The drive from Lisbon down to the Algarve takes about three hours, and I had planned the whole thing around the assumption that the hard part was the driving.
My husband was in Lisbon for work. We'd done the long flight together, the way we always do, and spent a few days in the city as a family before he peeled off into meetings and I took the children south. That's the honest answer to the question people ask me most, which is how I travel alone with two babies. I only half do it on my own. I don't fly internationally alone with both of them. I take the second leg alone, once we're already on the ground.
The other half of the answer is that I choose the place carefully. When it's me and a two-year-old and a five-month-old for four days, the accommodation isn't scenery. It's amenities and staff. It's whether I have to cook (Airbnbs). It's whether there is anywhere my daughter can be a two-year-old that isn't going to make me stressed. At Domes Lake Algarve, that was going to be the crèche, and I had booked a residence because until that point — having only traveled out of the country with both kids once prior — I believed a dishwasher and a wall between the two kids while sleeping was all I needed.
I chose it the way I chose hotels in the past when it was just my daughter and I traveling: by looking at square meters, hotel amenities, and the restaurant menus.
The arrival
We pulled in with my daughter waking just twenty minutes prior, missing her favorite human, Dada, and crying for food.
Not fussing. Not asking for a snack. Crying, in the particular register a two-year-old finds when she has been in a car seat too long.
My son, awakened by his sister, needed feeding as well. Both of them needed a diaper change. And so I stood at the check-in desk trying to look like a functional adult while pushing a double stroller with two crying kids with one hand and pulling our two suitcases with the other. Where was the doorman?
Somewhere in that, I was told two things. That the restaurant was about to be between service periods. And that the crèche was closed for renovation.
I heard both, but I needed to get all three of us into a room where I could put the baby down and change my daughter and take a deep breath before I could process what that would mean for the next four days.
I want to be clear that I had tried to find this out. A few days before we left I'd come across a Reddit thread suggesting the crèche might be shut. I went looking on the property's own website and found nothing — no notice, no seasonal dates, nothing but the same four-months-to-four-years that had been there when I booked, and a dream that I could drop both for an hour so that I could get some work done and maybe, MAYBE even use the spa for an hour. By then we were well past the point where the reservation was refundable. They apologized for that afterward, and the website has since been updated. But standing at that desk, I had a closure I'd half-suspected, no confirmation of it, and two children who needed lunch.
We took the keys and were shown to our residence.
The room I'd chosen for space
It was on the ground floor.
I hadn't thought to ask. Truthfully, I love a ski-in ski-out on the ground floor. A resort with a private pool on the ground floor. A South American boutique hotel with indoor courtyard access on the ground floor. A Tuscan villa that opens onto a winery on the ground floor. It took about ninety seconds in that room to understand why it mattered now. The windows looked straight out onto a path. Anyone walking past could see in, and could see specifically that this was one woman on her own with a baby and a toddler and four days of luggage. I closed the blinds.
Then I looked at the sliding door, which opened onto grass, which ran down to the lake.
A two-year-old can cross that kind of distance faster than you can put down a baby. So the door stayed shut too, which meant no air, and no letting her out to burn off three hours of car, and no version of the afternoon where I sat outside with the monitor while she ran around in front of me.
The room I had booked for space turned out to be a room I kept sealed.
It also sat a good walk from the hotel itself. From the restaurants. From the lounge. From anything I might conceivably want at four in the afternoon. Which meant that every time we needed food, both children had to be shoes-on, coats-on, baby-in-the-carrier, toddler-negotiated-out-the-door, and walked. In January. Twice a meal, there and back.
You can absorb that when there are two of you. On your own it's exhausting.
The pool bar was open — that was the one thing I'd understood clearly at the desk. So we did the whole production, all three of us out into the afternoon, and walked over.
The kitchen had closed. Minutes before. I still quietly maintain I had a couple of minutes in hand, and I also know I could not physically have moved faster than I did.
The other restaurant would open in an hour.
Standing there doing math
I had two options and I could see both of them clearly.
The first was to put both children back in the car, drive to a grocery store, shop for the quick four days we were in this location, drive back, unload, and cook. In a kitchen I had specifically booked simply for bottle-cleaning ease, in a week where the entire point was to have less to do rather than more.
The second was to put both children back in the car and go find a restaurant, assuming one within reach was serving at four in the afternoon in January, and walk into it with a tired, hungry two-year-old and a five-month-old and try to hold the whole thing together at a table by myself.
Both options took the reason I'd chosen this place and quietly deleted it. I hadn't booked a resort because I wanted to be at a resort. I'd booked it because it was supposed to make four days on my own with two babies workable, and standing outside a closed pool kitchen it was doing the exact opposite.
So I picked a third option, which was to leave.
I walked back across the property with tears sitting in my eyes and a plan to find somewhere that could actually help us, and I went to the front desk.
