This two-week journey is designed for those seeking a more luxurious style of travel, with 5-star hotels and bespoke food and wine experiences. Over 14 days, you'll partake in gastronomic walking tours, a premium port wine tasting, a hands-on cooking class, and dine at Michelin-starred restaurants. Explore the captivating cities of Lisbon and Porto, savor the natural wonders of Serra da Estrela, embrace the historic charm of Évora, and unwind in the coastal elegance of Cascais.


  • Delve into Lisbon's seafaring history with a tuk-tuk tour of Belém
  • Learn to cook Portuguese favorites under the tutelage of an expert chef
  • Escape to a remote mountaintop hotel in the Serra da Estrela Nature Park
  • Discover the best riverfront port wine cellars in Porto's Gaia neighborhood
  • Dine on Michelin-starred cuisine amid a historic seafront fortress in Cascais

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Lisbon, Free Time to Explore Lisbon
Day 2 Lisbon Walking & Tasting Tour, Dinner & Fado Performance Lisbon
Day 3 Exclusive Tuk-Tuk Tour of Belém, Portuguese Cooking Class Lisbon
Day 4 Day Trip to Sintra's Palaces & Parks, Dinner at Fifty Seconds Restaurant Lisbon
Day 5 Transfer to Porto via Óbidos & Nazaré Porto
Day 6 Gastronomy & Culture Tour, Port Cellar Tasting, The Yeatman Restaurant Porto
Day 7 Day Trip to the Douro Valley, Wine Tasting & River Cruise Porto
Day 8 Day Trip to Braga & Guimarães Porto
Day 9 Transfer to Serra da Estrela Nature Park, Free Time to Explore Serra da Estrela 
Day 10 Serra da Estrela Guided Hike & Picnic, Dinner at Puro Restaurante Serra da Estrela 
Day 11 Transfer to Évora via Marvão Évora
Day 12 Tour Historic Évora, Dinner at Divinus Évora
Day 13 Transfer to Cascais, Dinner at Fortaleza do Guincho Cascais
Day 14 Transfer to Lisbon, Depart  

Detailed Itinerary

Day 1: Arrive in Lisbon, Free Time to Explore

Luxury Meta: Premium Guided Walking Tour with Delicious Portuguese Flavours
Step beneath history at the Rua Augusta Arch near Praça do Comercio

Olá and welcome to Lisbon, the colorful capital of Portugal. On arrival, a private driver will be waiting to transfer you to one of Lisbon's newest 5-star hotels, The One Palácio da Anunciada. Set within a 16th-century palace, you'll spend the next four nights soaking up the luxurious interiors, which emphasize the building's original beauty. Drop your bags and explore the 27,000 square foot (2,500 sq m) gardens and its hundred-year-old dragon tree, then explore the city.

Lisbon is one of Europe's most charming capitals, with friendly locals, delicious cuisine, and gorgeous terracotta-roofed buildings that cling haphazardly to its seven hills. You'll step out of the hotel close to Avenida Liberdade, Lisbon's chic tree-lined avenue with top restaurants and luxury boutiques. Follow the flow toward Baixa-Chiado, where you'll find souvenir shops, small markets, and centuries-old delicacies. If you have your walking shoes on, continue down to Praça do Comercio and the Tejo River, where you can watch sailboats and the sunset.

Day 2: Lisbon Walking & Tasting Tour, Dinner & Fado Performance 

Duck into the city's best specialty shops and sample local treats on today's gastronomic walking tour

Today you'll experience the best of Lisbon with a private gastronomic walking tour. As you explore the historic neighborhoods with a knowledgeable guide, you'll pause to taste gourmet delights. Wear good walking shoes to traverse the hilly streets as you visit iconic landmarks and learn about the city's history and culture. You'll explore Baixa-Chiado, where the great 20th-century writers and philosophers used to gather, and Alfama, one of the oldest districts in Lisbon. You'll end at a beautiful winery where you'll taste a range of wines paired with Portuguese delicacies.

After lunch, return to your hotel to refresh ahead of this evening's special dinner experience. A private driver will collect you for the transfer to a fado house, where you'll experience one of Portugal's greatest art forms. Everything stops when fado is performed. Silence rules the room, the lights dim, and only then the show begins. More than a traditional style of music, fado is an emotional experience that will be further enhanced with your creative and contemporary Portuguese meal. Enjoy each course with paired wines, then wait for the show to begin.

