Beautiful beaches. Clear waters. Marine life all over. Palm trees, sun, and a light breeze. These are all the things that make Hawaii so magical and are a few of the reasons so many Americans choose to vacation in Hawaii year round.
Maui is my favorite island out of all the Hawaiian islands. For me, it offers all the things I want in a boujee vacation—great golf courses, incredible fine dining, spectacular beaches, clear water and good shopping. That’s not to say that’s what I want to have everywhere I travel, but when I go to Hawaii, these are the things that I enjoy the most. Oahu is too busy and too touristy (full of--and I know I am going to get shamed for this--overweight, pale Americans wearing tube socks and fanny packs) and islands like Kauai, Molokai and Lanai are too rural and don’t have much to do. The Big Island is too barren on the west end where all the nice resorts are and although quite lush and tropical on the east end, it's a bit of a trek to get there. There's also just not as much to do. Now, don’t get me wrong—there is a time and a place where a rural, serene location might be what you want but I actually like Maui because it has all the action you want AND the calm, peaceful options for those wanting to relax. It’s really the best of both worlds.
Another great thing about Hawaii in general is that you can pretty much visit year-round. While there is such thing as a high season, there is no such thing as a time not to visit. I’ve been to Maui more than a half dozen times and whether I go in June or November, the weather is always incredible. Sure, you might get your occasional rain, but that’s pretty standard for anywhere in the tropics.
Things You Should Know
Don't worry about what your weather app is telling you! Just like any tropical island, it rains often in Maui. However, it's often short-lived and sporadic, with periods of sun and warmth in between. There's a very high likelihood that if you go during the rainy season, you could get a weather forecast pop up on your phone that shows rain every day. Don't panic--this doesn't mean it's going to rain all day every day (unless there's a significant storm or something). Most likely, you'll experience brief periods of showers, followed by sun the rest of the day.
Maui is also known for being the windy island. Due to where it sits, the west end of Maui (where all the resorts are) often gets quite windy in the afternoons. Plan activities like golf around the wind (translation: play in the morning for a more enjoyable time). Mornings are typically quite calm, and then the wind generally picks up in the mid to late afternoon.
Renting a Car
My strongest piece of advice is to rent a car on Maui... and rent one in advance! Especially if you're traveling to Maui during one of their busier times of year (Thanksgiving, Christmas, spring break/Easter and the summer months), it will be important to rent a car ahead of time to: a) avoid exorbitant prices and b) make sure you can even get a car. Yes, I mean it. When we traveled to Maui for our babymoon in April of 2021, they actually ran out of cars on the island. Not only were the prices insanely expensive when I looked again about a week before our trip (try $4,000 for a car for the week), but by the time we got there, they had completely run out. Friends we met at Kapalua ended up getting stranded because of Covid, and were shocked when they were told by nearly every rental company that they were booked solid, with no available vehicles to rent (not even the expensive ones).
And while we're on the topic, expect to pay a premium for a rental car in Maui. This is because you really do need a car to get around the island, and if you want to do the infamous "Road to Hana" (see below), you really need to rent a car. Cars range between $700-$1000 for the week in Maui, but it's worth it when you consider the flexibility it gives you to see other beaches, drive around the island, get to hiking trails and more. Ubers are not only expensive but not always readily available. And most likely, wherever you've chosen to stay on the island, it's probably at least a 30-50 minutes drive from the airport.
Thankfully, Kahului Airport (OGG) has made some awesome improvements in recent years. The best being their new rental car terminal, which is accessible by tram. While you used to need to wait to get on a shuttle bus and then go off property to each of the different rental car agencies, the new rental car terminal means you either hop on the tram (or walk the 3 minutes to get there) and find most of the big-name rental agencies all under one roof. That means easier returning too.
Leaving the airport though, plan for long lines at check-in and security (even for TSA PreCheck!). I'm not sure why these lines always take forever, but they just do. So give yourself extra time when you are heading out so you make sure you don't miss your flight home.
I always choose to rent with Hertz, because with my Gold Membership (which is free to join), all I do is reserve ahead of time, look for my name on the board upon arrival, and then simply walk to my car and leave. No standing in line to finalize the check-in process. Then when I return, you just drop the car in line at the airport and leave. It's SO easy!
