Luxury Journey Through Portugal & Spain: Culture, Countryside & Gastronomy - 14 Days

Day 1: Arrive in Porto (Portugal), Explore the UNESCO City

Welcome to Portugal! Touch down in Porto, the country's second-largest city. Porto is beloved for its Ribeira (riverside), packed with port cellars and cafés, and the colossal Dom Luís I Bridge, which spans the Douro River. Don't miss the Livraria Lello, a bookshop with a distinctive spiral staircase said to be one of the real-life inspirations for "Harry Potter's" Hogwarts.

Upon arrival, your driver will drop you at The Yeatman Hotel, which lies on a hillside above the south bank of the Douro River. The wine hotel and spa sprawls over 7 acres (3 ha), with a decanter-shaped infinity pool, mammoth wine cellar, and spa offering wine-inspired treatments, from grapeseed oil massages and facials to barrel baths. Settle into your luxury room or suite, drinking in city views from your private balcony. 

You can dine at The Yeatman Gastronomic Restaurant this evening, which was awarded 2 Michelin stars for its inventive Portuguese cuisine. Celebrated chef Ricardo Costa offers a menu of national dishes with a modern edge, focusing on fresh fish and produce from the region, paired with a selection of fine wines. Try the acclaimed tasting menu for a gourmet dining experience. 

Day 2: Porto World Heritage Tour & Wine 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 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, get an introduction to Portuguese wines with a private tasting session. Sample six top bottles derived from the nearby Douro Valley, which has one of the most diverse collections of grapes in the world, and the southern Alentejo region. An expert sommelier will teach you about the different varieties and answer any wine-related questions. 

Day 3: Portuguese Cooking Class, Art Museum Visit

Start today with a private cooking class with a top Portuguese chef. This hands-on workshop introduces you to Portugal's cuisine and the cooking techniques for local favorites such as grilled sardines and piri-piri chicken. Start with a trip to a local market for seasonal ingredients and enjoy a memorable meal paired with dynamic local wines and spirits.

This afternoon, soak up some culture with a visit to Porto's new Museum of Contemporary Art in Serralves Park. Located in the city's center, the park covers 45 acres (18 ha) of various gardens, including a rosarium, woodlands, and pasture, complete with a tranquil lake. At the park's heart, the modernist museum hosts world-class, cutting-edge exhibits.

Day 4: Train to Lisbon, Food & Cultural Tour

Today, you'll take a 3.5-hour train journey to Lisbon, traveling in first class. 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.

Meet your driver, who'll take you to the city's main square, 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.

Freshen up before your private tour of the city, which explores two of Lisbon's most ancient neighborhoods, Mouraria and Alfama. Stroll from 12th-century alleys into the modern-day city, reveling in the laid-back vibes of each area and stopping along the way to sample authentic Portuguese dishes and snacks. You'll also learn about Mouraria's roots as the birthplace of fado, a Portuguese music form that dates back to the 1820s.

Day 5: Explore Lisbon's Highlights Independently

Spend today roaming Lisbon at your own pace. Famous sites include the Elevador de Santa Justa, a thin iron elevator built in 1902, which you can ride to the top of a 150-foot (45 m) tower showcasing views of the city and the sea beyond. Pass through the grand archway, Arco Monumental da Rua Augusta, which leads into Praça do Comércio, and discover the colorful Chiado district and Bairro Alto's hilltop views over the city.

For some retail therapy, 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. Pause for a coffee and sweet treat, and perhaps head out to the Belém neighborhood to visit UNESCO-listed Torre de Belém and Mosteiro dos Jerónimos.

Day 6: Visit Sintra's Palaces, Castles & Forests

Escape the city today with a private day trip that takes you half an hour west to the UNESCO World Heritage Site of Sintra. Set among cool, forested hills, Sintra acted as a summer retreat for Portuguese royalty and, as such, is dotted with turreted palaces, villas, and fairy-tale castles. These enchanting landscapes, which you'll delve into on the tour, served as inspiration for Lord Byron's poems.

