The Region That Makes Euro Summer Feel Easy Again

My checklist for a good trip has always been short: breathtaking, beautiful and worth the journey. But in my brief tenure as a parent, the list has grown.

Convenience matters now, too. I don’t know when I’ll opt for a layover or a second flight on a smaller plane again, and my family’s road-trip bandwidth is somewhere under three hours. So when I started looking for an off-the-beaten-path trip to Europe—a breezy nonstop flight from New York, somewhere that wouldn’t put lingering spritzes and pebbly, clothing-optional beaches at the center of the itinerary—I landed on Portugal’s Alentejo region, specifically the Beja District, around two hours southeast of Lisbon and roughly 90 minutes from the Algarve coast.

Alentejo doesn’t get the same attention as either, and that’s precisely the point. Culture and coast are both within reach whenever you want them, but the real invitation is to slow down. To embrace the borderline spiritual amount of flexibility that traveling with a kid can demand: no spontaneous detours, no lingering over wine until the restaurant kicks you out. But also no rushing, no feeling like you have to see everything or you’ve wasted the trip. Just presence. Just this.

I’ve used the word “pastoral” before, offhandedly. But after bouncing in the back of a custom jeep, my daughter strapped in beside me, driving through sprawling vineyards with birdsong and the occasional rustle of wind through cork trees in the background, the adjective really earned its meaning. Alentejo turned out to be exactly what I was looking for. The food exceeded expectations. Resort staff anticipated our needs before we voiced them. The landscape gave us room to breathe. And my daughter, who spent most of the trip asleep on my chest, blissed out poolside or staring wide-eyed at olive trees, seemed to agree.

Where to Stay

We planned a four-night trip, which might just be the ideal length for travelers from the East Coast to Europe, since it lets you adjust to jet lag and make it home without missing too much. We arrived in Lisbon in the morning, with enough time to order a frothy cappuccinos before boarding our transfer to Alentejo.

The feeling you get from the moment you arrive at Herdade da Malhadinha Nova, a member of The Edit by Chase Travel in Alentejo’s Beja District, is less of checking in to a hotel and more of a homecoming. Guests are greeted with warm, traditional Portuguese pastries and glasses of wine from the vineyard that stretches across the landscape outside.

Accommodations are divided up among five different sites. In the Casa do Ancoradouro, where we stayed, suites open to a shared living space complete with dining tables, a bar and a piano—and then onto an infinity pool magnificent enough to practically erase the memory of any other pool before. The suites’ private outdoor space is ideal for prebreakfast coffee. Request a crib if you need one; it arrives fully assembled, home to a friendly stuffed bear. If wine is more of a priority, nearby L’AND Vineyards is also worth considering as a base. Expect opulent breakfast spreads and a serene swimming pond. And if you have time to add a night en route between Lisbon and the Beja District, Vermelho Melides Hotel—whose façade is decorated with ceramics by the sculptor Giuseppe Ducrot—is at the top of my list.

Eat and Drink

Local cheese, served for lunch.

Alentejo cuisine is straightforward in the best way: pork, bread, olive oil, cured meats. No fuss, no foams, just ingredients good enough to carry a dish on their own. Eat outside every chance you get. We enjoyed breakfast on the terrace, lunch under the pergola and every dinner at the in-house Malhadinha Nova Restaurant, where wine pairings are served from the oak barrels just a few hundred feet away.

The best meal, as these things usually go, wasn’t from the tasting menu. It was a picnic arranged at a vista shaded by a massive tree. Fresh salads, pineapple skewered with cured meat and sandwiches laid out artfully. Don’t leave without arranging one.

Around the region, excellent food is as inevitable as breathtaking scenery. In Lisbon, try Prado Wine BarOpens overlay and Tricky’sOpens overlay for a slice of the slower life, or opt for O Velho EuricoOpens overlay if you’re looking for a classic Portuguese gem (and can show up early to snag one of just 30 seats). L’AND Vineyards’ reputation precedes its impeccable dishes, while in Évora, Restaurante O Moinho do Cu Torto’s servers will point you in the direction of the freshest tapas on the menu; just don’t miss the grilled pork. For a taste of true countryside soul, try the no-frills O Chana do Bernardino outside Évora for a hearty lunch.

Things to Do

From the moment your feet hit the hand-cut terra-cotta tiles at Herdade da Malhadinha Nova in the morning, there’s no shortage of wholesome, delightful activities to fill your days. Tour the 1,800-acre property and walk among the horses; stop to pet the soft noses of lambs that roam free. Off-property, you can find any number of farm tours around the Beja District and broader Alentejo region, including themed journeys focused on olive oil, cork trees or sustainable agriculture. Back at the hotel, take a tennis lesson in the afternoon heat, then a horseback ride through the olive grove. Book a pottery lesson with Rita, the hotel’s CEO, and enjoy the conversations that drift through the front door as her dogs and children run in and out. Don’t skip the spa, where the subterranean glow makes you feel underwater in the best way. Be sure to slip into the sauna, with a massive window that offers one of the best views of the property.

For a day trip, the ancient city of Évora is about a 90-minute drive north by car. Cobblestone streets, Roman ruins and life in abundance—hanging laundry, wandering cats, neighbors in warm embrace—await. Avoid Sundays if shopping is on your agenda, but if you just want to enjoy the architectural splendor, any day of the week will do. Walk through the local university, where pigeons lift off to perch on columns overhead. The first-century temple is awe-inspiring, even for those among us who required an emergency bottle on a nearby park bench. The Cathedral of Évora, towering and Gothic fortress–like, stands in stark contrast to the open fields you’ll have spent the past few days wandering through. Enjoy the Manueline chapel and Baroque altar, and take it all in with an espresso from Café Arcada. If you prefer to leave the logistics to someone else, book a guided tour of the mystical megaliths at Almendres Cromlech, which pre-dates Stonehenge by thousands of years, through Chase Travel.

Know Before You Go

Take a guided horseback ride through Herdade da Malhadinha Nova’s vineyard.

Dress for the relaxing lifestyle you want, not the calendar packed with meetings you usually have. Pack linen layers and flowy tops that can transform from frolicking to dinner with just a jacket. Bring jeans if you plan on horseback riding, and this isn’t the time for delicate sandals—thick soles and sturdy support are your best friends.

You’ll be communicating with most local guides and establishments via mobile messaging apps. Trains run multiple times per day between Lisbon and Beja, with a connection. Renting a car is also an easy way to approach the two-hour journey. Use the $100 you receive when booking through The Edit for on-site activities like tennis and pottery, both of which feel much less high-stakes when based in the Portuguese countryside. Reservations usually start around 7:30 p.m. for dinner, which is particularly of note if you have a sleepy baby in tow.