A grand tour of contemporary Portugal will take you to the country’s lively cities and through its food and wine backroads. Start in grand Lisbon to discover a food scene both cutting-edge and classic, the wild coast of Setúbal and plenty of hilly atmosphere. Wide-open luxury awaits in the Alentejo, inland Portugal’s heartland of wine, olives and whitewashed estates. Switch gears into northern Portugal as you head to Dão, a land of green hills and superb perfumed wines. Finally, finish your journey back by the ocean in Porto, the storied city that Port built, for history, wine and food.

Day 1 – Lisbon: Portugal’s Food Capital

Start your trip in Portugal’s hilly Atlantic capital Lisbon. Full of atmospheric corners and grand squares, Lisbon combines old-world Portuguese charm, imperial history and electric modernity. A local insider will take you to see the city’s key spots and difficult-to-reach viewpoints; it’s important to get elevation for perspective in Lisbon. With appetite awoken, there’s nothing for it but a food tour. Lisbon is packed with traditional gourmet shops, wine bars and petiscos places serving Portuguese tapas. Cheese, charcuterie, canned fish (the aperitivo trinity in Lisbon), cod fritters, savory pastries, sweet pastries, grilled peppers, grilled sausages, maybe even some garlicky clams. In one of the most wine-loving countries in the world, all these bites go down better with a glass of Portuguese wine in hand. Your guide will make sure you hit the ground running with classic wines made from those infinitely varied local grapes.

Take the afternoon to unwind at a café or stroll the city. In the evening, you’ll get a taste of modern Lisbon with dinner at Tasca Bica. With a Brazilian chef who worked in Shanghai, this Japanese-inflected hot spot embodies the excitement of Lisbon’s local-international scene (not all new: the former Portuguese colonies have been influencing Lisbon’s food for centuries). Expect creative salads, cod, duck ham and frango. Frango: chicken in Portuguese, prepared a few ways at Tasca Bica but the best is dry-aged in ham fat, smoked, roasted, barbecued with a special selection of herbs and spices. Drink Portuguese wine from small producers if you like, but might want to start with a cocktail!

Day 2 – To the Sea

Despite news to the contrary, Lisbon is not actually on the ocean. To see open Atlantic freshness you’ll be heading to the Setúbal Peninsula, just a short drive across one of the extra-long bridges that intersect the Lisbon riverfront. This is wild wide-open coastal country, little fishing villages and white-sand beaches–not urban at all despite being nearly Lisbon itself if measured in miles. Your guide will take you into the Setúbal fish market, where an infinite variety of fish and lobsters and clams and other sea creatures are sold. Portugal loves seafood as much as anything, with lots of fine-grained distinctions between slightly larger red things with claws and slightly smaller pink things with claws. Anyone who sees a Portuguese fish market might want to try all the product, so the best course of action is to head to one of the Setúbal seafood restaurants where gourmet lisboetas come to eat. Expect simple preparations and the freshest fish anywhere, old-school Portuguese waiters and ice-cold local white wine from the vineyards of Setúbal.

Setúbal has been famous for its wine for centuries, sweet long-aged fortified stuff. The Atlantic breezes keep the vineyards here refreshed and a little salty. Head to a little winery specialized in the local sweet wine for a tasting before heading back into the city. Oficio awaits for dinner. It’s a cozy spot with young chefs in charge and a menu where you want to order everything with plenty of Portuguese vegetable dishes, raw/smoked/baked fish and some shockingly good meat dishes.

Day 3 – The Alentejo Expanse

Today, leave the city behind: you’re heading into the open country of the Alentejo. This is Portugal’s wild Southeast, flat and dry, a land of cork oaks and olive trees and blinding sunshine. It’s also one of the country’s beating hearts, where tradition is alive and powerful. You’ll start your rural time in the countryside itself, at a typical alentejano estate producing cork, olive oil, walnuts and wine. You will tour the estate and have a light lunch with products produced there. Then it’s on to your countryside hotel Torre de Palma, in the northern reaches of the Alentejo where the good wine is. The hotel is a winery, so on arrival you’ll have a wine tasting. Unwind before heading down to dinner at the hotel’s restaurant for updated Portuguese dishes with lots of local product and produce from the hotel’s garden.

Day 4 – Alentejo Wine & Évora

Now in the heart of Alentejo, you’re ready for some off-piste exploration. Start at the truly scenic Dona Maria winery, where the land-endowed owner will show you the place (sprawling and whitewashed), and lead a tasting of numerous wines. On to the town of Évora, with its narrow streets and Roman ruins. Dive into an arch-traditional eatery in the old town for a light lunch (as light as the food-loving locals allow). Relax for the afternoon at Torre de Palma. Your guide, a real Alentejo insider, will pick you up for dinner in Estremoz, site of food pilgrimages from both sides of the Portugal-Spain border. Dine in a former prison on grilled vegetables, grilled meat, grilled fish, in very respectable quantities.