Accompanied by an expert guide, you'll hike through forest trails to explore Sintra's architectural wonders. These include a Moorish castle dating back to the eighth century and Palacio Nacional Pena (Pena Palace), a 19th-century romanticist building that blends Moorish and Portuguese late-Gothic architectural styles. Afterward, return to Lisbon for a final evening in the capital. 

Day 7: Transfer to the Alentejo, Explore the Hotel's Grounds

This morning, your driver will take you 1.5 hours east into the Alentejo, Portugal's largest region. The fertile landscape is carpeted with vineyards, cork plantations, olive groves, and wheat fields. Among the rural splendors, you'll find medieval cities like Monsaraz, which are surrounded by imposing walls and topped with a castle. São Lourenço do Barrocal, your chic hotel, lies in the shadow of Monsaraz, surrounded by unspoiled countryside.

Spend the rest of the day relaxing at your hotel, a whitewashed former farmhouse that's been in the same family for over 200 years. The property has a selection of barns converted into luxurious rooms and cottages by renowned architect Eduardo Souto de Moura. Room highlights include traditional red floor tiles and wooden shutters combined with modern comforts like underfloor heating. 

Windows look out over the 1,927-acre (780 ha) estate, which you can explore on foot, bike, or horseback. Discover olive groves, vegetable gardens, a pool, and a vineyard where you can enjoy a wine-tasting session. Head to the spa for a decadent massage; try the signature Barrocal Purifying Massage, delivered with herbs grown on the estate. End the day with some farm-to-fork dining at the on-site restaurant.

Day 8: Alentejo Jeep Tour with Winery Visit

Uncover the natural wonders of the Alentejo today on a private Jeep safari. Head out with a local guide to experience the beauty of the countryside, bumping through forests of cork and holm oak trees, where Iberian black pigs snuffle for acorns and farmers harvest cork. You'll learn the story of an English family that planted roots in the Alentejo in the 19th century and discover the secrets of olive oil and cork production. 

Continue to nearby vineyards, where you'll learn about the production process, from vine to bottle, and hear about how the Alentejo region's clay-lime soils and climate combine to produce award-winning varieties. Taste everything from syrah and Alicante Bouschet to Touriga Nacional and Aragonez. Return to your hotel afterward for a final night in the peaceful Alentejo.

Day 9: Transfer to Seville (Spain), Jamón Tour & Tasting

Today, you'll say goodbye to Portugal and transfer three hours over the Spanish border to Seville, the capital of Andalusia, which blends Gothic cathedrals with stately mansions and palaces. An hour north of Seville, you'll stop at Aracena to meet a guide for an Iberian jamón (ham) tasting experience. 

Aracena is a mountainous area known for producing Iberian ham, which is cured in the mountain air for up to three years and is considered by many people to be the jewel in the crown of Spanish gastronomy. Visit a family-run farm to see how pigs are reared, then continue to the town of Jabugo to witness the meat-curing process, followed by a ham-tasting session and glass of fino or manzanilla wine. 

Enjoy a gourmet lunch at one of Aracena's top restaurants, feasting on everything from locally-produced wild mushrooms and cheese to Iberian pork and asparagus—all of which are fresh and seasonal. Sip fine Spanish wines and indulge in a dessert before walking up to the town's castle. Join your driver for the final hourlong journey to Seville in the late afternoon. 

Stay at Hotel Alfonso XIII, an iconic city landmark built in 1929 by King Alfonso to host esteemed guests and royalty. The hotel's grand Andalusian design, complete with Moorish details, has been restored, and its sumptuous rooms offer marble floors, crystal chandeliers, and azulejos (Spanish and Portuguese painted tiles). Savor the ambience in this 5-star Luxury Collection Hotel, which features a garden shaded with palm trees and a pool.

Day 10: Seville Historical Tour, Gourmet Tapas & Wine Tasting

Delve into Seville's 2,000-year history today on a private walking tour. Your guide will cover highlights such as UNESCO-listed Seville Cathedral, a 15th-century Roman-Catholic church home to the tomb of Christopher Columbus and recognized as the world's largest Gothic church. Admire the cathedral's looming bell tower, La Giralda, built as a minaret for the Great Mosque when the Moors ruled Andalusia.

