The Windward Coast: Lanikai & Kailua

The south side of the windward coast of Oahu is known for some of the most beautiful beaches in the world: Lanikai and Kailua. These beaches are frequently ranked the top in the U.S. The beaches are tucked into beautiful neighborhoods with very nice houses, and it comes with a really cute downtown area (Kailua) that has great food and adorable shops! Read more to find how to spend your time wisely over on this part of the island.

What to Do

Lanikai Beach

Ahhh Lanikai… I’m dreaming just writing about it. This beach is often ranked #1 for the best beach in the world. Tucked into an isolated, upscale, and safe neighborhood, with mountainous cliffs behind and the beach in front, the softest light sand you will ever touch, two small islands off in the distance, and clear turquoise blue water with sea turtles often swimming around, Lanikai Beach is a dream spot. Recently I overheard a tourist sitting on the beach say, “We almost didn’t come here and were planning to stay in Waikiki but I’m so glad we changed our minds, this is the best part of the trip!” Be sure to bring snorkel gear in case you see a sea turtle swimming by. Tip: get here EARLY; parking can be difficult. Park your car on the street in the neighborhood but pay attention to the signs; the residents speak up if you are parked incorrectly. Also, there are NO bathrooms here. Kailua Beach is close by and has bathrooms; go there first if you need to go!

Lanikai Pillbox Hike

One of my favorite hikes on the island is the Lanikai Pillbox Hike. This 1.6 mile there-and-back trail is STEEP, especially at the start of the trail. I recommend using a trekking pole in one hand and your other hand to hold onto trees as you go up/down the beginning section. Bring water, wear appropriate shoes, sunscreen, and enjoy this marvelous hike! As one commenter on the All Trails website stated, “Million dollar views at the top.” “Pillbox?” you may ask! A pillbox is a WWII observation post for military personnel. There are many of these scattered around the islands. Pretty cool to see some history while hiking. Parking is the same as Lanikai Beach. If you plan to do both, you can stay parked in the same spot. Just remember, no bathrooms here!

Kailua Beach

Walk along this 2.5 mile long stretch of beach with turquoise blue water to feel like you are in an entirely different country. As this is on the windward side of the island, this beach is known for windsurfers, which are super fun to watch from the beach unless, of course, you want to join in! This beautiful beach has bathrooms, and a parking lot. You’ll still want to avoid getting there midday as it might be tough to find parking at that time.

Manoa Chocolate & Wine Bar

We were so glad to have just happened upon this place when looking for parking at Rise & Grind Coffee Bar (see below). Manoa Chocolate & Wine Bar was a great find! You will get a FREE chocolate tasting, and will probably want to try some of their wine too (not free) to go along with the chocolate samples. It was pretty cool to learn about how chocolate is made too! This little place has delicious chocolate from cacao beans grown on most of the Hawaiian islands which makes for great gifts (and great chocolate for yourself too).

Mt. Olomana Hike

AKA the Three Peaks hike… at the start of this hike they warn you that multiple people have died going to the second and the third peaks. Although I have seen many people do the trek to all three and they’ve had no issues. But getting to the first was good enough for me! A steady but steep ascent through the forest leads to hiking with ropes to assist you due to an incredible incline as you get closer to the top. At the very top is slightly like climbing a rock/being on the edge but once you get that 360 view, it will all be worth your efforts! Try to go when it hasn’t rained a lot as this could be dangerous if it’s muddy.

Where to Eat

Rise & Grind Coffee Bar

After living in Washington state for 6 months, I got to know really good coffee. After drinking coffee here, I had to know more; come to find out the owners of the Rise & Grind Coffee Bar in Kailua are from Washington! So, they know really good coffee too. A quaint little coffee shop to start your day will wake up all of your senses especially with their adorable decorations, plants in the courtyard out in the back, good coffee, and yummy breakfast sandwiches. Bring quarters as you will have to park in the metered parking garage behind the cafe.

Paia Fish Market

This fish market is also in Waikiki, but I typically like to go to the Kailua location since the line is usually shorter here. Plus, I can’t get enough of this place! I enjoy their fish tacos or the lunch plate with sauteed mahi mahi. Locals tip: Paia is pronounced “PUH - EE - UH” and is named after the town where the original Paia Fish market is on Maui, near the start of the Road to Hana.