Centuries blur together on the streets of Lisbon. A maze of 18th-century cobbled streets is alive with color and chatter while the Bairro Alto is the bohemian hangout for the 21stcentury. Chiado is older but now brings a new world suave that has its roots in tradition. Your hotel is between these two neighborhoods within walking distance of both, or you can take the tram, with lots of wine bars for your enjoyment. Your local guide will meet you at the airport and will help you check into the hotel. After a brief orientation tour, the evening will be free with your guide offering ideas for restaurants and other places to start exploring the city’s culture.

Wake up late and take it easy this morning. Set out, and you will soon see Lisbon’s affection for espresso and pastel de nata, a custard pastry that originates here, as well as the city’s slow pace of life. Spend the day exploring Lisbon and travel to local neighborhoods and the grand monuments. Enjoy Se Catedral, the old castle, the rambling streets of Alfama, and the opulent boulevards of Baixa. As the afternoon drifts into evening, you can go tasting at one of Lisbon’s finest wine bars, a place to start tasting the differences between DOC regions. Wine bars are a new feature of Lisbon, but as the country’s wine industry garners international acclaim, they have become a means to celebrate the hundreds of small producers that are shaping Portuguese wine.

Out of Lisbon, you will drive into the hills as a salty Atlantic Ocean breeze brushes the vineyards. Arrive first to Bucelas, the wine region adored by British royalty during Elizabethan times, and home to semi-dry whites with a very vibrant history. Taste and taste some more, and then travel closer towards the coast and Quinta do Gradil, where wines are paired with food in a rustic chateau. Walk it all off at the gardens of Quinta dos Loridos before another Lisbon wine tasting with semi-dry whites again the focus, but there are also some soft reds worth exploring from this DOC region. Around late afternoon, you will be in Obidos, a charming place of whitewashed walls and cobbled lanes and perfect for walking off the wine and food before heading back to Lisbon nearby.

They have been making wine in Setubal for 4,000 years now, evidence suggesting this was the first world region to produce muscat style wine. Jose Maria da Fonseca is the world-famous producer here, and you will tour the vineyard with the cellar master before tasting the range of wines that have been produced since the mid-19thcentury. Quinta da Bacalhoa dates to the Avis Dynasty and really celebrates the history of the peninsula, both through the wines and through the estate itself. Explore its galleries and the lounge around the palace before a wine tasting with striking views out across the gardens. You will be back in Lisbon around mid-afternoon, so the rest of the day is free to see more of Portugal’s capital.

Travel east into Alentejo, where the sun-parched plains are most famous for leading the world’s cork production. Vines thrive here as well and carpet the hilly slopes to create a scene that seems quintessential for Southern Europe. Join a winemaker and tour the Monte da Ravasqueira vineyard, learning about production in Alentejo. The wines are diverse here, as a lot of grapes do well. Production is high, and quality has risen significantly in recent years, as demonstrated by a wine tasting that is paired with a picnic. Continue your journey through Alentejo and go tasting in the Cartuxa Cellar, delving into different vintages to explore the aging potential of the region’s DOC wines. End the day at a 15th-century convent in Evora, a place historically used by visiting royalty that has become a five-star hotel and spa.

Spend a morning in the spa with an olive oil treatment with lemon and rosemary to get the body going, and then take a walk through Evora. A Roman Temple still stands after 2,000 years, and a nearby church is packed with dramatic frescoes. There is a chapel decorated with human bones, skulls creating pillars and femurs crisscrossing above the altar to create a surreal atmosphere in a sanctified space. The afternoon is flexible, and your guide can take you to several vineyards, including those who sell their wines around the world, along with more small-scale productions that have been making waves in and around Portugal. Evora is a delightful place to spend the evening, and especially after Lisbon day-trippers have left. Walk the medieval lanes, relax on outdoor restaurant terraces, and toast to the Alentejo region.

Your senses will be on overload as aromas float through the cellar of Herdade do Sobroso. This country house in remote Alentejo takes you into the nuance of local wine production, teaching you the enological basics of becoming a winemaker. In particular, see how to test wine from oak barrels to determine its future quality. Like everything in Portugal, you will have a laid-back and informal experience with plenty of laughter and as much tasting as you can handle. Eat lunch in a village nearby, and the rest of the day is all about Moorish history as this region dotted with whitewashed towns where the mosques still call to prayer. While many visit Evora, few get out to Alentejo’s other old towns, so expect a local experience and opportunities to sit around old plazas with the locals.

