Avoid Tourist Crowds At Hawaii's Captivating 'Pineapple Isle' For A Romantic Getaway

Sometimes it seems like the world is so connected that finding a place to get away from it all is impossible — at least without spending days venturing via plane, train, automobile, and, who knows what else to reach some remote hideaway. But, there's a place in the US fitting that bill, and it's a reasonably easy-access destination. We're talking about the Hawaiian island of Lanai. Located about an hour by ferry from Maui, Lanai is a 140-square-mile island (about the size of Las Vegas) with a year-round population of about 3,200. The ferry also connects Maui to the island of Molokai, home to a pristine and uncrowded beach known for its vibrant sand.)

Approaching Lanai by ferry, you'll notice there are no high-rises lining the shore. In fact, there are only three hotels on the entire island. Two are luxury resorts operated by Four Seasons. The third, Hotel Lanai, is a six-room boutique hotel with a deep connection to the island's history.

Let's take a quick look back in time. Indigenous people began settling on Lanai as far back as the 13th century. By the late-18th century, the island boasted a thriving community of about 6,000. Things took a downturn for the local population in the late-19th and early 20th-centuries when outsiders became interested in developing the island for ranching and farming. In 1922, James Dole, founder of Dole Food Company, bought the bulk of the island for $1.1 million, with an eye toward creating the largest pineapple plantation in the world. At the height of its success, Dole Food Company employed a staff of 3,000 workers who produced about 75% of the world's pineapples. Citing rising costs, the company ceased operations on Lanai in 1992, but its legacy remains.

When Dole shuttered its business operations on Lanai, the company left behind more than 20,000 acres of pineapple fields and Lanai City, an entire infrastructure built to accommodate employees. Today, Lanai City remains the only official town on the island. The aforementioned Hotel Lanai, located in Lanai City, was originally Dole Club House, a purpose-built facility constructed to house the company's management-level employees and James Dole's personal friends and associates. Built in 1924, the wood-framed structure reopened in the 1950s as the island's only hotel — a title it held until 1991 when the Manele Bay Hotel (Four Seasons Resort Lanai since 2005) opened on the island's south coast. Hotel Lanai underwent a complete renovation in 2018. Rates vary by season, but hover around $500 per night, about 75% less than the average per-night rate at Four Seasons Resort Lanai.

Lanai City is about as far from being an actual city as it can get, village is more accurate. Located near the island's center at an elevation of about 1,700 feet above sea level, average temperature in the six-block commercial center tends to be cooler than the coast. The town centers on Dole Park, a green oasis surrounded by interesting shops and restaurants.

Take a stroll through Lanai Art Center to check works by local artists, encompassing everything from wood carvings and textile art to paintings and artisan-made jewelry. The Local Gentry is a boutique clothing store, and the International Food and Clothing Center, an old-fashioned shopping emporium, is the go-to source for anything from wine and beer to fishing gear. Grab a bite at Blue Ginger Cafe or Ganotisiʻs Pacific Rim Cuisine, then head over to Lānaʻi Culture & Heritage Center for help planning further activities.

Lanai may be small, but that doesn't mean it's lacking in things to do. For a romance-themed itinerary, plan a short hike to Pu'upehe. Also known as Sweetheart Rock, the 80-foot natural rock formation juts dramatically from the surf about 150 feet off the island's south coast between Mānele Bay and Hulopoʻe Bay (one of the most beautiful US beaches for snorkeling).

According to local legend, the moniker comes from a tale of star-crossed lovers, a warrior and a maiden. When the warrior discovered the maiden had drowned near the rock, he climbed to the top and threw himself to his death in the sea below. The oft-photographed landmark makes a stunning setting for photographs, especially at sunset. Another landscape with ties to local legends, Keahiakawelo, also known as Garden of the Gods, is about 45 minutes from Lanai City. As the story goes, the windswept expanse punctuated by boulders and rock towers is the result of a fiery standoff between mythical island leaders.

Early risers may want to plan an excursion to Koloiki Ridge. The moderate 4.5-mile hike reveals panoramic vistas of Molokai and Maui and is particularly stunning at sunrise. If lounging the day away on a secluded beach is your idea of heaven, Polihua Beach may be right up your alley. It takes a bit of effort to get to the north shore sanctuary — probably why it's rarely crowded — but the payoff is basking in the sun on a pristine two-mile stretch of the Lanai coast. Even more indulgent, book a spa day at Four Seasons Sensei Lanai. Ranked among the most highly rated hotels in America with a spa, it's located in Lanai's forested uplands.

If a spa day at Four Seasons Sensei Lanai sounds intriguing, consider a multi-day couple's spa retreat. The secluded adults-only sanctuary will curate a personalized experience based on your wellness priorities. Lanai also boasts two golf courses. Cavendish Golf Course in Lanai City is a nine-hole, par-36 course constructed in 1947 as a recreational outlet for Dole Food Company's workers. The free-to-play course — that's right, free — is maintained by a group of local golf enthusiasts.

The other option, Mānele Golf Course, is a Jack Nicklaus-designed, 18-hole, par-72 course built on lava outcroppings overlooking Hulopoe Bay. Known for its stunning vistas, the Four Seasons Resorts-affiliated golf course is only open to guests in residence at one of the island's two Four Seasons Resorts. Another Four Seasons diversion, Lanai Adventure Park is open to the general public on specific days each week. The complex gets rave reviews for its roster of activities, including ziplining over the lush, mid-island valley of Kaiholena Gulch, navigating an aerial adventure tower, and testing your mettle on a spine-tingling challenge course.

And then there's the ocean. The crystal-clear waters surrounding Lanai are ideal for snorkeling. Book a snorkeling excursion and you may even see sea turtles and spinner dolphins frolicking in the surf. Planning to frolick in the surf yourself? Head to Kaiolohia on the island's north shore (also known as Shipwreck Beach). Surfers hail the spot for its consistent and reliable waves year-round. Headed the other way, Hulopoe Bay on the island's south shore is an easy-access surf spot popular in summer for reliable swells. In addition to ferry service from surrounding islands, inter-island flights connect Maui Kahului Airport (OGG), about 35 minutes, and Honolulu's Daniel K. Inouye International Airport (HNL), about 50 minutes, to Lanai Airport (LNY).