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Both have their pros and cons, and it helps to weigh these up when thinking about the best option when living in Wellington.
Of course wind is a factor, so getting something that stays put and doesn't fly away is pretty high on the list! Shade sails need to be anchor mounted, but in a strong southerly it pays to have had the mounts fixed strong! Shade sails have a permanent coverage, with the amount of shade depending on the angle of the sun. Umbrellas, can be moved around especially if it is a cantilever umbrella in an umbrella base.
The cost, of course, is another major factor. To install a quality shade sail is expensive, and the fixings permanent. An umbrella can go where you want it, and depending on the style, or if you're near the coast, it can either have a wooden or aluminium base or frame. Umbrellas also come in a variety of colours making them an aesthetically pleasing option.
Wellington BBQs and Fire have shade umbrellas and can offer advice about their use during the great Kiwi summer.