Traveling north the hills will grow higher as the wind starts to blow, an arid continental climate meeting the Atlantic Ocean weather. Hidden here are the vineyards of Dao, and tucked away on sheltered slopes, the vines thrive in the adversity. Grapes respond to stress, and in the Dao Region, they produce heavy exotic flavors. Single varietal wines are too intense, but classic Portuguese style blends do well with Touriga Nacional as the dominant grape. Think black cherry and cocoa on the nose, with a long oak-influenced finish. These are wines paired best with food, so you can sit down to lunch at an estate and taste your way through the vintages.

Stop in Dao on your route north to the Douro Valley, the darling of Portugal’s wine industry. The country’s recent viticulture acclaim can be heavily attributed to the Douro, a region that has started to produce stunning red blends, in a similar style to the most famous wines across the border in Spain, Rioja, and Ribera del Duero. Check in to a wine estate hotel and check out the view from your room that runs down and across the vineyards to the Douro River far below. You will dine at the estate, and it is an excellent way to compare the flavors of the two neighboring regions as you explore Dao and the Douro Valley.

The Douro was the world’s first demarcated wine region, which illustrates the area’s dedication to quality. Most of today is dedicated to two wine estates that have become synonymous with Portuguese red wine. Both date back to the 18th century but have only really entered the scene in the last 20 years. Quinta do Crasta is an opulent estate, and you can tour the facilities, including the 70-year-old vines so revered in Wine Spectator magazine. The cellar-master leads the way at Quinta Nova, great collections of oak barrels providing a musty smell before you dip into the luscious wines. If there is time, you might also visit a smaller producer, perhaps one that has switched from port-focused wines in recent years. While the same grapes as a port, and on the same slopes, the grapes are just cultivated in a different style.

The sail ruffles as you drift upriver and deeper into the Douro Valley. Your wooden boat has quite a history as a renovated craft that once transported grapes down to Porto. It is a timeless vessel for tasting amid nature, a breeze past your ears as the captain introduces wines from all three Douro Valley sub-regions. Disembark at a vineyard and admire the terraces, as because machinery cannot access the steep mountain slopes, everything is done by hand, right down to hacking through the schist and granite terroir. Vines stretch 20 meters beneath the ground, clinging on the near-vertical slopes. It will be a beautiful sight, the wine terraces extending skywards in a way not dissimilar to the riverside rice paddies of Asia. You can spend most of the day on the boat, indulging in the wine and food, before a relaxed evening at the estate hotel.

Spend the morning in the Douro Valley villages, places of serenity, and the surreal atmosphere of centuries past. Dive next into nearby Porto, a World Heritage city that wears its age with pride. Mosaics of azulejo tiles cover most of the buildings, and artistic facades found down streets that are too steep and narrow for vehicles. Wine bars are tucked away along cobbles, and restaurants are perched over the Douro River. This afternoon is left free, a time for you to go explore and make your own impressions in the city. In places like Porto, you will not need a map or a plan, so you can just go walking and soak up culture and style that has barely changed in three centuries.

Now it is time to move into the port cellars, iconic structures that stand side by side on the Vila Nova de Gaia side of the river. Great rows of oak barrels fill these cellars, aging port for up to 40 years. The tip-tap of a cooper’s hammer adds to the musty smells, and when you emerge from the cellar, you can take a vintage masterclass tasting in an old-world reception room. You will learn the vintages and styles, taste the same grapes as in the Douro Valley, and explore the role of port in the history of Porto and Europe. Visit two cellars and then board a wooden rabelo for a cruise on the Porto side of the Douro, tasting different ports as you travel on the vessel once used for transporting barrels.

Your final day on vacation will be very relaxed with the program mostly tailored around your energy levels and interests. You could choose to take a trip to nearby Minho, a wine region producing crisp green wines, low-alcohol whites that are best for a hot summer day. You could explore the old city, walking part Clerigos Tower to the wooden bookshelves of Lello, and then through the cobbles and stairways to the fabulous azulejo mosaic at Sai Bento Station. Porto Cathedral showcases the city’s history as it was built across three different eras, while the Palacio da Bolso suggests the city’s dedication to being unique. Spend some time in a wine bar on the river, trying wines from regions that haven’t featured on this tour, and dine at a Michelin-starred restaurant high above the river.

Leave Portugal from Porto’s international airport, and the day is left free until your private airport transfer.