Day 3: Exclusive Tuk-Tuk Tour of Belém, Portuguese Cooking Class

Tower of Belém
Now an icon of Lisbon, the Belém Tower was built in the 16th century to defend the city

This morning you'll explore Lisbon's vibrant streets in a fun and unique way—with a charming tuk-tuk ride! Your open-air chariot will collect you from your hotel, taking you on a scenic journey to historic Belém. Explore the neighborhood's famous monuments with your private guide and driver, who will share stories of how great Portuguese explorers embarked on dangerous and ambitious voyages. You'll cruise past the towering Monument to the Discoveries and the soaring Jerónimos Monastery and finish with Portuguese custard tarts at the original historic bakery.

In the afternoon, you'll roll up your sleeves for a special gastronomic journey. Your private Portuguese cooking class will be a personalized, hands-on encounter with the country's rich culinary heritage. Under the guidance of a skilled chef, you'll explore the secrets of Portuguese cuisine, and together, you'll cook a multicourse meal using high-quality, locally-grown ingredients. When your delectable dishes are ready, sit down with premium paired Portuguese wines and enjoy a special dinner.

Day 4: Day Trip to Sintra's Palaces & Parks, Dinner at Fifty Seconds Restaurant

Sintra's hilltop setting near Lisbon
Palácio da Pena (Pena Palace) sits on top of Sintra's highest peak near Lisbon

Today you'll experience the magic of Sintra and its crown jewel, Palácio da Pena (Pena Palace), in the lap of luxury. A private driver will collect you for a full-day tour through the enchanting landscapes and historic wonders. Journey from Lisbon to the picturesque mountain town, starting with a visit to the fairy-tale Pena Palace. After exploring the famous red-and-yellow romanticist creation and surrounding Pena Park, venture into the historic Sintra village for lunch and delicious local pastries. Continue exploring winding roads through the verdant Sintra-Cascais Natural Park, then head to the coast.

On the return journey to Lisbon, your private driver will stop at the towering cliffs of Cape Roca, the westernmost point of continental Europe, and then follow the coast south, past the surfer's paradise of Guincho Beach. Back in Lisbon this evening, you have a reservation at Fifty Seconds, a Michelin-starred restaurant with panoramic views and exquisite food. The chef marries Portuguese flavors with international influences, resulting in a memorable meal.

Day 5: Transfer to Porto via Óbidos & Nazaré

Get lost in the charm of Óbidos, a medieval walled village
Get lost in the charm of Óbidos, a medieval walled village

After breakfast at your hotel, it's time to make the journey to Porto, Portugal's second-largest city. A private driver will make a day of the three-hour drive by stopping at the medieval village of Óbidos and the fishing town of Nazaré. An hour north of Lisbon, Óbidos is a charming medieval walled village where the historic center is a small maze of cobblestoned streets and flowerbeds, and the whitewashed houses are livened up with dashes of vivid yellow and blue paint. Try the local liqueur—ginjinha—a sweet, sour cherry drink often served in a small chocolate cup.

Continue north to Nazaré, where you'll stop for lunch. The coastal town is famous for its long, sandy half-moon-shaped beach and some of the biggest waves in the world. Admire the beautiful wooden fishing boats and the local women who still wear the traditional seven skirts. If you're lucky, the world-record-breaking waves might be pumping, attracting top surfers from all over the world. Finally, continue to Porto, where you'll check into The Yeatman, an elegant 5-star hotel with spellbinding views over Porto's Old Town from its location across the river in Gaia.

Day 6: Gastronomy & Culture Tour, Port Cellar Tasting, Dinner at The Yeatman Restaurant

End your flavorful tour of Porto with a port wine tasting across the Douro River
Plan your trip to Portugal
Chat with a local specialist who can help organize your trip.

Get to know the city of Porto and its most famous monuments on a three-hour private walking tour this morning. Your local guide will lead you past the Cathedral, Torre dos Clérigos, the São Bento train station, famed for its elegant azulejo tiles. From bustling central squares to treasured secret corners, you'll quickly see why Portugal's "capital of the north" is worthy of its UNESCO World Heritage Site designation. Best of all, as you explore, you'll get a taste of the city as you pause to try traditional jams and jellies, port wines, cheeses and sausages, cod fish and rojões (fried pork).

