Short on time? Follow this link to a Google Maps version of our guide of things to do in Wailea, Maui with all of our favorite spots labeled! You can “follow” the guide, and the saved locations will automatically transfer to your own Google Maps account.
More posts from this trip:
I’m writing this blog post from my couch while shoveling popcorn into my face, but my heart is in Maui.
Tyler and I used to be so smug about Hawaii. Neither of us had never been, and there were always just so many other places we’d rather go. All of our friends and families are obsessed with it, but we always just thought, “How great can it be?” We considered ourselves more adventurous for preferring other destinations. I know, we are the worst.
But don’t worry, we’ve changed. We’ve seen the Maui sunset golden light and have spent the last three weeks since our trip eating our words and dreaming about our four short days in paradise.
We thought Maui would be the perfect place for a short, relaxing babymoon, a chance for us to connect and unwind before we really get ready for a big life change this fall. We went into the trip not really knowing what to expect, as we are typically not the best relaxers or biggest beach people (I burn in 30 minutes).
It took us three seconds to fall in love with Maui. In fact, I think the flight in really did it for us. As our plane descended through a bright pink sunset past the rolling green mountains, we looked at each other and just started laughing.
Since our trip was so short, we spent most of our time exploring the Wailea-Makena and Kihei areas and didn’t have a chance to venture up to Lahaina or Kaanapali. We didn’t do the famous road to Hana, as even driving through a parking lot is enough to give me the urge to projectile these days. All things on our list for next time.
These are our recommendations that came from this trip, though we know Maui has SO much more to offer. We also decided to save our food recommendations for Kihei for a separate post since that list was getting a little obnoxious.
We splurged on our hotel for this trip. We justified it with the following: we paid for our flights with credit card points, this would be our last romantic trip just the two of us for likely a very long time, and we only had four nights to pay for so it didn’t end up being that expensive. Just give me a call the next time you’re laboring over a purchase.
Also, we booked through Costco Travel and found an amazing deal for the Fairmont Kea Lani in Wailea. We paid over $200 less per night than any other site listed. I am HYPED on the Costco Travel game–thank you to my bestie Regan for that suggestion.
Back to the hotel. OMG. The Fairmont Kea Lani was magical. I mean, it was TRULY such a dream to experience. Our other besties, Joe and Kate, honeymooned here a few years ago and were extremely persistent that we prioritize it for our babymoon. They were SO right.
I barely know where to begin with this hotel.
Every single person we met, from the folks in guest services to the bellhops, was SO kind and welcoming. I was really starting to feel like Meghan Markle herself when I noticed that they actually treated every guest like royalty, not just me.
The guest services team even went out of their way to help us find out if our baby is a boy or girl! (You can read about that and watch the video here).
Every room at the Kea Lani is a suite, which made our stay all the more luxurious. Our ocean-view patio provided us with sweeping views of the Pacific, and we woke up early each morning to watch the sun’s warm glow rise over the beaches.
The Fairmont Kea Lani has three huge, gorgeous pools (one of which is adults only, can you say LAST HOORAH), and it also has its own little private beach. The property was definitely lively every day, but it never felt over-crowded.
In fact, we walked the ocean trail over to the Grand Wailea, another hotel that a lot of people recommended, and it was a ZOO, like a full-on waterpark. The Kea Lani seemed like a tranquil oasis compared to the Grand Wailea, and we were were so glad we booked it instead. (Although I will say the Grand Wailea is gorgeous, so definitely at least walk the grounds. The snorkeling there is supposed to be the best in Wailea, too).
The Kea Lani property is absolutely stunning, and it is the most perfect place to escape and relax.
After I explained that Tyler and I wanted to explore but that I didn’t want to get too hot or sweaty doing so (pregnant card), a coworker of mine recommended we check out Iao Valley in Maui.
We made the forty-five minute drive from Wailea early one morning–and by early, of course, I mean at 7am and with a strategic coffee stop in Kihei. We were delighted to find the little trail through the valley almost empty.
