Here’s what to see and do around Kailua’s windward side (Updated 2021)

Kailua is very cool and a fun mix of old and new, uber trendy and old school, rich but also local spots, there’s so many things to do in Kailua for everyone to enjoy on the windward side of Oahu and just a short trip from near by Hawaii Kai or downtown Honolulu.

This ever-evolving town is one of the hippest places to visit on the east side of Oahu but still maintains it’s small town charm that you’ll want to go out and explore when you visit Oahu.

You’ll enjoy exploring the town, doing some outdoor activity the area is known for or just hitting the fabulous beach scene in the area.

Whatever your mood is for the day, go visit Kailua and check out all these fun places to visit and activities to get your real taste of paradise on the windward side of Oahu now.

Top things to see Kailua

Wondering what to see in Kailua on the Windward side of Oahu?

Table of Contents

    Where is Kailua Hawaii located?

    Where is Kailua Hawaii located?

    Kailua town is located on the windward side (eastern side) of Oahu island and about 15 miles east of Waikiki area. What’s not to love here with the best of the ocean vibes, hip shops and delicious eating venues in town. Check out the best things to do in Kailua now.

    What is the weather like in Kailua?

    What is the weather like in Kailua?

    Almost perfect is the word with windward skies that blow in fresh air from the east and a natural air conditioning system that everyone enjoys on the east side. Average temperature in the area is in the low 80s with summer to early fall the dryer times of the year.

    Check out the best things to do in Kailua now

    Go shopping in Kailua

    Go shopping in Kailua

    Even thought the little town of Kailua, Oahu has its own Whole Foods and Target store, it still maintains its small-town vibe with unique mom and pop shops, art galleries and boutique stores and attractive shopping venues that you’ll enjoy visiting and supporting local vendors and shops in the area. With gentrification and prices of Kailua real estate hitting over the top rates, Kailua has been the trendiest and upscale town to visit and shop at the many cool stores and venues in town.

    Adventure fun in Kailua Hawaii

    Adventure fun in Kailua Hawaii

    Water fun in Kailua

    The beaches in the Kailua area are really spectacular and popular with locals and visitors to the islands. The two main beaches that are worth hanging out in the area includes Kailua beach park and Lanikai Beach.

    Kailua Beach Park

    Kailua Beach Park

    Kailua Beach is a nice long strip of beach (over 2.5 miles in length) with plenty of room to spread out, but be warned, the parking lot fills up early so get to the beach early or maybe head out later to enjoy end of day and sunset time on the beach. Some parts of the beach area have nice shady ironwood trees to hide under the hot sun when you need some shade from a day the beach.

    Kailua Beach Oahu 20

    Lanikai beach

    Lanikai beach is a smaller beach in a quiet and tony neighborhood of Lanikai. A popular and gorgeous white sandy beach with fantastic views of “The Mokes” islands in the distance that are easy to get to via kayak.

    Both beaches have the softest powdery white sands facing gorgeous aqua, blues and greens of the ocean that truly dazzles everyone visiting the beaches here.

    kayak to the Mokes isles from Kailua

    Head to the Mokes

    The islands just off of Kailua are a popular and fun kayaking adventure experience. You can easily rent kayaks from the beach (Kailua Beach Adventures) and head out by kayaks on relatively flat and beautiful aqua colored ocean waters that makes this a fun outdoor experience you’ll really enjoy. The two twin islands are called the Mokulua islands and locally called “The Mokes” with the largest island called Moku Nui and a fun kayaking challenge for more experienced kayakers. Beginners can kayak to the closer island called Flat Island which is just off the coastline.

    Check out this fun video of tours offered with Kailua Beach Adventures below

    Surfing fun at Kailua

    If you’re looking for some surfing action in the area check out the Castle breaks at the north side of Kailua beach. You’ll enjoy some cool surf and best time to avoid the crush of locals is usually mid-day when everyone is still working. Check out all the surfing fun in Kailua on this video highlights below.

    Watch the “Paddling” action at the Kailua beach park

    Watch the “Paddling” action at Kailua Beach Park

    After hours, the canoes come out for some paddling workouts from local canoe clubs. Head out to the canal at Kailua Beach Park to watch all the local outrigger teams practice with all their team mates and enjoy this local scene after hours.

