To start off, I’m going to state the obvious. There are a lot of great places in Hawaii. Exotic beaches, jagged green mountains, charming local towns, VOLCANOES. That’s undeniable the best part of Hawaii…the real Hawaii. But there’s another part of Hawaii that I love too. 

Resort Hawaii. 

Planned resort communities designed and laid out with tourist conveniences in mind. 

Filled with luxury resorts, sparkling pools, golf courses, tennis courts, restaurants with ocean views, shopping, and the whole thing landscaped and manicured to perfection. 

It may not be the “real Hawaii” but it’s pretty awesome.

All of the Hawaiian Islands have resort areas…little bubbles of tourist paradise…but in my opinion, the best resort area in all of Hawaii is in Maui…in Wailea.

If you’re never been to Maui before, chances are it’s exactly what you think Maui would be like – manicured and lush, quiet and luxurious with gorgeous beaches and world class resorts. 

It’s definitely not “local,” but it’s the stuff Hawaii vacation dreams are made of. 

Plus, unlike some resort communities on other islands, Wailea isn’t super isolated. It’s right next to Kihei, a more local (albeit very touristy) town, and conveniently located for exploring the island.

So if you’re lucky enough to be staying in Wailea, keep reading for my list of favorite things to do…

Things to Do in Wailea

This post may contain some affiliate links, which means I’ll make a little money on anything you choose to purchase. But of course, I only recommend my absolute favorites to you. Thank you for supporting the brands that make HulaLand possible.

Be a Beach Bum

Let’s start with the obvious. Wailea has some of the loveliest beaches on Maui. 

Wailea, Polo, and Mokapu/Ulua are the major beaches in the area (all with nice resorts situated on them). 

Keawakapu is a long (and often quiet) stretch of sand between Wailea and Kihei that’s one of my favorite spots for a long walk. 

Big Beach is one of Maui’s most stunning beaches (it has huge waves!), Secret Beach (just past Big Beach) is a cozy little cove and the most popular spot for weddings on the island, and Maluaka beach is likely the best spot for turtle sightings (it’s very near Turtle Town). 

Read this post for an in depth breakdown of Wailea and Kihei’s best beaches including info on public parking and access points. 

Wailea Beach Walk

This is one of my favorite parts about staying in Wailea. 

This beachfront walkway between Polo beach (Fairmont Kea Lani) and Mokapu beach (Andaz) is 1.5 miles of beachfront and cliffside beauty. Whether you’re a jogger or just a stroller (or using the path to hop from happy hour to happy hour), you’ll definitely want to explore the trail.

If you’re not staying on the walkway in Wailea, there are public beach parking lots at Polo Beach, Wailea Beach and Ulua/Mokapu Beach where you’ll be able to access it. 

Tikehau Lounge Happy Hour

There are far fewer “tiki bars” in Hawaii than most people would expect, but this craft cocktail lounge in Wailea fills a major void on the island. 

Their drinks here are FAR superior to the often “ho hum” drinks you’ll find poolside at the resorts in and touristy oriented restaurants and at a much better price. 

Go for their happy hour for before dinner drinks, but their food is actually really good too. Their kalua pork sliders are amazing. 

Kilolani Spa at the Grand Wailea

With so many luxury resorts, you KNOW there have to be some cushy spas on Maui, but the Kilolani Spa at the Grand Wailea is pretty special. 

The Grand Wailea has always been known for having a “grand” spa, but it just opened after an EXTENSIVE multi year renovation and it’s probably now the best in Hawaii. 

Even if there’s a spa at your resort, it’s probably worth coming to the one at the Grand Wailea instead. 

Watch Sunset

Wailea has a prime location for viewing the nightly sunset whether it’s from a high end restaurant, the infinity pool, a spot along the beach walk, or with your feet in the sand. 

Tennis

The Four Seasons is the only resort in Wailea with courts and a tennis program (some of the condo complexes have a court or two) but it’s open to non guests as well. Find their daily clinic schedule and rates for lessons and court time here. 

The Wailea Tennis Club also hosts clinics and lessons and has 11 hardcourts plus a pro shop. 

And it has such a dreamy setting! Find out more info here. 

Fancy Brunch at Ka’ana Kitchen

Nothing says “living resort life” like a lavish breakfast buffet. I’ve tried out most of them, and  Ka’ana Kitchen at the Andaz Maui is my favorite breakfast buffet in Wailea (which makes it the best on Maui). 

It’s about $50/person (the going price), but I think they have the best offerings, best quality, and best service. The restaurant also has a great view and even on a non-weekend/brunch day it’s probably the place that feels the most like a special experience (even for $50/person some resorts just feel like they’re shuttling a herd of guests through the buffet before they leave for their daily adventures). 

