Winter on the Windward side is always going to be a riskier bet than Honolulu; however, more often than not, it's pleasant, mild and sunny to partly sunny. I was there this past winter in Feb for 9 days and we had one day of rain. The windward side is green and lush for a reason, but I wouldn't let the rain scare you away. If there is rain in Kailua, you usually just drive over the Pali to town and there's plenty of sun.

if your coming during Thanksgiving again expect rains, grey skies and rougher seas. still a beauty of a town with an excellent beach that will be very different from Waikaloa. if the weathers nice its good to wake up early and catch the sunrise on the beach.

"Rough" seas is a bit of an exaggeration. There is a reef outside of Kailua Bay that keeps the waves down. It's never really rough in the Kailua/Lanikai area.

Hi,

rough seas may be a stretch but could be prevelant in faster sets rolling in and being more choppy. what I was really driving at was activites like kayaking and boating. this is my home town as well and have lived directly on the beach (yellow house's was the beach name).

did many launches from the boat ramp and can say that there has been some rough seas just inside the islands so yes it happens and more in the winter months.

I would never take anything away from Kailua and even watching storms roll in is nice. lived in Lanikai as well and never seen there rough as its reef extends to the Mokulua islands from just offshore and has little clearence from the surface. the reef in Kailua is much different and has multiple terrains and has deeper waters passing Flat Island on the inside and heading towards the marine base that enables the water to get ruff.

a great walking beach anytime of the day. if younger kids are coming, they would like nights on the beach with flashlights chasing down the sand crabs.

It can be pretty much anything and no one here can predict that it will be sunny, calm, rainy, windy,or otherwise more than a few days in advance.

That said, November is the start of the rainy season here which simply means that it is more likely to rain during that time than in the official non-rainy season. Kailua is on the windward, rainier side of the island to begin with. As KailuaBred said, you might be able to go over the Pali and find sunshine even if it's raining in Kailua. But not always, especially during the rainy season.

If a storm system moves in it can cover the whole island chain and it can certainly rain island-wide.

It can get rough enough in Kailua Bay to make it unpleasant for kayakers, as QFOX said. Windy enough to make it unpleasant for beach-goers. Heavy rains also cause brown water conditions (read: pollution).

We're into our thirteenth year living full-time in Kailua, if that makes any difference. I realize there are lots of folks who come here and report that they were here for a limited amount of time (or lived here decades ago) and offer advice based on anecdotal experiences but the fact is that nobody can offer anything but generalities this far ahead of time.

Not even those who actually live here. ;-)

Thank you so much to everyone for your replies. We are excited to visit Kailua and will probably brave the weather to enjoy the area. That said, it is good to go with the right expectations.

We look forward to our trip!

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