In south-central Portugal, to the right of show-stealing Lisbon and above the summertime fun of the Algarve, the underrated and understated Alentejo region packs a punch.

Technically two regions, Alto and Baixo translating to higher and lower, The Alentejo is awash with Roman and Moorish history, designated dark sky star-gazing reserves and countless grapes hanging from vines ready to be turned into one of Portugal’s greatest exports, and my favourite refreshment, wine. This is, of course, one of the most celebrated wine regions in Portugal.

The visitor count might not be as high here as other parts of the country, but that is very much its charm. Cruising along a near-empty motorway for a weekend escape, the rolling green countryside of vineyards with the odd castle provided a refreshing vacation from the bustle of the city.

The resort I picked for this weekend had to stand out, be quirky and ultimately a real gem of a place. I got scouring’s range of properties in Portugal, from hotels made of another Portuguese staple, cork, to restored palaces, the options were surprisingly endless.

L’AND Resort

I finally settled on L’AND Resort, situated just an hour from Lisbon in Montemor-O-Novo. Complete with a hot air balloon, Michelin star restaurant, retractable skylights for star-gazing and wine-production that happenesd inside the resort, I knew I had found my soulmate in hotel form.

Pulling up to the L’AND vineyard resort, the first thing you notice is how un-noticeable the resort is. The leading lines of the white buildings which centre around a lake sink into the green vines and trees that surround them. Not only is the stylish design aesthetically pleasing, but the integration with nature also makes the resort feel much smaller than it is. From the balconies, you can’t see other peoples accommodation, and this added to the sense of privacy and escape that the location of the vineyard offers.

Star Gazing in Alentejo

I’ll jump to my favourite bit about the resort and region as a whole, the star-gazing. Although Montemor-O-Novo doesn’t technically fall into the official Dark Sky Reserve, a dedicated area in Alentejo, the night skies were nothing short of incredible.

The resort with limited light pollution and far enough away from the town is nearly dark at night, and there are plenty of ways to enjoy mother natures nighttime show.

If you book a sky-view suite, then a remote-controlled ceiling pulls back to reveal the twinkly stars straight above your bed for some duvet style sky viewing. In the summer months, the actual glass is also removed from the roof which allows for a better view. To be honest, this was one of the things that disappointed me with the hotel; it’s not made clear when booking that the glass is there for part of the year, and at a premium price, this is something they should make known at booking.

Another option is your outside private plunge pool, which is enclosed on your balcony and more of a deep-bath. You can run the hot-tap and soak away to the magical view above.

Or your balcony, or the hotel rooftop, or by the lake (my favourite), or next to the vines… wherever you go, as long as there are no clouds expect amazing star-lit skies..

Vineyards in Alentejo

Red, white, rose and sparkling; they are all on production and offer in Alentejo with L’AND resort seasonally producing all the still wines in small batches. You could traipse off to explore multiple vineyards, or simply settle into wandering the vines that literally start outside your front door here.

L’AND offers various ways to sample both their wines and other wines from the region. With a glass of wine at check-in, a free wine and cheese pairing at 4 pm and other complimentary wine tasting options depending on the day, you’ll be off to a good start.

More in-depth wine tasting with professional notes can also be arranged, from just their own through to the whole regions. And if you head to the restaurant, the pairing flights can’t be missed.

Fine Dining in Alentejo

The food scene in Portugal is usually highlighted by Piri Piri Chicken and Egg custard tarts (Pastel de Nata) abroad, but the bar is continually being raised by some very talented chefs here and Miguel Laffan is one of those.

His Michelin Star restaurant at L’AND resort offers two menus, seasonal at €75 and the chefs menu at €105. Feeling like five courses would suffice, I went for the seasonal menu which included fresh oysters, deconstructed Portuguese style Bouillabaisse and a tender cut of Pork before two perfect desserts. The focus is on local produce, with the aim to source everything within 50km of the resort and the quality of the dishes was excellent. The matching wines and information that came with them were well worth the extra cash investment.

Miguel himself was in the dining room, running plates and chatting with the guests which was nice to see. Breakfast, a mix of buffet and a la carte the next morning was also of high quality.

L’AND Resort
L’AND Resort

L’AND resort review

With both a heated indoor and natural temperature outdoor pool between the 22 suites, there is plenty of place for R&R. The outside pool was empty of water on my visit, even in May, and this was another annoyance when paying for a premium hotel having a big empty hole in the lawn. The sauna looks out across the pool and vineyards, and the spa looked pretty fancy, although I didn’t have time to make use of it. The resort can also arrange a hot air balloon ride for you direct from the hotel to see Alentejo from above, prices are from €625 per trip as they don’t offer group flights.

Overall I loved the resort but wish I had seen it at it’s best, with the fully retractable windows and the pool open. It’s a pricey place to stay but even if you don’t book in, do try to get a reservation at the restaurant as it was genuinely excellent. You can see more of L’AND here.

But what else is there to discover nearby?

The Alentejo region of Portugal is vast, but here are a few highlights you could easily visit from the resort.

Montemor O-Novo

The small city of Montemor-O-Novo is a quick five-minute drive from the resort and can be seen in the background from the main dining room.

The cities main feature is the ruins of the Roman castle which sits atop the hill and although the walls have fallen in many places, inside you’ll find a convent and church in pretty good condition. The views are also excellent and stretch well beyond the city from the viewing point.

Montemor-O-Novo is pretty compact and can be easily walked in a couple of hours between the squares and churches down below. I wanted to visit the Escoural Cave, complete with prehistoric art but discovered you need to call ahead to arrange access.


Évora is the capital of Alto Alentejo and the principal city of the region, by car it should take around an hours drive from Montemor-O-Novo.

The historic centre is surrounded by towering stone walls and viaducts, and I loved the afternoon exploring here.

Start off in the Royal Palace gardens where peacocks casually stroll past the buildings before ducking outside to the Chapel of Bon, also known as the bone church as many skeletons decorate the building following a mass exhumation in years gone by.

Évora Cathedral is a large Gothic construction dating back to the 12th century and the nominal entrance fee which includes inside the church, the courtyard and the fantastic views across the city from the roof-top is a must do

Just along from the Cathedral is the Roman Temple of Évora which stands in excellent condition and would look more in place in Italy than a rural Portuguese city. The history of Portugal is often glossed over in favour of its beaches, but the more I explore the country, the more in awe I become of its fascinating collection of historic architecture.

The main square is a great stop to grab a bite to eat, listen to local musicians and people watch before strolling through narrow side streets of cobbles and whitewashed homes.


Another one hour drive brings you to Beja, the capital of Baixa Alentejo, and smaller than it’s counterpart Evora.

When I arrived, they were hosting ‘The Festival of Tiles’ which I’m assuming isn’t a year-round event, but traditional Portuguese tiles were permanently adorning many of the buildings throughout the city.

In Beja be sure not to miss out on the traditional market around the castle if you arrive on a Saturday morning. The 13th-century castle also boasts panoramic views from its tower.

The main square, a small affair, is shadowed by the Igreja de Misericórdia church which started its life as a meat market and the domed porch at the front often has local artwork on show. There are a few churches and galleries in the city, but you’ll need less time to get under the skin of Beja as you do in Évora. From Beja, you could continue your road-trip on to the Algarve’s coastline in under two hours and check out all my favourite Algarve hidden gems!