One thing I really like here is that omelet and made-to-order egg requests are handled through your server and brought to your table so you don’t have to stand in line and wait for them to make it. 

Ride in an Outrigger Canoe

Most resorts offer rides in outrigger canoes (sometimes they’re complimentary for hotel guests if you sign up in advance). 

I’ve never done it but it looks fun!

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Akamai Coffee

Arguably Maui’s best coffee spot, Akamai has a few locations now. I like to try a different signature drink or special every day ; ) 

The Wailea location is also a great spot for a full breakfast. 

Walk from Mokapu Beach to Kihei

I grew up going to beaches in Florida where you could walk for miles, and I do kind of miss that with Hawaii beaches. They tend to be more “cove” like which doesn’t lend itself towards long walks on the beach. 

But the best exception I’ve found is in the north end of Wailea and the south end of Kihei. Mokapu Beach in Wailea (in front of the Andaz) connects to Keawakapu Beach which is pretty long and dreamy and from there you can walk past Kamaole I, II, and III beaches in Kihei through a series of little pathways that connect them.

La Perouse Bay & Lava Fields

I love a good scenic drive, and the drive down to the end of the road through Makena is one of my favorite parts of Maui. You’ll pass through some of Maui’s most high dollar real estate (rumor has it Aerosmith’s Steven Tyler has a place in Makena) where the road hugs the coast just feet from little coves and beaches before you drive through a lava field (from Maui’s most recent volcanic eruption) and end at La Perouse Bay.  

La Perouse Bay is usually a good spot to see spinner dolphins and you’ll find some ancient Hawaiian archaeological sites including heiaui (a temple/altar). 

It’s also the trailhead for the Hoapili Trail (the most accessible portion of the ancient King’s Highway that circumnavigated the island). 

Big Beach

Also called Makena State Park, or sometimes Makena Beach, this is one of Maui’s most beautiful beaches. It’s a long stretch of golden/white sand with beautiful blue water. There’s a strong shore break here (as the life guards will often remind you) so be careful when entering and exiting the water. 

At the far north end of Big Beach, there’s a rock formation you can climb up (the views are amazing!) and over to get to Little Beach which has the reputation for being a nude beach/party beach with locals. 

There are two parking lots at Makena State Park (and usually a few food trucks) and no restrooms or showers but there are porta-potties. 

In April 2021, entrance AND parking fees were introduced (although reservations are not required). $10/car to park plus $5/person (under 3 are free) to enter. Fees are paid at the pay station in the parking lot. 

Secret Beach

Also called Pa’ako Beach, Secret Cove, and Makena Cove, this is where 98.9% of the weddings on Maui happen. Just kidding, but it seems like it sometimes. 

This tiny postage stamp of a beach is the first “shoreline access” sign you’ll see after you pass Big Beach headed south. There’s limited street parking in the area. 

It requires climbing down a little path to get to it, so it feels like a “secret” once you find it. Makena Cove is lovely (although very small) but the “secret beach” is actually around the corner to the right. You’ll need water shoes to climb along the lava rocks to get there but once you do, you’ll usually have it all to yourself. And from there you can keep making your way north and you’ll connect to the south end of Big Beach. 

Molokini Snorkel Trip

Hands down one of the most popular things to do on Maui is going out on a snorkel tour to Molokini. This partially submerged volcanic crater has some of the best visibility for snorkeling and diving anywhere in Hawaii. 

My personal favorite way to go is with Kai Kanani on their Sunrise Snorkel Tour. 

It leaves from Maluaka Beach in Makena (just about 5 minutes from the resorts in Wailea) which is the closest launching spot on Maui to Molokini (this means it’s a super quick ride compared to some of the companies that leave from much farther away). 

In addition to Molokini, Kai Kanani also makes a stop at Turtle Town so you can snorkel with the Hawaiian Green Sea Turtles! 

Read my full review of snorkeling Molokini with Kai Kanani here. 

Mai Tais at the Monkeypod

If there’s one thing you’re going to want to do in Wailea, it’s hit happy hour at the Monkeypod. Now I will preface this by saying that there’s now a Monkeypod in Ka’anapali at Whalers Village and that one has ocean views so if you’re staying on the west side then I would probably hit that one instead, but the Monkeypod in Wailea is the original and it’s pretty much my favorite restaurant in Hawaii. 

When I lived on Maui, we would stop at the Monkeypod in Wailea for happy hour all the time after a beach day so it feels a bit like tradition. 

Anyways, they’re famous for their mai tais which have a lilikoi foam on top and they do a really good happy hour. Check the recent hours but there’s usually an early one from 3ish to 5ish and a later one after 8 or 9. Besides pretty good deals on drinks, most of their appetizers and pizzas are half off. 

