Kailua is the perfect weekend getaway destination. With its sandy beaches, beautiful weather, and abundance of activities, there is always something to do in this small beach town. Here’s a great way to spend one weekend in Kailua.
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Table of Contents
How do I get to Kailua?
You’ll arrive on the island of Oahu at the Daniel K. Inouye International Airport in Honolulu. Formerly the Honolulu International, if the name confuses you!
If you’re renting a car, you’ll take a shuttle from the median just outside the arrivals terminal. Just look for the van with the name of your rental company.
It’s also easy and inexpensive to get from the airport to Kailua on The Bus, as it’s called. It will cost US$6, and take about 1.5 hours. This sounds like a long trip for what is about a 40-minute drive, but it’s a good way to take in some of the sights as you sit back and cross the island. Just look for Bus 20, pop your head in, and ask the driver if you can get to Kailua on his bus. He’ll fill you in on transfers.
You can also take a taxi, Uber, or Lyft, which will be a bit pricey or arrange in advance for a shuttle for around US$65. Google is full of them.
What is the best time to visit Kailua?
Kailua is absolutely beautiful all year round. Winter is the rainy season, but the average winter sees far more sunny days than rainy ones.
Temperatures are a bit cooler, but the Hawaiians are the only ones who notice. Anyone coming from below-freezing weather will love the balmy weather! Hawaiians dream about the snow, like other people in warm places, but you know better.
Summer (June-August), Christmas, and Easter are the busiest time of year in Kailua. Whenever the kids are out of school, families looking to take a vacation come to visit.
However, there’s a lot of room in Kailua, so you might not even notice. This side of the island is very different from the Waikiki side. That’s where the crowds hang out.
Kailua is a bit of a hidden gem, and there really is no bad time to visit!
Where should I stay in Kailua?
There are no hotels in Kailua. What we do have is an amazing selection of vacation rentals and bed and breakfasts. A search on any of the popular internet sites will give you many choices of accommodation, from budget to luxury. And if you have just one weekend in Kailua, why not treat yourself?
There is no “bad” place to stay in Kailua as far as the distance from the beach or town, especially if you have a car. The Bus also runs throughout Kailua.
The town is large enough to have whatever you need but small enough that everything is easily accessible.
If you’re looking for luxury and very close proximity to Kailua’s amazing beach, I suggest that you look for a place in Lanikai. This is an upscale neighborhood of Kailua, and you can find some extravagant places here. But if you look, you can find some more budget-friendly options that are a bit more basic.
Some great mid-range options are the areas of Kailua Estates and Kuulei Tract. Pull up a Kailua Neighborhood map to help you out with these.
Now let’s get on with your weekend!
Sample 3-Day Kailua Weekend Itinerary
* The activities are all dog-friendly (except some of the restaurants), but dogs must be leashed.
Day 1 in Kailua:
Morning:
Roll out of bed a smell the fragrant air. Spend a moment feeling happy to be here. Then make your way into Kailua Town, as the main core of Kailua is referred to, and stop at Morning Brew on Kailua Rd. Indulge in their decadent selection of baked goods and a sublime coffee drink of your choice.
Be sure to sit at one of the little tables outside so you can enjoy the sunshine and people-watch. Once you’ve finished your second baked treat, wander through the nearby shops and pick up a few souvenirs and gifts. This will take the rest of your morning. Don’t just stick to the main street, either. Cross over and see what you find.
Afternoon:
Lunch! Across the street from the spot where you found Morning Brew is Fat Boys Restaurant. Get a real Hawaiian plate lunch – I recommend the garlic chicken – and have a seat at an outside table and watch the world go by, as you wonder where plate lunch has been your whole life.
After you’ve polished off lunch, take a right down Kailua Road to the intersection and make a left. Carry on until you reach Kailua Beach Adventures. Stroll in and ask for a kayak to rent for the afternoon.
Kailua is THE best place to kayak, beating out even my favorite spot at Pelican Point in Walvis Bay, Namibia, which is saying a lot. Wear something you don’t mind getting wet! The great folks here will get you everything you need, and point you toward the beach, just past the shop.
This is perfect for everyone, whether you’ve kayaked before or not. Head for the Twin Islands (aka the Mokes)!
Looking for a more guided experience? Check out some tours here!
Evening:
Now that you’re all salty and tired, head back to the same street where you discovered Fat boys. Across the street is the fabulous Maui Tacos. You’ll want to take the salsa bar home with you. As always, sit outside! It’s beautiful, and you need to soak it in.
If you’re up for it, take a walk on Kailua Beach before you crash. If you have just one weekend in Kailua, try to spend as much time on the beach as you can!
Day 2 in Kailua:
Morning:
Roll out of bed a smell the fragrant air. Spend a moment feeling happy to be here (you’ll do this again tomorrow!). This morning put Boot’s and Kimo’s into your GPS at 1020 Keolu Dr., and taste your first Macadamia nut pancakes.
Spoiler alert: the pancakes don’t have nuts, but they’re served with a mac-nut sauce that you’ll want to bathe in. Everybody loves them, so leave a bit of time to wait for a seat.
Stop back at Kailua beach for a swim, or take the approximately 2-mile walk down to the end of the beach. This is the best beach walk in the world (IMHO).
Afternoon:
Lunch at Teddy’s Bigger Burgers, because sometimes you just need a really fantastic burger.
