Maui to Oahu via tiny Lanai: A seven-day summer island hopping itinerary
While each Hawaiian island could be explored for weeks or even months and still offer up new experiences, most people don’t have that long.
And, for those looking for some laid-back relaxation while still getting a taste of what’s on offer, going luxury on the hotels and getting smart with the exploration is the play.
For a 7-night dream itinerary, we explored via three of the islands’ five-star hotels - and explored the islands using an innovative self-driven tour guide app to help us get out and about on this island-hop adventure.
All three hotels have their own unique features and vibes - from Lanai’s utter seclusion, Maui’s awe-inspiring infinity pool and cabanas, and Oahu’s dining options that raise the bar on hotel food.
You can re-work these into a different order based on preference, or even skip one of the islands to spend longer at another.
The island-hop began with a short connection from Hawaii’s main airport to Maui, the island known for its Road to Hana - one of the most beautiful drives on Earth.
A short cab ride from the airport took us to the Four Seasons Resort Maui at Wailea. It’s tucked into the west side of the island overlooking Wailea Beach, and the elevated north-western part of the island in the distance.
The hotel makes the most of these views - and the pools at this resort are mind-blowing. The main saltwater pool is arranged around a large fountain and is surrounded by an abundance of complimentary cabanas.
There are additional ‘oceanfront sanctuaries’ tucked into recesses of land overlooking the beach, which offer an additional level of privacy and calm.
High above, there’s an adults-only infinity pool that was so discreetly hidden I didn’t even realize it was there during my first morning at the resort. Tucked around the edges are loungers with panoramic views of Lanai and the West Maui Mountains, and the swim-up bar was a cool spot to hang out and chat with fellow guests.
We hired one of the large paid-for cabanas one day and were grateful to have a shady, fan-cooled place to lounge between dips in the infinity pool - while taking in some TV when things got really hot.
As for our room, we were in one of the deluxe ocean-view rooms, which are on the hotel’s middle-to-higher floors. It featured a king-size bed, big sofa bed, and was around 600-square-feet with an oversized marble bathroom.
The bathroom was gigantic, with deep soaking tubs, a separate powerful shower, double-sink vanity, and a separate toilet. And one small feature that had an outsized effect on my relaxation was the sound system, which pipes in a handful of music styles on-demand. It’s not radio, and it’s not quite Spotify. It’s just a ‘set it and go’ situation - a simple and stress-free way of choosing a vibe and forgetting about it, which in the streaming era often leads to decision fatigue.
The hotel has a U-shaped layout which broadly faces out across the ocean. We were on the south side of the hotel, which gets beautifully drenched in sun in the morning, meaning that even if you arrive in the off-season, you’ll still be bathed in rays even if a little cloud cover rolls in around noon.
One really unique feature at the resort is an IV infusion facility from Next Health, where you can lay back in soft leather recliners while vitamin infusions steadily drip into your blood stream.
I got the energy booster infusion with an add-on of NAD+ (Nicotinamide adenine dinucleotide). In all, it cost around $500. So, ‘does it work?’ is the obvious question. Well, while the hit wasn’t immediate, we both felt incredibly refreshed the next day despite some pretty heavy drinking and a heavy meal.
In terms of longer-term effects, it was hard to tell, but there were repeated customers who swore by it and I could picture getting one of these again on the first day of arrival to counteract the effects of jet lag.
Now, I also appreciate a lovingly assembled hotel gym, and the open-air cardio section facing the ocean, plus a well-stocked weights room, was a genuinely enjoyable way to work up a sweat while on vacation.
The hotel also has outrigger canoeing in the mornings, which is super popular and requires early reservations. Unfortunately, some gusty trade winds meant it was canceled while we were staying at the resort, but people we spoke to who’d partaken said they loved it.
There’s also scuba, water aerobics, whale watching and paddle boarding to be had, as well as fun little events like hula classes that take place throughout the day.
The employees at this particular property stood out for their friendliness and helpfulness - literally everyone who works there comes to say hi, and ask how your stay is going.
