January
January can be two things in Portugal. It can be very sunny with blue skies, or sometimes it can be very rainy throughout the whole month, especially up north. Either way, it will probably be cold. Do bring a warm coat and a hat. You won’t freeze to death or need special equipment for the cold.
Quick travel tip: If you have a car, this is the time it will get covered in frost overnight… if it’s parked outside. If you plan to use it in the morning, cover the windows the night before with cardboard or even that shiny silver sunshade cover thing (if you come from a sunny place, you know what that it).
Boots are always an option in January, but don’t expect snow or ice on the roads unless you’re in Serra da Estrela, the highest mountain in Continental Portugal, or in the interior regions like Guarda, Bragança…
February
Portugal has been facing droughts and so February has been clear of rain. However, it is usually a rainy month and it is still cold. Winter clothes are the best choice: woolen jumpers, warm socks, a scarf, a hat…
Portuguese people don’t usually walk in the rain or care to wear impermeable clothes, so if you don’t want to look like a tourist stay clear of rain capes and opt for an umbrella instead.