I have been three times on the top of PICO island, the highest point of PORTUGAL a little more that 2300 m.
Is not a easy climb but honestly the descend is more difficult and need attention and precausion.
Know we are obligate to pay a fee and honestly we can climb by our one but is recommended to use a guide :-)
People are incredible and there is markers during all the climbing to sinalize were to go.
On the top there is a incredible view waiting for us, all the 5 island of the central group of azores, and honestly if we have the opportunity try to climb on an hour that allow you to the the sunset and sunrise, honestly you will not forgott :-). The way up is not made only by fine road there are rocks, and places that we need to use our hands in way to pass the objects but should not be a reason to not to go :-)
In terms of material i recomend to bring one impermeable jacket, water, and some energetic bars ou chocolate bars if your objective is to climb and came down in the same day. If you choose to spend the night on the top covers and warm clouthes is a most and a tend is not a bad idea, but watch out for the wind, use some rocks inside for the tend dont fly and precipitacion may occur. The advantage is that when you awake at 6:30 am, climb what we call the small pico and watch the sunrise all the cold, and stress is forgott and a big smille in your face can be recorded by your friends
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