Luxury Portugal Escape: Porto, Douro Valley, Serra da Estrela, Lisbon & Madeira - 14 Days

Day 2: Porto Architecture Tour, Taylor's Port Tasting

Today, you'll take a private walking tour of Porto's UNESCO-listed city center. Your guide will introduce you to the city's architectural highlights, including the Rivoli Theater, the Art Deco-style Cinema Batalha, and Centro Português de Fotografia, set in a former prison. End with a stroll along the Douro River and the Rua da Reboleira to see the rehabilitation of the Ribeira neighborhood.  

Spend the afternoon as you please; retire to your hotel for a decadent massage or pool session, or continue exploring the city independently. Admire the Ribeira's colorful dockside houses and warren of windy streets. Stop for a coffee and a pastel de nata (Portuguese custard tart) while watching the boats glide down the river.  

This evening, you'll enjoy a two-hour port tasting at Taylor's, one of Portugal's top wine cellars. Visit the atmospheric 17th-century cellars in Vila Nova de Gaia, which have been operating for four centuries, and browse an innovative museum. Your expert guide will show you the winemaking process at this historic winery, founded in 1692, ending with a tasting of Taylor's signature ports.

Day 3: Kayaking & Hiking in Peneda-Gerês National Park

Leave the city today and visit Peneda-Gerês, Portugal's only national park. Set 2.5 hours north of Porto, the park is filled with mountains and river valleys covered with native forest home to rare European animals like wolves and wild boar. The forests are crisscrossed with hiking paths that lead to 12th-century granite villages where you can enjoy typical Portuguese meals.  

Begin your outdoor adventures with a private kayaking trip on the Caniçada Reservoir, floating past wooded banks shadowed by peaks. For more adrenaline-pumping action, you can go standup paddleboarding, cliff jumping, or swimming in hidden waterfall lagoons. Take guided hikes to beauty spots and panoramic viewpoints that showcase the highlights of Peneda-Gerês before returning to Porto.

Day 4: Scenic Drive to the Douro Valley Wine Region

This morning, pick up your rental car and make the scenic 1.5-hour drive into the mountains and valleys of the famous Douro Valley wine region. Sections snake alongside the Douro River, surrounded by terraced vineyards and olive farms dotted with family-run quintas (estates). Stop off at sweeping viewpoints and riverside cafés to drink in the views; the town of Amarante is a favorite for its iconic bridge and streets lined with cute cafés.

Continue to the lavish Six Senses Douro Valley, a wine and spa resort set in a restored 19th-century estate in the hills overlooking the river. Admire the views from your luxury suite, which has a terrace hot tub, then take advantage of the resort's award-winning Six Senses Spa, where you can enjoy everything from a Himalayan salt sauna to a Roman laconium (sauna). Book a massage and decompress in the heated pool, which features floor-to-ceiling windows overlooking the valley. 

For dinner, take a seat at the Vale de Abraão Restaurant, with its vineyard views, flickering fireplaces, and 18th-century azulejos (traditional Portuguese decorative tiles). Feast on seasonal tasting menus or opt for the Open Kitchen Experience, where you can enjoy an a la carte menu and chat with the chefs while they prepare your meal. Of course, pair your dishes with some of the Douro Valley's finest wines.  

Day 5: Scenic Drive to Serra da Estrela Nature Geopark

Start the day with a two-hour drive south to the Serra da Estrela. This geopark is home to the tallest mountains in Portugal; the highest is Torre, with a 6,538-foot (1,992 m) peak. Hikers are drawn to the Serra da Estrela for its challenging trails, which pass rural villages, glacial valleys, and forests scattered with waterfalls.

Check into the luxurious Casa de São Lourenço, a traditional Portuguese pousada established in 1948, which has been renovated into a 5-star hotel. The prime attraction is the views; floor-to-ceiling windows showcase the jagged peaks of the Serra da Estrela, the mountain town of Manteigas, and the Zêzere Glacier Valley. 

Settle into the hotel's cozy alpine vibe with decor by renowned Portuguese designer Maria Keil. Relax with a coffee on the outdoor terrace or curl up on a sofa in front of the blazing fireplace in the indoor lounge. The hotel offers complimentary daily afternoon tea and a spa with a sauna and a large heated indoor pool leading to an outdoor whirlpool tub with mountain views.

Day 6: 4WD Tour of Serra da Estrela's Landscapes & Villages

Take to the mountains on a private 4WD tour with an expert guide. Follow rugged trails to the sky-scraping peak of Torre, where you'll enjoy 360-degree views of the mountainous landscape. Pass through valleys carved in the ice age, stopping to marvel at various springs, crystal-clear lakes, and the Zêzere River along the way. 

