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 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 & Cooking Class
  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.
  
  Our afternoon cooking class transforms us into temporary Portuguese chefs, learning to prepare traditional dishes using ingredients grown in quinta gardens. The class culminates in our own feast, paired with estate wines while sunset paints the terraced landscape in shades of gold and burgundy.
  
  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 - Train to Porto
  Today's train journey from Douro Valley to Porto follows the river through increasingly dramatic gorges, revealing why this route ranks among Europe's most scenic rail experiences. Porto emerges gradually - first industrial suburbs, then elegant 19th-century neighbourhoods, finally the UNESCO World Heritage Ribeira district where colourful medieval houses lean precariously over the Douro's final kilometers.
  
  Portugal's second city pulses with different energy than laid-back Lisbon - here, granite architecture speaks of mercantile wealth earned through centuries of port wine trade with Britain. We begin in Ribeira, where Roman foundations support medieval walls that witnessed everything from Moorish sieges to English trading partnerships. The neighbourhood's narrow alleys lead us to riverside cafés where locals debate football over espresso, their conversations punctuated by seagull cries and the rhythmic clatter of vintage trams.
  
  Our introduction walk covers 4 km (2.5 miles) of gentle urban exploration, including São Bento Station where 20,000 azulejo tiles depict Portuguese history in blue and white ceramic masterpieces. Each panel tells stories of royal processions, rural festivities, and maritime discoveries, creating a visual encyclopedia of national identity.
  
  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 neighborhoods, 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.
  
  Afternoon Options: Cross the bridge's upper pedestrian level for spectacular river views and guided tastings at historic port lodges like Sandeman or Graham's.
  
  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. Our gentle 3 km (1.9 mile) orientation walk through the marina and 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.
  
  The Mercado dos Lavradores showcases Madeira's incredible fertility - passion fruit, cherimoyas, and dragon fruit pile alongside traditional vegetables, while fish vendors display catches from Atlantic waters where deep ocean currents create some of the world's richest fishing grounds. Madeira wine, aged using unique heating processes developed for long sea voyages, offers complex flavours that pair perfectly with local specialties like espetada (beef skewers) and bolo do caco (traditional bread).
  
  Our oceanfront 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: 

  Levada Trails & Ancient Forests
  This morning we depart for Madeira's mountainous interior to explore the legendary levada irrigation system - 16th-century water channels hand-carved into cliffsides that create hiking opportunities found nowhere else on Earth. Our destination, Levada do Caldeirão Verde, leads us through UNESCO World Heritage Laurissilva forest, a living remnant of subtropical forests that covered southern Europe 20 million years ago.
  
  The journey follows mostly flat terrain beside the flowing levada, passing through hand-carved tunnels where headlamps are essential. Ancient laurel trees tower 40 metres overhead, their dense canopy creating unique ecosystems in perpetual shade. Wildlife includes the endemic Madeiran firecrest, Europe's smallest bird, and the Trocaz pigeon, found only in these ancient forests.
  
  Waterfalls cascade from heights invisible above the canopy, creating a symphony of falling water throughout our journey. Our primary destination is a stunning waterfall at the 4km mark - a perfect reward for our efforts and an ideal spot to rest and appreciate this remarkable ecosystem. This UNESCO Biosphere Reserve protects species that survived the last ice age in Madeira's stable subtropical climate. The levada system represents humanity's ingenious adaptation to challenging terrain, allowing agriculture to flourish across dramatically varying rainfall zones where windward and leeward slopes create distinct microclimates.
  
  Hike Summary: 2.5-3.5 hours on mostly flat levada paths covering 8km total. Minimal elevation change with 2 tunnel sections requiring headlamps. Well-maintained paths with some narrow clifftop sections. Distance can be extended based on group energy and weather conditions.
  
  Overnight in Funchal.

   

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

  Vereda do Larano Coastal Trail
  We journey to Madeira's dramatic northeastern coast to discover Vereda do Larano, one of the island's most spectacular yet peaceful coastal trails. This historic path once connected local communities across rugged terrain, following ancient routes where merchants and farmers navigated between Porto da Cruz and Machico for centuries.
  
  Our coastal adventure begins through enchanting Laurissilva forest, where dappled sunlight filters through ancient laurel canopies providing welcome shade. The well-maintained trail emerges onto dramatic clifftop paths offering breathtaking views across the Atlantic, where azure waters stretch endlessly toward the horizon. Unlike many of Madeira's popular hikes, this gem remains refreshingly uncrowded, allowing us to truly connect with the island's raw natural beauty.
  
  The trail winds along where volcanic geology creates stunning contrasts between red and black rock formations and the brilliant blue ocean far below. From elevated viewpoints, we glimpse the distinctive silhouette of Ponta de São Lourenço peninsula, the towering Penha d'Águia (Eagle Rock), and on clear days, the distant outline of Porto Santo Island floating on the horizon.
  
  Our destination, Boca do Risco viewpoint, rewards our efforts with panoramic vistas over Madeira's northeastern coastline, where mountains plunge dramatically into the sea. This peaceful spot, far from tourist crowds, provides the perfect setting to appreciate the power and beauty of the Atlantic meeting volcanic landscapes shaped over millions of years.
  
  The return journey offers entirely different perspectives as we retrace our steps through this geological wonderland, understanding why this route has captivated travellers seeking authentic experiences away from the beaten path.
  
  Tonight, our farewell dinner celebrates two weeks of discovery across Portugal's mainland mountains, river valleys, historic towns, and this remarkable subtropical island where volcanic landscapes meet Atlantic waters.
  
  Hike Summary: 3-4 hours covering 10km on coastal paths with forest sections. Easy to moderate terrain with 250m total elevation gain. Mix of well-maintained shaded forest trails with spectacular ocean views.
  
  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.