Alentejo sunsets always feel a little unreal – like someone’s nudged the saturation just slightly too far. That warm evening glow was our welcome to Hotel Convento de São Paulo, a place that had felt like a myth in my mind. We arrived as the sun was dropping low behind the Serra d’Ossa, after a slow drive along winding roads thick with eucalyptus, cork trees, and scrubby native brush.
Years ago, I’d heard about this independent convent-hotel filled with historic tiles located somewhere in the Alentejo, and ever since, the idea of staying there has lived rent-free in my head. What I didn’t realise from the pictures is that the convent is an 800-year-old building tucked deep in the wild hills of the Serra d’Ossa.
Here’s what it was like to enjoy a slow, long weekend stay at the Hotel Convento de São Paulo.
This review is not affiliated or sponsored by the hotel. I stayed and paid independently via Booking.com.
The drawcard: an ancient convent and its 54,000 tiles
What initially drew me to this hotel was its collection of tiles – some 54,000 blue-and-white illustrated azulejos. It turns out it is the largest private collection in Portugal.
Thousands date back to the 1700s, including the tiles lining the staircases and corridors that stretch on forever. It was incredible to soak in the history, wander the cloisters, and discover historic fountains. During your stay, you’ll have free run of the place to explore the many halls, chapels, corners, and common spaces.
I loved staying here, and beyond the architecture and azulejos, what will guarantee my return is the tranquil, natural setting. The convent is set within a 750-hectare (approximately 1,853-acre) property with gardens and woodland. When we visited in spring, we found a lush green landscape in bloom with colourful wildflowers everywhere and trails to explore.
Overall, it’s a well-maintained, but in no way glossy, hotel. It’s a place that takes you back in time, ideal for dreamers, history lovers, and appreciators of heritage.
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What’s the story behind the hotel?
Back in 1182, a group of hermits, known as the São Paulo Ermita Monk Order, retreated into these hills to live in silence. Over the centuries their spiritual outpost grew into a fully fledged monastery layered with thousands of azulejos, frescoed ceilings, and walls we wish could talk. They’d tell tales of Portuguese kings and queens who once stayed here, including Dom Sebastião back in 1577.
The convent was abandoned in the early 19th century, when Portugal’s ruling royals dissolved religious orders. A private family eventually restored the Convento de São Paulo, which is home to the largest private collection of tiles in the country. Now the extensive property is both a hotel and museum of sorts, with cloisters, grounds and woodland to explore, adding to the fun of your stay.
Where is the hotel?
Hotel Convento de São Paulo feels remote, but it’s not isolated. It’s set on a quiet road between Estremoz and Redondo, two gorgeous Alentejo towns that offer plenty of things to do.
Estremoz, about 20 minutes away, is known for its Saturday market, marble quarries, and a whitewashed old town wrapped around a castle. Redondo, smaller and sleepier, is famous for its pottery workshops and slow village rhythm. I’ll share more about both below.
Read next… Bottomless wine and secret cellars: Redondo’s tasca and talha trail
What’s it like to stay there? The room and service
We stayed in one of the annexe double rooms – just outside the main building, across from reception. It was quiet and comfortable, but a little detached from the action. To reach the cloisters, restaurant, pools, or breakfast refectory, you have to pass through reception and cross the main entrance. Next time, I’d choose one of the 40 rooms tucked within the old convent itself for a more immersive experience.
The rooms are traditionally styled, with dark wood, metal furniture, and a touch of old-world charm. Ours came with a pink marble-clad bathroom I was oddly obsessed with, and a firm but comfy double bed – a classic Portuguese hotel setup. I find it rare to get a queen-size bed here. We’re a bit fussy about pillows, but reception sorted us out with extras, no problema. I loved the vintage touch of a real candlestick and a branded matchbox to light the candle.
The staff were super kind, very helpful, and on hand 24/7 should you need anything.
What can you do around the property? A world in itself
We stayed for three days, two nights and used the middle day to simply enjoy the estate. After a big, slow breakfast in the old monks’ refectory (buffet-style, with scrambled eggs, yoghurts, cakes, croissants, cereal, and more), we set off on one of the hotel’s two marked walking trails.
The easier loop – around 6km – takes approximately 90 minutes, passing through forest, woodlands, and fields. We noticed we were close to the nearest village around lunchtime, so we detoured slightly for a spontaneous meal at Restaurante Serra d’Ossa. The service was a little brisk, but the food made up for it – don’t skip the grilled black pork, if it’s on the menu, and finish with a slice of sericaia (a cinnamon-loaded sponge cake and my favourite Portuguese dessert).
That afternoon, a sudden spring high made for a perfect tanning day. We could have borrowed bicycles, or used one of the four padel courts or the tennis court. Instead, we camped ourselves on sunloungers alongside the adults-only pool with a panoramic view and ordered G&Ts made with a local Alentejo gin. For the kids, a second pool is on offer.
What was great about our spring stay is that the property is so large you’ll often feel like you own the place (but thankfully it’s not creepy quiet). Around sunset, we ordered another G&T to enjoy alone on a terrace beneath an orange tree, heavy with fruit, before retreating to a common lounge where the fireplace was roaring and others had gathered.