    Lanikai Pill Box hike in Kailua area

    Go out hiking in Kailua area

    Lanikai Pillbox hike

    The Lanikai Pillbox hike is also called the Kaiwa Ridge trail is a popular local favorite hike with spectacular views. Less than an hour hike with a steady uphill grade, it is considered an intermediate hike. With gorgeous visuals worth capturing of Lanikai, Kailua and the gorgeous coastlines and mountains, you’ll love all the spectacular views from this hike.

    Check out this cool video on doing the Lanikai Pillbox hike below.

    Olomana Trail

    A nice hike here affords gorgeous views of Kailua and Waimanalo. This more advanced hike is a strenuous 4.5 round trip hike starts in a nice forest grove of ironwood trees and ferns and turns quickly uphill trek and through some large rock wall terrain with the help of ropes to get yourself up. There are three peaks here of which the first is the recommended and not the other which are extremely dangerous.

    Check this video highlights to the Three Peaks HIke at the Olomana Trail below.

    Hike to Maunawili Falls outside Kailua

    Hike to Maunawili Falls

    Lush jungle terrain located in a valley, you’ll find this beautiful waterfall and swimming hole. The hike to Maunwili falls is located in a neighborhood between the Ko’olau and Olomana Mountains and is about 2.5 miles roundtrip.

    Tip – it is muddy so wear appropriate shoes and bring bug spray for those pesky mosquitos.

    Check out this cool video highlight to visiting Maunawili Falls below.

    Other outdoor adventures in Kailua

    Go Bicycling in Kailua

    Forget all the traffic and parking issues in town and just rent a bike for the day at the Bike Shop and you can take your cruiser bike to all the fun hot spots around town, to the beach areas and other fun biking venues

    Golfing in Kailua

    With lush views of the Ko’olau Mountains in the background, golfing here takes on a cooler mountain vibe that is pleasant and relaxing. You have two choices of golfing venues here at the Royal Hawaiian Golf Club or the Mid Pacific Country Club

    Enjoy Sunrise on the windward side

    Enjoy Sunrise on the windward side

    The sunrises are best here on the east side at Kailua, pick a spot on the hill or the beach areas and you’ll enjoy some of the best sunrise views around Oahu here plus parking is so much easier this early in the mornings around town.

    Time to eat in Kailua

    Time to eat in Kailua

    Have a delicious Shave Ice

    After a fun day outdoors at the beach or some outdoor adventures, it’s time to cool off with some cool shave ice dessert to enjoy in Kailua. The best place you’ll find here is Island snow which is the perfect combination of ice cream and shave ice. Located next to the Kailua Beach adventure rentals, it’s the perfect stop after an active day kayaking, swimming or outdoor adventure

    Check out the Kailua local farmers markets

    Check out the local Kailua farmers markets on the windward side

    Do you love visiting farmers markets? Kailua loves fresh and local foods and island grown and you’ll find plenty of farmers markets to visit on the windward side. Check out the following markets for enjoying farm to fresh, local arts and crafts and other artisanal finds.

    1. Hawaii Farm Bureau Market (Thursday evenings at Kailua Town Center Garage)

    2. The Peoples Open Market (Thursday mornings at Kailua District Park)

    3. Lokahi Kailua Market (Sundays at Ulunui Street)

    Check out this video of the Lokahi market with artisanal foods, craft makers and other fruit and vegetable vendors from the area.

    Places to eat in Kailua Town

    Looking for someplace to nosh or even have some local Hawaiian food? Then head out to these favorite spots in Kailua to fill your hangry needs. You can do some easy local dining or take out food, brew hopping or even swanky fine dining venues for the foodies looking for farm to table dining service. Kailua at night happens to many of these fun places to explore in the evening.

    Maui Brewing company – What’s not to like with some cool brews and easy bistro fare, how about visiting 3:30 – 5:30 pm for their happy hour deals

    Lanikai Brewing – Tap and Barrel a popular and local favorite hangout to enjoy some local craft brews and seasonal offerings.

    Boots and Kimo Homestyle Kitchen– Homestyle cooking and comfort food at it’s very best for local’s and visitors looking for hearty food.

    Kalapawai Market and Café – Another local island mom and pop shop with fast take away food and deli to more wholesome diner food to enjoy

    Goen Dining + Bar – hang out at the fun and trendy Roy Yamaguichi restaurant with casual dining indoor and outdoor at it’s very best in Kailua and beautiful, tasty and fine dining with a casual vibe.

