Hawaii is a great place to go kayaking. The warm waters in Hawaii make for an kayak paradise - all year round. Most destinations like Kailua and Lanikai are reef protected. No currents or breaking waves make it into Lanikai or Kailua. The kayaks most suitable are sit on tops. Easy to get in and out. Hassle free kayaking and even surfing waves. You can strap a cooler on your kayak, a large dry bag or mount some fishing gear. Sit on tops are the most user friendly kayaks out there and are gaining popularity elsewhere not only in Hawaii. There are a lot of kayaking destination on the island of Oahu. Kailua is definitely the number 1 with its islands and miles of sandy beaches. Kaneohe is another good one. You can also do coastal kayak runs. Make sure to ask about offshore winds and keep a close look at the weather forecast.