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Nicknamed "The Pineapple Isle," Lana'i is the 6th largest of the Hawaiian Islands and the smallest island accessible to the general public. A notable characteristic of the island is that 97% of the island is privately owned by Larry Elison, the founder of Oracle. This fact does not take away from the shear beauty of the island, great for anyone looking to get away from the crowds and simply do some exploring. Just know if you want to make the trip and stay in one of the few hotels, it will not be cheap!


I always tell my mainland friends who consider visiting Hawaii, to first do it (obviously), but also if you can afford it in the way of time and money, don't just see one island. See multiple. Because each island has it's own personality-- the people are different, the landscape is different, but they are all very beautiful in their own way.

After living here for almost 2 and a half years, I've been fortunate to be able to see 5 of the Hawaiian islands (including Oahu). I walked through the other worldly Haleakala Crater on Maui, saw the mesmerizing Waimea Canyon on Kauai, explored the famous Kalauapapa Lepur Colony on Moloka'i, and even hiked the highest peak in all of Hawaii on the Big Island. However, my Hawaii journey would feel incomplete if I didn't visit the last accessible island, Lana'i. When a free long weekend came around, I packed my bag, hopped on a plane with my friend Danielle, and took off, eager to explore my final island.

Our flight touched down at Lana'i Airport around 9am. If you've island hopped before, specifically to the Big 4 (Oahu, Kauai, Maui, Big Island), you know that you can get flights pretty much any time of day. This is not the case for Lanai. There are only about 5 flights a day and they only leave from Oahu. Just a helpful hint for planning purposes.

Our first stop for our trip, to get our rental car. I highly recommend getting a Jeep to maximize your exploring ability. We rented our jeep from Dollar, but there are many places to rent from on island. The most important thing about driving here is knowing which roads are open to vehicles. Some of the dirt roads on the island can get very muddy and soft, which would make the risk of getting stuck that much higher. This is one of the most common tragedies that can happen while exploring this little rock, so be careful!

Our first adventure-- hiking the beautiful Koloiki Ridge Trail, a short ridge hike, located just north of Lanai City.

The seclusion and beauty of this area were just amazing.

A gorgeous valley, with views of both Molokai and Maui. Only a few hours in and I'm already in awe of this place. (For more on this hike, check out my full writeup).

Despite the ease of Koloiki, we had worked up an appetite, so we decided it was time for lunch. We stopped in Lanai City, which is pretty much the only place to get food on the island, outside the hotel. Despite the name, this place definitely doesn't qualify as a city, it is a town. But it is very pleasant. Right in the middle of the town is Dole Park, named after non other than Dole Pineapples. It was a beautiful grassy area filled with massive Cooke trees. It makes for a great place for a picnic.

Which is exactly what Danielle and I did. We stopped at Richard's Market for some poke bowls and some "Buch," as Danielle always calls it. No matter what island I go to, the poke always amazes me. Fresh and flavorful, without masking too much of the delicious ahi taste. Not to mention, you get so much fish! Poke has begun sprouting up on the mainland in places like DC, NYC, and the west coast. The bowls are more customizable (think Chipotle), but you only get a few pieces of fish. And it's expensive! I think Hawaii poke is one of the greatest things ever, so everyone who eats fish should try it if you visit. But be careful, poke anywhere else will never taste as good.

Enough of my poke rant. It was time for us to make our way to where we would be staying for the night, the famous Four Seasons at Manele Bay. The drive out there was intriguing enough as we were surrounded by vast fields of flat land, allowing you to see all the way to the ocean. This section was very interesting as the road was lined with these large Cook Island Pines. It was if the trees were guiding us to paradise.

Because the Four Seasons is exactly what you picture when you think of paradise. I knew instantly this would be the nicest hotel I'd ever stayed in, and probably will be for a long time. Full service towels and water by the pool, SUPs and snorkel gear to borrow, comfy robes and Nespresso in the room, and even a toilet with a bidet. What more could you want?

And of course, it wouldn't be Hawaii if we weren't greeted with Leis. We even got some pineapple-guava juice as a bonus! I felt out of place with my sweaty hiking clothes in this stunning interior.

