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One thing you need to remember is that casual dressing in Cuenca is a part of life. Jeans, casual slacks, jogging pants, etc. are worn day and night and are acceptable for both men and women. I have seen very few skirts, although I brought a couple. You never know when you might need one.
When visiting Ecuador, you are allowed 90 days within the country without fee or penalty. If you would like to stay longer the easiest solution is a tourist visa, which will allow you six months in Ecuador. It is best to do it the legal way to avoid any problems later at your departure or border crossings. have lived in Cuenca for 6 months and we have had 3 days when the sun was out all day and a scattered cloud. 99% of the time it has cloud cover. Not partly cloudy or mostly cloudy but completely cloudy. It can rain at any minute for 5 minutes or all day.