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I have been to Portugal more times than I have been to any other country, and I have never once gone in August. That was not a decision I made on purpose. It just kept working out that way. Now that I am thinking about the best time to visit Portugal with kids instead of the best time to visit Portugal with a backpack and nobody waiting on me, I am glad it did.
Lochlan is twenty months old. We have not taken him yet. The trip we are planning is for next year, and the first real choice I had to make was not where we were staying or how long we were going for. It was when. Every other decision bends around that one, and with a toddler it bends harder.

The short version
May. If you have any flexibility at all, go in the second half of May. The days are warm without being heavy, the Algarve water is cold but you can get in it, the Lisbon hills are walkable at noon, and you are ahead of the crowds and the prices that land in late June. Late September is the other right answer, and the sea is warmer then. If a school calendar locks you into summer, aim for the last week of August into the first week of September rather than the first half of August.
That is the whole answer. The rest of this is why, and what I am actually doing about it.
Why May is what I would book
The average high in Faro in May is about 74F. The sea sits around 65F. Rain is down to roughly an inch for the whole month. Lisbon runs a little cooler than the Algarve and gets a breeze off the river, which matters more than the number does.
Here is what those numbers mean when you are the one carrying the child. At 74F you can be outside at one in the afternoon. You are not hunting for shade every ten minutes or deciding whether to call the day early. In my honest take on whether Portugal is good for families I said the real difficulty in Portugal is terrain, not heat, and that holds. The streets are steep and the stone is slick. I have climbed to Pena Palace three times without a stroller and I have no idea yet how we are doing it with one. What I do know is that I would rather do that hill at 74F than 85F.
May also gets you the version of Lisbon I like best. The viewpoints and the miradouros are busy but not shoulder to shoulder. You can walk into most of the restaurants I come back to at seven without a reservation, which is the hour a toddler eats. And the sun is still up past eight, which sounds lovely until you are the one trying to get a twenty month old to sleep with light coming around the edges of the curtain. More on that later.
The other thing May gives you is price. A sea view apartment in Cascais in May is a different number than the same apartment in July. Cascais is where we are basing ourselves for four nights, flat and sheltered and forty minutes on the train from Lisbon, and the spread between a May week and a July week there is the single biggest line on our budget.

Late September is the other right answer
September is the month people forget about, and it has one clear advantage over May. The water is at its warmest. The sea off Faro runs about 71F in September, which is six degrees warmer than May, and six degrees is the difference between a child who gets in and a child who stands at the edge for twenty minutes.
Air temperatures are still around 80F in the Algarve. Rain is under an inch. European families go back to school in the first week of the month, so the beaches empty out noticeably between the first week and the third.
The catch is early September. Lisbon in the first week can still feel like August, hot and crowded and expensive, so if you are going for the cities rather than the coast, push to the back half. I would not book a week that starts on the first of September and expect shoulder season.
Here is how I decide between the two. If the trip is mostly about water, I take late September. If the trip involves carrying a toddler up a hill in Sintra, I take May.

What the weather actually does, month by month
These are averages for Faro, which is the Algarve coast. Lisbon is a few degrees cooler in summer most days and a few degrees warmer in winter, and it can spike much hotter than Faro during a July heat wave because it is a city and it holds the heat. Madeira is its own climate entirely and barely has a winter.
January and February. Highs around 61F, sea around 62F. Rainy, quiet, cheap. Lisbon is genuinely pleasant for walking. No beach.
March. Highs around 66F, sea still 61F. A good city month. The Algarve is lovely to look at and too cold to swim in.
April. Highs around 69F, sea 63F. Easter moves around and takes crowds and prices with it, so check the dates before you book anything.
May. Highs around 74F, sea 65F, about an inch of rain. My pick.
June. Highs around 80F, sea 68F, almost no rain. Early June is genuinely excellent. Late June is where the crowds start and the prices follow. There are also two nights in the middle of June I would plan around, which I will get to.
July and August. Highs around 85F, sea 70 to 71F, essentially no rain at all. The busiest and the most expensive.
September. Highs around 80F, sea 71F, under an inch of rain. The warmest water of the year.
October. Highs around 74F and the sea holds at 71F, which surprises people. But the rain more than doubles to around two inches, and it tends to come in bands rather than drizzle. A good gamble, not a safe bet.
November and December. Highs in the 60s dropping into the low 60s, and December is the wettest month of the year at around three and a half inches. Cheap and quiet. This is when I would look at Madeira instead, which stays mild all winter and is a separate trip rather than an add on.

