How They Compare—and The Best of Both Worlds
Maui’s iconic leeward coast is what Hawaiian postcards are made of: Buttery-sanded beaches, leggy palm trees, glitzy resorts, humpback whales breaching from the water—and heaps and heaps of sunshine.
And while the leeward edge presents several similarities across its stretch—from Makena to the south and Kapalua to the west—there are distinct differences between its southern and western ends.
Whether you’re struggling to decide between staying in Kihei or Ka’anapali, or are simply scheduling a fun-packed Maui day, here’s how the two sides compare so that you’ll know what to expect. You should also listen to The Aloha 360 Podcast, where John and Leslie have done their takes on perfect day itineraries for each region of Maui.
Weather
It’s no secret that Hawaii’s climate is one of its biggest draws, particularly during the winter. And while Maui’s northern and eastern shores—to say nothing of “Upcountry”—boast countless merits of their own, the island’s leeward side is famed for its predictably beautiful weather.
Still: Kihei—the South Side’s largest town—claims an average annual temperature of 84 degrees, just a smidgen cooler than Lahaina, the West Side’s urban center. Both tend towards dry, hot, and dusty during the summer months, with nearly impeccable weather during Spring and Fall. (Yes, Maui winters do exist.) Their outer regions—for South Maui, that would be Wailea and Makena; for West Maui, it’d be Ka’anapali, Napili, and Kapalua—are prone to nippier spells with greater cloud covering; Makena, for example, is known for its signature cloud. Napili and Kapalua, meanwhile, see more tropical showers, with an annual rain fall of 22 inches. (By comparison, Kihei experiences a mere 12.) One thing to keep in mind when making plans, however: Lahaina translates to “cruel sun”—and its name often justifies itself with relentlessness.
In Sum: Your Best Bet
Visitors seeking heat and ample sunshine will be stoked with both Kihei and Lahaina; those sensitive to hot temperatures—or those who want a cooler and lusher experience—will find much to love in the communities of Napili, Kapalua, and Wailea.
Accommodations
The lion’s share of the island’s resorts, condos, and Airbnbs rest on the leeward side, where several of Maui’s most acclaimed beaches are fronted by glam resorts replete with verdant landscaping, pools, and restaurants. Ka’anapali went down in history as Hawaii’s first master-planned resort community, and the organization it implemented in the 60s persists today with one hotel after the other bridged by a boardwalk facing the Pacific.
Wailea—one of the island’s poshest parts—took its cue from its western cousin, presenting hotels that range from the uber-chic Andaz Maui at Wailea Resort to the ever-elegant Four Seasons Resort Maui at Wailea (these resorts, too, are connected by a wonderfully-walkable path that parallels the ocean).
The primary difference between Wailea and Makena rests in price. The average cost of a night in Wailea is $400, while you can score a hotel room in Ka’anapali for as little as $200. Additionally, given that Ka’anapali was conceived of and created when most of Wailea was little more than a kiawe forest, Wailea’s resorts, from the Marriott Wailea to Hotel Wailea, are newly refurbished and more luxurious. The Sheraton at Black Rock is situated directly on our famous Kaanapali Beach. Head past Ka’anapali, however, and you’ll be presented with two of Maui’s most opulent venues: Montage Kapalua Bay and The Ritz-Carlton.
But outside of these “resort” communities, you’ll find condominiums that may not offer valet or manmade waterfalls but are economically feasible. Kihei tops with its bank of condos, most located on or across the street from the beach. Lahaina, on the other hand, rules when it comes to laidback inns that are less spendy than resorts but big on charm. (Check out The Plantation Inn for reference.)
In Sum: Your Best Bet
Keen on having a resort experience, but at a lesser cost? Head to one of the mega hotels on Ka’anapali Beach—you won’t be disappointed. Interested in having the most upmarket experience around? Book a room in Wailea or Kapalua. Singletons will be pleased with staying at an Airbnb in the super-cruisable Lahaina, while families with keiki will get the best bang for their buck by renting a condo in Kihei. Just stay south: Kihei beaches tend to get murky for snorkeling and swimming past Cove Park.
Another major factor to consider is proximity to the rest of Maui. If you're looking to do sunrise at Haleakala, drive the Road to Hana, or do a discovery flight from Kahului, you'll be much closer for this kind of exploring in north Kihei than you would in Kaanapali.