After we dropped our stuff off at the hotel, we decided to do a little pre-dinner sunset hike in order to burn off the many calories we were about to consume. Our destination was Pu'u Pehe, more commonly called "Sweetheart Rock", a beautiful rock formation located just off the coast. Getting there is very easy from the Four Seasons, simply walk across Hulopo'e Beach and you will hit the trail.

Hulopo'e beach, I might add, is a stunning beach. The sand is very soft and the waves crash sharply near the beach, creating that soothing ocean sound. You can also camp at this beach (it does require a permit), so if you are looking for a significantly lower budget way to experience this island, I recommend that.

There it is, Pu'u Pehe. There's a lot of beauty and history to this spot, which you can read more about in my separate post.

And it makes for an absolutely stunning sunset spot.

And drone spot, if you are into that sort of thing.

We ended our night with a luxurious dinner at the ONE FORTY, American Steak Hawaiian Seafood. I won't say how much it costs, I'm far too embarrassed to admit it. Let's just say I won't be going out to eat for about 6 months to recover from that expense. But it was amazing. Bellies full and a little alcohol buzz going, we retired to our beds, ready for the next day's adventure.

We began day 2 with a bang, waking up to catch the sunrise at Pu'u Pehe. The sunrise was just as spectacular as the sunset, as the sun rose between the two peaks of Maui.

And the morning light made for some great aerial photography. This photo helps captures the layout of this part of Lana'i. The iconic Pu'u Pehe, Hulopo'e Beach, the Four Seasons and the southern coastline, all in one shot.

We continued our active morning with a short stroll along the Fisherman's Trail, conveniently located on the other side of Hulopo'e Beach. It's a great little rocky coastal trail, that gives you a different perspective of the coastline, sea cliffs, and neighboring islands (full writeup here). I love how many activities there are in proximity to this luxurious hotel.

We took a quick morning dip and lounge by the pool following our hike. I am still in awe at how beautiful these views are from this hotel. I guess that's why it doesn't come cheap!

With our flight heading back to Oahu in the evening, we had to maximize the amount of time for activities. So we checked out of the hotel and made our way back towards Lana'i City. But first, we needed some calories. We stopped at the Blue Ginger Cafe, where I proceeded to order this Loco Moco. If you've never had one, it's a popular local fare, typically made of hamburger patty, a fried egg, and brown gravy, served over rice. I've had them before, and I wasn't crazy about it. But I will say this one was delicious. Besides, it was a ton of food! With that many calories, I won't have to eat for the rest of the week!

Bellies full, we began our drive up to the Northern Shore of Lana'i. Our destination was here, Shipwreck Beach. Its name comes from the numerous vessels that have wrecked here, due to the harsh tradewinds and swells (full story here). It provides an awesome beach walk giving you a gorgeous vantage point of Maui and Moloka'i.

But most importantly, a cool look at the famous YOGN-42 wreck. This photo makes getting shipwrecked look not so bad right?

As the sun began to lower, we knew our time on Lana'i was coming to an end. However, there was one more destination I wanted to hit, the Kaunolu fishing village. It was a favorite spot of King Kamehameha, a place he retreated to after conquering Maui, Lana'i, and Moloka'i. The journey out to this village is not at all easy. The road is extremely rocky and uneven with many ups and downs. I had never driven a road like this, not to mention we were cutting it close for our flight. Let's just hope we don't blow a tire or get stuck somewhere.

We made it down to the village with about 10 minutes to enjoy before we would have to jet up that rocky road to the airport. I hopped out of the car and sprinted along the trail to its terminus-- this lookout point, often called "Kehekili's Leap," where warriors would jump the 60 feet into the water below to prove their bravery.

With the water crashing below me, the sun beginning to set on the horizon, and the golden glow illuminating the beautiful cliffs, I felt a calm rush over me. Even though I could only enjoy it for a moment before sprinting back to the car, it was worth every second. Despite Lana'i being my final island, I still feel like I have so much left to explore. With the time I have left here, I will continue to do just that, so I can continue to unlock Hawaii's many secrets.

Enjoy this post? Leave a comment below!

Also Check Out:

- Go Hawaii's information about Lana'i


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