Kailua Oahu

Activities in Kailua + Windward Oahu

The most beautiful part of Oahu is the wind-side. On the upwind side, the primary target is the city of Kailua (and neighbouring Lanikai), but I will also plan to stop at stations just south of Kailua (down to Koko Head Marina) and just to the North Bank of Kailua if you want to make a outing!

Frequently described as "the largest small seaside city in the world", Kailua is a favourite of local people and visitors who are looking for a break from Honolulu but still appreciate the amenities of the "city" (hello Costco and Target!). When you drive from Honolulu to Kailua, take the H3.

Are you unfamiliar with Oahu? Find out about the location of the (is)land and where you can spend the night, as well as my favourite seaside resort, budgeted hotel, airbnbs, honeymoon resort, family-friendly resort, luxurious resort and boutiquehotel. This is Lanikai Beach: Lanikai is beautiful as a photo on the list of the largest bays in the canal. It' not the most comfortable but it' definitely a worthwhile one.

The Lanikai is a small neighbourhood right next to Kailua Park and there are not many car parks. You' re not going to find facilities like this one, so wrap everything you need. This is Kailua Beach: Whilst the neighbouring Lanikai shore is the pride of the islands, the Kailua shore is not exactly the ugliest underling. There are so many walks on Oahu, but that's my favourite!

You will find the starting point at Kaelepulu Dr in Lanikai. "Only 30 minutes from Lanikai there is a small landing spot and lots of entertainment. They can hire a kayak in Kailua, but the best place to start it is Lanikai. The Kailua is known for its breakfasts.

Cinnamon' s is a Kailua institute (and Hawaii famous), but I've never had a great one there. There was only "meh" the first and the second one was quite poor. I have my favourite Kailua breakfasts at Moke's Bread and Breadfast. There are so many sweet shops in Kailua, but my favourites are on Hekili Street.

At the I Lorraine Guave Shop (the shop is located in Haleiwa on the northern shore). I got a really funny blanket, some golden bracelets and way too many things with pom-poms. You will find the city of Waimanalo (a very small city with wonderful beaches) just down the road from Kailua, and if you go further southwards, one of Oahu's best trips.

I am not sure if this part of Oahu is part of the upwind side from a technical point of view (it is more likely to be lumped together with eastern Honolulu), but I will tell you in this article because I think it goes well with a full days out to Kailua when you come from another part of the isle.

If you leave Waimanalo and head southwards, the first big point you come to is Makapu'u Point (vice versa if you come from Waikiki). It is a long walk (with a good incline) to get to the top (where you can see a light house and breathtaking vistas of the weather ), but it is completely cobbled.

Oahu's most beloved snorkel site, Hanauma Bay, is now a protected area and they are trying to rebuild the site after years of use. But if you are not an avid snorkeller, or just don't have enough free play, you should still see the view. Head Koko Crater: Occasionally shaded by Diamond Head, this craters is a favourite walk, but I've been informed that it makes Diamond Head appear as such.

When you get there, you're near the Koko Head Marina, so stop at Kona Brewing Co for a cold drink (or lunch!). Leonard's (famous for his malasadas-Portuguese donuts) is also known to be occasionally stored in this mall.

I will also keep you up to date on the latest bookings and offers and every weekend I will be highlighting some of my favourite holiday apartments. If you leave Kailua and head northerly, you are on the best trip on Oahu. Cruising along the weather coastline to the northern bank is one of my favourite pastimes on Oahu.

You will find the famed Crouching Lion walk along this mountain range, as well as a spectacular sandy area. From there you can go on to the northern bank (which I enter in another post!). Do you feel a little overburdened with trying to find the ideal Oahu route? The Oahu Bound! I' ve put together the BEST Oahu Routes you'll find everywhere!

They are the routes I use on my travels to Oahu (plus a few optimizations because the 20/20 review is right?) and they are great for the first timers and returnees who want to see the best of Oahu. I' ve recorded everything from the best snorkel sites, shores and walks, and it's all sorted by each part of the islands so you don't have to spend your own tracking in.

Oahu Bound gives you a 3, 4, 5 and 6 day route and I am not just referring to a to-do enumeration of todos. You' ll also get a travel templates that you can use to create your own route, along with detailed hints for building your own route, a vast repertoire of things you can do on Oahu, and instructions for building your own Google Maps.

For the Oahu Bound travel package, click here.