[SINTRA, PORTUGAL] — Sintra is not just a single town, but an entire wooded (unusually so in these arid parts) nature preserve about an hour and a half outside of Lisbon. It’s the perfect daytrip from Lisbon or the perfect day trip from Cascais. Definitely well worth the drive and easy to find — all the roads and signs in Portugal are outstanding. It’s a big riot of color and architecture, surrounded by hundreds of acres of gardens and forests. Plan a half a day, at least, or preferably a whole day, to make the loop through the forest and the half dozen towns and castles and sites within the preserve. It is very busy. Very touristy. But very cool to see. Think of it
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[CASCAIS, PORTUGAL] — About a half-hour outside of Lisbon, Cascais is a great little beach town along the coast and the perfect long weekend base to explore the entire Lisbon coast. What to do in Cascais. Where to stay in Cascais. Where to eat in Cascais. It’s hard to picture such a cool little beach town as a suburb of Lisbon; it feels like a world away. Where Lisbon opens onto the Targus river, Cascais is further out on the peninsula, just past the Monaco-like wealth enclave of Estoril. Out here, you are more open to the blue waters of the Atlantic. [Note: a lot of people think that Portugal is a Mediterranean country, but it actually doesn’t even touch the Mediterranean Sea, it opens
[CASCAIS, POTUGAL] — Only an hour or so outside of Lisbon and just 5km and 10 minutes from the sunny Lisbon beach suburb of Cascais, Praia do Guincho. Guincho Beach. Rated as one of the best beaches in Portugal and on top ten beaches in the world, it’s a dream. Strong winds, perfect sand — a contrast to the rocky beaches of France and Italy — large waves and incredible sunsets, it just all adds up. It’s easy to get to, with parking along the road and multiple coves (I’m actually not 100% if there is one single Guincho, or a bunch) you can just drive, park and burn. If you’re staying in Cascais, you can rent a bike and it’s an easy flat ride, take
[LISBOA, PORTUGAL] — In planning for a trip to Portugal with a bunch of friends last month, I was in charge of looking for a cool boutique hotel. Some in the group I knew, others were going to be New Friends. Some I assumed were wanting somewhere special, others (cough cough) were a little more “I’ll just use my points.”-type. The pressure was on… Holy cow (✞🐄) it’s amazing how fast Lisbon changes. I remember the first time I went in 2013 and Baixa was mostly boarded up and there just wasn’t much to do down in that grid of slick stoned streets. Now you can’t swing a cat without hitting a spanking new hotel or IKEA-bedecked Airbnb. The question was which one. I stumbled
[DOURO VALLEY, PORTUGAL] — After a harrowing Google Maps-led hair-brained shortcut through curvy mountains roads (umm guess who was Navigator 🙄), we arrived with our seasick passengers… ready for a drink. We drove through a gated entrance to a wine estate, wound up the road straight into the vines. A teeny sign on the right said “Reception ↘︎”. We slammed on the brakes. (Groans from the back) “That can’t be it…”. What we couldn’t see was the building built into the side of the cliff below us. Unlike Google Maps, we trusted this little sign. We fell out of the rental van, stumbled down the flinty steps and KABOOM. The view we were looking for. Just as Ana has prescribed. We walk into the
[DOURO VALLEY, PORTUGAL] — I see all these Instagram peeps hitting Porto taking pictures of the big bridge, climbing up its steep hills, drinking some port and then bolting. But really what they’re missing is a day trip (or longer) up the Douro River to visit the incredible, hilly stair step vineyards of the Douro Valley, one of the prettiest places I’ve ever been. I dunno, I’m over wine tours, once you see a few, they’re all the same to me — “Is that French oak or American? How long in stainless??” — poke me in the eye with a stick…but that’s just me… But the Douro Valley is different. Hilly. Steep. Flinty mounds of luscious green heaven pouring down to a mellow meandering river.