Today you have the choice between three spectacular hikes.
(1) The Olomana Hike is a moderately difficult, pretty vertical one. The 380º views from the top are unbeatable. It does involve driving back down the Pali a bit to the Royal Hawaiian Golf Course’s loop road. Your GPS knows.
(2) The Maunawili Falls Trail, also familiar to your GPS, is an easy hike and goes on for about 10 miles. But you don’t have to do the whole thing. The perfect distance for me is to the lovely little waterfall. Have a swim and cool off before you head back.
(3) The Lanikai Pill Box trail, also known as the Kaiwa Ridge Trail, doesn’t involve the drive, and if you’re staying in Lanikai, it’s practically on your doorstep. On the far side of the beach, stroll down Kaelepulu Drive until you see the sign next to a private drive. It’s a bit steep, but not too difficult. You’ll see a couple of shells of war-time bunkers, and the views from the top are magnificent.
Evening:
If you’re feeling fancy, step into the Uahi Island Grill, on Aulike Street, for dinner. Try the poke or the Kalua pork for some ono (delicious) island flavors.
After dinner, have a few Kona beers at the local Kailua Town Pub and Grill. Located on Hoolai Street, they have rotating craft beers and a selection of all the best island cocktail favorites. And if you’re still hungry – pub food! Their fish and chips is the best you’ll ever eat.
It can be a bit confusing – the grill is in front, and the pub is in the back. If you’re NOT feeling fancy this is a great alternative to Uahi’s for a meal, too.
Day 3 in Kailua:
Morning:
Wake up and run through a few ways you could escape your old life and stay here forever. Then, as it’s Sunday, grab your reusable bag and wander down to the farmer’s market.
You’ll find it just around the corner from Boot’s and Kimo’s, where you had the amazing pancakes. The market runs from 8 am to 12pm and sells produce, artisanal products, and crafts.
Then take your last morning to relax at home with the fresh pineapple, local mango, and papaya you’ve just picked up.
Afternoon:
Have lunch at the market. They have fantastic dishes – wander around and try to decide. It’s not easy!
This afternoon, head back to the beach for some snorkeling! Lanikai is the place to go. If you don’t have snorkel gear, ask your host. Rentals often come with these types of beach toys. If yours doesn’t, head back to Kailua Beach Adventures, where you rented your kayak. They’ll fix you up.
Evening:
On your last evening, you get to go to Buzz’s. This small but popular restaurant is just across the road from Kailua Beach Park. It’s a little pricey, but the food is good, and they make a great mai tai. They are pretty strong though! For a milder version, but still potent, try the BFRD, which stands for Big F*@>&%g Rum Drink.
This is a great time to take one last moonlit walk on the beach. If you’re lucky enough to be here on a full moon, try to catch the moon rise. It’s spectacular.
Other things to do in Kailua:
Kailua is the ideal location for all types of water sports. Kite surfing is especially popular on Kailua Beach. In the winter, it’s perfect to learn how to surf, as the waves are small and close to shore.
Body surfing or boogie boarding is fun here too. With just one weekend in Kailua, try to squeeze a few of these in!
This beach town is also a great jumping-off point for activities all over the island. It has easy access to The Pali Highway and the H2, so it’s easy to get anywhere from here.
Click here to see more adventurous tours near Kailua!
Where to Eat in Kailua:
- Morning Brew: a great coffee shop with sublime baked goods, perfect for breakfast.
- Fat Boy’s Restaurant: a casual “plate lunch” style place. Served in take-out containers, you can sit outside to eat.
- Maui’s Tacos: great Mexican food with an addictive salsa bar. Try the fish tacos!
- Boot’s and Kimo’s: famous for their macadamia nut pancakes, but open for lunch, too.
- Teddy’s Bigger Burgers: because sometimes you just need a great burger.
- Uahi Island Grill: a bit less casual, with an ono selection of island and mainland dishes.
- Kailua Pub and Grill: the spot for a cold craft beer and some pub food favorites.
- Buzz’s Steakhouse: a great location across from the beach park, and over-the-top mai tais.
Other Tips to know before visiting Kailua:
There is also a town called Kailua on Hawaii’s Big Island. This can be confusing for people – when you book your trip, make sure you’ve got the right Kailua!
If you are hoping to explore the whole island of Oahu, I recommend checking out Gypsy Guide’s self- guided tour! It’s super affordable and will point you to all of the best stops around the island!
3-day Kailua Weekend Trip Itinerary Recap:
- Day 1: Morning Brew, Kayaking, Fat Boys for lunch, and Maui’s Tacos
- Day 2: Boots and Kimos, Hiking, and Uahi for dinner
- Day 3: Farmers Market, Snorkeling, and Buzz’s
Keep Reading::: Maui Bucket List
One Weekend In Kailua Isn’t Enough
As you can see, there’s SO much to do in Kailua that one weekend would never be enough to see it all. You can customize your 3-day Kailua itinerary based on what interests you. No matter what you’re looking for, you’ll find plenty of entertaining activities to create your own fun-filled, jam-packed adventure weekend in Kailua.
What else would you add to this “One Weekend in Kailua” Itinerary?
Tip! Make sure to follow me on Instagram for more USA weekend getaways and dog-friendly adventures!
Happy Travels!
Contributed by Deb Hendricks of Introvert with Itchy Feet
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