A Portugal Road Trip from the Algarve to Lisbon

With all the twists and turns of the last two years, I was prepared for any and all birthday getaway plans to fall through, but stars aligned, or rather variants abated, to give me a lucky European travel window in October. Meeting up with my Munich-based sister, we chose Portugal for myriad reasons, namely we’d both drooled over the images of its dramatic coastline and we admired the country’s extra efforts to keep travelers safe. So, we charted a two-week road trip, arriving in the Algarve, ending in Lisbon and stopping at as many of the countless, breathtakingly beautiful beaches as we could along the way.

ALL THE VILAMOURA

On our trip to the Greek Islands, we’d figured out the best vacation order—start with a longer string of days at a bigger resort so the only thing you really have to think about is relaxing. Enter Anantara Vilamoura Algarve Resort. Just a 30-minute drive from the Faro Airport, the Anantara had us checked in and soaking up our arrival day’s last rays in no time. We spent the first half of our five days just sitting by the pool, sitting in the pool, devouring books, ordering pitchers of sangria and fries to our loungers and, come evening, putting on nice dresses and hilariously taking a zillion pictures of ourselves in them until we got one good one.

Once we’d achieved chill mode, we ventured out. We enjoyed a day at a nearby beach club—it’s free for Anantara guests—and had a delicious dinner at Salmora near the harbor.

On another day, we had the concierge book us on a boat tour. Starting from the harbor and following the coast, it culminated with the Benagil cave. I didn’t expect our big boat to be able to tuck into the opening for a better look, but it did, and it didn’t disappoint. Afterwards, the boat anchored off-shore and anyone who wanted to could jump in for a swim.

On our final night, the concierge worked a little last-minute magic to get us into the beachside Restaurante Rocha Baixinha for sunset. Speaking of magic, the whole evening was—crossing the river bridge, strolling along the oceanside boardwalk and dining on fresh seafood perched above the sand as the sunset traded its color for twinkling stars.

MILLIONS OF BEACHES

While Portugal doesn’t technically have millions of beaches, it can sure feel like it. After checking out of Anantara, we picked up our rental car and, taking the coastal route, plotted stops at some Instagram legends and some unexpected gems. Both Marinha and Camilo have been well documented, so they were understandably busy. By the time we reached the latter, we were hungry and thankfully there’s a cute little restaurant right above. After more fresh seafood and a glass of wine, we tackled the 200 steps down to the tiny beach for a refreshing dip.

Reaching Sagres, Europe’s most southwesterly point nicknamed Promontorium Sacrum or “the end of the world” before explorers crossed the Atlantic, we hit up more beaches. First, Tonel, a popular surf spot—we hadn’t planned to surf, so instead enjoyed a cold beer at the beach bar and watched the action. Next, we headed down the road to Beliche, popping into Artesanato a Mó on the way to buy some of Portugal’s famed pottery. You don’t have to head all the way down to appreciate Beliche, like so many Portugal beaches, the view from the above is a big enough wow.

We continued north through the Parque Natural do Sudoeste Alentejano e Costa Vicentina—say that three times fast—a long stretch of protected coastline home to, you guessed it, many more beaches. Along the way we stopped at Bordeira, the most wild, expansive beach we’d seen so far. Taking the long, sandy walk to the water felt like a scene from Dune.

From there, we continued north and stopped to take in Arrifana from above and have a bite to eat at the adorable Sea You Surf Café. Along with Bordeira, my favorite beach was one we tried on a whim. I’m keeping the name a secret, because some beaches should be rewards for those who stumble upon them. To get to this beach, we had to do a bit of a hike in and gosh was it worth it—only a handful of people, incredible rock formations and even a trickling waterfall. We put our towels down and decided to stay awhile.