Fine Dining at the Hotel Wailea Restaurant

There is no shortage of high end restaurants in Wailea, but the restaurant at the Hotel Wailea is SPECIAL. If you are a foodie, you appreciate the finer things in life, and you’re okay dropping some $$$ on a special occasion dinner, then you simply must make a reservation here. 

I’ve compared it to Mama’s Fish House, but it’s just different. It’s going to appeal to a more niche audience, but honestly it’s more elevated than Mama’s. It just doesn’t have that beachfront location. It feels more like a hideaway. 

It’s $125/person with a choice of a first course, second course, and dessert and options are plentiful for all three. And this isn’t one of those fancy schmancy expensive places with tiny portions. The food is substantial here. 

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Snorkel at Turtle Town

Turtle Town is one of the best places to swim with turtles on Maui. 

There are some underground caves offshore in this area (plus a lot of algae that they feed on) that attract a large number of turtles so it’s pretty reliable to spot them swimming in the area. 

A lot of the Molokini snorkel boats make a stop offshore in the area for snorkelers, but if you know where to go you can snorkel in the area from the beach too. 

In general, “Turtle Town” is roughly the area of Makena Bay from Makena Landing Park (on the north end) to Maluaka Beach (on the south end). And the two best access points are at Makena Landing and Maluaka Beach. 

The turtles swim around so there’s always a good chance of spotting one wherever you are, but for the best odds you’re going to want to swim out away from shore a bit. 

It’s not necessarily unsafe and a lot of people snorkel in this area on their own, but I would recommend staying a little closer to shore than you see the people snorkeling on the boats maybe unless you have a paddleboard. 

I’m also generally a fan of wearing a flotation belt when you’re snorkeling (especially if you’re not on a tour), and of course making sure there’s somebody on the shore who is tracking where you are. 

If it were me, I would enter the water at Makena Landing and swim a bit south/away from the shore from there. It’s a fairly protected area and there’s often other snorkelers there. Also, you could sit and wait for a snorkel boat to pull up and swim over to check out what they’re looking at. 

Kayak Eco Adventure

If you like adventure, book a kayak eco tour to Turtle Town with Maui Kayaks. They launch from Makena Landing and have at least two snorkeling spots. Besides turtles, they often spot dolphins, rays, octopuses, and whales in season! This is a great alternative if you don’t want to go all the way out to Molokini, and you’d like to visit Turtle Town but aren’t comfortable swimming out from the shore on your own. 

Go Resort Hopping

So back to hopping from happy hour to happy hour…whether you’re staying at a resort in Wailea, or you just want to get the full “Wailea experience,” everything here revolves around the resorts. 

There are five major resorts in Wailea and they’re all connected to the Wailea Beach Walk which means they’re all easily accessible whether you’re coming up from the beach, from the resort you’re staying at, etc. 

From north to south you’ve got the Andaz, Wailea Beach Resort, Grand Wailea, Four Seasons, and the Fairmont Kea Lani. 

The Andaz sits on Mokapu Beach, the Wailea Beach Resort is in between Ulua and Wailea Beach, the Grand Wailea and the Four Seasons are on Wailea Beach, and the Fairmont Kea Lani is on Polo Beach. 

Besides each resort having valet or self parking (which they’ll validate if you’re having a meal, shopping, etc.) each of those beaches also has public parking. And you can pay by the hour to park at the Shops at Wailea (they’ll also validate with a purchase). 

All five resorts are places that are worth checking out. Generally speaking, Grand Wailea is the most jaw dropping and impressive. They’ve got several shops, a large lobby bar, plus a lowkey poolside bar/restaurant (Bistro Molokini). 

I think having a drink at the Lobby Bar at the Four Seasons is a must do Wailea experience. It’s just so…civilized. 

The Andaz is probably the most impressive property on Maui. It’s modern and sleek and drinks or lunch at the Bumbye Beach Bar is a great way to see the place. 

The Wailea Beach Resort is probably the most lowkey resort in Wailea, but they’ve got the best “Instagram setup.” Their giant ALOHA sign is a big crowd pleaser (this is super close to the Shops at Wailea-if you’re parked there you can walk down to the resort) and Kapa is a great place for a more affordable resort lunch/drink/casual sunset dinner. 

The stretch of the Wailea Beach Walk between the Four Seasons and the Fairmont Kea Lani is probably the most dramatically beautiful part of the 1.5 miles so if you like beautiful scenery and cliffside views, you’re not going to want to miss that. 