The resort boasts some really impressive views from its eateries - there’s Ferarro’s, which hugs the shore for picture perfect views of the sunset. It served Italian delights like warm homemade bread with nduja pork butter, roasted garlic and fried rosemary. Sublime - a must-try.
The best entree was the bowl of paccheri with Italian sausage, fennel, broccolini, and garlic crumb. It’s quite heavy, so not somewhere to go if you want a light bite - but for those with an appetite it’s a great option. Pizzas from its wood-burning oven also looked great.
Then there’s Wolfgang Puck’s Spago, the elevated, breezy, glass-walled offering from the celebrity chef. If you can, request the furthest corner of the restaurant, beyond the other diners, for an entirely unobscured view of the ocean and the stars.
Ahi cones were a twist on the ubiquitous Hawaiian dish - served in sesame miso cones which worked well with the tang of fresh tuna. Hamachi with avocado and maui onion was also super-fresh, super-light highlight. But it’s hard to go wrong with the Hawaiian-Californian fusion menu.
The resort’s signature Duo Steak and Seafood restaurant - featuring local seafood and premium steak cuts - is great, and served up a simply grilled opakapaka fish, a divine New York strip, alongside some decadent sides like truffle Mac and cheese, and caramelized crispy Brussels.
But the restaurant really shines at breakfast. Alongside the typical breakfast buffet options, the pancake and omelette station really shines. The pancake special on the morning I sampled Duo was a carrot cake pancake which absolutely slapped; crumbled up carrot cake that sunk deep into the pancake batter as it cooked, before being sprinkled with macadamia nuts. Incredible.
The breezy open-air lobby is half-indoor, half-outdoor, and the lack of any obvious boundaries makes the huge space feel even bigger. While most hotel lobbies are spaces to pass through, the lobby at Maui is a place we actually hung out, post-dinner.
The next stop was the Four Seasons Resort Lanai, which offers super-cool private charter flights from Oahu - but if you’re arriving there from Maui, the transfer is less glamorous but equally fun.
A cab ride to Lahaina takes you to a ferry port, and the 45-minute journey across the water ends with you cutting in alongside dramatic cliff faces to shore.
The transfer at the other end is seamless, with Lanai hotel staff on hand to tag your luggage, and direct you to the waiting bus for the five-minute ride to the property.
Lanai is a unique island which was once the preserve of the Dole empire - where 80% of the world’s pineapples were grown. It’s now the home of two Four Seasons hotels … and very little else in the way of development. Even the downtown ‘Lanai City’ is little more than a few blocks of low-rise plantation town-style homes, with no traffic lights. It makes the contrast with the hotel all the more dramatic.
The Four Seasons resort here is one of the world’s most exclusive - where Bill Gates had his wedding, and where Elon Musk (according to DeuxMoi) stopped by shortly before we visited.
It’s a sprawling but serene property with a clifftop location overlooking a beautiful, white-sand beach - whose waters can be explored with the hotel’s complimentary snorkel equipment.
Our jaws dropped at our room, which featured darker jungle-chic wood finishes - teak and zebrawood - that are a step change from the typical beach resort vibe of whites and blues.
High-tech fixtures and fittings elevated the experience; including an electronically controlled bidet; one-touch lighting and window shade mechanisms, and a Dyson hairdryer that delighted my wife.
We stayed in a garden-view room, meaning instead of rolling waves we had leafy, shaded outdoor space. To me, this was just as cool, and even more unique; thriving tropical foliage made me feel like I was holed up in a private mountain retreat, rather than steps from a beach.
Even the stroll to the room is an event, with a meander through themed gardens featuring koi ponds, rescue parrots, waterfalls and peaceful nooks.
The property opened at the Manele Bay hotel in 1991 and became a Four Seasons in 2005. A Google search of the old layout shows fairly meh grounds - a large pool, little foliage - which has since been transformed into two lagoon-style pools, cascading waterfalls, a nook cave, winding paths, and secluded dining spots.
The prime spot, for me, was the two rows of 20 or so beach chairs, slightly distanced from the rest of the resort, which lay in near silence - no music, no loud chatter - with only the crashing waves down below for company.
Given the island’s lack of development, all of best dining on the island can be found here, and we found it to be a seafood lover’s dream.