What they did
I asked, calmly, whether I could check out.
That's genuinely all I asked. Not for a refund, not for a different room, not for anyone to fix anything. Just whether there would be a penalty if I left now. I had already half-decided where we'd go — an Octant property about an hour away. We'd stayed with Octant for our babymoon and the service had been extraordinary, and we were booked into another of their houses later in the same trip. I knew what I'd be getting.
They asked if everything was all right. I said it just wasn't what I'd expected, in the flat voice you use when you are holding yourself together in a lobby.
They got the manager.
She asked me to explain properly. What had happened, what I'd expected, what wasn't working. And that was the end of holding it together. Five months postpartum, jet-lagged, on a different continent, alone, with a toddler crying for food beside me, I burst into tears in the middle of the lobby and told her all of it. The restaurant. The crèche. And the thing underneath both, which was the sheer physical labor of getting two children dressed for outside every single time I wanted to leave the room, over and over, for four days, by myself.
She listened to the whole thing. She didn't interrupt to defend anything.
Then she asked, quietly, whether the female concierge could hold my baby and entertain my toddler.
Please.
What happened next took about four minutes and changed the entire trip. She walked us into the indoor lounge — the one that would have food in an hour — and asked the bartender to bring me a menu immediately and to get something made for my daughter as fast as the kitchen could manage. Then she told me to make sure I ate too, which is not a thing hotel managers usually say, and is exactly the thing nobody says to you when you are five months postpartum and running on nothing.
She produced a kids' kit: a matching tiles game, crayons, a coloring book, a few other things. My daughter was occupied inside a minute. My son was in eyesight, with a group of women cooing over him. There was a glass of wine in front of me and food coming.
I had gone from standing outside a closed kitchen with no options to sitting down, with both children handled, in less time than it takes to load a car.
The conversation
Once everyone had calmed down, we actually talked, and this is the part I think about most.
She asked where I'd been planning to go. I told her about Octant, and about the babymoon, and why I trusted them.
Then she apologized, and not for the thing I expected. Not for the crèche being closed, which was a maintenance decision made months earlier by somebody else. She apologized for the handover. Because the front desk should have given me the kids' kit at check-in. They should have walked me to the guest lounge and told me it had cold bites available all day, which would have solved my entire afternoon before it happened. They should have mentioned the playground. The walking trails. How to get down to the beach. And the small kids' room they had set up specifically because the crèche was being renovated, which nobody told me existed.
All of it was there. Every single thing I needed was already on that property — maybe not to the extent that I had expected, but enough that I wouldn't have panicked.
I told her, honestly, that I suspected the front desk had rushed the conversation because my children were crying and I was very visibly desperate to get to a room. Which is what happens. Nobody was careless on purpose. But that gap, when young kids and jet lag are involved, can change everything.
She left me with the food and the wine and said she'd go find out about processing a refund, in case I still wanted to leave.
She came back a few minutes later, while we were still eating, and offered to move us into the Absolute Family One Bedroom Suite inside the main hotel. At no charge.
No going outside to eat. No going outside for the kids' room. Club access included, which meant warm and cold bites, beer and wine, around the clock. Whatever happened, at whatever hour, there would be food.
And then she said the thing that actually won me:
"I can take you to see the room. You can even try it for tonight — if it doesn't work, you can check out and we'll refund the rest of your stay. We'll pack up your things in the residence and move them so you don't have to, and I'll do a final check of the condo myself to make sure nothing's left behind. A woman's eye."
She had taken every remaining piece of effort off me. Including the packing. Including the last look around the room that I would otherwise have done with both kids in tow, the baby desperate for the next nap.
The room they moved us to
It was extraordinary, and it was extraordinary in the specific ways that matter when your children are this small.
There was a pull-out bed. My daughter sleeps in a Montessori floor bed at home and rolls the way two-year-olds roll, so I said I'd put pillows around the edge and we'd be fine. They refused. They brought in a twin mattress and put it on the floor instead, because that was actually safe rather than approximately safe.
A crib went into my room. Which meant there was still a wall between the toddler and the baby — non-negotiable for us at that stage, and the difference between one child waking and both, which I'd told the manager when explaining why I had booked the residence in the first place.
And there was a balcony, overlooking the pool and the lake, so that once they were both asleep I could sit outside with a book and a glass of wine and have an hour that belonged to me.
Jokes on me. I spent it out there working and watching the Steelers lose a playoff game, but it was quite nice nonetheless.
After that it was small things, repeated daily, which is what good service actually is. Staff who noticed us and checked in. Someone who played with my daughter while I handled the baby. Someone who held my son so I could eat with two hands. One place where a toddler was occupied and food was available at the same time, which sounds like nothing and is everything.
I got to take a breath. That was the whole thing. That was what I'd come for.
