Luxury One-Week Portugal Food & Wine Tour

Lisbon enchants from first glance as grand townhouses stretch out through the center with plazas finding their way onto almost every street corner. Before you lies the Tagus River, while on either side of you the hills will rise and you will see tightly packed clusters of colorful buildings. Touch down this morning and check into a hotel in Alfama, where the winding lanes hold their history with pride. After some time to freshen up, you will start exploring, first up the hill to Castelo de Sao Jorge, and then to the clanging bells of Se Cathedral.

Broad boulevards fill Baixa, your next stop, where you will learn the Lisbon love for espresso and glamorous cafes. Renovated after an earthquake, Praca do Comercio is one of Iberia’s great squares, a symbol of design and indulgence. Tucked into its western corner, you will find a wine tasting room and opportunity to compare iconic wines from Portugal’s different regions. This should leave you ready for a local lunch that can also be enjoyed on the square.

Belem is home to Lisbon’s most famous attractions, notably Jeronimos Monastery and Belem Tower, and it is also where pastel de nata, or pastel de Belem as it was originally known, comes from. Come here in the afternoon and visit the patisserie that invented the snack. By now you will be tired, so you can retire to Chiado, a lively old neighborhood packed with wine bars and tapas-style food joints. After the journey and a day of exploring, Chiado is where you sit back and watch Lisbon unfold with a glass in hand.

Vineyards swathe the plains outside of Lisbon, jutting up against the coast and tumbling beneath the castles. These are the vineyards that were acquired by notaries like the Marquis of Pombal and various Portuguese kings, and the vines that introduced Portuguese wine to the rest of the world. Rolling across the sun-baked hills of Alenquer, Quinta da Chocapalha is where you will begin today’s tasting, enjoying the history of the recently renovated cellar. Further across the hill is Quinta do Gradil, where the estate’s most excellent wines are paired with five beautiful courses of traditional Portuguese fare. Casa das Gaeiras is a place to then rest from the morning’s indulgence, gazing across the gardens and feasting on the estate’s history.

After all of this wine tasting, you will probably be in a state of lethargy, which is not a problem because the medieval village of Obidos is best when you have completely slowed down. Here you will find mazy streets of whitewashed houses, a fairytale setting made complete by the horse carriage that takes you around. Superbly preserved in its 12th-century state, Obidos is a vestige of a long-gone era. You will be effortlessly transported back in time, clip-clopping around the village before a toast of Obidos ginjinha. The evening will be left free in Lisbon, and your guide will inform you about the four Michelin-starred chefs who have food stalls in Time Out Lisbon.

The sultry scent of fermenting grapes will greet you in Alentejo while forests of cork punctuate the vineyards and villages cling to their hilltop perch. This region produces more wine than any other in Portugal, and its reputation has soared over the last 20 years to now be known for quality along with quantity. At L’AND Vineyards you will have a private wine course including a tour of the cellar and estate, plus a tasting of varietals synonymous with the region. While yesterday’s wines were marked by an old-world opulence, those from Alentejo are more accessible, and there is a greater variety of flavors on the palate. L’AND Vineyards also has a spa where you can literally bathe in the grapes after a wine massage.

Entirely rested and very relaxed, you will enjoy late lunch courtesy of Michelin-starred chef Michael Laffan. His creations are contemporary, using raw Alentejo ingredients in styles unheard of before. By late afternoon, you will be rolling into Evora, where two millennia of history proudly unfolds through a UNESCO World Heritage center. You will see the Temple of Diana with its Roman columns and mysterious tales, and then the Loios Church and Evora Cathedral, two of the most beautiful architectural works anywhere in Portugal. And then the Chapel of Bones, where skeletons fill the cloisters and skulls provide a macabre atmosphere. This is a lovely city to walk around without a map, checking out the eclectic architecture, choosing your dinner from one of many small home-style restaurants.

It will be all about Alentejo wine today, on a private tour that weaves across the plains and into the mountains. The flavors reflect the region’s atmosphere and heritage as the bold red wines feel just right against the Moorish castles that hang sporadically on the rooftops. As you explore more of Alentejo, you will find that the accessible early flavors of yesterday hide the bolder tastes of tradition. Monta da Ravasqueira is a great example of this, one of the region’s oldest estates and a throwback to early production methods, so you will find the wines to be vastly different from the new-world L’AND. After your tasting, you can take a gourmet picnic into the vines, dining with a beautiful view across rural Portugal.

