Rekindling a Romance With Maui’s Island Neighbor, Lanai

Lanai Four Seasons Dock

A text popped up on my phone before taking off at SFO, “You’ll meet your guide at the airport for your connection to Lanai Air.” Nice, I thought, as I daydreamed of the deep blues and glorious greens of my future. An hour later, due to various shades of gray of SFO, my flight was delayed. Ugh, I thought, as my cortisone levels shot up. I can’t miss my connection.

As soon as we touched down in Honolulu, I texted my greeter. “I’m coming through — O.J. Style!” Her reply was simple, “Mahalo, see you soon.” Turns out my stress was unnecessary, Lanai Air is a private airline, consisting of Pilatus PC-12, Swiss turboprops that run as needed. I was scooped up in the main terminal along with another passenger, and we were driven to the hangar in a plush SUV. Then I had to explain to our 20-something greeter that O.J. Simpson was in a TV commercial where he ran through the airport jumping suitcases like hurdles on a track field. She smiled politely. Upon arrival at the large Lanai Air private terminal, another greeter handed me a mini bag of Skinny Pop and a chilled Pellegrino — cortisone decreased.

Flying Lanai Air, which is included in the Four Seasons room rate, means you skip going into the Lanai Airport, and instead a luxury car awaits your arrival at the tarmac. Traveling from another island via air or ferry is an option on your own dime.

This was my second visit to the property. The first was immediately after Larry Ellison famously purchased 99 percent of the island, and selfishly, I was hoping this acquisition would bring the America’s Cup to the Hawaiian Islands. (It hasn’t yet). Back then I met Kepa Mala, who was heading up the newly created Pulama Lanai. This land and resource management company was set up to implement goodwill improvements around the island, such as maintaining trails, managing deer population through their hunting program, working with FDA to certify venison for sale at hotels and protect endangered species on the island.

Nearly ten years later I was curious to see how the island had evolved. Besides my favorite family-run poke spot being gone, everything else felt like positive changes. Pulama had rebuilt the public swimming pool, fixed up the movie theater, updated Lanai City Bar & Grill Inn and Richards, the grocery store. I also noticed some new housing near the upcountry property, now called Sensei Lanai, A Four Seasons Resort, but otherwise, the quaint town centered around a large square felt as mellow as I remembered.

While the former Koele Lodge had always been a popular destination for locals who enjoyed the cool air and bountiful gardens, Sensei Lanai is now a 24-acre adults only sanctuary, which has become increasingly popular for couples who want to get back on track (physically and emotionally). With Larry Ellison at the helm, the wellness offerings are the latest and greatest combination of eastern and western modalities. A trained team of practitioners offer sessions on mindset, fitness, nutrition and yoga. Besides the spa treatments, guests can also partake in golf, tennis, hiking, archery, sailing and horseback riding. The half of the upcountry golf course has become a small 18-hole complimentary putting course, and the Lanai Adventure Park, which includes a multi-element aerial adventure course, large zipline and a private challenge course experience, where couples can partake in programs including reframing resistance, communication through challenge and building effective relationships.

Another noticeable addition to both properties is the world-class art work on display throughout both. Aptly, there is a tour dedicated to the Sensei collection, including names like Fernando Botero, Marc Quinn and Urs Fisher — my favorite was the two giant heads by Jaume Plensa. I had just seen Plensa’s 80-foot Water’s Soul on the Hudson, which seems to be shushing NYC, so being able to just walk up to his 30-foot Talaia in the tropical garden setting felt surreal.

There are a handful of new offerings at the beachfront Four Seasons Resort Lanai, including an open-air concert pavilion and a 40-inch telescope housed in a two-story domed structure where guests are guided through the stars to learn about Hawaiian celestial lore. The newly opened Cultural Garden is inspired by a kauhale, or kitchen garden, where one can learn about native plants integral for cooking, construction and well-being in Hawaiian daily life and can join in crafts classes. However, what I love most about this property has been here since the beginning: the location just above idyllic Manele Bay with access to the ocean.

Speaking of the ocean, Lāna’i is surrounded by a marine preserve, which means snorkeling and scuba will not disappoint. Our group opted for a sunset cruise on a catamaran, which for Instagrammers offers the absolute best golden hour photo ops. As I was sipping a glass of bubbly, I learned that there are three commonly seen species of dolphin off of Lāna’i; Hawaiian spinner dolphins, Pantropical spotted dolphins and common bottlenose. On our sail, we ran into a pod of over 200 spinners who acted like they were as happy to see us as we were to see them. Captain Kristin Belew, who is also a scuba instructor and marine naturalist, filled us in on dolphin trivia.

Why do they spin? Researchers do not have a definitive answer and the only other probable theory is that they jump and spin for some sort of communication purpose. Belew likes to say, “Because
they can and because it is fun!” During the peak whale season (mid-January to early March) she says, “We often see whales on every trip and we offer specific whale watching trips to find, watch and listen to the humpback whales.”

The most interesting thing she’s seen was actually under the sea, where she officiated an underwater wedding at one of the island’s famous dive sites called First Cathedral. “It is a beautiful site,” she recalls. “It features a lava chamber where a giant shaft of light beams down through the ceiling and light also shines through a series of small holes in the back wall which results in a stained glass effect.”
As our boat eased back into the dock, the sun was setting and our hearts were full from excessive dolphin sightings.

The evening had just begun, as we had dinner plans at Nobu Lanai, followed by stargazing. Just another day in paradise.

Romance Across the Islands

Looking for romance on the islands? We’ve curated a list of the top spots on each island.