Visiting Covão d'Ametade is a highlight, a birch forest on the banks of the Zêzere, set in a glacial depression 4,921 feet (1,500 m) above sea level. The site offers views of the Cântaros granite outcrop and is the starting place for hikes and rock climbing. 

Continue to mountain villages, where you'll taste local dishes paired with wines from the nearby Dão area and learn how the region's famed burel wool is produced. Afterward, return to your hotel for a final evening in your mountain retreat, savoring elevated Portuguese cuisine with untamed views at the on-site restaurant.

Day 7: Drive to Lisbon, Cooking Class or Dinner with a Michelin-Star Chef

Leave the mountains this morning and embark on the four-hour drive to Lisbon. Portugal's vibrant capital is full of winding cobbled streets traversed by yellow trams, with medieval towers, Baroque palaces, and dome-topped monasteries. That's not to mention world-class restaurants, buzzing markets, and a busy bar scene.

Head to Praça do Município, where you'll check into the luxury hotel AlmaLusa Baixa/Chiado. Settle into one of the boutique rooms or suites in this 18th-century building, which offers everything from original fireplaces and flagstone floors to supreme city views.

Tonight, enjoy a private cooking class where you'll learn to prepare a traditional Portuguese meal, complete with both a fish and meat dish, followed by dessert. Alternatively, opt for an exclusive fine dining experience, where you'll enjoy a meal prepared by a Michelin-starred chef in their culinary lab, who creates new recipes for award-winning restaurants. 

Day 8: Tour Lisbon with a Local, Evening of Fado

Discover more of Lisbon today, starting with a private tour of the city. Stop at the Elevador de Santa Justa, a thin iron elevator built in 1902, which you can ride to the top of a 150-foot-tall (45 m) tower showcasing city views and the sea beyond. Pass through the grand archway, Arco Monumental da Rua Augusta, which leads into Praça do Comércio, and visit the colorful Chiado district and bohemian Bairro Alto for hilltop views over the city.

Your guide will end with restaurant recommendations, and you can explore independently. Stop for a coffee and pastel de nata and perhaps head out to the Belém neighborhood to visit UNESCO World Heritage Sites like Torre de Belém and Mosteiro dos Jerónimos, a formidable monastery built in 1501 in a blend of Gothic and Renaissance style. 

Spend the rest of the day roaming Lisbon at your own pace. Trawl for treasures at the Feira da Ladra flea market on Tuesdays and Saturdays, where you can find everything from vintage clothing to quirky antiques. Then there's the daily Mercado da Ribeira and all kinds of food under one roof at the Time Out Market next door. End the day with dinner and a fado performance, a Portuguese music form that dates back to the 1820s, in the Bairro Alto. You'll dine on local dishes at one of Lisbon's top restaurants, accompanied by the sounds of traditional singing and guitars.

Day 9: Sintra & Cascais Tour with Coastal Cruise

Escape the city today and travel half an hour west to the UNESCO World Heritage Site of Sintra and the nearby fishing town of Cascais. Set among cool, forested hills, Sintra acted as a summer retreat for Portuguese royalty and, as such, is dotted with turreted palaces, villas, and storybook castles. These enchanting landscapes served as inspiration for Lord Byron's poems.

Accompanied by a private guide, you'll visit the Palacio Nacional da Pena (Pena Palace), a 19th-century romanticist castle that blends Moorish and Portuguese late-Gothic architectural styles. Next, explore Cascais and its famous Citadel, a set of formidable fortifications that date back over 500 years, built to protect Lisbon from pirates. Stop at Hell's Mouth, a dramatic chasm in the seaside cliffs. End with a private cruise along the coast of Cascais and Estoril, taking in views of secluded coves and golden beaches. 

Day 10: Fly to Madeira, Funchal Food & Cultural Tour

Say goodbye to Lisbon this morning and fly 2.5 hours southwest to Madeira. This small volcanic island lies off the northwest coast of Africa and enjoys a warm, spring-like climate. Its diverse scenery ranges from black-sand beaches to organic vineyards, laurel forests scattered with waterfalls, and botanical gardens bursting with flowers. 

Arrive in the capital, Funchal, where your driver will be waiting to take you to Reid's Palace, a luxury Belmond hotel. The property lies among gardens dotted with a heated freshwater and saltwater pool that offers views of the sparkling Atlantic Ocean. Check into your room in this historic hotel, which dates back to 1891 and has hosted famous guests like Winston Churchill and George Bernard Shaw, who both have suites named after them. 