Many of Alentejo’s modern wines are blends, but at Monta da Ravasqueira you can drink the single varietals. Monte Seis Reis is similar, enabling you to distinguish Portugal’s native grapes. After this second vineyard stop, you will wind into Estremoz, a dazzling old city along the frontier with Spain. There will be time to stroll across the old town at your leisure, perhaps with coffee at a castle and photographs down streets that are constructed entirely from marble. Eat locally tonight in a home kitchen that will serve up specialties that you will struggle to find outside of Alentejo, including dogfish in cilantro sauce and black pig stew. This cuisine is very distinct from Lisbon and has more in common with the Spanish region Extremadura.

The gastronomic journey will continue over the hills and along the Spanish frontier to Belmonte. A castle dominates the town here, providing endless views into two nations. Listen to the sound when your shoes meet the cobbles and hear dramatic historical tales from your local guide. Trancoso also illustrates the region’s frontier past with a fortified village suggestive of quarrels that took place across rural Iberia. But while Spain and Portugal may have rivaled over the land, the people have a similar dedication to fine cured food. For lunch, you can take a cold lunch of cheeses and hams on Trancoso’s small main square, with the aged jamona particular highlight.

Winding further north, you will enter the UNESCO World Heritage Douro Valley vineyards. A steeply terraced landscape surrounds the Douro River, with vineyards clustered onto small squares of flat land. Making wine is difficult here as everything must be done by hand as the vineyards are too steep for modern machinery. Plots are small, and there is a real skill to marrying grapes from vines receiving different levels of sun and light. Attention to detail is essential, and that is one of the reasons Douro introduced a DOC system. It was the first region in the world to introduce quality standards, a system subsequently copied by France and Spain. Arrive at a Douro vineyard, and you can taste this overarching quality from the start.

Vines must be hardy to survive here as their roots stretch over ten meters down into the terroir, which contributes to a richness and boldness of flavor. Settle into Quinta da Pacheca and feast your senses on different wines with the winemaker or cellar master opening up past vintages. You will be staying in a vineyard for the evening at a country retreat with expansive views over the river. You can stroll into a nearby village or relax by the water before dinner is served in the vineyard’s restaurant. It will be an indulgent affair, with multiple courses designed around the wine.

Small wooden vessels have cruised the Douro for centuries to transport grapes and wine barrels to Porto. These are called rabelos, and the boats evoke the romance of a long-gone era. A rabelois the only way to enter Porto on a Portuguese food and wine tour as it is slower than the bigger cruise ships, but you can dock at vineyards on your route, and there is a beauty to the languid pace. Drift through the landscape and dine as you go, eating on the shaded deck as the guide points out famous estates you pass through, like Quinta das Carvalhas. Slowly you wind towards Porto’s bridges, crossing beneath their iconic frames before docking beside a port cellar.

Porto’s port is actually located in Vila Nova de Gaia. More than three centuries ago the cellars were banished from Porto, sent across the river as they were taking up too much space. They did not move more than a mile, and now they dominate the landscape along the river’s southern bank. You will be staying on this side of the river but will dine in Porto, where the traditional recipes have been updated by another of the country’s Michelin-starred chefs. Tonight, your meal will be heavily influenced by port and by seafood with thick sauces and liberal use of nuts and fruit. The restaurant is one of the country’s finest and a superb example of regional flavor for a fitting final dinner on this one-week tour of celebratory moments.

Spend some time exploring Porto this morning as you wander the steep maze-like streets to Se cathedral and Stock Exchange Palace. A UNESCO World Heritage Site and one of Europe’s best-preserved urban centers, Porto is a lovely place to walk without a map. When you get lost, you can just walk downhill, orientating yourself against the bridge to Vila Nova de Gaia and you will be back at your waterfront hotel in no time.

Later this morning you cross the river by paddle boat and take a private tour of a port cellar. Musty fragrances fill the actual cellar, where endless corridors of barrels proudly display their year of production. Back upstairs, in a light and airy tasting room, you can get to know different ports. Taste your way through different ruby ports, including vintage and late-bottled vintages. Compare the flavors with the nutty, caramel tones of a tawny port with your guide likely to open a number of older ports so that you can compare vintages. This will be followed by a gourmet lunch overlooking the River Douro with more cuisine from the north of Portugal and a number of dishes that can be finished with a light glass of port. You will be transferred to the airport later in the afternoon.