Things to Do in Kailua & Windward Oahu

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 (with neighboring world famous Lanikai Beach), 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! Add these things to do in Kailua to your list for sure:

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Kailua & Lanikai

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.

Things to Do in Kailua

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 Drive 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.

Ho’omaluhia Botanical Garden: Just north of Kailua in Kaneohe you’ll find the Hoʻomaluhia Botanical Garden. Admission is free and the gardens are lovely, but the real star is the drive back to the gardens. The mountains are beautiful and seem to rise up right in front of your vehicle.

Shopping: 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.

Kailua Restaurants

Cinammon’s: This is probably the most popular and talked about breakfast spot on the island (at least in Kailua). They’re famous for their pancakes, and the guava ones are my favorite. Go early (when they open) or expect to wait in line. They’ve recently opened up a location in Waikiki.

Boots and Kimo’s: Another famed breakfast spot in Kailua, Boots and Kimo’s is best known for the macadamia nut sauce they put on their pancakes. Again, go early or expect to wait in line.

Moke’s Bread and Breakfast: Probably the most underrated breakfast spot in Kailua, even though it’s rated very highly on TripAdvisor! It doesn’t get the attention that Cinammon’s or Boots and Kimo’s gets, but it’s fantastic. The best lilikoi pancakes period.

Kalapawai Deli: This old general store is the perfect spot to grab breakfast, lunch, or snacks when you’re heading to Kailua Beach. It’s actually right on the beach, which makes it super convenient, but the food is great. There’s also a smaller restaurant in Kailua town.

Island Snow: My personal favorite shave ice on Oahu (everybody has their own). It’s not far from Kailua Beach.

Chadlou’s Café: The place to go for specialty coffee drinks in Kailua. They also do breakfast, lunch, ice cream sandwiches, and snacks (think PB & banana toast).

Nalu Health Bar and Café: This Instagrammable café serves fresh acai bowls, smoothies, juices, and sandwiches. Everything is fresh, fresh, fresh, and tasty.

Lanikai Juice: Now with locations all over the island, this is a go to spot for smoothies, juice, and acai bowls.

Egghead Café: A great spot to grab a quick, healthy, and tasty breakfast before heading to the beach or out to explore. Breakfast bowls, sandwiches, waffles, and salads.

Teddy’s Bigger Burgers: This local fast food chain serves up delicious burgers, fries, and shakes throughout the islands.

Haleiwa Joe’s: The location in Kaneohe (Haiku Gardens) is one of the loveliest spots on Oahu. The food is delicious, and the atmosphere feels special but not pretentious. It’s a favorite spot with locals to celebrate special occasions.

Waimanalo 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. I did this in flip-flops, although I wouldn’t really recommend it. It’s an easy enough hike, but a pretty good incline going up. The hike only takes about an hour, but bring plenty of water.

Things to Do in Kailua & Windward Oahu

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 and entry is limited so arrive early! Currently, here are the details: admission is $12, parking is $3 and it’s open everyday (8AM-4PM) but Monday and Tuesday (no one in after 2PM though). They’re also only allowing a max of 120 people in per hour. These restrictions were put in place upon reopening after COVID, but because of massive crowds in recent years and the aforementioned conservation efforts, expect some of these operational changes to stick around for awhile. Also, you’ll have to monitor the conditions at Hanauma Bay closely before your trip as it’s becoming more difficult to access. While it’s always closed on Mondays and Tuesdays, it can also close spur of the moment due to jellyfish (which sometimes has to do with the tides and moon phases and other times just seems random), and earlier this year experienced a more prolonged closure due to high bacteria levels in the water. Needless to say, snorkeling here can be hit or miss due to conditions, but it truly is a special place.

Side Note: If you’re looking for a rental car for your trip, I LOVE Discount Hawaii Car Rentals. They’re seriously the only company I ever use. They’ll give you the very best prices, you don’t have to reserve with a credit card or pay until you show up, you can cancel and re-book anytime if you find a better rate, and they usually have a special that adds additional drivers for no fee. It’s a no brainer. Click here to check rates for your trip.

RELATED: 15 Things to Do on Oahu

Where to Eat on Oahu

Oahu Travel Tips

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.

To the North Shore

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. In this area you’ll find one of the most stunning hikes on Oahu, Crouching Lion. It’s been officially closed, but it’s still quite a popular little hike. Full disclosure: I don’t really recommend doing this hike…GO AT YOUR OWN RISK. That being said, here’s the deal: Parking is at Swanzy Beach Park. From there, walk north up Huamalani Road to the trailhead. I recommend only going as far as the first mini summit (less than half a mile) as it gets pretty dicey past that. It’ll only take you 30-45 minutes to get to the top, but it’s a pretty steep incline. You’ll be rewarded with the best views of Kahana Bay and the mountains in the background. Don’t go if it’s been raining and even then plan to get dusty/muddy.

Mokolii Island (Chinaman’s Hat): Pull over at Kualoa Park for great views of this funny shaped island just offshore. You can kayak out to Chinaman’s hat and hike to the top, but it’s not really an adventure for beginners (and you’d have to rent a kayak elsewhere and bring it out), so if you’re interested I’d book a guided tour.

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!).