We had dinner at Ermita, the hotel’s restaurant – a dream of antique tiles and candlelight – before heading to the games room for a few games of pool.
Read next… 18 best places to visit in the Alentejo: prettiest villages, towns and cities
The food: the restaurant and breakfast buffet
Breakfast is served in the old monks’ refectory – a grand, tile-lined room with plenty of light and some slightly mysterious symbols on the ceiling. The breakfast buffet is exactly what you’d expect (in a good way): a hot station with scrambled eggs, bacon and mushrooms, alongside croissants, homemade cakes, cereals, yoghurts, fruit, and spreads – including honey produced on the property.
The hotel restaurant, Ermita, is set inside the former Capela do Bispo, which is lined with tiles and has frescoed ceilings. By candlelight, it was a genuinely beautiful place for a relaxed dinner, and the young server was formal but delightful.
Foodwise, I’m a former food critic, and I usually avoid hotel dining, so I had my expectations in check. The two soups we tried were forgettable, and the wild boar a little dry. But the black pork was fantastic – grilled over charcoal with the layers of fat rendered beautifully. And the sericaia – my soft spot dessert – was everything it should be: a spongey just-baked cake topped with a thick layer of cinnamon and served with an Elvas’ plum and syrup.
Things to do nearby
Close to Hotel Convento de São Paulo
Within five minutes of the hotel (if you can tear yourself away), a handful of small detours are worth making.
- For hikers: Walk the Passadiços da Aldeia da Serra – a boardwalk trail and staircase that should be easy to navigate. You might be able to detour via the boardwalk on the shorter hotel trail.
- Full-day cork safari & wine tasting: Explore the Herdade de Maroteira estate in a classic open-top Land Rover to learn about Portugal’s cork production and ecosystem, followed by a wine tasting at the estate (with generous cheese and charcuterie). The tour ends with lunch at a traditional Alentejano restaurant.
- For history: Make a detour to the Anta da Herdade da Candeeira, a megalithic dolmen dating from 4,000 to 3,000 BC. You might be able to visit the neighbouring Herdade da Candeeira, which produces beautiful wines too.
Estremoz – the marble town
A marble town with a castle at its crown, Estremoz is an Alentejo gem that offers more than meets the eye. The best time to visit is a Saturday morning when a huge market selling antiques, pottery, and fresh local produce takes over the main square. From there, you have two choices: wander up through the old town’s tight cobbled streets to reach the pousada hotel, housed in a former palace. (Ask to climb the marble tower to take in panoramic views of the Alentejo.) Or, discover one of the largest private tile collections in Portugal at the Berardo Museum Estremoz. Set in a palace, this azulejo museum is a must-see for tile lovers.
Where to eat: Venda Azul, Mercearia Gadanha, Larau
Redondo – famous for pottery
Smaller and sleepier, Redondo has more of a laid-back country town vibe. It’s best known for its ceramics – terracotta pieces thrown on the wheel and hand-painted in a beautiful, rustic style. With about half a dozen pottery workshops and studios to visit, you’ll be able to see the makers in action and collect a souvenir with heart. It’s also worth popping into the local pottery museum.
Where to eat: Celeiro do Pinto
Read next… Explore Redondo, Portugal’s best-kept pottery secret
Need to know about Hotel Convento de São Paulo
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Getting there: You’ll need a car – this isn’t a place you stumble upon by accident. It’s roughly 2 hours from Lisbon, and the drive gets prettier the further east you go.
Rooms: There are 40 rooms in the main building and a few in the annexe (where we stayed). If you can, book one inside the convent proper – it’s worth it for the full atmospheric experience.
When to go: I think spring and autumn would be the best times – warm days, cool nights, and fewer people. If it’s warm enough, relax by the pool; if it’s cool enough, cosy up by one of the fireplaces. We stayed a Thursday and a Friday night, and it was noticeably quieter on the Thursday – so go mid-week for quiet stays. In winter, I imagine you’ll have the place to yourself.
Bring: Walking shoes for the trails, layers for cooler evenings, and something to read by the pool or fireplace. The rooms have spa robes and little toiletries.
Read next… Portugal & Spain Road Trip: Where to stop between Lisbon and Seville
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That’s my experience at the beautiful Hotel Convento de São Paulo in Portugal’s Alentejo region. Let me know if you plan to stay in the comments – I’d love to hear what you think of it too…
Keep reading…
- Explore Redondo, Portugal’s best-kept pottery secret
- Bottomless wine and secret cellars: Redondo’s tasca and talha trail
- The average person’s guide to A-list Comporta: Portugal’s luxe beach town
- 20 best things to do in Évora, the Alentejo capital
- How to spend 48 hours in Évora
- Where to eat in Évora: The Best Restaurants, Cafés & Sweets
- Portuguese artisans: 10 traditional crafts from the Alentejo
- Portugal’s pottery village: Why you should visit São Pedro do Corval
- The best things to do in Estremoz
