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Second cities: Destinations to add onto a trip to Lisbon

Sept. 15, 2019
10 min read
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Welcome to TPG's series Second Cities. The series is designed to help travelers find smaller or less-popular-but-equally-amazing places to visit that are no more than a few hours by air or land from your original destination so you can maximize your itinerary.

Although you can spend a trip to Portugal exploring all the hidden corners of Lisbon or lounging on a picturesque beach, the country's small size makes it the perfect destination for active travelers and explorers wanting to cover a lot of terrain.

Portugal is roughly the size of Indiana, making it fairly simple to get from A to B. Although flying makes sense in some cases, in general, renting a car or hopping on a bus or train out of the country's capital affords you a number of other dynamic Portuguese adventures you may not have if you only spend time in Lisbon.

Lisbon, Portugal. (Photo by Sean3810 / Getty Images)
Lisbon, Portugal. (Photo by Sean3810/Getty Images)

Day trips to Sintra's famous palace and the beaches of Cascais are an easy feat, just 30-45 minutes by car from Lisbon, but if you'd like to spend a little more time in spots farther outside the capital, here's where you should go.

Porto & Douro Valley

Porto, Portugal and the Dom Luís Bridge over the Douro river. (Photo by Sebastien GABORIT / Getty Images)
Porto, Portugal and the Dom Luís Bridge over the Douro river. (Photo by Sebastien GABORIT/Getty Images)

While Portugal's second-largest city may seem like an obvious choice, Porto and the surrounding Douro Valley are delightfully underrated and much less visited than Lisbon.

Getting there: Take advantage of TAP Portugal's newly launched routes from Chicago (ORD), Washington, DC (IAD), and San Francisco (SFO) to Lisbon on the A330. You can build in a stopover in Lisbon up to five nights, and then continue onto Porto (OPO). Or, organize a multicity adventure flying the airline's first Airbus A321-LR out of Newark (EWR) nonstop to Porto (OPO). Then, head over to Lisbon (LIS) on a 55-minute flight and then back to the US out of Lisbon. By car, the ride between the two cities is about three hours.

Where to stay: The InterContinental Porto Palacio das Cardosas (rates start at $175 or 50,000 rewards points per night) is located at the edge of the city's historic center — and just down the street from one of the world's most beautiful McDonald's. Yup, you heard right. Take a moment to pop into the familiar golden-arched fast food joint — even if it's just to ogle and not to eat. This particular location doesn't boast the typical plastic décor: it still retains stained glass and chandeliers from its former glory as the Imperial Cafe.

What to see and do: Start by wandering around Porto's historic streets, admiring the faded tiles crumbling from the city's buildings and sampling Portuguese tarts. Walking across the Dom Luis I bridge is a must, and make sure to cruise underneath on one of many boats offering one-hour cruises along the Douro.

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Port wine tasting in Vila Nova de Gaia on the other side of the towering bridge is ideal for an early happy hour. Take the cable car running along the wineries and the river's edge for breathtaking views of the bridge and then hop from Sandemans to Calems and beyond, sipping tawnys, rubys and white ports along the way.

Sandeman Wine Cellar. (Photo by John B Hewitt / Shutterstock)
Sandeman Wine Cellar. (Photo by John B Hewitt/Shutterstock)

Bookworms should visit the Lello Bookshop to admire the intricate woodwork and impressive staircase. The entry fee is worth it if you plan to buy something as it goes toward a purchase. Wandering through the Clérigos Church will offer some insight to Portuguese baroque architecture, and make sure to wind up the tiny staircase to see the view from the top of the bell tower, looking out over the red-tiled rooftops, Douro River and beyond.

Outside of the city, visit the many quintas, or wineries, located throughout the Douro Valley. Or, enjoy day- or weeklong cruises up the Douro River.


Riders on the toboggan in Monte Sledge. (Photo by Nikiforov Alexander / Shutterstock)
Riders on the toboggan in Monte Sledge. (Photo by Nikiforov Alexander/Shutterstock)

While beach-lovers can always head to Portugal's lengthy coast or to the islands of the Azores, Madeira is a spot often overlooked by the average traveler. Although many of the beaches are pebbly, the island's volcanic pools and wineries tucked away into the hills may just be more intriguing than a stretch of sand, especially if you're visiting during cooler months as Madeira is known to be the land of eternal spring.

Getting there: Flights from Lisbon to Funchal (FNC) are available nonstop on TAP Portugal or on low-cost carrier EasyJet. The flight is under two hours.

Where to stay: Although Madeira is lacking in points hotels, you can have a classical, luxurious stay at the Belmond Reid's Palace (approximately $320 per night), which is set on a cliff overlooking the Funchal Harbor. The hotel is bookable on, and if you pay with the Capital One Venture Rewards Credit Card through Jan. 31, 2020, you can earn 10X per dollar spent.

