5-7 Day Guide to The Alentejo Region of Portugal

You’ll need a rental car either from the airport or the center of town. Head towards L’AND Vineyards which is also a design forward, luxury hotel. Depending on what time of day you arrive, you can stop in for a meal and/or wine tasting or hang your hat there for the night.

If you decide to move on to the next destination, go check out the town of Evora. It’s a charming town with narrow streets and far quieter than the hustle and bustle of Lisbon. You’ll feel like you are in the “real Portugal.” In fact, Conde Nast just named this “underrated” town one of Portugal’s prettiest.

You’ll want to check out the infamous Chapel of Bones and the Roman Temple and spend time wandering the area. Absolutely have dinner at Origens. It's a special restaurant run by a husband and wife team who are very passionate about their craft. After dinner, head to your hotel, Octant Evora which is about an 18 minute drive east of town. There’s nothing in town in the way of luxury hotels and this is the best option.

Today, make your way to São Lourenço do Barrocal (under an hour away) to drop your bags before heading to spend the day checking out another beautiful city that is even quieter and more charming, Monsaraz. After exploring, head back to your hotel and enjoy dinner on property at their lovely restaurant, A Terra.

The next morning head out to do some wine tasting before you make your way to the next property. I really enjoyed my stop at Quinta do Quetzal.

You can have a wine tasting, visit their art gallery or have a full lunch among vineyard views. Another option is Quinta do Paral. While I didn’t make it there because they were closed on Sunday, it looks like a larger operation. Evidently, they are building a boutique hotel and restaurant. If you have the opportunity, do both!

At your leisure, head towards my favorite hotel in Portugal, Herdade da Malhadinha Nova. If it’s available, book room #4 in their modern area, unless you are traveling with a group or children, they have a wide availability of options with only 26 rooms. For this estate, there really isn’t a reason to leave. The menu of activities is endless for the small number of keys. The property itself is over 600 acres and has a working horse stables and a highly acclaimed vineyard, not to mention, a Michelin recognized restaurant. I recommend a two night minimum here if your schedule permits and sometimes they even require a two night minimum during certain seasons.

Now we say goodbye to the countryside and venture towards the coast stopping at the tiny little town of Melides, about an hour and fifteen minute drive. The town is quite small and the main draw is Christian Louboutin's Hotel Vermelho. It’s a unique stay and the town of Melides is mostly about the hotel. If you don’t want to stay the night, at least have lunch at their restaurant Xtian.

From there, head towards Comporta, about a 25 minute drive. Comporta boasts some of the most breathtaking beaches in Portugal, characterized by their vast expanses of soft golden sand and crystal-clear waters. You will sense tranquility and seclusion, making it a favorite destination for those seeking a peaceful getaway. Portugal has made this beach a preserve and there are no houses or hotels on the actual beach giving it the feel of a wild, unobstructed vibe. The village maintains a low-key ambiance, with traditional whitewashed houses, charming cafés and boutique shops dotted along its narrow streets. Made famous for it’s bohemian chic feel and a heavy artistic influence. I stayed at Sublime Comporta and the rooms are spacious and well appointed. It boasts the nicest gym I have seen in Europe. Their beach club is super chic and about 10 minutes away. Sublime offers three restaurant options and they are all good. “Food Circle” is a unique experience only offering 12 seats and a tasting menu in the garden.

When you are ready, begin your hour and 45 minute journey back to Lisbon to return your rental car. I highly recommend dining at Belcanto, a two Michelin starred restaurant on your final night in Lisbon before heading to the airport in the morning.