While there’s no single “best place to stay” on Maui, Wailea and Ka’anapali are two of the more popular options. In this quick post, we’ll break down the major differences to help you decide where to stay on your next trip to The Valley Isle.
It’s not only first-time visitors to Maui who struggle to decide whether to stay in Wailea or Kaanapali. While both locations offer plenty of vacation rentals and resort options, access to fantastic beaches, and great restaurants, they feature completely different vibes. Making the best choice for your next Maui vacation is all about understanding each location’s strengths and matching them up with your personal vacation priorities. Wailea is more spread out, quieter, wilder, and a bit upscale. Kaanapali is dense, mostly walkable, affordable (relatively speaking), and very close to Lahaina.
Accommodations: It Depends, But Probably Wailea
While you’ll find plenty of luxury accommodations for rent in both Wailea and Kaanapali, floor plans in Wailea tend to be a bit more spacious. The main complexes in Wailea, including Ekahi Village, Elua Village, Ekolu Village, Grand Champions, Wailea Point, Makena Surf, and Polo Beach Club are all low rise developments that sprawl over finely landscaped acreage. The Kaanapali area offers far fewer low-rise options, in favor of 5+ story hotel complexes with familiar names like Hyatt, Westin, and Marriott.
Most lodging options in Kaanapali are only a few steps from the sand. That means you probably won’t see the inside of your rental car as often and you can swim in the ocean at only a moment’s notice. But the sheer density of the resorts lining Kaanapali Beach also means you’ll nearly always have plenty of company in the pool, at restaurants, and even in the elevator.
That’s just not the case in Wailea, where the condos, pools, and beaches are spread out across a much wider area. In Wailea, we’re biased towards Grand Champions, mostly because you get more for each dollar you spend on accommodations. It’s a bit further from the beach than some of the other condo options, but nightly rates are often 30% less than Ekahi and Elua Villages. Across the board, you’ll find more serenity in Wailea than Kaanapali, with quieter resort pools, wider beaches, and more golf options.
If higher end hotels are more your speed, then Wailea also has you covered with a collection of beachfront resorts unmatched anywhere else on Maui. These include Four Seasons Resort, Grand Wailea, Fairmont Kea Lani, Andaz Maui (Hyatt), Wailea Beach Resort (Marriott), and the adults-only Hotel Wailea.
Beaches: Wailea Wins
Black Rock Beach in Kaanapali is justifiably famous. The high lava rock cliffs stand out against the golden sand and blue sky like sentinels. It’s also one of the more popular cliff jumping spots on Maui. The snorkeling ain’t bad either. But the unspoken secret about the other (southern) end of Kaanapali Beach is that it’s slipping through our fingers as we speak. Forty years of erosion has taken its toll and it’s now a thin razor of sand in some places. It’s still beautiful but the swimming can be a bit rocky at times and you’ll find that most tourists simply opt to spend the day at the resort pools doing laps on the waterslides and pounding piña coladas in the grottos.
Heading 15-20 minutes north from Kaanapali in your trusty Maui rental car, you’ll find a cluster of fantastic cove beaches in the Kapalua area, including Napili, Kapalua, and Oneloa beaches. Napili is the quintessential image of a Hawaiian Beach – a distinct cove with a slightly crescent shape, packed with beach umbrellas and swimmers frolicking in typically calm waters. Kapalua Beach is similarly lovely with crystal clear water and solid snorkeling on calm days. North-facing Oneloa can be windswept with bigger waves and is nearly always uncrowded. Continuing north, the few remaining beaches at this end of Maui are increasingly remote, rocky, and tricky to access.
Wailea, on the other hand, has an embarrassing surplus of amazing beaches lining the coast from Kihei all the way down to Makena. Starting with Kamaole III at the south end of Kihei, the parade of easy-to-access beaches includes Keawakapu (pronounced “keava-kapu”, Mokapu, Ulua, Wailea (sometimes ranked the best beach in all of Hawaii), Polo, Palauea, Po’Olenalena, Chang’s, Maluaka, Oneuli, Little, and finally Big Beach (aka Makena State Park). If the parking lot is full at any one of these Wailea beaches, you can just pop over to the next one. And while it’s a bit further afield, Big Beach is almost never crowded and is a great place to mix with the locals on weekends and holidays. Some of these beaches are so close to each other that you can simply walk between them, especially at low tide.
In our humble opinion, the sheer number and close proximity of world-class beaches in Wailea/Makena gives South Maui a clear edge over West Maui when it comes to enjoying sand and surf on vacation.
Ocean Activities: Kaanapali Wins
Kaanapali’s close proximity to Lahaina Harbor gives it a strong edge when it comes to accessing key ocean activities like snorkeling/scuba trips, sunset cruises, fishing charters, whale watching, parasailing, submarine excursions and ferry passage to Lanai. South Maui is much closer to Molokini but staying in Kaanapali puts you only a 10-minute drive from nearly all other top ocean excursions. In fact, we once spent 75 minutes stuck in traffic trying to get from Wailea to Lahaina in time for a noon sport fishing departure. We missed the boat, lost the $1,000 pre-paid fee (no refunds!), and then had to sit in traffic all the way back to South Maui. My kids still haven’t forgiven me.
If you’re planning to make on-the-water excursions a big part of your Maui vacation, pick your activities well in advance, make reservations, and then decide how often you really want to drive from Wailea versus simply staying right next door in Kaanapali.