Frequent visitors to Portugal (and other spots in Europe such as Spain and the Netherlands) may want to consider staying at one of the popular Pestana Hotels, which offer its own loyalty program, the Pestana Priority Guest. Soccer fans will enjoy a stay at Pestana CR7 Funchal, a collaboration between Portuguese footballer Cristiano Ronaldo and the hotel group (rates start around $125 per night).

What to see and do: Madeira is made up of two islands: Madeira and Porto Santo. If you're visiting in the summer and you want a traditional beach scene, take a 20-minute flight to PXO on Binter Canarias or a 2.5-hour ferry from the Funchal Harbor. Porto Santo's 6-mile-long stretch of golden sands is one of the most beautiful beaches in all of Portugal.

Those who prefer to see the sea from atop rocky volcanic cliffs should stay in Madeira and explore the small villages and natural wonders located around the island. The first order of business should be to take the cable car up in the island's capital, Funchal. Then, get pushed back down the curvy, winding roads in a wicker sled (known as the Monte Sledge). Nothing says 'Welcome to Portugal' like being raced down a hill in a toboggan basket by two grown men using their boots as brakes. While sandy beaches are far and few between on the island, it may be even more fun to swim in natural pools formed by volcanic rocks and lava at Porto Moniz.

Hiking the volcanic peaks of the island such as Pico Arieiro and Pico Ruivo are energizing ways to spend your trip — your reward being sky-high views of the island and its surrounding Atlantic waters. Or, check out Cabo Girão, one of Europe's highest cliffs. The glass-bottomed skywalk at the top of the cliffs gives you vertigo-inducing views of the sheer drop to the sea below.

Cabo Girão on the Island Madeira. (Photo by PleskyRoman / Getty Images)
Cabo Girão on the Island Madeira. (Photo by PleskyRoman/Getty Images)

If hiking isn't your idea of a relaxing vacation, get those cliffside sea views while wine tasting at many of the hilltop wineries around the island. Madeira wine is a fortified wine — its dry, strong taste comes from repeatedly heating it during the creation process. It's difficult to find in the US, so tasting (and bringing some home) will be a memorable experience.


Coimbra. (Photo by ipinto / Getty Images)
Coimbra. (Photo by ipinto/Getty Images)

Portugal’s interior provides a vast relief from the all-inclusive, cookie-cutter resorts that are descending on the southern Algarve coast. If weaving past small villages throughout the heart of Portugal sounds like a dreamy escape, make your base the enchanting medieval town of Coimbra.

Getting there: For prime exploring, rent a car and drive the two hours to Coimbra from Lisbon. Once there, so many other villages, beaches and towns are within a short drive. The train also takes about two hours.

Where to stay: Both of Coimbra's Baixa and Alta (low and high) neighborhoods offer plenty of accommodation options. The Alta neighborhood, once reserved for the more aristocratic, is home to the family-owned Sapientia Hotel, which features a stunning rooftop with river views. Staying at an Airbnb in Baixa area gives you easy access to many of the town's historical sites. Or, cross the river and stay in the fancier Santa Clara neighborhood at the Quinta das Lágrimas, a stunning garden villa that recently joined Hyatt's Small Luxury Hotels of the World program (rates start at $165 or 20,000 points per night).

What to do: Whether you spend one night or seven in Coimbra, the town and its many surrounding hilly villages emit a rustic charm designed to woo you. You can use the town as a base and once you've seen its gardens, Roman ruins and crumbling Medieval walls, plan to visit Fátima (less than a one-hour drive), one of the world's most famous pilgrimage sites where the Virgin Mary reportedly appeared in 1917. Or, head to the "Venice of Portugal," Aveiro (also less than a one-hour drive), known for its colorful Portuguese-style gondolas (called moliceiros) that navigate the canals (once used to gather seaweed), taking you past eclectic art nouveau architecture.

Aveiro, Portugal. (Photo by Bet_Noire / Getty Images)
Aveiro, Portugal. (Photo by Bet_Noire/Getty Images)

Just a short drive away, you can discover a number of Portugal's schist villages. The name comes from the construction of the village, made from a special “schist” rock, a metamorphic, horizontal stone easy to split and build with. The schist architecture is unlike any other, and lazily wandering these small, hilly villages is a true escape for those needing a break from a busy urban lifestyle.

Back in Coimbra, make sure to see the São Sebastião aqueduct, which dates back to the 16th century. Or, admire the collection of over 40,000 books at the Biblioteca Joanina, a baroque library that seems more like an elaborate palace or cathedral that happens to be filled with books. See the library as part of a tour of the University of Coimbra, a UNESCO World Heritage site and Portugal's oldest university.

Featured image by (Photo by lili popper / Unsplash)