Next, wander to the orange-tree-filled Santa Cruz neighborhood, which lies in the old city center. Take a break for some tapas and wine at one of the area's cute cafés, then continue to the Royal Alcázar, a set of palaces and gardens recognized by UNESCO for its synthesis of Christian and Muslim cultures. Finish your tour with a walk along the banks of the Guadalquivir River.

This evening, get a taste of Seville with a private tapas and wine-tasting experience. Head out with a foodie guide, who'll take you to bars and bodegas loved by locals, where you'll enjoy tapas paired with Andalusian wines. Finish with a full dinner at one of Seville's top restaurants, sampling typical dishes such as salmorejo (cold tomato soup), espinacas con garbanzos (spinach with chickpeas), and presa iberica (pork shoulder). 

Day 11: Andalusian Olive Oil Estate Tour, Michelin-Star Dinner at Abantal

Venture out of Seville this morning for a private tour of an Andalusian olive oil estate. Soak up countryside views on your way to a famous estate where Christopher Columbus's son, Hernando, began producing and exporting olive oil to the New World in the 17th century. Tour the estate's old manufacturing center with its 16th-century oil presses, wander the rows of emerald olive trees, and learn about the entire production process. End with a tasting session of the estate's top olive oils.

Return to Seville for a free afternoon; ramble through the historic city streets independently or relax by the pool at your hotel. The day ends with a lavish dinner at Michelin-star restaurant Abantal, known for its innovative Andalusian cuisine. Sample a tasting menu that captures southern Spain's iconic dishes with a contemporary edge, devised by acclaimed chef Julio Fernández.

Day 12: Transfer to Granada, Alhambra & Generalife Gardens Tour

Start the day with a scenic, three-hour transfer through the Andalusian countryside to Granada. Set in the foothills of the Sierra Nevada, the city is renowned for its Moorish architecture and history, as well as its bars and flamenco venues. Check into your 5-star hotel, Parador de Granada, which lies within the city's most famous landmark, the Alhambra. 

Set on a hill above Granada, this Muslim fortress dates back to the ninth century but was rebuilt in the 14th century by the Nasrid Dynasty. The dramatic landmark was a Moorish palace until the Christian reconquest in 1492 when it became the Royal Court of Ferdinand and Isabella. Your elegant room in the palace features original tile work, antiques, and views of the Generalife Gardens. 

Once you've settled in, take a private tour of this UNESCO World Heritage Site's grand buildings, which include striking examples of Moorish history. Observe features such as the hand of Fatima on the gateway of the Puerta de la Justicia (Gate of Justice), fingers outstretched to ward off the evil eye, or the extravagant design in the Patio de los Arroyanes (Court of the Myrtles). This evening, you can dine on Andalusian and Moorish-inspired dishes at the on-site restaurant, which sprawls onto a terrace overlooking the flower-filled gardens. 

Day 13: Explore Granada, Hammam Session & Flamenco Show

Explore Granada independently this morning. Highlights range from the city's oldest square, Plaza Nueva, to the medieval center Albaicín. Take a walk through the Jewish Quarter, Barrio Realejo, and visit the 16th-century Granada Cathedral, the city's largest and most opulent Roman Catholic church.

This afternoon, you'll relax with a steam bath at one of Granada's traditional hammams. Hop between different rooms with varying temperatures for a detoxifying steam, then soak in hot and cold baths, followed by optional massages and treatments.

End the day with a flamenco show in a Sacromonte cave. Flamenco is the ultimate artistic expression of Andalusia, and Granada's Sacromonte neighborhood is one of the best places to explore this art form. The area is the birthplace of the zambra, a flamenco dance party that dates to the 16th century, and the marital rituals of the Moors. Between the 18th and 19th centuries, locals waited at cave entrances, ready to perform their flamenco show for travelers.

Day 14: Train to Madrid, Depart 

Today, your luxury tour of Portugal and Spain comes to an end. Your driver will take you to the train station, where you'll board a train for the 3.5-hour journey to Madrid. From here, you'll take a private transfer to the airport in time for your homebound flight. Safe travels!

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