Get a Picnic from Spoon & Key Market

Spoon & Key Market in Wailea is the perfect spot for a quick breakfast or lunch or to grab a picnic lunch for the beach. When I’m staying in Wailea, I love stopping at Spoon & Key Market for lunch on my arrival day. 

Their ahi melt is spectacular. 

They also do a special sunset menu on Wednesdays and Thursdays plus an amazing looking pre-fix menu on Fridays and Saturdays that changes weekly. 

Snorkel at Mokapu Beach

There are so many great spots to snorkel off the beach in South Maui, but my favorite is off Mokapu Beach right in front of the Andaz. The rocks hook around a bit and form somewhat of a protected area and since it’s right in front of the resort there’s usually plenty of people out there snorkeling which is a GOOD THING. 

You don’t need to be that person snorkeling way out by yourself. We call them shark bait ; ) 

Also, the best snorkeling conditions are going to be earlier in the morning. Plan to be finished by 11AM. 

If you’re staying close by in Wailea, walk over on the Wailea Beach Walk with your snorkeling gear. If you’re not, there’s a public parking lot for Ulua and Mokapu Beach just south of the Andaz. 

Golf

The Wailea Golf Club has three championship golf courses which is more than enough to keep even the most avid golfer busy on vacation.

Shop til You Drop

There’s plenty of shopping in Wailea. The most obvious place to hit is the Shops at Wailea. This open air shopping mall has everything from high end luxury brands (Louis Vuitton, Gucci, etc.) to surf shops (Billabong, Roxy, etc.) and a few local shops as well. 

The Lululemon has a Hawaii exclusive line, and I also love Whalers General Store and Island Gourmet Market for souvenirs, prepared food, and light groceries. 

Besides the Shops at Wailea, I really like the Wailea Village where my FAVORITE Bikini Market is located. 

But honestly, I think the best shopping is at the resorts. Every resort has at least one boutique (the Grand Wailea has several) and they have the best stuff. 

Snorkeling at Ahii Nature Preserve

On your way to La Perouse Bay, pull over to the side of the road to snorkel in one of the pristine and calm pools at the Ahii Nature Preserve.

Go to a Luau

While I personally think the best luau on Maui (heck, in Hawaii) is the Old Lahaina Luau (which HAS reopened after the fire), if you’re staying in South Maui it’s a bit of a drive over to that side of the island. 

If you’re looking for a luau to enjoy that’s within walking distance (or a quick drive) of the Wailea resorts, you’ve got options!

The big three resort luaus in Wailea are 1) Grand Luau at the Grand Wailea, 2) Te Au Moana Luau at the Wailea Beach Resort, and 3) Feast at Mokapu at the Andaz. 

They’re all pretty high quality (with price tags to match). 

For a more budget friendly option, I already recommended the Hula Show at the South Maui Gardens. That’s a great event. 

You didn’t hear it from me ; ) but all three resort luaus are in open spaces where you could easily watch part of the show from a distance. There’s a free Polynesian Show at the Shops at Wailea a couple of nights a week plus the Four Seasons Maui has live music and a hula dancer most evenings in the lobby bar. 

Dinner at Humuhumunukunukuapua’a

I like to do at least one “fancy” dinner on vacation and Humuhumunukunukuapua’a at the Grand Wailea has such a dreamy atmosphere that it has to be on the short list. 

It was just recently reimagined (top to bottom, including the menu) as part of the resort’s renovation, and they really nailed it. 

Bigger parties may want to request a table back in one of the “huts” overlooking the lagoon, but if you have four or less, I love sitting right on the railing next to the aquarium bar. 

It’s a stunning view no matter where you look!

P.S. I travel to Hawaii multiple times a year, and let me tell you a secret…I do most of it for FREE using credit card points and miles. 

I have a somewhat intricate system that I’ve fine tuned over the years to maximize earning points and how I cash them in, but the short version is:

I use THIS Marriott Bonvoy Boundless card for free Marriott nights. The sign up bonus alone on this card will get you 3 (sometimes 5!) free nights at hotels in Hawaii like the Sheraton Maui, Royal Hawaiian (Oahu), Sheraton Kauai Coconut Beach Resort, and the Waikoloa Beach Marriott (Kona). 

And I use THIS Southwest Premier Rapid Rewards card for free flights on Southwest. The sign up bonus will get you at least one round trip flight to Hawaii (possibly two depending on where you’re flying from). 

The combo of these two cards will have you most of the way to a free trip to Hawaii right out of the gate. Again, you can sign up for the Marriott Bonvoy Boundless >> HERE and the Southwest Premier Rapid Rewards >> HERE
And if you’re really serious about getting into the travel hacking game, read this post for a more in depth look at how I maximize credit card points to book travel.