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One of the most gorgeous parts of Oahu is the windward coast (east side). It’s famous for its jagged green mountains (the Ko’olau range) and laidback towns with gorgeous beaches. The main destination on the windward side is Kailua town (and neighboring Lanikai), but I’ll also be including stops south of Kailua (down to Koko Head Marina) and north of Kailua (to the north shore) in case you want to make a day out of it!
Often referred to as “the world’s biggest little beach town,” Kailua is popular with locals and tourists who are searching for some respite from Honolulu, but still like some of the conveniences of “town” (hello Costco and Target!).
Getting there: If you’re heading to Kailua from Honolulu, be sure to take the H3. It’s got to be one of the most beautiful highways in the US and you’ll have AMAZING views of the Ko’olau Mountains.
RELATED: Not very familiar with Oahu? Read up on the lay of the (is)land and where to stay plus my favorite beach resorts, budget hotels, Airbnbs, honeymoon resorts, family friendly resorts, luxury resorts, and boutique hotels.
Lanikai Beach: THIS is why you come to Hawaii. Regularly found on lists of world’s greatest beaches, Lanikai is picture perfect. It’s not the most convenient beach, but it’s worth it. Lanikai is a small neighborhood right next to Kailua Beach Park and there’s not much parking. There’s no parking allowed on the side of the street with the bike path, and you obviously can’t park in people’s yards or driveways, so you may have to hunt for a spot. You also won’t find any amenities as this beach, so pack in everything you’ll need.
Kailua Beach: While next-door Lanikai beach is the island’s crown jewel, Kailua beach isn’t exactly the ugly stepchild. It’s gorgeous! And it has great amenities. You’ll find restrooms, showers, picnic areas, rentals, and the Kalapawai Deli. There’s also plenty of shade.
Lanikai Pillbox Hike: There are so many hikes on Oahu, but this is my favorite! It’s fairly short, but it’s got a good pay off. You’ll find the trailhead on Kaelepulu Dr in Lanikai. All of the parking is on the road. This hike only took me about an hour up and back, but you really have to scramble in some places. The first part is by far the steepest.
Kayak to the Mokulua Islands: If you love to kayak, paddleboard, or are just looking for an ocean adventure, you’ve got to paddle over to the “mokes.” Just a 30-minute paddle from Lanikai beach, there’s a small beach to land on and a whole lot of fun to be had. You can rent kayaks in Kailua, but the best place to launch them from is Lanikai. I haven’t done this yet, but I enjoyed reading this post about kayaking over on Memorial Day.
Where to Eat: Kailua is famous for its breakfast places. Boots and Kimo’s has a crazy good macadamia nut sauce they use on their pancakes. Show up right when they open or you’ll be waiting in line for a while. Cinnamon’s is a Kailua institution (and Hawaii famous), but I haven’t ever had a great experience there. The first time was just “meh,” and the second time was pretty bad. But people LOVE it (and their guava chiffon pancakes) so maybe I’ve just caught it on a bad day(s). My favorite breakfast in Kailua is at Moke’s Bread and Breakfast. Their lillikoi pancakes were insanely good and we didn’t have to wait at all.
Where to Shop: Kailua has so many cute boutiques but my favorites are on Hekili Street. It’s a great little strip with tons of cute boutiques and snack spots. I LOVE Guava Shop (the original is in Haleiwa on the north shore). Everything in that shop is bright, colorful, and cheery. I’ve bought a super fun beach sheet there, some gold bangles, and way too many things with pom-poms. Also, online retailer Bikini Bird opened up their very first brick-and-mortar a couple shops down.
To the South
South of Kailua, you’ll find the town of Waimanalo (a very local town with beautiful beaches), and if you continue south, one of Oahu’s best drives. I’m not sure if this part of Oahu is technically considered part of the windward side (more likely it gets clumped together with east Honolulu), but I’m going to tell you about it in this post because I think it pairs nicely with a day trip to Kailua if you’re coming from another part of the island.
Makapu’u Point and Trail: Leaving Waimanalo and heading south, the first major spot you’ll come to is Makapu’u Point (reverse this section if you’re coming from Waikiki). You’ll see a turn off with cars parked along it and a small parking lot at the bottom. It’s a mile hike (at a decent incline) to get to the top (where you can see a lighthouse plus epic views of the windward coast), but it’s entirely paved.
Halona Blowhole: Blowholes always draw a big crowd in Hawaii, and this is one of the most easily accessible ones you’ll find. You just have to fight off the crowds from the tour buses to get a look! There’s a turnout on the highway with a few parking spots.
Hanauma Bay: Oahu’s most popular snorkeling spot, Hanauma Bay is a nature preserve now and they’re making attempts to restore the reef after years of abuse. Parking is limited and is usually filled up by 9 so arrive early! Admission is $7.50, parking is $1 and it’s open everyday (6AM-7PM) but Tuesday. If you’re not a keen snorkeler, or you just don’t have time, you should still see the overlook. They’ll refund your $1 for parking if you leave within 20 minutes.
RELATED: 15 Things to Do on Oahu
Koko Head Crater: Sometimes overshadowed by Diamond Head, this crater is a popular hike, but I’ve been told it makes Diamond Head seem easy. It’s 1000 steps (on old railroad ties) straight to the top.
Where to Eat: If you’ve made it this far, you’re pretty close to the Koko Head Marina so stop by Kona Brewing Co for a beer (or lunch!). Leonard’s (famous for their malasadas-Portuguese style donuts) food truck is also known to be parked in this shopping center from time to time.
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To the North
Leaving Kailua and driving north, you’ll find yourself on THE best drive on Oahu. The drive along the windward coast towards the north shore is one of my favorite things to do on Oahu. You’ll be sandwiched between majestic green mountains on one side and stunning white sand beaches on the other.
Kahana Bay: This beautiful bay is such a gorgeous spot to pull over and make a pit stop. You’ll find the famous Crouching Lion hike along this ridge, as well as a phenomenal beach.
Chinaman’s Hat: Pull over at Kualoa Park for great views of this funny shaped island just offshore.
Kualoa Ranch: One of Oahu’s biggest tourist attractions can be found on this stretch of road. While you can stop in to check out the gift shop and restaurant, pretty much all of the tours at the ranch require reservations. Check out this post for 5 things to do at Kualoa Ranch.
At this point, you can continue on to the north shore (which I’ll get into in another post!).
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