A property that is "kid-friendly" means nothing when your kids are under four. Every hotel looks capable in high season with school-aged kids, or with two parents and a nanny in tow. What tells you the truth is what happens when it goes wrong at three in the afternoon, in low season, when you're outnumbered and both physically and mentally exhausted. Domes got the arrival wrong and then handled it better than most places handle an ordinary Tuesday.
A word in defense of shoulder season
I want to be careful here, because the lesson of this trip is not "don't travel off-peak." It's close to the opposite. I push clients toward shoulder season constantly, and I'd push you there too.
May, June, September, October. Fewer people in the places worth seeing, noticeably better rates, and — the part most people miss — far more availability at the properties that are booked solid a year out for August. If your children aren't in school yet, you have a window most families would trade a great deal for. Use it.
What I walked into wasn't shoulder season. January in the Algarve is deep off-season, and that's a different animal. Off-season is when properties do their annual maintenance, cut restaurant hours, and close the things that require staffing. The weather is still lovely. The resort is running at a fraction of itself.
The line between the two isn't on a calendar, and it moves by property. Which is exactly why it's worth asking rather than assuming.
Is the childcare operating on my dates? Are all the restaurants on full hours, or are any closed for the season? Is anything else shut — the spa, the pool, the kids' club? Ask those before you pay a deposit and you get the emptier, cheaper, better version of the trip with none of what happened to me.
What I'd do differently
Book for proximity, not square footage. This is the one that was genuinely mine. With a five-year-old, a residence is a gift — the access to the outside spaces, the ability to cook a lunch. With children under three, proximity based on the situation is key. If this had been high season and warm, I wouldn't have been stressed about walking to every meal. In fact we loved being away from everything when we stayed in Mexico.
Tell them ahead of time that you have young kids, and say what you're expecting from the trip. This one is for your travel agent. A quick email explaining how excited I was for the crèche, and noting that I'd be doing this alone, could have moved me into the right room before I ever arrived.
Get childcare confirmed in writing, by a human. A website tells you what a property offers. It does not tell you what is running the week you arrive. Mine said four months to four years and said nothing at all about January. The only version worth trusting is a named person confirming your specific dates in an email you can point at later. This is now the first thing I do for every client traveling with a child under four, and it takes ten minutes.
Ask what's open when, not just what exists. In low season, restaurant hours contract and gaps open up between service periods. A two-hour window where nothing is serving is a mild inconvenience at thirty and a genuine crisis with a hungry toddler.
Ask what happens after the kitchen closes. Lounge access, in-room dining hours, whether anything at all can be had at four in the afternoon or ten at night. That one question would have prevented my entire first day.
Ask what they'd give a family that they don't advertise. The kids' kit, the play room, the lounge with the all-day bites. None of that was on the website. It existed because somebody at that property had thought about parents, and I only found out by falling apart in the lobby. Ask up front. It's a normal question, and the answer is often the reason to choose one hotel over another.
What actually matters, with children this small
- Service. Not turndown and a chocolate. People who look at you holding two children and think to offer something before you have to ask. The person who takes the baby for ninety seconds so you can eat is worth more than every amenity on the list combined.
- Childcare. Genuinely open, on your dates, at your child's actual age, confirmed by somebody who works there. Everything else in this article follows from that one sentence.
- A place for you to relax. Somewhere that becomes yours the moment they're both asleep, without leaving the room. A balcony, a terrace, a lounge you can reach on a monitor. Without it, bedtime is the end of your day too.
- Excellent food, available without leaving the property. Across the whole day, not only during service periods, with something on the menu a two-year-old will actually eat. Distance to food is the number that decides your week.
Everything else is decoration. If you're traveling on your own with young children, or if the whole point of the trip is that you get a break too, those four things are the brief.
Would I send you there
Yes. Without hesitation, and the people are the entire reason.
With conditions, because that's the job. Book inside the hotel, not a residence, if your children are under three. Go in shoulder season — you'll have the place half to yourself for less money — and confirm the crèche is running and the restaurants are on full hours before you pay anything you can't get back. Budget for the Mini Club, which carries a fee for under-fours, though the club for 4–12s is free. And know the spa is adults-only from sixteen, in case you were picturing a thermal afternoon with a nine-year-old.
The trip I'd book you now is a suite in the main building, with childcare confirmed in writing, club access included, and all restaurants open. That's a genuinely lovely week, and it's the week I thought I was booking.
But truthfully, it ended up better than the one I'd planned.
Tell me what you're planning
Pick whatever applies. I'll send what's useful and nothing else — no weekly emails about nothing.
I check these things so you don't find out on arrival
Crèche opening dates, restaurant hours in low season, which room category is actually near the food. Booking a hotel through my platform costs you nothing and still gets you breakfast, an upgrade when it's available, and perks that aren't on the website. Having me plan the whole thing is $250 per adult over eighteen.