The Best Small Town In Hawaii For A 3-Day Weekend
While most will settle on a Hawaiian weekend getaway within Maui’s beaches or on Oahu’s dynamic vibe, they miss what is quietly extraordinary on the island of Lanai, where a plantation town called Lanai City exists some 1,600 feet up amidst Cook pines. This is no ordinary Hawaiian destination. You won't be overwhelmed by tourist traps and shops catering to visitor traffic. Lanai City offers something increasingly rare in Hawaii: a small-town experience that remains devoted to its incredible landscapes amid resort development.
The Town That Dole Built
Lanai City exists because James Dole purchased Lanai Island in 1922 and turned it into the world's largest pineapple plantation. The city is a company town, organized around a grid system centered on Dole Park, a square bounded by towering Norfolk pines. The date of the community's original development seems pulled right from the earlier half of the 1900s, as evidenced by the architecture.
The closing down of pineapple operations in 1992 could have left Lanai a ghost town. Still, somehow it has survived between two large resort properties, where people maintain their deep heritage by speaking Tagalog and operating from several mom-and-pop storefronts along Seventh Street.
Where to Stay Without Breaking the Bank
The Hotel Lanai is directly on the main street and provides everything you need to make a long weekend work. Originally erected in 1923 to provide housing for pineapple executives on vacation, this historic gem boasts ten rooms that evoke the plantation style, complete with wood floors, patchwork bed coverings, and the type of screen lanai you actually want to sit out on in the evening. The prices are reasonable compared to other options, and you can't beat being a thirty-second walk to the best restaurant on the island, also on the property.
If you are looking to splurge but do not want to pay resort prices, the Four Seasons Resort Lanai offers lodge-style luxury on the outskirts of town. The resort goes big on plantation-style décor with its great room highlighting stone fireplaces and oversized leather furnishings. You get Four Seasons’ legendary service while still easily accessing the town on foot.
Eating Well in a Very Small Place
The Lanai City Grill, located at the Hotel Lanai, packs a big punch. They are led by Chef Christian Page, whose cooking, honoring Hawaiian regional cuisine, is done effortlessly. The fish arrives according to what arrived on the boats that day. Their signature dish is the grilled ahi with wasabi butter.
Blue Ginger Cafe serves breakfast and lunch with a level of efficiency honed by serving bustling locals. The restaurant is open early, offers huge portions for less than $15, and boasts a burger worth the trip. The décor is no-frills, but this is a place that serves what you need after hiking or hitting the beach.
The Landmark That Holds It All Together
Dole Park isn't historic in the technical sense of commemorating a battle or a signing, but it is just as significant. The park encompasses most of downtown, with its towering Norfolk and Cook pines that cast enough shade to chill the air. Dole Park is what keeps this town together. This is where you can find locals walking their dogs early, children playing soccer in the afternoons, and blankets spread out on the grass where families gather to have picnics in the evenings.
Natural Wonders within Twenty Minutes of Town
The Munro Trail traverses across the island’s highlands, ascending to Lanaihale, which is the highest peak on this island at 3,370 feet. The trail offers a clear view of the other five islands in Hawaii in the morning. The trail is approximately 13 miles long and passes through eucalyptus and pine trees that resemble those found in Tasmania and Northern California.
A trip to the Garden of the Gods provides you with this island’s most surreal natural environment with very little exertion on your part. Daylight hours are best spent here because you can watch the rocks change colors to darker shades of orange and red when the sun sets. It is worth hanging out to see it at least once.
The Festival That Actually Matters
The Pineapple Festival takes place on the July 4th weekend annually at Lanai City, which rings a bit cheesy until one understands it is actually the island’s biggest community event. The festival floods Dole Park with live entertainment, food stands, craft vendors, and a pineapple-eating contest that contestants actually train for. However, what makes this festival special is how it serves as a kind of homecoming celebration for those plantation islanders who left to find work on mainland planes. The festival promotes the heritage of the entire region.
Why Three Days Hits Different Here
Lanai City is ideal for a long weekend because it doesn’t fill up every minute of every hour with activities. A hiker can hike Munro Trail one day, read a book at Dole Park during the next couple of hours, and dine well for supper, and that’s enough to make it a successful day. The next day could involve traveling to Hulopoe Beach to swim and snorkel, then returning to town for lunch at Blue Ginger. There is no FOMO because there aren't 17 restaurants you need to visit or 12 beaches you need to go to. These restrictions can actually become liberating factors. You find yourself moving at a slower pace because there is no need to hurry somewhere, and this change in tempo is more relaxing than any massage.
