We are halfway up the narrow stone steps of the Moorish castle’s crenulated walls when my wife shakes her head and tells us to go on without her. Heights bother her, and the fortifications that run along the ridge of this mountain are precariously high indeed.
If this were the U.S., the castle’s al-fresco stairs would be roped off, or metal guard rails would be installed throughout. But the castle’s natural state is an example of one of the things I love about Europe: User beware. Tumble off and 200 feet down — and it’s your own problem.
So instead, my five-year-old son, Max, and I continue on our own: up, up, up the high steps, reaching the tippiest-top portion of the castle’s tower outlook. Max is all smiles. He wants to sit in one of the archery slits, but even I get a parental, existential tremor. I grab onto his belt as he leans out into the splendor.
Family vacations need not suck. Instead of Disneyland’s castles, we decided to do the find real castles. Portugal may have not seemed the most obvious of choices for castle hunting, but that’s the thing: The country has long been ignored by the international jetset, its national treasures and surprising diversity largely overlooked.
And so we decided to turn our Portuguese into an eight-day road trip, borrowing a brand-new Bentley Continental GT, a spectacular grand-touring coupe with equal parts power and comfort. Even better, it would take us to properties which are in themselves national treasures. We’d be staying in former castles, houses of royalty, historic buildings, and monasteries, all converted into five-star hotels.
The three of us landed in Lisbon, picked up the Bentley and immediately drove west to Sintra. From there, we’d eventually travel north along the seaside to Porto and surrounding regions, and then eventually back south to Lisbon itself.
Beginning in Sintra, as it turns out, was a very good decision. Sintra is about an hour outside of Lisbon; the kind of mountain town where the royals escaped the summer heat.
The region has three magical castles, all clustered within a mile or so, each radically different from one another. There’s the Castle of the Moors, which we’re atop now. In the near distance, the Pena National Palace shimmers in the sunlight with its kaleidoscope of brightly-colored walls. It really does look like a Disney castle. And down below us, at the bottom of the mountain, is the Gothic styled Quinta da Regaleira, which has a mysterious gardens and slightly creepy, labyrinthine caves which visitors are allowed to explore.
From the Moorish watchtower, we can actually spot our hotel down below, shining in the greenery: the Tivoli Palace de Seteais. Such is both its grandiosity and its prime location just outside the old town.
It had taken some wrangling to arrive to the property itself. The local government had recently changed the flow of the old town’s streets, making many one-way. This wreaked havoc on our GPS maps on both car and phone, which didn’t yet have those updates. So we did circles through the town in the Bentley, being mindful not to scrape the immaculate bumpers of the $220,000 machine, until we finally arrived at the great gates of the Tivoli Palace.
It soon proved worth the trouble, with the kind of welcome — fresh lemonade and a snack as you check in, sitting upon an antique settee — that comes with a property keenly attuned to guests’ needs.
The Palace was built in the late 1700s as a private house of royalty. The topiary maze in the gardens is original, as are the archways. It eventually went unused for a century before it was taken over by the Tivoli properties in 1955. Now the Palace has 30 elegant rooms, many overlooking the town of Sintra itself. The food is excellent and the service personal and attentive. It is, quite simply, a fabulous hotel.
That level of service is something we soon learn is endemic to the country itself. Waiters and the like take service seriously. But it is usually delivered with an easy sense of graciousness that only comes with a culture where hospitality is both ingrained and enjoyed.
That night, we have dinner at Romaria de Baco, a casual spot recommended by the Tivoli, and the owner himself is soon at our side, recommending local cheeses, and the marvelous waitress, Margarita, has taken our son outside to play on the concrete steps
Two swift days pass in Sintra, and it’s still nearly not enough time to fully explore the castles, but we get into the Bentley and spirit north, stopping at a seaside town to get fresh fish on the beach. The food is delicious, and Max plays happily in the water. Back at the Bentley, I carefully brush his feet off, not wanting to get sand all over the perfect leather on the seats.
The Bentley is both an ideal foil on winding mountain roads — where the suspension takes to the curves with aplomb — and the freeways, where the 626-horsepower W-12 engine eats up miles with ease. I can’t think of a better car to swish about in Europe.
And so it seems like no time at all we arrive into Porto, crossing the bridge and the Douro River on the way to our hotel, the Pestana Porto – A Brasileira. Though the 100-room hotel only recently opened, it is in a storied building more than a century old, which also housed the famous local A Brasileira cafe. The cafe had been a fixture in town, and it too has recently reopened, a happy pastiche of white tile and aromatic coffee and baked goods.