Golf: Wailea All The Way
While Kapalua’s famous Plantation Course gets most of the press, Wailea’s Gold, Emerald, and Blue courses team up to make Wailea the true epicenter of golf on Maui. With three distinct 18-hole layouts featuring stunning views of Kaho’olawe, Lanai, and Molokini, Wailea keeps golfers entertained all week long. If you’re a PGA Tour fan and want to walk in the footsteps of the best golfers on the planet, Kapalua may certainly still be worth the effort, although it’ll set you back more than $450. Wailea’s three premier courses clock in under $300, with significant discounts available if you tee off after 12PM.
True golf fanatics will also appreciate Wailea’s relatively easier access to other fun tracks like Maui Nui (10-minute drive) and The Dunes at Maui Lani (25-minute drive). In contrast, both courses are at least 40 mins from Kaanapali, with travel times extending to an hour or more in typical Honoapi’ilani Highway traffic.
Restaurants: Kaanapali Has The Edge
It’s no secret that dining out in a post-pandemic world is something of a double-edged sword. An experience that once defined the very essence of a relaxing vacation has become a total crapshoot. Will enough of the kitchen and waitstaff show up for work? Is the restaurant operating anywhere near its actual capacity? Do I have to spend the first ten minutes staring at my phone or can I get a real menu to hold in my hands? Fortunately, restaurants on Maui have started to answer these questions in the right way and things are (slowly) returning to something that vaguely resembles “normal.”
Wailea’s languid sleepy pace is something of an achilles heel when it comes to dining out. The resort hotels offer some fantastic dining options as does The Shops at Wailea, but the menus tend to be very similar and the prices are higher than a Mexican fan palm. Wailea Kitchen offers a unique indoor/outdoor setting, Monkeypod is a perennial favorite, and Lineage sports creative cocktails and an Asian-fusion menu. Also in Wailea, The Market serves up excellent sandwiches to go. Their Gino’s Dakine steak sandwich is our go-to favorite to devour by the pool or take to the beach.
It’s not that Wailea doesn’t have some fantastic dining options, it’s just that the Kaanapali area has more variety across all price points. That’s why West Maui ultimately gets the nod when it comes to restaurants. The higher density accommodations and the ease of access to Lahaina mean that you’ll simply have more options for both lunch and dinner when staying in Kaanapali versus Wailea.
There are simply too many restaurants in the Kaanapali area to cover them all, so we’ll just mention a few of our favorites. For less-pricey dinners, there’s something for everyone at the Hoopiilani Food Truck Park. It’s casual, family-friendly, and delivers a nice respite from the heavy richness of too much hotel food. Get there early to avoid long wait times! Beyond food trucks, the sky’s the limit for West Maui dining.
Monkeypod is a popular option in Whaler’s Village, as is Hula Grill and Leilani’s. Duke’s Beach House is a bit further north and serves up classic tropical fare like panko crusted fresh fish and coconut shrimp. A further jaunt to the north brings you to Miss Arepa, a more casual option for a gluten-free South American-inspired lunch or early dinner. The Fish Market Maui is also up this way and features amazing poke and all sorts of other fresh-catch options.
And then of course Lahaina is only a few miles south and offers more than 100 restaurants across all categories. Some are better than others, but that’s a topic that deserves its own dedicated post.
Nightlife: Kihei & Lahaina
Nightlife in Wailea is a mongoose crossing the road after dark. Seriously, there are some very nice hotel bars in Wailea but they are spread out and fairly quiet. Monkeypod Kitchen, just around the corner from our Grand Champions condo, has a great indoor bar that serves up their famous foamy mai tai until last call just before 10pm. Those are your best bets for nightlife in Wailea, although you can always head north into Kihei to find a more active bar scene at spots like South Shore Tiki Lounge, Lava Rock Bar & Grill, and VIBE Bar.
Kaanapali itself is similarly challenged. Most of the bars and restaurants lining the beach peak in the late afternoon through sunset and then quiet down by 9pm. Nearly all are connected to a hotel so the crowd is usually 100% tourist. Our favorite spots right in Kaanapali include the northern outpost of the aforementioned Monkeypod Kitchen, the popular Barefoot Bar at the Hula Grill, and the Ohia Bar at Duke’s.
Lahaina was where the action was back in 1846 when 700+ whaling ships docked there in a single year, and it’s still the place to be seen and heard after dark. The restaurants and bars that pour out onto Front Street took a big hit during the pandemic but have started to bounce back with the elimination of restrictions on indoor gatherings. The Dirty Monkey is always a solid choice with DJs, live music, plenty of dancing, maybe a few too many TVs, way too many whiskeys, and a game room too. Hit the Sly Mongoose for an authentic dive bar experience and some local flavor. Also be sure to check out Down the Hatch for some adult-flavored shave ice and Fleetwood’s on Front Street for rooftop views.
Wherever you end up, keep an eye out for the ghosts of 19th century pirates, rascals, and scallywags roaming the wharves.
Wailea vs Kaanapali: And The Winner Is…
You. Seriously, you really can’t go wrong whether you decide to stay in Wailea or Kaanapali. Both are worthy of your hard-earned vacation dollars and both offer easy access to all the things Maui is most famous for – sandy beaches, tasty mai-tais, swaying palm trees, pristine golf courses, and so much more. BUT, there are significant differences and for those that know exactly what they want from their next Maui vacation. Making the right call can elevate your experience from merely memorable to totally shaka.