We dined at the rooftop Nobu restaurant, where the black miso cod is the star of the show, and an omakase menu is available for $198 per person. Our favorite dishes were the ultra-fresh yellowtail sashimi with warming thinly sliced jalapeño, delicate spicy hand rolls, and cod marinated in black miso before being fired in the oven.
The following night we settled in at One Forty, where we were very impressed by the wine selection - particularly the chardonnays - and took on a giant seafood tower together, featuring incredibly delicious lobster, a fresh tuna tartare, delicate oysters, chunks of king crab, and fat juicy shrimps. It was elevated simplicity.
We kept things simple for breakfast at One Forty, sampling perfectly cooked omelettes, among other items, and highly recommend the oatmeal which was finished with kiwi, mango, bananas, blueberries, almonds, roasted coconut and local honey.
Lanai is known for its Jack Nicklaus-designed golf course, which is built on lava outcroppings and hugs the stunning coastline. And while course access is limited to hotel guests, the writer - despite his best efforts - is dangerous with a golf club.
To get acquainted with the island, we took the Holoholo tour instead. It involves two jeeps, one driven by a hotel employee and the other one driven by the hotel guest, tailing behind. Both cars are equipped with short-wave radios, so the driver of the lead-vehicle can give you a continuous guided tour throughout.
There are stops along the way - including the moonscape-like Garden of the Gods - and a delicious fresh lobster roll lunch. And no matter where you land on the island - from dramatic valleys, to the sandy beaches overlooking a WW2-era shipwreck - it all feels like a private space to which you temporarily have access.
Close to the hotel, a short walk past the pristine white-sand beach, are the cliffs closed to Puu Pehe, or Sweetheart Rock.
It’s the perfect spot from which to watch the sun rise over Maui in the distance, and it’s entirely worth the 4.30am alarm in summer, followed by a wander through the dark.
There’s all sorts of other activities - from sailing to hiking trails - if you’d like to mix it up.
The exit from the island was very slick - a hotel-arranged connection to the local airport, where the vehicle pulls up right beside the charter aircraft. No waiting, no security, and you’re up in the air to Oahu within a few minutes. It allowed for a lot of extra pool time at the resort, and made for some great vacation photos.
Ko Olina is about 30 minutes in a cab from the airport, and Four Seasons Oahu is a resort on an epic scale, sitting on the rugged western coast of the island overlooking a peaceful man-made lagoon with bright blue waters.
It’s a large resort, and what’s lost in intimacy is made up for with vacation options. It’s got something for everyone: a genuinely private adults pool where even the loudest child’s screech wouldn’t reach; tons of activities for young kids and a pristine kids club area; hidden huts for couple’s massages, huge add-on areas where corporate events can take place; and a magical glass-fronted chapel overlooking the sea, for on-site weddings.
The vibe (outside of the adult pool) is higher energy than the other two hotels, and that’s what you’re coming to Oahu for; livelier vibes, with all of the beauty of Hawaii. And if you’re hanging out on Oahu, staying at Ko Olina is the way better play than Waikiki, which is just oppressively touristy these days.
Oahu, being a tall structure, has the benefit of height to make the most of the impressive ocean view. Our high-up West-facing room - with a long stretch of floor-to-ceiling windows overlooking a balcony and the water beyond, was bathed in a warm glow in the morning and a late afternoon burst of sunlight gave way to a magical sunset.
The balcony was large, and as it’s west-facing, the light wasn’t too overpowering in the morning, and meant that after a day at the pool, a trip up there for sunset provided dramatic views across the Pacific Ocean.
The room featured once super-comfy king bed, a huge TV, tasteful furniture, and comfortably sized marble bathroom. And while the section of hotel that I stayed in overlooks, in the distance, a privately owned event space that was very noisy on night one - that died down on future evenings.
We spent the days by the adults-only infinity pool, with refreshing cool water and a funky swim-up bar - a retro truck called Dr. Mai Tai’s, from which libations are served.
There were three other pools - including the outdoor pool at the spa. Top tip: It’s rarely busy there, so if you really want to get away from it all, that’s a great spot to do so.