Enjoy up to 25% off the base rate when you book now
Where to Stay
Four Seasons Wailea
The Four Seasons is probably the most exclusive resort on the island, though not necessarily the nicest. Don’t get me wrong—it’s a beautiful resort and has all of the usual Four Seasons amenities and that exemplary Four Seasons customer service, but I think for the money you can get better. It just sort of depends on what you plan to do while in Maui. If you want to be right in the heart of all the action, this is probably one of your best best (along with the Andaz, the Marriott, and the Wailea Beach Villas).
Located right in the heart of Wailea, staying at the Four Seasons is probably the most convenient and is one of the nicest hotels among the string of resorts that line the beach in Wailea. They definitely have some of the best restaurants too, so staying here means that you can eat at a different restaurant each day and still probably not have to leave the resort at all. There’s Wolfgang Puck’s Spano (we even saw Wolfgang hanging by the pool with his family on one of our recent trips), DUO steakhouse, Ferraro’s, and The Beachwalk Cafe. Their spa is great and the best beach is right out in front of the Four Seasons, so you don’t even have to walk far to get there. It’s generally crowded though, so keep that in mind. And it's spendy: you pay a premium to stay here. Rooms during high season typically start at about $900 a night.
Ritz Carlton Kapalua
The Ritz Carlton is probably my favorite hotel on the island, but might not be my first recommendation depending on what you are planning to do. It’s pretty far out there, away from most of the action, so if you are wanting to dine at the best restaurants, shop, and do touristy shit, the Ritz is not your place. If you’re just looking to chill by the beach or relax by the pool, get spa treatments, or play golf, the Ritz Carlton at Kapalua is your best bet. They have a giant pool, as well as an adult pool that features great cabanas with all the amenities. Or if you're looking to sun by the beach, they also have chairs at the beach. The rooms are spacious, the beds are super comfortable (so much so that we bought a Ritz bed several years ago!) and the service is top-notch.
With that said, I do have some advice for getting the best room here though: pony up for the apartment-like rooms at the Ritz Carlton residences or ask to be placed in a quiet room on a high floor. The first few times we stayed here, we weren't picky and got a base-rate room overlooking the golf course (so "no view" by the hotel's standards). We didn't mind though, because there are beautiful trees and it's really tranquil. On our trip we took in April of 2021, we actually were put in an upgraded "Premium Ocean View" room, which we really didn't like. Though it had views of the ocean, it also overlooked the pool, and since it was quite busy when we were there (Easter week), the pool noise was quite loud and there were clearly a lot more people staying in that part of the hotel. When we asked to be moved to a quieter part of the property, they moved us to a golf course view room that actually had a better ocean view—just in the opposite direction. This meant we got the sunset—along with peace and quiet—and the beautiful golf course instead of the pool.
This hotel is on the up and up. They just completed a very long renovation project, which was not only desperately needed but also mandatory if they want to compete with the neighboring hotels. Thankfully now the resort has more modern rooms, better restaurants and better pools. The food is WAY better than it used to be. The adult-only pool with the cabanas is really great—quiet and peaceful with incredible views. Their scuba facility is actually pretty decent (I learned to scuba dive for the first time there several years back) and their new water park for the kids looks pretty nifty. I also love that they offer oceanside yoga in the mornings and full use of kayaks and paddleboards.
The Marriott Wailea has been my go-to Maui hotel for years—not just because it’s part of the Marriott brand and therefore a destination I can rack up points and elevate my Bonvoy status, but also because it’s centrally located in Wailea. The Marriott sits between the Andaz (where my favorite Maui restaurant is) and the Four Seasons and the Fairmont, so if I’m in Maui for a conference it’s the perfect place to stay away from all the other conference attendees but still be close enough to walk. It’s also walking distance to the Wailea shops, the golf course, and a short drive (or longer walk) to Monkeypod.
My main complaint today would be that it doesn't have any fine dining restaurants like its neighbors (the Andaz has Morimoto and Ka'ana kitchen, the Four Seasons has Spago and Duo, the Fairmont has Kō and Nick's Fishmarket, the Grand Wailea has Humuhumunukunukuapua'a). I would not call Humble Market Kitchen fine dining. And the spa isn't that great either. I always have to head over to the Grand Wailea or the Andaz if I want a good spa treatment. Another bummer is that because they're usually so busy, if you're a Marriott Elite Rewards member don't expect an automatic upgrade—I've only been lucky enough to get one at this property on one occasion, despite the fact that I almost always get upgraded when I travel to other Marriott properties.
