Most of the most coveted private hotel pools are well monitored to ensure they’re used only by guests, usually through wristbands. Fortunately, the ocean is better, and free.

I was able to use the pool at one of the big resorts at Poipu in Kauaii. We had stayed at a hotel on a different island and had taken some beach towels from them. We went to visit and walk around the hotel/resort one day and saw that the towels the resort used were the same as the ones we had taken. We came back and used the pool area the whole day (brought our towels with us), did not need a wrist band, purchased food/drinks without a problem. It can be done. This was a total fluke for us – but it was all possible because of our similar towels.

You might try to get in when the hotel is having a luau. Most of the big hotels have luaus every so often. We got into one of the big hotel luaus for free – we just walked in from the beach (as long as there’s no big gates blocking off the hotel’s section of the beach or something), it was very easy, since they were having the luau in their courtyard connected right to the beachfront, and there’s so many people around. We got a free banquet, pao, roast pig, entertainment :) You could probably easily slide into the luau and then into the pool.

I don’t mean sneaking in (I do believe the pools deserve the money :), but just buying a day pass.

I checked the websites of some of the pools but they didn’t seem to offer a pool-only day pass, so I called them today, 2010-Dec-02.

Here’s the deal about day passes at Hawaii’s most coveted private pools, as of 2010-Dec-02.

Maui

• Called Hyatt Regency Maui Resort & Spa at 808-661-1234. They no longer sell day passes.
• Called Grand Wailea at 800-888-611 and spoke with the concierge. They stopped selling day passes 2 years ago due to crowding.
• Called Westin Maui at 866-500-8313. Asked to be transferred to reservations, then to front desk. Day passes are from sunrise to sunset, cost $150 and can’t be booked in advance. You need to call that morning and they’ll tell you if there’s space.

Big Island

• Called Hilton Waikoloa Village in big Island (+1-808-886-1234). Plenty of day passes are available (no reservation required). $80 for a party of 4, 11am-7pm.
• Call the Sheraton Keauhou Bay Resort & Spa at +1-808-930-4900 and speak with the concierge (press 2) about pool passes.

If you aren’t staying in a hotel you have no business sneeking in to use their pool. The guests staying there are paying top dollar and it’s not fair to them to be paying for YOU because you can’t afford the good things on your own. Not to mention it’s those people who are usually the obnoxious, loud, and disruptive ones too. And now because of the abuses most hotels have banned the “day pass” policy. So here’s an idea, stay at a hotel you can afford, or just STAYHOME until you have enough saved up. The people who post ideas on how to “sneek In” should be ashamed of themselves and embarrassed. Go stay at the HO JOs!!