SUBLIME COMPORTA INDEED

Having driven through forests, small towns and farmland, we arrived to the cork tree-flanked country roads of Comporta to kick up our sandy feet for a few days at Sublime Comporta. Sublime is one of many superlatives to describe the place. Its 45 rooms, suites and villas are spread out across 17 hectares to feel at once private and connected. We opted for one of their cool Bio Pool Suites which all open to freshwater pools kept clean solely by surrounding aquatic plants. Since the sun was still shining on it, I immediately took a plunge then enjoyed some of our welcome bottle of champagne while I watched and listened to the frogs. Here, you get a side of wildlife with your swimming and sunbathing—I was in proverbial heaven.

Wanting to be thorough, we also tried out the more standard main pool and it was equally lovely. In keeping with the overarching sublimeness, all the dining is top-notch. If you have a bigger group you can book a private dinner at their Food Circle, a beautiful space encircled by their food gardens. Every night we walked by it envious.

Many inland resorts have affiliated beach clubs and Sublime Comporta is no exception. With its own chic and delicious restaurant, we lunched here al fresco on spaghetti alle vongole and vinho verde before strolling down the beach for a swim. One of the days we were there, a pod of dolphins swam by close to shore.

Since we’d seen dolphins without trying, we instead booked a horseback riding experience at the nearby Cavalos na Areia. Crossing over muddy farmland and up over a crest, we were met with a staggering view of the open ocean and white sands that stretch on—then we rode alongside the lapping waves. Cheesy as it sounds, I felt like I was in a movie, and for those who pay extra for it, you can have a dramatic mini movie of it complete with drone footage—I really should’ve dressed for the part. After dismounting our horses, Chanel and Shakira respectively, we got back on the road bound for Lisbon.

BOM DIAS IN LISBON

Ditching our wheels—we didn’t want to bother with a car in the city—we promptly checked into The Vintage Lisbon. Decked out in mood-boosting hues and mid-century decor, the boutique design hotel is just our style. We immediately went up to the rooftop bar for a happy hour drink, but it was full, so in the meantime we made our complimentary in-room cocktail—a fancy gin and tonic—and flung open the big balconette windows. Charming moment made.

We made it back up to the rooftop bar a few times. It was the perfect place to wind down after days of exploring. Exploring which included a morning at the popular LxFactory. The complex of shops, restaurants and maker studios is full of eye-candy and a great place to score cooler than your average souvenirs for friends and family. We also made a point of finding a +351, the clothing brand founded by Lisboan Ana Penha e Costa and made in Portugal.

For dinners, we tried two different vegetarian restaurants. Arkhe was a fine-dining experience, with multi-course menus of rich, complex flavors, and Senhor Uva was more casual, tapas style. A small space below street level, Senhor Uva doesn’t look like much but it was the last and best meal of our trip—the service, the food, the wine pairings, all outstanding. For an aperitif, we cabbed over to Toca da Reposa, a cool bar that makes most inventive cocktail places look pedestrian—whirling away in the window is a science lab-type contraption for doing special infusions. A note about restaurants in Lisbon: being a big city lauded for its food scene like New York or Paris, reservations are a must. We made ours two weeks ahead and lots of spots were already booked up by then.

MINI TRIP TO SINTRA

We would’ve loved to keep the Portugal party going with a stay in Sintra or Cascais but since they’re both so close to Lisbon we could tuck in a day trip. On the excellent recommendation of our hotel concierge, we booked a private tour with Hello Portugal Tours. Because there was just the two of us, we got to do the tour in a MINI convertible.

After our careful tourist driving, it was a thrill to rip along the winding roads with the top down to Pena Palace, Azenhas do Mar, Cabo da Roca and through Cascais with someone who knows them like the back of his hand. When they aren’t leading tours, our guide, Gonçalo, and his wife Rita, are real estate agents. So not only do they have a wealth of knowledge about Portugal’s history and landmarks, they can also help people get into the market if they wish. After a couple weeks here, we wished it. Although if we bought here, that would deter us from staying in more of the country’s amazing hotels. A home is so much more upkeep—we’ll stick with hotels.