But it was the food at Oahu that made the stay really special. Of the three options we tried, two of them were spots we’d make local detours to revisit, when next in the neighborhood.
Take Mina’s Fish House, a breezy beachfront spot with its own ‘fish sommelier’. Yeah, the twist-on-the-sommelier thing was stretched to breaking point when that water sommelier guy got big on TikTok - but this guy’s the real-deal. He’s a local fisherman with a sideline at this restaurant, explaining to diners the best way to choose, prepare, and eat various fish.
As someone who loves seafood but is sometimes reluctant to tackle a whole fish, his advice was a great help in trying something new. The cocktails are inventive too, and included a Mai Tai - the classic cocktail of Hawaii - served in an (empty) can of Spam, the ubiquitous lunch meat popular on the island.
Another highlight is the table-side tuna tartare preparation. Tuna is ever present on Hawaii’s menus, so figuring out a way to elevate it into something special is an impressive feat. The other was Noe, an Italian restaurant from Ryo Takatsuka where the tasting menu is the order of the day, allowing you to sample entrees like the signature tagliatelle with truffle and mushroom, and the amazing scallops with white polenta, mushrooms, and charred asparagus.
Before our arrival, concierge made it super-simple to book a very reasonably priced hire car, which was delivered and picked up by the valets. It was great to have for a couple of days, allowing us to take a 30-minute drive to downtown one day, followed by a loop of the stunning north shore the next.
We do recommend the Shaka guide app, which is a paid-for app with audio and GPS guided routes around both Maui and Oahu. You hook it up to a car’s sound system and it’s intuitive from there. In Oahu, it took us on a stunning loop from our hotel, via Pearl Harbor, and on to the stunning north shore where the surfers hang out.
The activities here were amazing, and really varied. One morning we set sail on a Wa’a traditional sailing vessel with two local guides - it roared out of the quiet lagoon onto wild bumpy waters and hugged the coastline along to the spot where we pulled on some scuba gear, dipped under the surface, and saw an array of incredible sea-life including sea turtles that were 100-years-old or more.
One evening, we wrapped up dining to head up to the hotel’s rooftop tennis courts for some late-night star-gazing with the hotel’s resident expert - who takes guests on guided tour of the skies with a mega-sized telescope.
There are other really thoughtful touches here, such as an artist-in-residence - currently Nick Kuchar, who creates vintage-inspired surf and travel art as an ode to Oahu. His work is displayed through the hotel’s ground floor level.
Meanwhile the hotel has partnered with Dana Childs, an energy healer, for on-demand guided meditation through the resort’s in-room media systems. There’s also an upcoming retreat in September featuring rituals and group workshops with Childs and special guests.
There’s also a funky HI Sessions concept, where local talent is celebrated with a live recording session featuring a special musical guest.
Now, I also tried the signature lomi mohala massage at all three resorts - it’s an ancient technique which uses special oils, rhythmic strokes, and leaves to help relaxation. The massage and spa at each hotel had something different to recommend it.
At Lanai, the massage felt like the most-skilled, from a reiki-master with years of experience. Oahu and Maui had the coolest settings - with thatched treatment huts right by the ocean, called hales.
The spa facilities at Oahu were sprawling and really high quality, and I ended up spending hours there after my massage.
Check-in and concierge at all three hotels is quick, friendly, and they’ll do what it takes, within reason, to make sure your stay is seamless.
At the Maui resort, I used the concierge team to help with booking some amenities and activities, and it was easy. Meanwhile the team at Oahu was excellent at anticipating my screw-up when I’d accidentally left the ‘do not disturb’ light on my room when I went out for the day. A text in the afternoon asked whether that was intended, and ensured I returned to a crisp, clean room despite this.
None of the restaurants disappointed - but as you’d expect, prices are high.
All resorts had solid 24-hour room service, and here’s my recommendation: get the Japanese breakfast. Miso Soup, broiled fish, onsen egg, and pickled vegetables aren’t the really the kind of comforting stodge that people tend to want when they’re pulling the pin on vacation - but it’s a bracing, delicious twist that sets the mood for wellness that The Four Seasons does very well.
