If you’re looking for a good hike on Oahu, that’s relatively short with big views, you’re going to love the Lanikai Pillbox trail on the Windward side of the island. 

Oahu has a series of pillbox hikes (bunkers from WWII posted in various lookouts around the island) and the Lanikai Pillbox is definitely the most famous one. Views don’t get much better than this!

It’s a moderately challenging, but short trail with incredible panoramic views, and a bit of WWII history. 

If you’re the type to fill your vacation with incredible hikes, you definitely want to put this one on your list. But even if you’re not, this one is worth adding to your vacation itinerary. 

Seriously, if I was only going to do one hike on my trip to Oahu, I think this would be it. 

Here’s everything you need to know before you go:

Hiking the Lanikai Pillbox Trail on Oahu’s Windward Coast

The Lanikai Pillbox Trail is located above world famous Lanikai Beach on the Windward (East) side of Oahu. 

The trailhead is located in a residential neighborhood in Lanikai (off Ka’elepulu Drive) and there’s very minimal parking here so I would plan to park at Kailua Beach Park and walk up. It’s about a half mile walk from the beach parking lot. 

The trailhead is easy to find. It’s a pretty steep initial climb along a fenceline before you’ll find the ridge.

The trail is only about a mile round trip to the first pillbox and back, but you can walk further along the ridge to a second pillbox (about 1.5 miles round trip). 

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. Most people stop when they reach the first pillbox, but you can keep going if you want to see them all. 

I wouldn’t say this is a “hard” hike at all, but the trail is a lot less defined and cleared than Diamond Head so you have to do a bit of negotiating. 

Because the view faces east, some people like to go for sunrise, but you’ll definitely need headlamps if you go that route. 

After you finish the hike, there’s plenty to keep you busy along the Windward Coast for the rest of the day. Check out this post for my favorite things to do in the area. 

P.S. I travel to Hawaii multiple times a year, and let me tell you a secret…I do most of it for FREE using credit card points and miles. 

I have a somewhat intricate system that I’ve fine tuned over the years to maximize earning points and how I cash them in, but the short version is:

I use THIS Marriott Bonvoy Boundless card for free Marriott nights. The sign up bonus alone on this card will get you 3 (sometimes 5!) free nights at hotels in Hawaii like the Sheraton Maui, Royal Hawaiian (Oahu), Sheraton Kauai Coconut Beach Resort, and the Waikoloa Beach Marriott (Kona). 

And I use THIS Southwest Premier Rapid Rewards card for free flights on Southwest. The sign up bonus will get you at least one round trip flight to Hawaii (possibly two depending on where you’re flying from). 

The combo of these two cards will have you most of the way to a free trip to Hawaii right out of the gate. Again, you can sign up for the Marriott Bonvoy Boundless >> HERE and the Southwest Premier Rapid Rewards >> HERE
And if you’re really serious about getting into the travel hacking game, read this post for a more in depth look at how I maximize credit card points to book travel.

P.P.S. Here’s one more really important thing you need to know before your Hawaii trip…

You’ve got your airfare, hotel, rental car and your big activities booked, so you should be good to go, right? Wrong!

Travel is BOOMING in Hawaii and a lot of state and national parks have instituted reservation systems at some of the island’s most popular spots to help manage the crowds and make things a little more sustainable. 

That means that there are now over half a dozen sites (beaches, trailheads, etc.) that require advance reservations. And some sell out well before you arrive on the island so you really need to have some sort of a plan. 

I recently saw somebody in a Hawaii travel group post in a panic that they didn’t know they had to make reservations for things in advance…they thought they could just show up and “go with the flow.” I was tempted to say, well, “as long as the flow doesn’t take you somewhere that requires reservations, you can!” ; )

But I don’t want YOU to be that person, so I’ve pulled together a list of all the places you need to reserve entry in advance (plus all the details on booking windows, price, links, etc.) and a handful of popular tourist hotspots that book out really far in advance too. 
Get that info >> HERE