges lined with terraced vineyards. By evening, we reach the heart of port wine country, where the rhythm of mountain silence gives way to the gentle flow of the Douro River, promising tomorrow's immersion in viticultural traditions dating to Roman times.
  
  Peso da Régua, the unofficial capital of the Douro wine region, is located at the confluence of the Douro and Corgo rivers, surrounded by UNESCO World Heritage terraced hillsides. This charming riverside town serves as the nerve center for port wine production, its 19th-century railway station still receiving barrels from quintas upstream, continuing a tradition that made the Douro the world's first demarcated wine region in 1756.
  
  Hike Summary: 2-3 hours of moderate mountain hiking covering 4-5 km/2.5-3 mi on granite plateau at 1000 metres/3,280 ft elevation. Well-maintained paths with moderate elevation changes totalling 150 metres/492 ft gain. Some rocky sections and granite steps. Route can be extended to portions of the longer PR14 CVL trail (up to 12 km) based on group ability and weather conditions.
  
  Overnight in/near Peso da Régua

   

  Included Meal(s): Breakfast and Dinner
• Day 8: 

  Douro Valley Walk & River Cruise
  The Douro River carved its valley through schist bedrock over millions of years, creating the stepped terrain that makes port wine possible. Our morning vineyard hike follows ancient paths between terraced quintas (wine estates), where families have cultivated grapes for over 2,000 years. The 5-7 km (3-4 mile) moderate route reveals the incredible human effort behind every bottle - these terraces, built entirely by hand, represent one of humanity's most impressive agricultural achievements.
  
  We visit a traditional quinta where the vintage rhythm continues unchanged: grapes still crushed by foot in granite lagares (tanks), juice fermenting in oak casks cooled by Douro breezes. The quinta owner, whose family has produced port for generations, explains how this harsh landscape - winter temperatures dropping to -10°C (14°F), summer heat reaching 45°C (113°F) - stresses vines into producing intensely concentrated grapes that create port's distinctive character.
  
  This afternoon we enjoy a peaceful scenic cruise along the legendary river that has shaped this UNESCO World Heritage landscape for millennia. We embark on a short but memorable journey floating past the terraced vineyards that cascade down steep valley walls like giant stone staircases, each terrace representing centuries of human determination to cultivate wine in seemingly impossible terrain.
  
  Our cruise reveals the intricate relationship between the Douro River and Portuguese viticulture—how these ancient waterways transported precious port wine from remote quintas to Porto's cellars for over 300 years aboard traditional rabelo boats. As we glide past schist slopes adorned with meticulously maintained vines, we understand how this dramatic landscape earned its designation as the world's oldest demarcated wine region, where Romans first planted grapes over 2,000 years ago.
  
  Hike Summary: 2-3 hours of moderate vineyard hiking covering 5-7 km/3-4 mi through terraced landscape. Gentle to moderate inclines on dirt vineyard paths and stone terrace steps with 200 metres/656 ft total elevation gain.
  
  Overnight in Peso da Régua

   

  Included Meal(s): Breakfast and Dinner
• Day 9: 

  Douro Valley - Camino Português Coastal Walk - Porto
  An earlier start this morning allows us to combine our transfer to Porto with an authentic Camino experience along Portugal's dramatic Atlantic coast. The Camino Português, one of the major pilgrimage routes to Santiago de Compostela, Spain, has guided travellers from Lisbon through Porto toward Galicia for over 800 years. Its coastal variant, established more recently but following ancient fishing community paths, offers pilgrims an Atlantic alternative to the traditional inland route.
  
  We depart Peso da Régua and travel to Vila do Conde, where the Ave River meets the Atlantic, and which has welcomed pilgrims for centuries along the Camino Português coastal route. This historic town developed around its magnificent Monastery of Santa Clara, whose 16th-century convent church dominates the riverside. Before our walk, we enjoy a brief orientation and a break for lunch, understanding how this settlement prospered through maritime trade and religious patronage.
  
  The waymarked route leads us along the Atlantic coastline - sometimes on beachfront boardwalks with ocean views, other times through coastal villages set back from the shore, but always following the yellow arrows that have guided pilgrims for centuries. This flat, easy terrain epitomizes the coastal Camino's character, where sand, sea air, and the rhythmic presence of the Atlantic accompany our journey.
  
