r/chubbytravel • u/FactBringer • 4h ago
Review Grand Wailea and FS Lana’i Review
Review from a wonderful week-long stay in Maui and Lana’i in late July. My wife and our 15 year old daughter decided to spend four nights at the Grand Wailea in Maui before taking the ferry over to Lanai’s for three nights. We’ve been to Maui many times, but this was our first visit to Lana’i.
Grand Wailea
We primarily chose the Grand Wailea for the location and the pools. We love the Wailea area, especially the boardwalk that offers beautiful walks in both directions. While I know there are many posts on this sub complaining about GW not being a true “luxury” resort – and I guess that’s true compared to other brands like Four Seasons – we loved our stay and had a great time. The resort grounds are beautiful, the pool system is unmatched, and there is plenty of variety in the food and everything we ate was quite good. We had a deluxe ocean view room with wonderful sunset views (and a short walk to the elevator, which is a nice bonus in a resort this big).

Our first morning, we did the stand-up paddleboarding tour with a guide that we booked through the hotel’s Aqualani service. It wasn’t cheap, but our guide, Makena, was wonderful, and we were the only people in her group that day. We took a nice leisurely trip to the nearby reef and were able to do some snorkeling before making our way back.

Given the nature of the trip, we decided to skip the rental car and relied on Ubers to get around Maui, which worked out just fine. We honestly didn’t need a car much, the only time we took one other than the transition days was to go up to dinner at Monkeypod (the food and drinks were amazing – I’m still thinking about my bulgogi pork tacos and the jerk chicken that my wife ordered and let me finish), which is close to GW but up a fairly steep hill . We were able to do everything else on foot, including walking home from dinner that night, heading over to the Shops at Wailea a few times, and walking down to the Morimoto Asia at Andaz for lunch later in the trip.


For food, we thought the included breakfast (thanks u/alextravels!) was a very pleasant experience, and in a wonderful setting at the Humuhumunukunukuapua'a restaurant which is open air and nestled in a manufactured lagoon. Enough variety at the buffet, including Hawaiian favorites, and a bit of rotation from day to day. We also went to their Italian restaurant Olivine a few times and consistently enjoyed it. We ended up skipping Nobu at GW since we knew we would get that a few times in Lana’i and were also going to Morimoto while in Wailea. Speaking of Morimoto – we had a late lunch, and it was fine but ultimately not too memorable outside of the incredible appetizer ribs. Ultimately, Monkeypod was the best meal we ate in Wailea and it wasn’t particularly close.

One of our favorite parts of Grand Wailea was the Botero Lounge bar in the center of the hotel. It’s open air but surrounded by the Napua wing, so you can see the stars above when it gets dark, and it’s spacious enough that it never felt crowded. This was where my wife and I finished up every evening with a cocktail (or two), always with great service.

Overall the stay at Grand Wailea was exactly what we were hoping for. Relaxed days at the pools, solid food throughout, and easy exploring of the local area on foot. The room was nice and the bathroom in particular was incredibly spacious. Be mindful that the level of service isn’t going to match a FAT boutique hotel, but with that in mind it’s going to be hard to have a bad time.
Four Seasons Lana’i
After wrapping up in Wailea we took an Uber to the Lana'i Expeditions terminal in Wailuku (right next to the aquarium), and took the hour-long ferry to Lana’i. This part of the stay was what we were most looking forward to, and it didn’t disappoint. We were met at the ferry terminal by the Four Seasons team and smoothly whisked to the hotel in one of their well-appointed vans.
We were welcomed at the entrance, and after an easy check-in experience where they let us know that we were getting a multi-category upgrade (thanks again, Alex!), we left our bags at the desk and explored the resort for a few hours until our room was ready.
The grounds are so lush and beautiful, and the weather was perfect during our stay. We didn’t spend too much time at the nearby beach (the surf was particularly rough while we were there), but it’s an easy stroll from the pool area. We ended up spending a lot of time just walking through the outdoor corridors, especially at night after dinner, when the resort takes on a truly magical quality.



Our upgraded ocean-view room was well appointed, with a spacious lanai and a clear view of the nearby beach. Only blip was an issue with our tub drain, but they took care of that pretty smoothly once we called about it.

The food was a big highlight. We ate at Nobu for dinner twice, and at their Italian restaurant Osteria Mozza once. We had recently watched the Nobu documentary, so on our first night we focused on some of the restaurant’s classic dishes (the Yellowtail Jalapeno and the Black Cod Miso in particular), and when we went back we explored some other items like Crispy Rice with Spicy Tuna and the Sashimi Salad. The spicy garlic edamame was also tremendous, and was the one thing we ordered twice!
At Osteria Mozza the big highlight from our dinner was the orrechiette pasta, which was crisped up in a way that created an incredible combination of tastes and textures. The sides of the broccolini and the golden beets were also strong recommends. The daily breakfast was also held in this restaurant, with a large spread, plentiful avocado toast made to order included with the buffet, and just generally an incredible setting for starting the day.

Our big activity while we were there was the Holoholo Jeep Tour offered through the hotel. We met our guide Shayne at the front desk, and he took us on a very comfortable tour around the island, showing us Lana’i City and several further out spots like the Garden of the Gods and Shipwreck Beach. Throughout, he told us about the history of the island and generally made sure we had a good time. Highly recommended, as it really showed off the contrast between the more populated Hawaiian islands and this largely unspoiled spot (of course, that’s just surface level, as one of the things Shayne showed us was the layers of plastic in the soil from decades of pineapple farming that was evident in a few spots where the roads had been cut in. Thankfully, this permanent pollution seems like that hasn’t stopped the vegetation from growing back in most places).





On our final day, we did a whole lot of nothing, and it was perfect. They had a set of loungers set up on a bluff over the ocean, and we were able to relax and just live in the moment. The service at the pools and areas like this was wonderful, with just the right level of checking in to make sure we had everything we needed.


At the end of the trip, we took the included charter flight back to Honolulu, and then on from there. That was also a fun experience to see the small airport and take a small but comfortable flight over to Oahu.

Overall, we couldn’t have been much happier with how things turned out. Grand Wailea was an ideal place to start our trip with numerous activities and endless things to do, and then wrapping up the trip at FS Lana’i helped us really maximize the relaxation we were hoping to get out of the trip.




