Short Oahu Escape
February 3, 2016 11:43 AM   Subscribe

Need help with itinerary!

I've been wanting to get away lately so I treated myself to a brief trip to Oahu in early March. I will be there for 3 nights, flying in on a Monday at 2:10 PM and departing Thurs at 3:00 PM (probably would have been better to stay longer, but that was the only free period I had). I know that that's not a very long time, so I need some help figuring out where I should stay and what to see/when to see it.

I'm definitely interested in:
Diamond Head Hike
Pearl Harbor (got USS Arizona Memorial reservations for 9 am on Thurs)
Snorkeling in Hanauma Bay
Checking out Kailua/Lanikai beaches
North shore
Lanai lookout
Koko Crater Hike
Laniakea Beach (turtles!)
Malasadas at Leonards
Getting good poke
Getting great Spam musubi
Good food in general


1) Where should I stay? I know most people would say Waikiki but I've also been grieving a recent death in the family and I'm don't know if I'm up for a super touristy, hustle-y-bustle-y atmosphere. I was thinking of something more quiet, maybe finding a legal rental close to Kailua beach, but is there anywhere else I should be looking? I will be renting a car.

2) How should I schedule things? I was thinking that I
Day 1: Fly in, eat somewhere, do some beach exploring/catch the sunset
Day 2: Do an early morning hike (it seems important to be super early to a lot of the hikes, to beat crowds), then a driving tour up through the North Shore
Day 3: Early morning Diamond Head hike, then over to Hanauma Bay for snorkeling. No idea what to do the rest of the day yet.
Day 4: Early over to Pearl Harbor (byy 8 AM), explore, get lunch, head to airport for 3 PM flight

Any suggestions/alterations? I wouldn't mind exploring Waikiki more but I heard traffic/parking is truly terrible (though I'm used to LA, so maybe not that different?)

3) I'm traveling as a solo female. I am generally an alert and mindful traveler, but are there any areas I should be extra careful? I heard that there can be quite a few car break-ins

This will be my first time on any Hawaiian island!
posted by sprezzy to Travel & Transportation around O‘ahu, HI (6 answers total) 3 users marked this as a favorite
I found a decent place via AirBnB that was near Waikiki (a couple miles) but not touristy at all. PM me if you want details.

If you want to explore the Waikiki beaches by foot, you can often find free parking in the lot off Monsararrat Ave. south of the Honolulu Zoo, in Kapiolani Regional Park. I was there the first week in January and was able to park there, no problem. Car break-ins are relatively common; good practice is to never leave anything that might look valuable visible in your car.

March is going to be the shoulder season, but my impression is that it really picks up in mid-March, so you may beat crowds. My experience driving in January was that in Honolulu you had to allow lots of time if you were driving anywhere in rush hour. Elsewhere, things are unpredictable. The traffic alerts in Apple's Maps app on my iPhone were pretty reliable.

If you like museums, consider a visit to the Bishop Museum. A little gem is the Japanese garden at the East-West Center, on the campus of the University of Hawai'i at Manoa.

And if time allows, there's a very nice hike at Ka'ena Point, on the far western end of the island (but not that long a drive from Honolulu). It's about 2.5 miles from the parking lot to the point, most of it on an old two-track road. Laysan albatrosses and other seabirds nest at the point; there is a fence with a double gate (like an airlock) that keeps dogs out. There's also a colony of monk seals at the point, and during whale migration season you can often see humpbacks in the ocean. My wife and I did that on our last full day on O'ahu and it was the highlight of our stay on the island. It's popular enough that it should be reasonably safe for a solo hiker, and there was AT&T cell service all the way to the point.
posted by brianogilvie at 12:01 PM on February 3, 2016 [1 favorite]

I got pretty good answers to my October question about a long weekend in Oahu, if you haven't seen it.
posted by charmedimsure at 12:43 PM on February 3, 2016

We were on Oahu in January. We stayed on the far end of Waikiki at the New Otani Kaimana hotel. It's a Japanese chain. Small sized modest rooms, but it's pretty peaceful. They have a good restaurant, excellent customer service, free beach towels and mats, and not super expensive room rates. And it's on a nice beach frequented by locals. This area is more quiet because it's separated from the rest of Waikiki by a large park (mentioned above). It's close to the Honolulu Zoo as well. They do charge for valet parking, but some people do get street parking.

You're also within a short walk of restaurants on Kapahulu Ave: Ono Seafood, Ono Hawaiian Food, Haili's Hawaiian Food, Rainbow Drive-In, Hawaii's Favorite Kitchens (Poke Stop/Shimazu Store), Leonard's Bakery, Da Hawaiian Poke Company, Side Street Inn, and more.

And there's more good places to eat on Montserrat Ave: Bogart's, Pioneer Saloon, Montserrat Ave Shave Ice, Diamond Head Grill and Market, etc. I also loved having the view of Diamond Head right there.

Another area at the other end of Waikiki is Ala Moana, as the beach there is much more chill than Waikiki. Even though you're by a mall, it's a pretty good food neighborhood (MW is basically right there, there's Shirokiya in the mall, we also loved a tiny mom and pop poke joint in the area called Fresh Ahi off the Boat - and they're open fairly late for a poke place). Ala Moana Hotel may work for you. Or one of the hotels fronting the marina. Definitely quieter on that side.

If you're going to be out and about a lot of the time, and going for only 3 days, I am not sure a rental is going to make sense for you given that there's a cleaning fee and many have minimum stay requirements. And I think you're aware of the huge illegal rentals problem on Oahu (esp. Kailua) from what you've written?