  We pass through Praia de Vila Chã and continue toward Mindelo, where traditional fishing communities maintain their Atlantic relationship. The walk reveals how Portugal's coastline shaped cultural identity - whitewashed houses facing the sea, boats pulled up on beaches, the distinctive light that has attracted artists since the 19th century.
  
  Our walk concludes at Praia da Azurara or Matosinhos beach (depending on group pace), where we pause at the Atlantic's edge before our bus transfer into Porto. in time to check-in and freshen up before gathering for dinner and anticipate tomorrow's exploration of Porto's UNESCO-recognized historic center.
  
  Walk Summary: 2.5-3 hours covering 6-8 km along coastal paths and beach boardwalks. Flat terrain with virtually no elevation change, well-maintained paths with some sandy beach sections. Atlantic breezes and full sun exposure typical.
  
  Overnight in Porto.

   

  Included Meal(s): Breakfast and Dinner
• Day 10: 

  Porto Discovery
  Morning finds us exploring Porto's UNESCO World Heritage historic center, where centuries of maritime commerce created one of Europe's most authentic urban landscapes. Our guided walking tour begins at the magnificent São Bento Station, where 20,000 hand-painted azulejo tiles depict Portugal's history in brilliant blue and white. These ceramic masterpieces, completed in 1930, transform a railway station into an art gallery celebrating everything from rural life to royal conquests.
  
  We ascend through Porto's layered neighbourhoods, discovering the Gothic Cathedral where Portuguese princes were baptized and the ornate Clérigos Tower, whose 240 steps reward climbers with panoramic views across terracotta rooftops to the Douro River. The baroque churches of Santa Clara and São Francisco reveal Portugal's golden age wealth, their gilded interiors glittering with New World gold.
  
  Our route winds through narrow medieval streets where traditional shops still sell hand-forged copper pots and embroidered linens, past colourful houses whose wrought-iron balconies overflow with laundry and flowerpots. At Livraria Lello, we glimpse the neo-Gothic bookstore that inspired Harry Potter's magical library, its crimson staircase spiraling toward stained-glass skylights.
  
  The morning concludes at Ribeira district's riverside promenade, where merchant houses cascade down to the Douro's edge. From here, the iconic Dom Luís I Bridge spans the river in elegant iron arcs, connecting Porto to Vila Nova de Gaia's port wine cellars across the water.
  
  Walk Summary: 3-4 hours covering 4 km through historic cobblestone streets and riverside areas. Moderate terrain with several uphill sections, stone staircases, and occasional steep climbs to viewpoints. Well-paved paths with some uneven medieval surfaces typical of UNESCO World Heritage centers.
  
  Overnight in Porto.

   

  Included Meal(s): Breakfast and Dinner
• Day 11: 

  Porto - Fly to Madeira
  Our 1.5-hour flight southwest carries us 978 km (608 miles) into the Atlantic, where Madeira rises from 4000-metre (13,123-foot) ocean depths like a volcanic garden. This subtropical archipelago, formed by underwater volcanic eruptions 20 million years ago, created landscapes so dramatic that early Portuguese explorers named it "Ilha da Madeira" - Island of Wood - for dense laurel forests covering its peaks.
  
  Funchal spreads up steep mountainsides from a natural harbour that sheltered Christopher Columbus during Atlantic voyages. The city's name derives from "funcho" (fennel), which covered these slopes when Portuguese settlers arrived in 1419. We should have some time on arrival for a brief orientation stroll; the old town reveals Madeira's unique position as a mid-Atlantic trading post - Moorish architectural influences mix with Portuguese colonial styles, while exotic flowers from every continent bloom in tropical abundance.
  
  Our hotel provides the perfect base for exploring an island where subtropical climate meets dramatic topography. Tonight, Atlantic breezes carry the scent of passion flowers and frangipani, promising tomorrow's adventure into UNESCO World Heritage forests that exist nowhere else on Earth.
  
  Overnight in Funchal.

   

  Included Meal(s): Breakfast and Dinner
• Day 12: 

  Madeira's West Coast Discovery
  This morning we journey into Madeira's dramatic western landscapes, where ancient volcanic forces carved Europe's highest sea cliffs and created the island's most spectacular plateau hiking. Our adventure begins through the traditional fishing village of Câmara de Lobos, where Winston Churchill once painted colourful boats resting in a natural harbour that has sheltered mariners for five centuries.
  
