My older brother has been visiting since August 12, and one of the activities we planned during his stay was a visit to Lanai. So, this past Sunday, August 15, we traveled to the smallest inhabited island available to travelers. Here was our experience.
About Lanai
It’s known as Hawaii’s “Most Secluded Island” and “The Pineapple Island” as it once hosted the world’s largest pineapple plantation. With only 5,000 residents, most of whom live in Lanai City, Lanai is an off-the-beaten-path destination.
How to Get to Lanai
Arriving at Lanai Airport
A ferry runs between Maui and Lanai, but to reach Lanai from Oahu, you must fly. So, we booked flights on Mokulele Airlines, which flies out of Terminal 3 at Daniel K. Inouye International Airport (HNL).
On Sunday morning, I made avocado toast for us to eat before heading to the airport, and we drove to the airport for the flight. We arrived early because I hadn’t yet been to Terminal 3. I wasn’t sure what the parking situation would be. To my delight, there was parking about 12 yards from the tarmac, and we would be able to walk up to the small counter from the car and over to where the plane was without any issue.
Our flight took off at 7:40 AM and landed at 8:25 AM. We flew on a small propeller plane that sat eight people. During this time, we saw numerous rainbows, and Jake said he saw another small plane in the sky that “made him think of WWII.”
Arriving in Lanai
Once we landed, I texted a driver that I had coordinated with the day before. We had decided against renting a car. Due to the limited number of rental cars on the island, any car I found was around $250. It didn’t seem worth it because there was a shuttle service for $10/person that could take us to everything we wanted to see. Throughout the day, we spent $40 total on this taxi service called Rabaca’s Limousine and were able to walk everywhere else.
Initially, we intended to go straight to the Four Seasons Resort to begin a hike I had found called Fisherman’s Trail. However, we first drove into Lanai City to drop off some other passengers who had taken Rabaca’s shuttle with us. Then, the driver asked if we could wait until 10 AM to go down to the Four Seasons as he had another ride to do at that time from Lanai City.
We were thrilled. We hadn’t originally intended to visit Lanai City because it was a bit out of the way of our itinerary, and we didn’t think there was enough to see/do to make the additional trip and expense worth it. However, because we were doing the driver a favor, he didn’t charge us anything additional, and we were able to see an additional part of the island.
Lanai City
It was early on Sunday morning when we saw Lanai City, so I don’t think it was indicative of how busy it could get (even for a small town). That said, we enjoyed walking around the town and stopped at Richard’s Market, which may just be my favorite grocery store in the entire world. It was lively and well-stocked. It had fun music playing, and it looked like the ideal place to go grocery shopping on a Saturday morning. I had gotten some peanut M&Ms out of a vending machine at the airport, and Jake bought a pack to match mine at Richard’s.
Visiting Richard’s Market
We then walked across Dole Park to a local coffee shop that was absolutely packed. I got a mango juice, and Jake enjoyed some black coffee. We walked up and down the streets checking out the school, post office, DMV, restaurants, and Catholic Church. While not much was open, it was a great opportunity to envision what the tiny city could be like during busier times of the week/year.
Walking through Dole Park to get coffee
Checking out the restaurants around town
The Four Seasons Lanai
We grabbed the shuttle when it was 10 AM to get down to the Four Seasons. The Four Seasons Lanai is one of only three places to stay on the island, and it comes with a hefty price tag (about $2,500 per night). And it was nice…but was it that nice? I’m not sure…maybe they’ll #sponsor a stay for me there one day, so I can find out.
Once there, we followed the path down to the beach to locate Fisherman’s Trail. It’s a coastline trail bordered by the Four Seasons golf course. While it was only about 3.5 miles out and back, it felt longer to me as we hiked it. By the end, I was ready to head back. The sun was beating down on us, and we ended up sunburned and sweaty from this hike. Fortunately, one of the highlights was procuring golf balls that had been hit off the course as souvenirs.
Based on the lack of people on the trail and the lack of signage, both Jake and I agreed that the trail wasn’t common knowledge. If you asked Four Seasons staff members about it, they would direct you to the right spot, but we doubted they were offering up that information. It was an absolutely gorgeous view from a hiker’s perspective, but for golfers, it had to have been awkward watching some sweaty tourists walking along the coastline from the course. Thus, we thought leaving the trail in place was probably a requirement for the hotel, but as a result, they didn’t promote the trail to their guests.
Jake asked how I found the trail, and it had just been a Google Maps find. I had zoomed in on Lanai and clicked around on different icons to see what there may be to do in the area, but I certainly hadn’t found it on any “must do/see” list.
Hiking Fisherman’s Trail
Eating Lunch at Views
Looking to cluster our activities in one spot, I had come up with the idea to grab lunch at the Four Seasons following the hike. A few days before our trip to Lanai, we had made reservations at Views, which was the only restaurant on the property that allowed non-guests. It was intended as dining for golfers, and it fit our needs perfectly because we were in fairly casual clothing.
As the restaurant was closer to the golf course than the main hotel, we weren’t sure how to get there. After our hike, we returned to the front desk and let them know the dilemma. We were directed to the bellhop station where they called one of the resort cars — a Tesla. This was my first time riding in a Tesla, and the ride took all but two minutes. Unfortunately, an employee found out we were not guests (oops!) and told us we wouldn’t be able to get a ride back down to the hotel.
Unperturbed, we proceeded to eat lunch at the Views with an amazing outlook of the water. The food was tasty, and we were recharged for the afternoon. Given our lack of a ride, we walked down the hill back to the Four Seasons to Hulopo’e Beach Park, which took about 30 minutes.
Drinking lemonade at Views
Relaxing at Hulopo’e Beach Park
Hulopo’e Beach Park is the only beach park on the island, and as all shorelines in Hawaii are public, this beach is used by the Four Seasons as well as locals. We crossed the beach park to walk out to Sweetheart Rock. We then retired to the beach for about an hour before we had to grab a ride back to the airport.
Visiting Sweetheart Rock
Originally, we coordinated with Rabaca’s to get picked up at the boat harbor so we could go back to the airport in time for our 5:55 flight. However, during this time, we saw a family from Austin that we had met during one of our other rides in the shuttle that day. They worked it out so that we could all get picked up from the beach park at a suitable time.
The family had two children, ages 7 and 8. During the car ride back to the airport, Jake and I enjoyed some avid conversation with the children. The daughter even gave us some classic lines that we’ve referenced many times since, “I love the Ritz,” and “My dad’s business partner works with Elon Musk.”
Kids…they say the darndest things.
Final Thoughts
We landed back in Honolulu around 6:30 PM, and I ordered Neapolitan pizza for us to pick up on the way home from Brick Fire Tavern. On the way home, Jake discovered his love of Taylor Swift’s Lover album. (Seriously, he’d been missing out for that long!)
Overall, Lanai is a perfect day trip. If you’re looking for a day packed full of adventure, you’re probably looking in the wrong place, but the island had plenty to explore in the time we had, and we even had some downtime to nap and swim at the beach toward the end. If I were to do it all over again (and Jake agrees), taking the ferry from Maui probably makes more sense than flying from Oahu or staying overnight on the island. It’s the cheaper alternative to both. Happy travels!
Check out other items on my Hawaii bucket list.