So you’ve made it here to the beautiful island of Oahu and you are looking for something a bit more adventurous to do. Sure Waikiki offers some fun activities, but you want to see the real Hawaii, the Hawaii outside of Waikiki. If you are up for a little day trip to the windward side of the island, then a Kayaking adventure in Kailua Bay is a fun, adventurous, and physical activity.
Your Kayaking day trip to Kailua will include scenic stops, that will allow you to view the windward coast, along with recommended stops at some of Hawaii’s little hidden treasure eateries. If you’re up for it follow these steps to enjoy.
Kayak Rental Reservations – First things first, you will want to reserve your kayak at least a day in advance, especially if you are heading out on a Saturday or Sunday. While there should be kayaks available if you walk up, it is always better to be safe and have one with your name on it ready to go. Try these places to book a kayak rental. Kailua Sailboards & Kayaks – 808-262-2555 or Twogood Kayaks Hawaii – 808-262-5656.
Get to Kailua with scenery – Get yourself, or your family on the road by 7AM. You want to get out of Waikiki and head toward the Pali Highway early. Follow the signs to get on H1 West from Waikiki and take the exit for the Pali Highway. If you’re going from any other way, just check out google maps for directions. Leaving early will give you a chance for a couple of recommended stops along the way.
On your way to the Windward side of the island, pull over on the Pali Lookout. Located towards the top of the highway, be prepared to pull off to your right about a quarter mile before the tunnels after the highway flattens out, there’ll be signs. The Pali Lookout will provide you with an astonishing view of the entire Windward side of the island. It will also provide a photo opportunity for you and whoever you’re with, be prepared.
Breakfast in Kailua – Getting hungry? We thought so. After leaving the Pali Lookout, you’ll continue on the Pali all the way into Kailua where you’ll take your first left after the first stoplight in town on Hoolai Street. At the end of that small cross street on the right hand side you’ll find the famous Agnes Portuguese Bake Shop.
Why not stop in and get a delicious malasada – or other delightful pastry or breakfast sandwich, before you continue. For more information on Agnes’s and to get directions check out our Agnes’s directory page.
Getting your Kayak - Once your stomach is full, head on to pick up your kayak. Depending on where you rented from your directions here may vary, but for simplicity we’ll just say you’ve rented from Kailua Sailboards and Kayaks. They seem to be pretty easy to navigate from. You will have a chance to stop and grab some snacks and treats for the kayaking trip because wherever you chose to rent your kayak from will be close to several convenience stores near by.
Once at the rental you’ll go through the usual. Place credit card in case you break the kayak, buy extras like a dry bag and what not for whatever you don’t want to leave behind, and of course, sign your life away. One that note it should be mentioned that most places will have you watch an informational/safety video regarding the kayak; from there you will be ready to go out.
Getting in the Water - From the beach you can kayak straight out to Flat Island which you are able to land on the island and explore a little if you want. On lower tides there is a patch of sand on the side facing Kailua Beach. To the left and right (facing the ocean) there is reef and sometimes surf and we caution against going on either side. Also, steer clear of the back and sides of the island as currents can pull you into the rocks.
From there make your way to the right, right around the bend and onward to Lanikai beach. Take some snorkeling gear with you so that you can jump out of the kayak and get some clear water snorkeling in. On your way to the beach you take note in the water around you, there will most likely be coral heads popping up with fish, turtles, and the occasional larger fish hanging around. Be careful to avoid these underwater obstacles as sudden shifts from waves can topple your kayak and cause injury.
For the very adventurous type you can head further out to the two islands off of Lanikai beach. These two islands are called the Mokulua Islands and we suggest only to go out to them if 1. you’ve watched the safety video from the rental shop, and 2. if you don’t mind a little extra paddle. But, be careful. Don’t go near the breaking surf to the far left (Lanikai reef) or between the islands. This is extremely dangerous and can turn your kayak over leaving you getting severely injured on the reef.
The rental shops should have directed you straight out from Lanikai beach for this paddle. There are a few openings in the reefs that allow you to get out. Also, once you reach the islands, you’ll only want to stay on the front side of the island and land at the small sandy beach. Don’t paddle to the back side as it can be pretty treacherous. Another bit of caution, only go to the left island (facing the water) as this is the easiest access.
Getting in and out of the Kayak on this beach can be a little difficult and can make for entertainment for those already out on the Island. Enjoy the view back to where you have to paddle. If you brought something to eat this can be a great time to take a break and enjoy.
When you have had your fill of water, kayaking, fun and sun, then go ahead and start heading back around the bend to the Kailua Beach area where you started. Be careful exiting and make sure not to paddle in the swimming area. Find your kayak cart or turn in spot and return the kayak.
After Kayak Nourishment – After turning in your kayak, you will probably be pretty hungry from your big adventure. There is a great little pizza place called Bob’s Pizzeria, located in the Kailua Shopping center right across from the beach. This is also the same shopping center that Kailua Sailboards & Kayaks is located in so if you went with this rental outfitter you’ll be right where you need to be.
Finally, if you want to chase your meal with a famous local treat, then head into Island Snow – located in the same shopping center, for a shaved ice treat. This is the same place the Obama’s visited during their winter vacation here in 2009. Who knew ice and sugar syrup could taste so refreshing.
When you’re done you should go ahead and make your way back to Waikiki. Try and leave the Kailua beach area by 4PM, you want to avoid traffic. You also want to get back to Waikiki before dark so you can plan your night out on the town!