    Cinnamon’s Restaurant – A local island favorite that is 34 years in the making with favorite breakfast foods like Eggs Benedict, pancakes and other breakfast specials or meals for the rest of the day

    Nico’s Restaurant – Local seafood is what you want to order here with fresh local catch of the day and other seafood specials on the menu

    Lanikai Juice – delicious and easy smoothies, juices or an acai bowl to go or just hang out for a bit

    Island Snow – perfect ice cream and shave ice that is so good especially with mixed tropical flavors to choose from a big selection of flavors to choose from

    Things to see around Kailua area

    There’s plenty of fantastic places to explore close to Kailua on the East side of Oahu. Consider visiting these cool attractions for a fun day exploring the area’s best attractions and historic sites.

    Kawai Nui Marsh

    Kawai Nui Marsh

    The largest protected marshland space in all of Hawaii encompassing over 830 acres of wildlife preserves. Home to several migratory and local indigenous waterbirds, fish and aquatic marine life. The Marsh has a paved area that is perfect for walking, jogging or biking the area.

    Hamakua Marsh

    Located close to Kawai Nui Marsh is this marsh land area that is a smaller wetland preserve for protected wetland and migratory birds and is a great spot to watch native birds in the area. You can see Hawaiian Moorhen, black necked stilt, and Hawaiian coons in the marshes regularly

    The Ulopo Heaiu in Kailua

    The Ulopo Heaiu

    Located on the edge of the Kawai Nui Marsh (eastern side) is the heaui with a large stone platform measuring 140 by 180 feet and reaching a height of 30 feet. The building stones were brought to this location from Menehune legend from 10 miles away in Kualoa area.

    What’s free to do in Kailua?

    No doubt that gentrification has brought better choices but higher prices for property, shopping and dining experiences in town. But you can still find cheap or free things to do in Kailua. Check out these great ideas below:

    1. Enjoy a fantastic sunrise on the beach
    2. Doing some of the great hikes around town
    3. Check out the nature preserves or the Ulopo Heaui
    4. Do an easy road trip down to Maku’u Point and all the way back through scenic Hwy 1
    5. Rent a kayak, wind surf board or boogey board for recreational fun
    6. Window shopping is free and cheap in Kailua
    7. Check out the farmers markets for free tastings and cheap fruits, veggies and take out food.
    8. Enjoy a nice walk on the beach

    Stay overnight in Kailua

    Where to Stay in Kailua

    With no hotels located in Kailua are, you’ll still find a variety of Kailua accommodates that may fit from small inns and Bnb and Kailua beach rentals available to stay overnight or a few days for a nice weekend getaway here.

    Paradise Palms Bed and Breakfast – A well appointed and comfortable Bnb with spacious rooms and on suite bathrooms, kitchenettes or fridge and coffee. Included basic and simple breakfast service.

    Pillows and Paradise Bed and Breakfast – A family friendly inn with pool, kitchenette, free breakfast fruit tray and parking and wifi

    Manu Mele Bed and Breakfast – close walk to the beach or use their private pool and gardens, the inn serves basic breakfast service with fruit, breads and yogurt along with hot drinks

    Check out all these top review sites through TripAdvisor here with current prices, availability and booking calendar.

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    Check out these other posts on Oahu

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    Things to do in Hawaii Kai

    Virtual tours of Oahu

    Free or cheap things to do in Oahu

    A Diamond Head Hike in Honolulu

    Family friendly beaches in Oahu

    Top things to do in Honolulu

    Explore and Hike Waimea Valley

    Horseback Riding in Hawaii

    Conclusion of best things to do around Kailua Oahu

    For Kailua fun, you’ll love explore all fun activities and attractions around this easy and walkable and beach areas of Kailua on the east side. Hope this gives you some great ideas of things to do and see around the town and outlying areas to visit.

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    Meet Noel Morata

    Noel Morata is the creator of This Hawaii Life along with a small team of contributors. Living on the Big Island and traveling regularly to the neighbor islands, Noel and team actively search and share the latest information and updates to Hawaii travel, food, adventure and various lifestyle activities on the islands for your planning and vacation. Aloha and enjoy This Hawaii Life.