[ALENTEJO, PORTUGAL] — Leaving the pine-canopied coastal lands of Comporta, you drive straight across the heart of Portugal’s beautiful Alentejo region. Covering 30% of the country, this is Portugal’s bread basket. 10,000+ square miles of endless fields of cork, olives, wine and wheat. When you read any article on Alentejo, you will undoubtably see bright photos golden wheat and dark green cork trees, mine will be no different. I’m here to visit one of Alentejo’s best boutique hotels. It almost feels like a movie filter, everything all gold, dark green and brown. The pounding sun almost making everything a little fuzzy. The uniform bright white architecture of Portuguese house of buildings, starkly contrasting with the golden fields and green hills. Driving Across Alentejo Driving
[Alentejo, Portugal] — From this hilltop, the highest in the region, you can see forever. That’s why this little town has been important throughout history. And not just history, but pre-history. Monsaraz in Alentejo is the site of one of the oldest settlements in Portugal, going back to neolithic times when people were tilting stones to the sky and calling it home. Or temple. Or tomb. There are some of the best neolithic sites in the world scattered all over this region. This was such a strategic location that it has been fought and won over many many times by the conquering hoards. First, the pagans, then Romans, then the Goths came and slaughtered, then the Arabs, then another collection of Arabs, then Jewish conquerors, Christians
[ALENTEJO, PORTUGAL] — The ancient town of Monsaraz sits high on a hilltop in Portugal’s Alentejo regio, the tallest point for miles around. Just miles from the Spanish border and surrounded by thick castle walls, it overlooks one of the most beautiful parts of inland Portugal, including the giant Alqueva reservoir — the largest manmade lake in Europe. Some consider Monsaraz one of Portugal’s most picturesque villages and it is one of it’s oldest. People have been living in this region since pre-historic times, with ancient monoliths strewn all over the land. Then the Romans came and took over, then Visigoths, the Jews, then Christians, then Muslims again… everyone wanting a piece of this strategic hilltop. Surrounded by thick protective walls, the castle goes back
[LISBON, PORTUGAL] — Here’s a great boutique design hotel to stay in Lisbon. The Lisboans. When I got out of the taxi, I noticed the small, discrete sign out front, The Lisboans. I rang the doorbell and was buzzed in. A gregarious Mario welcomed me like a brother “You’re Dan?, we’ve been waiting for you, welcome to The Lisboans“. He brought me through a small door into a room full of six or so people at open desks, working on their computers. “Everyone, this is Dan.” “Hi Daaan.” they all replied, with smiles. “Welcome to our Nerve Center where everything happens’”. Everyone goes back to clacking away. Reservationists. Web people. Housekeeping. All right there. So refreshing. On the wall was a big grid on a whiteboard,
[LISBON] — There are lots of great restaurants in Portugal, but I’m just going to talk about two must-visit restaurants in Lisbon that I recently went to. Restaurante Prado and Horta dos Brunos. Two fantastic and completely different experiences. When I was in the beach town of Comporta, Yasmine, a very tasteful Belgian Instagram friend direct-messaged me this tip: And then, when I was in the far rolling hills of Alentejo, my friends Neil & Lisa texted me: “We went to that Horta dos Brunos your friend recommended. Wow. Fantastic. So full. Can’t walk.” When I finally arrived in Lisbon, I knew I had to go and made reservations. When I got in my Uber and the non-English speaking driver saw the destination on
[ALENTEJO, PORTUGAL] — Driving out of Lisbon airport in your rental is absolutely crazy, with GPS or not. After an overnight flight (or two) you exit the terminal into the bright Portugal sun all bleary eyed, you get your car and just go. The GPS is playing catch up, while the traffic is not, bearing down on your tail like a dog in heat. The roads are like a plate of dropped spaghetti, turning off in every crazy direction, with signs that don’t match what the GPS is telling you. After a couple of roundabout orbit corrections, you finally break free of the tangle and head south for the Tagus River. Suddenly, the bright blue sky opens up, the traffic disappears and you’re back to
[ALENTEJO, PORTUGAL] — It’s the pine trees that get ya. They are everywhere in Comporta. Big billowy umbrella pines that quietly sway in the breeze. Besides the rice fields, Comporta is known for its pines. And because development has been strictly controlled, the remain its dominant feature. There are no massive hotels or major housing estates, just slivers of streets carved out of the trees, often with protective easements that protect the privacy forever. When I first saw this villa on Airbnb, I thought “Oh wow, this is nice…” and kinda like finding a puppy at the pound, I knew this would be the place we’d rent. Wasn’t quite sure of the area at first — had a hard time figuring out distances on Google