The Great Outdoors
Maui’s leeward side inarguably presents the best beaches on the island—if by “best” you mean golden sand, perfectly-swimmable waters, outstanding snorkeling opportunities, lulling waves gentle enough for first-time surfers, and sunshine in spades. (Those drawn to more radical beaches, with craggy coastlines, epic swells, and dramatic weather, will find their thrills on the northern and eastern shores of the island.) Both the South and West Sides offer gorgeous coves, from the miles of stunning beach that make Keawakapu Beach where Kihei and Wailea meet to the world-renowned Napili Beach north of Lahaina.
South Maui, however, has the highest number of sunbath-able white-sand gems, include the three winners of Kamaole Beach Parks I, II, and III; situated side by side, and you can beach-hop without having to step foot into your car. With a boating ramp (with snorkeling trips to Molokini by Redline Rafting) between the latter and Keawakapu, what follows is another string of beaches that are, well, sheer perfection. The beaches in Lahaina are excellent options for beginning surfers, but narrower and usually more crowded than the Southern sands.
Both the South and West Sides provide boatloads of ocean activities, including snorkeling, surfing, stand-up paddling, outrigger canoeing, and daily jaunts to the outlying volcanic caldera (and snorkeling mecca), Molokini. By far, the outdoor experience we tend to move towards the most is on the Kai Kanani out of Makena for their sunset sail. This is one of those trips you can take year-round and have an incredible time.
Beyond the sand and sea, however, the West Side rules in terms of non-beach outdoor activities. Lahaina offers cultural walks that allow visitors to get a glimpse into its past as the former capital of Hawaii. Hiking opportunities also abound, from the Lahaina Pali Trail to Mahana Ridge. More intrepid travelers will also find, on the west end, the Nakalele Blowhole (and Point) and parasailing. The South Side, meanwhile, possesses the splendid and hypnotizing Hoapili Trail—a path that’s part of the ancient King’s Highway—and Kealia Pond National Wildlife Refuge. Both are fantastic, but non-oceanside activities on the South Side are fewer.
In Sum: Your Best Bet
Visitors eager to spend most of their vacation soaking up the sun from the comfort of their towel will be delighted with the South Side’s numerous jewels. Those hoping for a greater diversity of activities will be captivated by the West Side’s offerings.
Entertainment and Nightlife
There’s no contest: Lahaina easily goes down as the island’s most electrifying place for after-dark adventures. As a former whaling port (and with the raucous rep it inevitably crafted), the town of 12,000 has maintained its lively status with bars, clubs, and restaurants that sure know how to party. Front Street is where it all takes place, from live music at Fleetwood’s on Front St. to late-night dancing at The Dirty Monkey. The West Side also boasts some of the best entertainment on the island, including the the Royal Lahaina Luau, Warren & Annabelle’s Magic Show, and Masters of Hawaiian Music Slack Key Show. What’s more, those staying on the strip of Ka’anapali can barhop at the resorts’ on-site taverns, settle in for a luau—and end it all with drinks and dessert at the perennially popular Duke’s Beach House.
The South Side, meanwhile, presents something of a split personality. While most of the island tends to shut down early—there are those ocean sports to be relished in the morning—Kihei’s Triangle often makes a ruckus into the wee hours. Situated in South Kihei, the cluster of bars includes a karaoke hubbub, an Irish tavern, two nightclubs that can be mad-fun for dancing, a tiki bar beloved by locals, a divey saloon cherished by Hells Angels, and a late-night happy hour spot that serves incredible sushi. Also, just down the street is one of our favorite spots to enjoy a different and more creative kind of fun at Island Art Party. Here you'll enjoy libations and snacks while being walked through making your own work of art. They make everything easy and fun, while helping you bring home a unique and personal souvenir.
Some of Wailea's trendiest spots—Monkeypod Kitchen and Pint + Cork—are a tad more sedate but no less fun. The Four Seasons and the Andaz also boast some of the loveliest bars on the island—complete with ocean views and live music by local talent—while Mulligans on the Blue presents a terrific weekly lineup of entertainment.
In Sum: Your Best Bet
Young and just want to have fun? Head to Lahaina; Front Street rarely fails in terms of action. More inclined to savor a glass of Viognier while gazing at the moonlit water from a palm-filled lobby? Enjoy all the plushness Wailea has to offer.
Dining and Shopping
It’s a tight contest when it comes to the dining and shopping experiences on Maui’s southern and western ends. To the south, and you’re given The Shops at Wailea, a two-story, immaculate plaza that boasts local wares, luxe designers, and the latest in beachy attire: Louis Vuitton, Cos Bar, Lululemon, Mahina, Quicksilver, and more. Art galleries dominate its second floor, where you can find everything from unique jewelry at Ki’i Gallery to stunning photographs at National Geographic. Shopping in Kihei proper, however, is sparser and less enticing, but Hi Tech sells excellent threads while Kihei Kalama Village offers a cornucopia of souvenirs (plus shave ice!)