Like the rest of the hotels which we’ll be staying on for the rest of the trip, the A Brasileira is a member of the Pestana Hotel Group. A family company based in Portugal, the group manages the Pousadas de Portugal, a collection of properties in historic buildings.
We arrive at a rather unfortunate time: Just before the start of a World Cup match featuring the national Portuguese team. (It’s a match they will lose, forcing them out of the games.) Everybody in the country will be watching the match, of course, and I feel bad about checking in just as the game begins. Nonetheless, the staff leap to help us, and one of the porters personally takes me to the nearby parking garage, ensuring I park in a safe spot.
We feast that evening at Rib, a “meat and wine” restaurant at Porto’s other Pestana property right off the Douro. The layout of Porto is not unlike that of Budapest — two halves of the city split by a gorgeous river — and there’s a deep delight to watching the city lights dance on the sliding waters of the river.
By day, too, we’ll find that Porto is a highly walkable city, with plenty of hills to traverse up and down. We almost do enough walking — almost — that I don’t feel guilty trying out the local delicacy, a sandwich called the Francesinha. It has at least three kinds of meat (ham, steak, sausage), covered in a bun, and then smothered in melted cheese. Even Max looks a bit horrified as I mop up the last of the juices with French fries.
Northern Portugal offers mountains, abundant greenery, winding roads, and tumbling rivers. It feels distinctly different than other parts of the country. It is also home to two towns, Guimarães and Amares, which I’d never even heard of before out trip. Both are worth seeking out.
The first, Guimarães, is known as being the actual birthplace of Portugal, owing to its royalty declaring the independence of Portugal in the 12th century. Guimarães itself is a busy city. But the historic center, a UNESCO World Heritage site, is a walled city from the middle ages, keeping urbanity at bay with its web of tiny cobbled streets and imposing castles. It makes a highly enjoyable place to stroll around on a sunny afternoon.
We stay several nights at its hillside property, the Pestana-owned Pousada Mosteiro de Guimarães. This rambling property, which includes acres of mysterious and lush gardens and grounds, has more history than any hotel has a right to. The former monastery has portions that stretch back to the 12th century.
But it is a sister property, the Pousada Mosteiro de Amares, that is unique. It too is a former monastery, this time a 12th century building of Cisterican monks. Amares, 45 minutes north of Guimarães, is a very quiet mountain village. And while the property has been beautifully redone by an award-winning architect, it retains the sense of quietude and solemnity of its previous inhabitants. It is imposing; The stone walls really do feel like they may speak at any time. The grounds and pool look onto the nearby mountainsides. I could imagine spending several days, reading books, and contemplating. (Though not with a five year old in tow.) We only have time for an afternoon visit, which includes a long and utterly delicious lunch. As we’ve come to expect, the service is both personable and impeccable.
It is well past midnight, and Max is playing “ninja spies” with my wife, a made-up game comprised of him dashing around the streets of Lisbon and pretending to hide from passers-by. The sight of a giggling boy crouched against a wall, many hours after an appropriate bedtime, almost universally creates a similar reaction from Lisbon’s late-night revelers. They start giggling themselves.
This is Lisbon: An infectiously happy town, riding high on a newfound popularity. The riverside city is now known for great food, fun bars, and cool people. You feel lucky to be here, at this time, sharing that food and drink and sense of merriment.
We spend our mornings and early afternoons wandering from neighborhood to neighborhood; each with its own particular feel. Lisbon is also a town of high hills, and often presents overlooks with spectacular views of the Tagus river. The old, tile-covered buildings are gorgeous in a slightly crumbling way, and it never feels too early to grab a wine or beer at an outside table and watch the world amble by.
As the afternoon gets hotter, though, we’re happy to retire to our perfectly-located hotel, the Pousada de Lisboa. It is a grande dame, painted imperial yellow and right on the central plaza, the Praça do Comércio. Since it’s both riverside and highly visible, you can never get so lost that you won’t find your way back. A former ministry building and national monument, it is of course historical and is stuffed with antiques, statues, and artwork.
In a city like Lisbon, you don’t want a place to hide away — you want comfort, insider knowledge, and an ideal location. The Pousada de Lisboa delivers all that in spades. I have a hard time imagining a better setup.
But, then, I also had a hard time imagining a better family trip — or a road trip. When it comes to both castles and magic, Portugal delivers.
For general information about Portugal, see Visit Portugal .Flights from the U.S. direct to Portugal are available on TAP Air Portugal . Click Here to book any of the Pestana hotels and here for the Tivoli Palace. If you can afford the Bentley Continental GT coupe we salute and encourage you.
By Jason Harper
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