Outrigger Reef Resort 

After a multi year, multi million dollar refresh, this oceanfront romance, popular for vowel renewals as well as first time nuptials is the darling of the Waikiki Beach featuring an expansive Monkey Pod restaurant right above the beach, pool, cabanas, legendary live music nightly at Kani Ka Pila Grille.

Pro Tip: Upgrade to the Voyager 47 Club access, for perks including happy hour overlooking the beach at sunset.  

Four Seasons Oahu Resort at Ko Olina

This expansive resort inside the upscale Ko Olina enclave west of Honolulu — known for calm, sandy lagoons and a championship golf course — boasts tranquil rooms, casual-elegant dining (including Mina’s Fish House), oceanfront pools, a sprawling spa, unique cultural activities and exclusive excursions.

Pro Tip: Book a suite that comes with a private oceanfront luxury cabana, or a couples’ massage in one of the spa hale (open-air huts). Sunsets on this west-facing resort are guaranteed to dazzle, too.

Turtle Bay Resort

Set on five miles of beach, the 850-acre Turtle Bay Resort is a natural playground on Oahu’s North Shore, just 45 minutes away from Honolulu.

Pro Tip: For more discreet lodgings, book one of the Ocean Villas, which have access to their own pool and courtyard steps from Kuilima Cove. Couples should also check out the spa’s 2.5-hour romance package, including a coconut lava shell massage and pedicure.


Hotel Wailea

This adults-only hotel features 72 one-bedroom suites designed to evoke the ultimate island-style pied-à-terre, spread across 15 acres on a secluded hilltop with sweeping views. Each one-bedroom suite has a separate living area, luxury linens, deep soaking tubs, kitchenettes and private lanais. Pro Tip: Couples can reserve the ultra-discreet Treehouse, nestled in mango trees with an ocean view, for a private, seven-course meal with wine pairings.

Hana-Maui Resort by Hyatt

Long known as the Hotel Hana-Maui, this serene enclave in remote East Maui has changed owners and management several times in recent years. Now part of Hyatt’s Destination Hotels brand, the 66-acre resort has maintained its romantic air of seclusion, offering 74 conterooms and suites, including airy oceanfront bungalows with dazzling ocean views and subtle island-inspired decor. Pro Tip: Opt for an Oceanfront bungalow with a Jacuzzi on their decks, ideal for warming up on a cooler misty evening. 

Montage Kapalua Bay

Starting at 1,250 square feet, its spacious one-, two- and three-bedroom units were built as residences with top-name appliances in full kitchens and deep soaking tubs and separate showers in marble-lined bathrooms.

Pro Tip: Opt for a coconut milk bath in a stone tub outdoors with a massage in the roomy outdoor hale (thatched hut).

Hawaii Island 

Mauna Lani, an Auberge Resort

Two beautiful new pools — one just for adults — beckon by a beach renowned for sea turtle sightings. Rooms have an understated but chic decor, while the soaring lobby spaces have become inviting, open-air living rooms infused with tropical greenery.

Pro Tip: After a “farm to spa” treatment with locally sourced ingredients in the couples’ room at Auberge Spa, plan a private “barefoot on the beach” dinner for two by special arrangement with CanoeHouse. 

Fairmont Orchid

First opened in 1990 as a Ritz-Carlton — which means it has good bones — this resort boasts a beautiful sheltered beach, a huge pool and great walking paths along the ocean for romantic strolls.

Pro Tip: The award-winning Spa Without Walls has eight private outdoor waterfall hales (huts) and six rejuvenating oceanside hales for maximum melting, relaxation vibes.

Outrigger Kona Resort and Spa

This oceanfront property is located on 22 acres of the Kona Coast, just south of the town of Kona on an ancient lava flow on Keauhou Bay. Built in the early 1970s as Kona Surf, the resort has gone through a few major renovations and was rebranded as the Outrigger Kona in 2020. Stay tuned for more improvements coming in 2024.

Pro Tip: Say “I do” in the resort’s wedding chapel overlooking the historic Keauhou Bay or “I still do” reaffirming your wedding day promises at Pa‘aki Point with sweeping views of the Pacific Ocean.


1 Hotel Hanalei Bay

Built into the cliffside overlooking Hanalei Bay, beyond scenic views, the hotel seamlessly blends comfort with sustainability. The latest renovations include landscaping with 70% endemic and indigenous plants that support local wildlife, rainwater irrigation reducing outdoor water consumption by 97%, support of local farmers, fishers, and growers, and much more.

Pro Tip: Book the Ku’uipo Sweetheart Getaway and watch love grow. The package includes a private ocean view dinner, couples massage and daily breakfast for two.

Waimea Plantation Cottages

This collection of restored vintage plantation-era cottages is on the dry, quiet West Side, near the road heading up to Waimea Canyon and Koke ‘e State Park and within striking distance of the 17-mile beach at Polihale State Park.

Pro Tip: Couples who aren’t off exploring can take advantage of the secluded setting with long walks on the driftwood-dotted, black sand beach or lounging in a free cabana by the compact pool.

The Grand Hyatt Kauai Resort & Spa

This 52-acre bluffside compound above Keoneloa Beach (Shipwreck Beach) in Poipu may be the largest on the island with 605 rooms, but it hosts many garden nooks where you can enjoy the sweeping ocean views in relative tranquility.

Pro Tip: The quieter expanse and expertise of Anara Spa draws patrons from all corners of the world. Refresh yourself with a massage, facial or body treatment that features a bounty of island-fresh botanical essences.