No visit to Porto is complete without sampling the local wines. Port wine is born in the Douro Valley, but the wine ages at cellars in Gaia, across the river from Porto. This afternoon you'll take a private tour of a wine cellar to learn about the famous export, then taste very special port wines that have aged for 10, 20, 30, and 40 years. After, return to your opulent hotel for a gastronomic journey. With two Michelin stars and panoramic views of Porto, enjoy a romantic meal as the sun sets at The Yeatman Restaurant.

Day 7: Day Trip to the Douro Valley, Wine Tasting & River Cruise

Douro Valley
Take an exclusive day trip to the beautiful Douro Valley and explore its famous wines

Explore the picturesque Douro Valley on a full-day tour from Porto, where you'll explore elegant wineries, savor a delicious lunch at a renowned quinta (a country estate), and unwind on a scenic river cruise. A private driver will take you from the city streets to the vineyards and valleys of the famous wine region, which is the oldest demarcated wine region in the world, dating back to 1756. You'll spend the day visiting wineries and learning about the region's fascinating UNESCO-protected wine heritage as you walk through the vineyards and taste local wines.

At lunch, you'll dive deeper into the region's winemaking heritage with a special tasting and sumptuous lunch at a local estate. Then it's time to hop aboard a boat for an hourlong cruise down the tranquil Douro River. Relax and soak up the lush scenery of the valley, where the vines roll down to the riverbank while sipping on a glass of port wine. At the end of the day, return to Porto.

Day 8: Day Trip to Braga & Guimarães

Braga's Arco da Porta Nova is a mix of Baroque architecture

Today's adventure delves deep into Portugal's incredible history. Your morning begins with a chauffeured ride to Guimarães, known as the birthplace of Portugal. Its UNESCO-listed historic center embodies the nation's formation and identity and brims with meticulously restored medieval structures. The 10th-century castle, perched atop a hill, stands as a symbol of its rich heritage. Explore the Dukes of Bragança Palace and the 13th-century São Miguel de Castelo Church, brimming with history.

Next, journey north to Braga, one of Portugal's oldest cities, once known as "Bracara Augusta" during the Roman Empire. The Braga Cathedral, built between the 11th and 13th centuries, is the nation's oldest and remains an enduring religious emblem. Uncover architectural gems like Braga Tower, the Archbishops' Court, and the opulent Palácio do Raio, once the grandiose residence of a prominent merchant. In the late afternoon, return to Porto to relax and enjoy your final night in the city.

Day 9: Transfer to Serra da Estrela Nature Park, Free Time to Explore

Dine among the mountaintops tonight at the Casa de São Lourenço Burel Panorama Hotel

Swap the city for continental Portugal's highest mountain this morning. A driver will collect you for the private three-hour transfer to Serra da Estrela, a mountain wonderland of clean air, crystal-clear streams, and free-roaming sheep. In the winter, the snowy peaks are a playground for skiers; in the spring, wildflowers grace its lower slopes; in summer, hikers will encounter shepherds and their flocks roaming the higher pastures.

Your driver will drop you off at the 5-star Casa de São Lourenço Burel Panorama Hotel, a luxurious but sustainable destination hotel that puts you in touch with nature. After checking in, take in the incredible views of the Manteigas glacial valley from your private balcony before deciding what to do with your free afternoon. You could make use of the wellness area, spa, and sauna, take a swim in the indoor pool, or venture out to explore the mountain on foot or by bike. This evening, enjoy a fine interpretation of traditional mountain recipes at the São Lourenço panoramic restaurant.

Day 10: Serra da Estrela Guided Hike & Picnic, Dinner at Puro Restaurante

Embark on a Breathtaking Guided Hike in Serra da Estrela with a Scenic Picnic!
You'll be rewarded with sweeping views, lush flora, and a delicious picnic

Estrela means star, and this mountain is full of sparkling gems waiting to be discovered. This morning you'll embark on a half-day hike with a private guide to explore glacier lagoons, sub-alpine meadows, peculiar granite boulders, and forested gorges. As you wander, look for dunnocks, dart ford warblers, and eagle owls in the forests, and kestrels and goshawks soaring above the highest peaks. Your reward is a picnic of local and regional produce, including the famous gooey Serra da Estrela sheep's cheese, considered one of the country's culinary treasures. 

