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Officially, the rainy seasons in Singapore are, December to March of the following year, and June to September.
My personal testimony, as someone who has lived here since 2013, the weather is pretty similar all year round. Hot and humid with a chance of significant rain every day.
Because of Singapore's proximity to the equator, it is very hot and humid here, so over the years, Singapore has made sure to plant a lot of trees for shade, and in addition, there are a lot of areas and attractions in indoor places. There is a lot to do in the indoor areas in Singapore, so there is not too much to worry about.
It is more recommended to walk outside in the morning or late afternoon.
Walking with an umbrella can also be nice as long as it is not a serious shower.
An umbrella can be purchased cheaply at any of the 7/11 branches scattered around the island.
What do you do when it's very hot or rainy?
Basically, you can always find shelter from the rain, enter a shopping mall or a good restaurant.
Here are some more recommendations:
Visitors to the magical domes of the Gardens By The Bay.
Embark on a journey through the glittering malls of Orchard Road. You get to the Orchard station by subway or to the ION mall by taxi, and from there you can connect through comfortable, air-conditioned underground passageways (there are usually shops in each passageway) to about seven more malls.
Visiting the big aquarium in Sentosa
You arrive at the City Hall or Esplanad train station and embark on a hopping trip between about six excellent shopping malls connected by underground passages. Marina Square Mall has a huge and crazy "gymboree" for children.
Visitors to the River Wonders zoo which is mostly adapted for touring in the rain and protected from the sun. You can also see the cute pandas of Singapore there.
As you understand, there are quite a few things to do and this is only a partial list.
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