Day 5 – Dão: Green Land and Fine Wine

Now that Alentejo has convinced you that Portugal is Mediterranean, you’re going north to be shown otherwise. Your destination: Dão, hilly country by the Serra da Estrela mountains that is green and wooded and dotted with villages and small vineyard plots. This is the start of the North, wet and cool and local and small-scale. Why are you here? For the wine, first and foremost. People call Dão the Burgundy of Portugal. After tasting at two mountainside wineries stop for lunch in the mountain wine village of Gouveia where everyone must make at least a little wine. Then you’ll settle in to your palatial hotel in Santar, enclosed by with gardens and terraces, and have dinner in.

Day 6 – Dão to Porto

One last winery stop before you head to notoriously wine-loving Porto. Caminhos Cruzados in Dão. This is a modern winery where you’ll have a wine-pairing lunch prepared by the on-site chef. Dão wines go great with food  and this lunch will show you why. After you arrive in the city, a local expert guide will pick you up for a tour of the city center. You’ll see some of the city’s famous corners as well as the atmospheric spots you’d be unlikely to find on your own. Dinner at Almeja will give you a taste of local products in creative dishes at the hand of local chef João Cura and paired with small-production Portuguese wines.

Day 7 – The Atlantic Side Of Porto

Porto may be a port, but the city is on the river, not the ocean. Today you’ll head to the Atlantic fishing port of Matosinhos just outside the city center. Matosinhos was long a center of the canning industry, but today it’s best known for bringing in fresh fish and seafood. You’ll visit the market, packed with untranslatable fish and shellfish. Then, it’s time for an extravaganza: lunch at Marisqueira A Antiga, arguably the area’s best seafood restaurant. Winemakers and lovers of good eating make their way out to Matosinhos to eat and drink here. Oysters and clams make great starters. Lobsters and shrimp in all sizes make their way into rice dishes. Subtle Atlantic fish are grilled or baked in salt. And the wine cellar is overflowing with rare wines from across Portugal and the world, including plenty of flavorful whites that pair splendidly with the food.

After lunch, your guide will take you to a family-owned winery in Vilanova de Gaia, the town across the river from Porto where Port wine shippers age their stock. You’ll taste fine Douro Valley wines with a member of the family.

Day 8 – Departure

Private transfer to the Porto airport or train station for departure.

An impeccably restored 19th-century palace turned boutique hotel in the upscale Príncipe Real district of Lisbon. Awarded the 2024 and 2025 Conde Nast Traveler's Readers Choice Awards and a spot on the Telegraph’s 50 Best Hotels in the World. The rooms and public areas are beautifully furnished and parts of the hotel feature original tile work. Rooms offer complimentary drinks, including wine, homemade treats and fresh flowers and fruit.

The heart of the hotel is the garden, an oasis in the heart of the city, with a pool and outdoor terrace to enjoy breakfast (served until noon), lunch or dinner or a glass of wine. The hotel’s EVOO restaurant serves meals all day long and Mick’s Bar is the spot for a late night drink. It’s almost like staying in a friend’s house in the heart of vibrant Lisbon.

Torre de Palma

This beautifully converted Alentejo farmhouse offers relaxation and luxury in the Alentejo countryside. Torre de Palma is a 5-star winery hotel, where you can immerse yourself in traditional Alentejo whitewashed architecture with modern twists. Wine tasting, wine blending workshops, wine-pairing meals, Lusitano horse experiences and spa treatments await. Chef Miguel Laffan’s on-site Palma restaurant showcases local sausages, cheeses and meats in the contemporary Alentejo cuisine.

This luxury countryside getaway sits in the heart of the Dão wine region. The hotel was a home of the Portuguese royal family, and the common areas still exude old-world charm. The hotel’s gardens are extensive, perfect for a stroll or a drink by the pool. The rooms have been tastefully updated to luxury standards, retaining historic charm. The on-site restaurant and spa make for a relaxing stay.

5-star luxury dead center in the heart of Porto, the One Monumental Palace Hotel offers elegance and good taste in a stately building from 1923. A spa with an elegant indoor swimming pool, a sauna and hammam, a one Michelin star restaurant, a Japanese restaurant and a cocktail bar mean you hardly need to leave the site.

Chef Julien Montbabut’s flagship Le Monument restaurant offers culinary voyages through the regions of Portugal. Yakuza Japanese restaurant serves sushi, sashimi and maki. American Bar serves traditional and creative cocktails as well as casual fare.

The hotel is on one of Porto’s central streets, Avenida dos Aliados, and is walking distance to iconic sites such as Lello bookshop, Torre dos Clérigos, the Bolhão Market and São Bento Station, not to mention the many nearby bars and restaurants.