This evening you'll make a special journey across the largest glacial valley in Europe—Zêzere Valley—to a renowned mountaintop restaurant. Puro Restaurante is a traditional mountain lodge that elevates regional cuisine, balancing modern sophistication and cozy comfort in an intimate setting. The chefs here use the finest and freshest local ingredients to craft dishes that tell a story and pay homage to the flavors of Serra da Estrela.

Day 11: Transfer to Évora via Marvão

Look out over Évora's ancient Roman aqueduct from your room at M'ar de Ar Aqueduto

After breakfast, it's time to make the four-hour journey to Évora, the capital of the Alentejo. In this region, time stands still, life moves slower, and the people are the warmest. En route, your private driver will make a special stop at Marvão, a charming and picturesque medieval village perched atop the stunning Serra de São Mamede. Wander through the timeless village, with its remarkably well-preserved architecture, cobblestone streets, and historic churches, and take in the views from the dramatic hilltop setting on the border with Spain.

Continue to charming Évora. Switch off when you enter the ancient town walls and check into the luxurious 5-star M'ar de Ar Aqueduto. Your room sits within a restored 16th-century palace, complete with the original chapel, vaulted ceilings, and Manueline windows. Take your time to refresh and relax by the hotel pool, which overlooks the 16th-century aqueduct that circles the city, then seek out dinner at one of the city's great contemporary restaurants such as Tua Madre, Híbrido, or Cavalariça.

Day 12: Tour Historic Évora, Dinner at Divinus

Beautiful and compact Évora is filled with landmarks and surrounded by gorgeous countryside

Évora is a UNESCO World Heritage site and the cultural and gastronomic capital of the Alentejo region. After breakfast today, you'll explore this ancient, compact city with a local expert. Wander past the well-preserved ruins of the Templo Romano, proof of Évora's Roman past, and witness the golden age of Portuguese maritime discoveries. Discover the hauntingly beautiful Chapel of Bones, an eerie yet fascinating ossuary adorned with human bones; delight in the architecture of the Sé de Évora (Évora Cathedral); and enjoy the grandeur of Praça do Giraldo, the city's lively plaza.

Find a local tavern or tasca for a casual lunch and the chance to try hearty Alentejo dishes, such as grilled black pork and seracaia (a flan-like dessert). Spend the rest of the afternoon wandering between whitewashed houses and shopping for artisan goods, or relax by the hotel pool, which overlooks the 16th-century aqueduct that circles Évora. Tonight you'll dine at Divinus, an upmarket restaurant at the Convento do Espinheiro, a 15th-century convent turned 5-star hotel. Born and raised in the Alentejo, chef Jorge Peças reinterprets regional dishes in a fine dining setting.

Day 13: Transfer to Cascais, Dinner at Fortaleza do Guincho

Tonight you'll watch the sunset from the famous Fortaleza do Guincho
Tonight you'll watch the sunset from the famous Fortaleza do Guincho

Today's final destination is Cascais, a former fishing village and 19th-century royal summer playground. A private driver will collect you from the hotel for the two-hour drive to the elegant beach town right next to Lisbon. Cascais attracted a summer-dwelling artistic community in the 1930s and has continued to charm locals and visitors since. Check into your hotel, the 5-star Pestana Cidadela Cascais. Set in a 16th-century seafront fortress, the artsy hotel combines contemporary comforts and creativity within an unusual and luxurious historic setting.

Freshen up, then step outside the hotel and into the Cascais Citadel. These 500-year-old fortifications were built to protect Lisbon from pirates and corsairs. Explore the Art District within the walls, then wander over to the historic center of Cascais for a late lunch. This evening you'll dine at Fortaleza do Guincho, a Michelin-starred restaurant set within a historic fortress with far-reaching views of the ocean and Guincho Beach. Chef Gil Fernandes puts an emphasis on seafood and Portuguese gastronomy, showcasing the freshest catches from the Atlantic Ocean. 

Day 14: Transfer to Lisbon, Depart

Wave goodbye to the blissful bays of Cascais
Wave goodbye to the blissful bays of Cascais
Your two-week adventure in Portugal comes to an end today. Depending on the time of your flight, you may be able to squeeze in one more walk along the coastline of Cascais or perhaps pick up some last-minute souvenirs. At the designated time, you'll be collected from your hotel by a private driver and transferred to Lisbon's airport for your onward departure. Safe travels!

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Map of Luxury Portugal Flavors & Culture Tour - 14 Days
Map of Luxury Portugal Flavors & Culture Tour - 14 Days