[ALENTEJO, PORTUGAL] — We’d spent our first day in Comporta at Pégo Beach, one of the best beaches in the area. Still a little jet-lagged after arriving the night before. We rented chairs and lulled ourselves to sleep with the waves while quietly reading/not reading our books. The sun was high, it was the end of June, but the steady breeze kept the temperature in the 70s. Unbelievably perfect. Families played beach games as we shake-and-baked in the soft warm sand — so opposite from the rocky beaches of France and Italy. Around about noon, my stomach growled. “I believe it is time for us to eat,” I said, knowing that one of the best restaurants in Comporta sat not 70 meters from where we
[PORTO, PORTUGAL] — The Bridge. The Bridge is everything in Porto. It looks like the Eiffel Tower on its side crossing the lazy Douro River — which makes sense since it was designed by Gustave’s company. It’s hard to believe that this beast has been carrying traffic since it was built in 1886. At that time, it was the largest bridge span in the world. Such a stunning setting, which is why, when looking where to stay in Porto, I found a hotel that had the above amazing view on TabletHotels, my favorite go-to hotel site. This was literally the view out my window of the Pestana Vintage Hotel. Can’t ask for much better. You can see why the city’s core is a UNESCO World Heritage
[NAZARÉ, PORTUGAL] — I’m not a surfer, obvs, but I’ve always been captivated by stories of Big Wave surfing, where weather-watching, nicely-tanned people drop everything and fly across the world to try to catch big swells. I’m fascinated by waves. Even have read awesome books like The Wave: In Pursuit of the Rogues, Freaks, and Giants of the Ocean (which I highly recommend). And most recently, this awesome new book on waves and water: How to Read Water. (more highly recommended, so enlightening.) One place that is almost always on the list is Nazaré on the west coast of Lisbon, where nearly every year there’s always some small article in the media with amazing pictures of beastly waves crashing high above the heads of huddled masses on
[OBIDOS, PORTUGAL] — About an hour south of Porto is the small castle town of Obidos. If you’re a Game of Thrones fan, which I’ve never really seen, you may recognize this place. But if you’re just a normal castle-loving gypsy, you can stay in the nice pousada inside and get an extra use out of your traveling Glastonbury/Burning Man/Coachella flower bonnet and feel like a queen. They charge extra for swords, I hear, but available. Ravens on advance request. A good friend of mine recently stayed in the Pousada Obidos and absolutely loved it. And all the tourists empty out at night and they had the whole town to themselves. Some great restaurants, too. Obidos is known for their chocolate, so there are oodles of chocolate
[Outside Santa Cruz, Portugal] — It’s the smells that hit you first… After pulling into a sparse car park, no sign of life. You walk up to the huge, heavy wood doors — all big and Asian-y and intimidating, makes you feel like a bible salesman at Larry Ellison’s house — and they’re locked. Oh no, are they closed? Did I get the date wrong? Then you notice the small buzzer. And buzz. A big clanking noise and the antique rusted door latch opens up for you and the big door swings open. And that’s when the smells hit. Wood fire. Strong rosemary. A waft of lavender. A swirling stiff breeze of scents that coarse through the gap and wallop your nose with calm. And that’s
[Lagos, Portugal] — The winding two lane highway runs all up and down the western coast, tucked just under a constant high berm of low hills that act like a windbreak from the coast. The car weaves in and out of clumps of wooly cypress trees, their wide trunks like the fuzzy legs of a herd of mammoths, crossing small bridges and dodging farm trucks heaving from the local fields. It’s kind of weird, actually. The sun is bright as can be, yet you’re in shadows most of the time in the early afternoon. You can feel the salty ocean breeze but that long forehead of low hills casts long shadows across the road, it’s hard to even get a view of the beaches you’ve read so
[EDITOR’S NOTE: AFTER POSTING THIS, I JUST FOUND OUT THAT THEY SOLD THE HOTEL AND WILL CONVERT IT INTO A PRIVATE VILLA RENTAL> SO BUMMED. OH WELL, ENJOY THE PICTURES!] [LAGOS, PORTUGAL] — After landing in Lisbon all stinky from the flight, you jump in the rental and haul ass straight down the A2, crossing the rugged mountains that keep all the cold air from the North trapped on the rightside of the equation and make the Algarve warm all year. You book across the Algarve on the A22, toll after bitchy toll, slavingly following the GPS because your brain is fried. And then you get off near Lagos, and enter the Twilight Zone. A big grey area on the map. Lots of blank space,