Relax in your elegant room or suite, which features a marble bathroom, hand-painted wallpaper, and a balcony or patio with ocean views. Later, you'll embark upon a private food and cultural tour of Funchal. Join your local guide to visit the city's most popular eateries, sampling 15 types of food and drink while learning the city's history. 

Day 11: 4WD Tour of Madeira 

Experience Madeira's astounding beauty on a private 4WD adventure tour. Head inland, passing through forests to viewpoints, traveling along sections of the Caminho Real, the 105-mile-long (170 km) royal path commissioned by the king of Portugal in the 19th century. Spiral upward, reaching 3,281 feet (1,000 m) above sea level, through forests of pine and fir trees, to the Abrigo do Poiso family restaurant, which offers sweeping island views.

Afterward, head to Pico do Arieiro, Madeira's third-highest mountain, which soars 5,965 feet high (1,818 m). From here, you'll soak up panoramic views of the island's central mountain range, with the glittering Atlantic Ocean beyond. Next, continue to Ribeiro Frio, a village in one of Madeira's 20-million-year-old laurisilva (laurel) forests, which are protected for their rare flora and fauna. 

Walk along one of Madeira's iconic levadas, a network of stone waterways built to funnel water south across the island. Follow a 1-mile (1.5 km) trail through the forest to the Balcões viewpoint, which overlooks the striking Ribeira da Metade Valley, carpeted with laurisilva forest. Hop back in the 4WD next, journeying inland along an exhilarating off-road track to Santana, a region famed for its quaint stone houses topped with spiky thatched roofs.

You'll return to Funchal along the east coast in the afternoon, pausing to sample local rum at the Engenhos do Norte distillery en route. You'll enjoy photo-worthy stops along the way, including at Guindaste and São Lourenço, which offer a dramatic glimpse of the coastline. 

Day 12: Madeira Leisure Day, Sunset Catamaran Cruise 

Today is yours to explore Madeira at your leisure. If you want to relax, lounge by your hotel pool or dive into the turquoise water from the oceanfront platform. Head to the hotel spa for an indulgent massage, savor Michelin-starred dining at the on-site William restaurant or enjoy a decadent afternoon tea on the terrace.

For city sightseeing, stroll into the capital, Funchal, where you can duck into the ancient Funchal Cathedral, famed for its intricate carved wooden ceiling. Wander along the harbor to the imposing São Tiago Fortress, which now houses the Contemporary Art Museum filled with Portuguese works. 

Venture farther afield to laze on volcanic beaches or tour sleepy villages like Curral das Freiras (Nun's Valley). The steeply-situated village—once the sanctuary for a convent of nuns hiding from pirates—offers a network of foot and mule trails with scenic overlooks, as well as local delicacies to try, like chestnut cakes and a cherry-infused liqueur.

End the day with a private sunset cruise off the coast of Madeira. Board a catamaran to sail along the south coast, looking for whales and dolphins playing in the waves. Your expert crew will point out cetaceans along the way, hoisting the sails as you glide across the ocean. Sip drinks while you watch the sunset, extinguished by the topaz water.

Day 13: Guided Hike on the 25 Fontes Trail

Lace up your hiking shoes today to tackle Madeira's famous 25 Fontes Trail with a private guide. This 7-mile (11 km) round-trip hike is one of the island's most popular, leading through lush laurisilva forest with impressive views over the Ribeira da Janela Valley and towering waterfalls. The pinnacle is a wall of 25 streams that cascade into a pool.

Begin at 3,281 feet (1,000 m) above sea level in Paúl da Serra, descending through Rabaçal Valley, where you'll follow a gushing levada to Risco Waterfall. Take a break to admire the water, which tumbles 328 feet (100 m) to the rock below, before continuing to the 25 Fontes Waterfall, where spring water cascades into a fairy-tale lagoon surrounded by giant ferns. 

During the trek, your guide will highlight flora such as rare besom heath and mountain mocano, features of the UNESCO-listed laurisilva forest. Watch out for exotic birds in the treetops, including the long-toed pigeon. After the trek, return to your hotel for a well-earned rest. Gorge on Italian cuisine at Ristorante Villa Cipriani and enjoy cocktails beneath the stars to celebrate your last night in Madeira. 

Day 14: Fly to Lisbon, Depart

Today, your luxury Portuguese adventure comes to an end. Spend a final few hours by the pool or shopping for souvenirs in Funchal before your private transfer to the airport, where you'll catch a flight back to Lisbon and your onward connection. Safe travels!

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