Despite the sign’s indication that the walk to the top of the lookout point would take thirty minutes, we made it to the top of the trail in ten. We loved this lush, green area and felt like we were walking through a jungle. Definitely recommend checking Iao Valley out.
A few friends suggested spending some time at Big Beach, just down the road from the resort area in Wailea. We pulled up at around 4pm one day and promptly turned around at the site of the completely packed parking lot and crowds of families spread out over the beach.
The next morning, our last before we had to get ready for the airport, we woke up at 6am and drove over to Big Beach to give it another shot. We had the entire beach to ourselves and spent the next hour in near tears (me) about leaving. This beach is truly stunning, and it was really special to experience it all by ourselves in the morning like that.
We made the mistake of heading to Makena Cove at sunset on a Friday evening, so we had to battle two entire wedding parties for views and pictures of the sunset dropping behind the palm-tree-lined cove.
We’d definitely recommend posting up at this tiny, picturesque cove for sunset, and it’s probably much less crowded on a week day.
We haven’t talked about this too much on Rome by the Hour, but Tyler is literally obsessed with golf. He doesn’t play that much anymore, but it’s pretty much all he talks about. I’ll let him take this one:
“I have rarely, if ever, splurged on golf. I played golf for my high school and basically got on most courses for free. The cost of golfing at nice courses was a shock to the system after high school, so I’ve really only golfed a couple times a year since then.
I knew that if we went to Hawaii that I would regret not playing a round. Wailea Golf Club turned out to be an incredible experience, and I am so glad I spent the money to play here. I recommend the Emerald Course not only because it’s stunningly beautiful with ocean views on nearly every hole, but it’s also a fairly forgiving golf course.
The best part was that Ruth came along to ride in the cart. She had never seen me play golf before. Despite my unnecessary competitiveness, ripping my pants on the 7th hole, and a lot of humidity, we somehow made it to the 18th hole with our marriage intact.
If you are into golf at all, this course is completely worth the splurge.”
My friend Kate, who honeymooned at the Kea Lani, aggressively insisted that we eat at Monkeypod. Kate is the same person who forced us to go to Giolitti for gelato in Rome, which is literally our favorite place on the planet. So we knew we needed to kick off our weekend with a Mai Tai topped with passion fruit foam…don’t worry I just smelled it, a pizza, and a cream pie from Monkeypod. Everything was absolutely incredible and reasonably priced (for Maui). We couldn’t stay away and went back for round two on our last night.
The Fairmont Kea Lani has a handful of restaurants on the property, but we decided to eat at Nick’s Fish Market one night because the reviews were SO over the top and everything on the menu looked insane. We split the steak and the mahi mahi and finished them both within minutes. (The portions are huge, but we rose above).
Nick’s is definitely the most expensive place we ate at ($40-50 each for entrees), but it was such a fun and romantic date night under the stars and beneath the glow of the tasteful tiki torches that I now need for my future backyard.
In order to compensate for our expensive dinner, we grabbed food at Island Gourmet Markets a couple of times. The market is conveniently located down the road at The Shops at Wailea, and they have everything from breakfast sandwiches to grab-and-go sushi (you know I was hitting the avocado rolls HARD). This is the perfect place to grab an inexpensive breakfast or lunch on your way to the beach.
The ideal night cap to any day in Maui: a scoop of ice cream from Lappert’s, specifically the cookie dough favor. Also in The Shops at Wailea, this place always has a line and never disappoints.
We actually ended up eating in Kihei, the little town nearby, at most of our meals. Kihei has a ton of hole-in-the-wall type places, so our absolute favorite thing was to grab food and take it to the beach. We decided to do all of those places in our next post, so keep an eye out for that.
It’s a pre-weekend pick me up: just a little note with links to the latest blog posts, what I’m reading lately, and products I’m obsessed with. Think of it as a friend dropping off a surprise latte in the morning--you know?