  Our route ascends to Cabo Girão's breathtaking clifftops, standing 580 metres above crashing Atlantic waves. The glass skywalk offers heart-stopping views over terraced vineyards carved impossibly into vertical cliffsides, while sea erosion has created caves and coastal terraces that local farmers still cultivate today, forming an incredible living watercolour landscape.
  
  The real adventure awaits on Paul da Serra plateau at 1,400 metres elevation—Madeira's vast "mountain plain" where ancient lava flows created a unique high-altitude ecosystem found nowhere else on the island. Here we embark on a section of the Levada Nova, following 16th-century irrigation channels through this otherworldly landscape where endemic plants thrive in volcanic soil and mist-fed meadows stretch toward distant peaks.
  
  Our moderate hike reveals how Portuguese engineers channelled precious water across seemingly impossible terrain, creating agricultural miracles in this subtropical paradise. The high-altitude environment supports unique flora adapted to constant Atlantic winds and dramatic temperature variations, while panoramic views stretch across Madeira's western valleys and dormant volcanic peaks.
  
  Descending toward the coast, we reach Porto Moniz, where volcanic activity created extraordinary natural swimming pools carved directly from black basalt rock. These geological wonders invite refreshing Atlantic swims after our mountain adventure, while the dramatic village setting demonstrates how Madeirans adapted to life at the foot of towering volcanic cliffs.
  
  Activity Summary: 5-6km (3-4 miles) levada hike on Paul da Serra plateau (2.5-3 hours) at 1400m elevation. Natural pool exploration at Porto Moniz.
  
  Overnight in Funchal.

   

  Included Meal(s): Breakfast and Dinner
• Day 13: 

  East Coast Wilderness & Coastal Drama
  This morning we venture into Madeira's untamed northeastern coastline for our adventure finale, where ancient Laurissilva forests give way to some of the island's most spectacular coastal hiking. Our destination, Vereda do Larano, follows historic paths where merchants and farmers once navigated between isolated communities across terrain so rugged it remained virtually unchanged for centuries.
  
  Our coastal adventure begins near Porto da Cruz, entering enchanting forest sections shaded by ancient laurel canopies—living remnants of subtropical forests that covered southern Europe 20 million years ago. The UNESCO World Heritage Laurissilva creates a natural cathedral where dappled sunlight filters through dense vegetation and endemic Trocaz pigeons find sanctuary in ecosystems unchanged since prehistoric times.
  
  Emerging from forest shade, our trail transforms into dramatic clifftop paths offering breathtaking Atlantic panoramas where azure waters stretch endlessly toward distant horizons. Unlike Madeira's popular tourist trails, this coastal gem remains refreshingly uncrowded, allowing genuine connection with the island's raw volcanic beauty and the sound of waves crashing against basalt cliffs far below.
  
  The path winds along striking geological contrasts where red and black volcanic rock formations create stunning visual drama against brilliant ocean blues. From elevated vantage points, we glimpse the distinctive silhouette of Ponta de São Lourenço peninsula and the towering Penha d'Águia (Eagle Rock), while clear conditions reveal distant Porto Santo Island floating mysteriously on the horizon.
  
  Our peaceful destination offers panoramic vistas over Madeira's northeastern coastline, where ancient mountains plunge dramatically into the sea. This contemplative spot, far from tourist crowds, provides the perfect setting to reflect on two weeks of discovery across Portugal's mainland mountains, river valleys, historic towns, and this remarkable subtropical island where volcanic landscapes meet Atlantic waters.
  
  Activity Summary: 6-8km (4-5 miles) coastal and forest trail (3-4 hours) with 250m elevation gain. Return to Funchal with free time for shopping, relaxation, and departure preparation.
  
  Overnight in Funchal.

   

  Included Meal(s): Breakfast and Dinner
• Day 14: 

  Departure
  Departure from Funchal.
  
  The journey home begins with hearts full of Portuguese warmth, cameras filled with impossible landscapes, and palates educated in wines that capture the essence of ancient terroirs where human tradition meets dramatic geography.
  
  "Boa viagem" - good trip!

   

  Included Meal(s): Breakfast

*The red tour trail on the map does not represent the actual travel path.