Here's a little tip for the Marriott: be sure to get an upgraded room. There is a HUGE disparity in room quality at this hotel, which is actually one of my primary complaints about the property. But if you are in one of their upgraded rooms, it's actually quite delightful. Book one of their suites for more space or an Oversized Lanai room for an outdoor space with loungers--often with ocean views. If you book on points, call the resort ahead of time and ask to pay a cash upgrade for a nicer room. Often times you can snag a really great upgraded Lanai room or suite for between $50-$150 a night.
Though it's not as nice as some of its neighbors (the Andaz and the Four Seasons are way better), it's a good option for the price. They have done a really great job with their recent improvements.
The Andaz is one of Maui’s newer hotels, and it’s definitely the coolest. With it’s modern design and layers upon layers of infinity edge pools, the Andaz is the place to stay if you like that modern, young, fun feel. The rooms are impeccably done—very minimalist with clean lines and colors but still with all the comforts and amenities that you could want. And the best part? It has two of Maui’s best restaurants on the island—Morimoto and Ka’ana Kitchen. Get one of the oceanfront rooms if you can.
This is one of my favorite hotels in Maui. It is new, clean, modern and has a bit of a sensual side to it. The cascading pools and incredible views, combined with spacious, tastefully decorated rooms and phenomenal restaurants make the Andaz THE place to stay. I would choose it over the Four Seasons and the Fairmont even. The fact that you just have to walk downstairs to get to two of the best restaurants in Maui (Morimoto and Ka'Ana kitchen) is a huge plus. And the price is very reasonable for what you get. I just want to stay in one of their villas one of these days... next time hopefully
This hotel would typically be on my “where NOT to stay” list, but if you are traveling with kids, this is probably actually one of your best options. This place is seriously like Disneyland (in all the good ways and the bad ways), so if you are NOT traveling with children, I would never advise staying here.
Though this wouldn’t be my first pick, there are, however, a lot of good qualities about the Grand Wailea. The spa is INSANE--seriously one of the best, if not THE best, on the island--and I've heard the rooms are actually really nice. Because they do cater to families, there are a lot of activities for the kids and I think they even have programs where you can drop the kiddos off with supervision so you can enjoy some time alone.
Wailea Beach Villas
If you’re traveling with a group of people, a large family or just want a lot of space, the Wailea Beach Vilas are a great option. They are a community of villas sandwiched in between the Marriott and the Grand Wailea, with 3 and 4 bedrooms. It’s like having your own home (with all the amenities of home like a full kitchen, multiple bathrooms and laundry), but with all the amenities you can enjoy at a resort, like daily maid service, pool and gym privileges, and staff who will set you up with loungers, towels and an umbrella on the beach. These places are spendy though, as they run between $700 and $1200 depending on the season.
Fairmont Kea Lani
Though I’ve attended several conferences at the Fairmont, June of 2019 was my first time staying there. Let me tell you—it did not disappoint! Though I had never been all that wowed by their restaurants, pool area and meeting rooms (they’re all nice but not particularly mind-blowing or different from the other hotels along Wailea), the room absolutely blew me away. I think I had a slightly upgraded ocean view suite, but it was more spacious than I could have ever imagined and extremely well-appointed. My suite had a large entryway with a mini bar, coffee area, counter and separate closet, and then a giant living room with a sectional couch, TV and desk area with a sliding glass door that opened up to the balcony. Next was the master suite—which of course also had a balcony—with a spacious king bed, two closets and another TV. I have to say, the bathroom was what did it for me: it was almost as big as the bedroom and had two sinks, a large walk-in shower, toilet room and giant soaking tub. For the money, the Fairmont is a good choice and the rooms are fairly comparable to the Four Seasons without the Four Seasons price tag.
If you are looking to stay closer to Lahaina or in Ka’anapali, the Westin is probably your best bet. Though not my first choice for a stay on Maui, if you insist on staying in Lahaina or Ka’anapali then the Westin is hands-down your nicest option. It’s right on the beach, has plenty of options for the kids, and has a nice assortment of restaurants to choose from.