Why I am not taking a toddler to the Algarve in August
I said this in the first post in this series and I will say it again here, because it is the question I get most. I would not take a two year old to the Algarve in August.
The heat writes off the middle of the day. You get a morning and you get an evening, and the five hours in between are spent indoors or in water or in a car with the air conditioning on. Prices roughly double. The beaches that are wide and calm in May are full in August, which matters when you are tracking a small person who moves fast and does not look back.
August does have one real argument in its favor and I am not going to pretend otherwise. The water is the warmest it gets, and if your child is the type who will not go past their ankles in 65F water, August solves a problem that May does not.
So if August is your only window, it is not a disaster. It just means you plan differently. Book a place with shade or a pool, not just a beach nearby. Flip the day, so you are at the beach by eight and back inside by noon and out again at five. Pick Albufeira with its resort setups over a town where everything closes at lunch. And I would skip Lisbon entirely in August and save the city for a different trip.
Everything in one place
All of this, plus where I would stay in each town and what I would actually do with a toddler in each one, is in my Portugal for Families guide. It is a 13 page PDF with the full 10 day itinerary and a section on each stop written for traveling with small children. I made it because I was tired of having eleven tabs open, and I figured I was not the only one.
The two nights in June I would skip
The Festas de Lisboa run all through June and peak on the nights of June 12 and 13 for Santo António. The street parties, the arraiais, fill Alfama, Mouraria, Graça, Bairro Alto and Santos. There are sardines on every corner. The marchas parade down Avenida da Liberdade starting at ten at night on the 12th, and Alfama is effectively impassable after dark and still packed past one in the morning.
It is one of the best nights in the city. I would also not be anywhere near it with a toddler, and I would not book a room in Alfama for the 12th under any circumstances. You will not sleep. Nobody sleeps.
If you want the festival, and it is worth wanting, there are smaller arraiais on the earlier weekends in June that are calmer and start earlier in the evening. Go to one of those, eat a sardine, and be back at the apartment by eight. Then stay somewhere flat and quiet on the peak nights. Baixa, or further out in Cascais with the train in.

If you are going for the cities and not the beach
The whole calculation changes if swimming is not the point. March and October both work well for a city trip, and both are a fraction of the summer price. Lisbon in March is mild and walkable and the queues at the big sites are short. Sintra and Óbidos are far better in March than in July, when the hill is hot and the lines are long.
Winter is the real sleeper. November through February in Lisbon is quiet and cheap, and the city is mild rather than cold. You plan around rain instead of heat, which with a toddler is honestly the easier of the two problems. There is always another cafe. Pack a rain shell, plan a couple of indoor stops, and read my full Lisbon guide for the ones that hold up in bad weather.
What I would not do in winter is go south expecting beach weather. The Algarve in January is mild and beautiful and the water is 62F. It is a walking coast in winter, not a swimming one. Lagos in February is lovely and empty, and you will not get in the sea.
A few things I am packing for the weather
🛒 What goes in the bag regardless of month
- A wide brim sun hat for him, because the Algarve afternoon sun is serious and a baseball cap does nothing for the back of a neck.
- A long sleeve UPF swim shirt, which I would rather reapply than sunscreen on a child who will not hold still.
- Mineral sunscreen. I use the low tox versions at home for my own reasons and I am not switching on vacation.
- A portable blackout blind. This is the one I would fight for. Sunset in Lisbon in late May is close to nine, and a room that does not get dark is a bedtime that does not happen.
- A packable rain jacket if you are going anywhere between October and March.
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How far ahead I am booking
For May I am booking about four months out, which feels comfortable. For June I would move faster. Central Lisbon apartments around the festival nights go three to six months ahead, and the good flat ones with two separate rooms go first. Where I would stay in each town has the specifics on which neighborhoods I would book and which I would not.
Timed entry tickets for Pena Palace are worth buying in advance in any month that is not January, and they are worth buying for the first slot of the day in every month. The hill is the hard part and it is harder at noon.
One more timing note that has nothing to do with weather. The time difference from Chicago is six hours, and the first two days are the ones you lose. Our 10 day itinerary has almost nothing scheduled for day one on purpose. I have an autoimmune disease and I have learned the hard way what happens when I plan a full first day, and that was before there was a toddler involved.
Questions I get about timing a Portugal trip with kids
What is the best month to go to Portugal with kids?
May, with late September a close second. May gives you warm days, manageable hills, low rain and lower prices. September gives you the warmest sea of the year and emptier beaches after the first week. Both avoid the heat and the crowds of mid July through mid August.
Is the water warm enough for kids to swim in May?
In the Algarve, yes, if your child is willing. The sea off Faro averages around 65F in May, which is cold when you first get in and fine after five minutes. Children tend to mind it less than adults do. On the Lisbon coast and in Ericeira the Atlantic is colder and rougher, so I treat those beaches as places to dig rather than swim.
What is the rainy season in Portugal?
November through March, with December the wettest month at around three and a half inches on the south coast. October is the turn, when rain roughly doubles from September. July and August are essentially dry.
When is Portugal cheapest?
November through February, by a wide margin. Flights and accommodation both drop, and the Algarve in particular empties out. If you are going for a city break and do not need a beach, a winter week in Lisbon costs a fraction of a July one.
Is Lisbon too hot in July and August with a toddler?
Hot enough that I would not plan it that way. Lisbon holds heat and the hills are relentless, and a stroller on a steep patterned stone street in the middle of the afternoon is a bad combination. If you are in Lisbon in high summer, do your walking before eleven and after six and keep the middle of the day indoors or on the water.
Should I plan around Portuguese school holidays?
A little. Portuguese schools break from late June to mid September, and that is when the Algarve beaches are busiest with families from Lisbon as well as from the rest of Europe. The first two weeks of September are noticeably quieter than the last two weeks of August for exactly that reason.

We are going in May. I have the dates circled and nothing booked yet, which is where I always am in October. If you are working out the same question, the rest of what I have written about the country is on the Portugal page, and I would start with the Lagos list if the beach is your reason for going.
Pick the month first. Everything else gets easier after that. Then work out how many days in Portugal with kids you actually need, which was the next thing I had to settle. After that came the money, and I put every line of it in is Portugal expensive, and what I am budgeting for our family trip.