It depends on you. I personally NEED an umbrella. Neither of us can take much sun any more. As far as renting from Craig, his umbrellas are pretty sturdy and if you get it firmly anchored, you should be ok, except on the windiest days. To me, I get one to use at Beachside Villas, because they don't provide umbrellas, but no way I would bother to lug it to another beach. If we go to another beach, we just rent chairs and umbrellas there. Usually it runs about $20 for 2 chairs and an umbrella for the day at most beaches, versus $20 or so for a WEEK from Craig. And I have to have a chair also, as I'm not comfortable sitting on sand. Be advised if you rent the chairs from Craig, that most of his chairs are 'sand' chairs, low to the ground, which don't work well for me. He does have a few regular chairs, I believe, so if you want one of those, you need to ask for it specifically. We always rent a cooler from him also, and we always request one with a FLAT top, so we can use it as a table at the beach..