You are on vacation take your time, do not hurry, there should be no issues with checking a bag outside of costs and a few minutes. Some rules to make life better. Never put anything in a checked bag that you cannot live without or if it is lost. Restated never put anything you would worry about in a checked bag. Two, carry with you a bathing suit and anything you must have. Credit card, cash, toothbrush, and a bathing suit that fits is all you really need anyway. Let the porters shlep the stuff you might want but do not need. We always check and we always carry a day's worth of clothes in the odd event the bags get delayed and catch up with us later. If you sweat any of this, you are doing it wrong. Any good airport process 100,000 checked bags a day. Some will get lost, some will simply disappear. Leave anything you care about at home so you and your mates do not have to worry about it.