Local’s Guide to Visiting Oahu

Local's Guide to Visiting Oahu

My dear friend Sarah Khandjian of Sarah Hearts will be visiting Oahu for the first time in May, so she asked for a few recommendations. Since we just got back from there (where my entire family still lives), everything was fresh in my mind–and I may have gotten a little carried away! If you’re looking for awesome places to eat, play, and shop that both locals and visitors enjoy, this is the post for you.

Honolulu: By Honolulu, I don’t mean Waikiki. I really don’t like to go to Waikiki because it’s such a weird place full of other people’s ideas of what they think Hawaii is supposed to be like. It’s fun for a couple of days and then it gets old. Here are a few places we love that are just outside of Waikiki, in the parts of Honolulu that locals actually go to

Kaimuki: A warning that this neighborhood isn’t very pretty but is chock full of great little gems. My sister lives around here, so we’ve done our fair share of exploring! Most of the things we love are food related. You can have breakfast, lunch, or dinner at Town (so delicious!), coffee at Coffee Talk, or dim sum at Happy Days. I adore the Sugarcane boutique. You can also drive up the road to Kahala Mall where there are more boutiques, a Whole Foods (if you want to stock up for your hotel/condo/cottage), and some good restaurants.

Hawaii Kai: Just past Kaimuki and Kahala is Hawaii Kai, home to beautiful beaches. If you like to snorkel, head to Hanauma Bay. You might even see some turtles there!

Local's Guide to Visiting Oahu

Chinatown: Eat lunch or dinner at The Pig and the Lady, visit the authentic lei stands (that locals actually go to!), and if you can, catch a show at the historic Hawaii Theatre.

Local's Guide to Visiting Oahu

The Windward Side: We always stay in Kailua, even though it’s not really near anyone we know, because it’s so beautiful. The drive in and out of the Windward side always makes us feel like we’re heading into Jurassic Park. If you’re in the market for accommodations, there are lots of good ones out here–usually $150 or less, with a kitchenette and free parking. This one has been our favorite. Here are some other things we love in this laid back area:

Ho’omaluhia Botanical GardensI’ll pause here to say that I’m not really a botanical gardens kind of person, but this place is so magical and breathtaking that we make an effort to go every time we’re in Hawaii. It’s tranquil and lush. There are lots of places to sit and enjoy the atmosphere, so it’s a great place to bring a picnic.

Valley of the TemplesWe like to go here because it’s a little like popping into some gorgeous part of Japan for an hour or so. You can ring the gong, enjoy the koi, visit the big Buddha, and take some incredible photos.

Lanikai Beach

Boots & Kimo’s and Cinnamon’s are both Kailua institutions for breakfast or brunch. You’ll need a nap after eating at either!



North Shore: You can drive from Kailua to the North Shore along Kamehameha Highway, which is very scenic. The route takes you along the perimeter of the island, through some VERY down home country towns. When we did it last week, we saw a bunch of signs that said things like, “Keep the country country!” Which probably sounds really southern, but actually means that they don’t want any strip malls on their beachfront properties.

Waimea Bay: Basically all you could ever hope for in a beach in Hawaii. I like to try to get there on the earlier side or else it can be difficult to find parking.

Hale’iwa Town: This is a little surf town and I just love it! If you only visit one of the places from this email, I think it should be Hale’iwa. It’s just so charming. We like Papoku’s for lunch (a real, Hawaii style plate lunch), Matsumoto’s for shave ice, and all of the little stores that line the streets.

Oh, now I’m homesick all over again!

P.S. Previous Oahu recommendations: Part 1 and Part 2

Travel Smarter, Not…Expensiver

I’m going to let you in on a secret: I almost didn’t write about going to Puerto Rico at all. I don’t want people to think we’re living some kind of luxurious lifestyle, when we really aren’t.

We’re lucky to be able to live comfortably — that fact was only made clearer this past weekend when the blizzard hit and we witnessed it from the centrally heated cocoon of our condo. But this trip to Puerto Rico is the result of a couple of weeks’ worth of research and price hunting. If you’re thinking of escaping the cold, it’s totally possible to have an amazing vacation on a budget. Here’s how we did it:

Don’t fall for the resorts. While it sounds great not to think about what you’re spending on food and drinks while you’re on vacation, the reality is that you’re paying for all of it and then some. It’s almost always a bad deal. We found a great hotel with a pool and four restaurants for about a third of the price of the nearby resorts — and on top of that, we have access to those same resorts because our hotel is a sister property. (What’s that? Cake? And we can eat it too???)

Read lots of reviews. The hotel and resort websites make everything look beautiful, but the reviews will tell you what’s behind it all. The one with the sleek pool may have terrible rooms or dangerous bathrooms. We almost booked one hotel, then read a handful of reviews that said the rooms smelled of mold.

Fly during the week. This is equivalent with buying fashion off season — the fewer people you’re competing with for the prices, the better. Avoid flying out on Fridays and returning on Sundays, when prices are bound to be more expensive because of commuters and weekenders. My favorite comparison tools are Kayak and Bing’s travel function. And in case you’re wondering, Bing didn’t sponsor this post (but thanks anyway, Bing!)

Search outside of packages. Sometimes packages are great deals. Other times, you’ll do a lot better booking the hotel and flight separately. This time, we got a much better deal by booking our flight through Jet Blue directly.

Look for specials. Hotels often have discounts for holidays and special occasions. If you don’t see one on the website, call and ask if they’re running any. We’ve gotten everything from free parking to 20% off to meal credits just by asking what deals the hotels have going on.

(And, yes, I know “expensiver” isn’t a word. But it should be.)

Have any travel tips of your own to share? Let’s hear ‘em!

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