(For those not aware, Oahu has a ton of illegal rentals in residential neighborhoods operating without the proper non-conforming use certificate with the letters TVU or BB. There are only 789 active TVUs and 33 active BB certificates on all of Oahu as of November 2014. Many of these are in/near Waikiki anyway. Renting an illegal rental only contributes to the affordable housing shortage in Hawaii. Oahu is facing a projected 26,000 home shortage in the next decade! So your cool non-touristy Airbnb unit is likely pushing out a full time resident (has happened to someone I know). Remember that if you can find a rental online, so can government officials.)

Monday: Pick up your rental car and drive to your accommodations. If hungry, many people stop at Nico's Pier 38 along the way. You probably won't get checked in until around 3pm anyway. I would drive up to Tantalus/Roundtop Drive and admire the scenic view for a little while. Then drive back down and have drinks and appetizers at House without a Key in Waikiki this night. It's serene and quintessential Waikiki - not hustle and bustle. Live music, hula, and sunset, all in a beautiful setting. Dependent upon how long your travel day way and adjustment to the time change, you'll probably crash early this night. Most likely, your body will wake you up on "home" time the next day.

Tuesday: A circle self-driving tour makes a lot of sense. I might skip the hiking on this day because there are a lot of sights you'll want to linger at, especially on the north shore! You'll want the full day available to you. You have some of my personal must-sees missing from your list above...

Note: hiking in the early morning is not only to beat the crowds, but to also hike before it gets too hot!

Grab a quick breakfast & start at the Spitting Cave of Portlock (mind the steep trail down). Then make your way to Lanai Lookout and Halona Blowhole, driving past Hanauma Bay. Drive to Makapu'u Lookout and see Rabbit Island. Then stop at Lanikai Beach (parking can be difficult on these residential block, and definitely don't leave anything of value in the car near Lanikai) and Kailua Beach. Then head off to Kualoa Regional Park and see Chinaman's Hat (a nice place to sit and think).

Now go up to the North Shore, where you'll see Laie Point (make sure you experience both sides of the view - gorgeous!), Sunset Beach, Banzai Pipeline, Waimea Bay Beach, and Haleiwa town. Grab shave ice at Matsumoto's. When we were there we saw no turtles at Laniakea Beach but I've heard that Haleiwa Ali'i beach has them. So keep that in mind. This will be a very long day. Grab something casual for dinner back in "town" (perhaps at one of the places on Kapahulu Ave).

During our self driving tour, the Spitting Cave was my husband's favorite stop, whereas my favorites were Kualoa Regional Park and Laie Point. I didn't see those on your list! :)

For lunch on this day, you could stop after Lanikai and Kailua Beach and grab some poke from Fresh Catch or Hibachi, both somewhat nearby. Or if you're not hungry, keep going until you hit the North Shore, and grab some poke and spam musubi from Kahuku Superette (so good!). Or one of the famous Kahuku shrimp trucks.

Wednesday: Your plan seems solid. Hike Diamond Head as early as possible. Then get to Hanauma Bay early before the parking lot fills (around 9am/9:30am). When it's closed, it's closed!

Afterwards, treat yourself to lunch at Helena's Hawaiian Food (do expect a wait, and definitely get the pipikaula ribs and squid luau) and then get some shave ice at Waiola shave ice (make sure to go to the original on Waiola Street, as the one on Kapahulu is not as good). Relax at the beach, take a nap. Maybe back track to a place you didn't spend enough time at on Tuesday. Or just chill and do nothing.

Thursday: Your plan seems solid. 8am Pearl Harbor, lunch (perhaps The Alley at Aiea Bowl), airport.

I'm not sure what airline you're flying, but we flew out of HNL on Hawaiian Airlines last month, and there was a bit of confusion at the check in area because many people are not used to self-tagging their luggage via a kiosk interface. Also the security line looked very, very long (are you PreCheck?). So add extra time for that.
posted by kathryn at 6:52 PM on February 3, 2016 [3 favorites]

Response by poster: Wow, thanks, guys! The answers were few but talk about quality over quantity :)

brianogilvie Thank you for the parking tips, as well as that hike suggested at the end (I hadn't heard of it yet!). I might just PM you about that Airbnb, since it comes recommended!

charmedimsure Thanks for linking! I had seen that before but it was good to look through it again!

kathryn Thanks so much for the thoughtful response! I am pretty acquainted with the illegal rental issue, yes, particularly because I lurk on the tripadvisor forum and they are quite vocal about that there--and I think I've seen you posting there, if you are the same kathryn in nyc. I really appreciated the day-by-day review, and the dining/sightseeing spots. Also huge thanks for the note about self-tagging, as I am flying Hawaiian for the first time and didn't know anything about that.

You guys are the best!
posted by sprezzy at 8:36 PM on February 3, 2016

If you are driving, do be aware that the North Shore (and Hawaii in general) has issues with theft. Keep your car keys on you at all times, or use a locker if you're going snorkeling. Don't leave anything in plain sight inside your car (get s car with a trunk, not a hatchback), because (after our rental car and all of stuff in it got stolen), locals we talked to were all too eager to share their stories of car windows getting smashed in and such.

Hawaii is a wonderful place, and we've been back several times since the time when our stuff was stolen (mostly because I was dumb), but it's not without some risks.
posted by Ghidorah at 3:15 AM on February 4, 2016

You're welcome! Definitely use your street smarts and common sense while traveling. And don't ever leave valuables in the rental car.

Even a car with a trunk won't necessarily you because it's so easy to pop the trunk after breaking in. Always bring any computers, tablets, cameras, cash, jewelry, watches, wallets, etc. with you when you else away from the rental car. And don't open the trunk, and walk away from the car, as you'll never know who else is watching. Even "paradise" has bad apples.

Have a great time!
posted by kathryn at 6:16 AM on February 4, 2016

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