Dining at The Shops—and on the South Side in general—is just as diverse. Wailea is home to several of Hawaii’s finest chefs and their award-winning restaurants, including Hawaiian Regional Cuisine pioneer Roy Yamaguchi’s Humble Market Kitchin at the Marriott Wailea, Bev Gannon’s eponymous bar and restaurant on the edge of Makena, and Peter Merriman’s perennially-packed Monkeypod Kitchen in Wailea Gateway Plaza. Kihei tends towards the more laidback end in terms of eats, with a fantastic brewery—Maui Brewing Co.—on the slopes above the town, a great tavern (with equally superb poutine and salads) called Shearwater, some of the island’s best sushi (Sansei and 5 Palms), and local eats that are easy on the wallet (Nalu’s, Da Kitchen, and Homemaid Bakery, to name a few).
Maui’s West Side also has shopping and dining opportunities galore. Browsing the 40 fine art galleries, boutiques, and surf shops along Lahaina’s Front Street, for instance, can be an all-day, enormously enjoyable affair, with stars that include Kush Fine Art, Tilly Timms (for those searching for eminently wearable shirts), and kiosks peddling locally-made soaps and accessories. Both essentials and extravagances can also be found at Whalers Village in Ka’anapali, including Sephora, Crazy Shirts, Tori Richards, and Kate Spade.
As for dining? The southern and western ends of the island are again in a stalemate. The restaurants along Front Street range from family-friendly, chain venues (such as Cheeseburgers in Paradise) to marvelously-appointed spots like Lahaina Grill and Mala Ocean Tavern. Those on the makai (ocean) side of the famed street have the advantage of being mere yards away from the water; even cafés on the periphery—such as Slappy Cakes—are downright memorable. Ka’anapali has dazzling fare as well, such as Japengo in the Hyatt (though obscenely priced), which was recently named the Best Resort Restaurant on Maui by readers of the rag Maui Time.
In Sum: Your Best Bet
Both sides have much to offer in terms of dining and shopping. Keep in mind, however, that most of the South Side’s best offerings are located not in Kihei but in Wailea.
Culture
While South and West Maui tie in nearly every category, the West Side takes the cake when it comes to cultural offerings. Consider it this way: With the exception of Makena (which, prior to weather changes that rendered the region dry and unfruitful, was a flourishing farming and fishing community), the South Side was, for a long time, nothing but arid land—so much so, native Hawaiians referred to it as “Kama’ole” (or “barren”). It wasn’t until the 1970s, when developers began building inexpensive condominiums near the coast (while water was piped in from the ‘Iao aquifier) that the desolate town began to fill with inhabitants and visitors; today, it’s the 12th most populated region in the state.
Meanwhile, Lahaina has enjoyed a rich and vibrant history—and long before the annexation of Hawaii. Prior to the arrival of missionaries, the district, originally known as “Lele,” was designated as the capital of the Kingdom of Hawaii by Kamehameha the Great while throughout the early 19th century its waterfront operated as one of the primary ports for the North Pacific whaling fleet, seeing as many as 400 ships in its wharf during whaling’s heyday. Home to Chinese immigrants who flocked to the island during the sugarcane boom, the buzzy town’s vivacity has endured throughout the centuries, from the opening of the now-iconic Pioneer Inn in 1901 (a National Historic Landmark that once hosted the likes of Jack London and Sun Yat-Sen) to the annual Halloween parade and street party as well as lauded Lahaina Luaus.
Much of this storied past can still be savored today. Visitors can take a peek inside Lahaina’s old prison house—which was built by Kamehameha III to detain disorderly sailors—or tour the Wo Hing Museum, a former “society hall” that served as a meeting venue for religious Chinese ceremonies. Other gems well worth your time include the Old Lahaina Lighthouse, the courthouse, Hawaii’s first stone church, the former home of Lahaina’s first Protestant missionary, a 12-foot bronze Buddha at the Lahaina Jodo Mission, and the aforementioned Pioneer Inn—where you can brush up on your Hawaiian history while enjoying one of their mouthwatering Bloody Marys.
In Sum: Your Best Bet
Happen to be a culture buff who loves to be surrounded by relics of the past? There’s no doubt about it: Lahaina is, in the parlance of the times, where it’s at. Far more interested in what’s new and fresh? You’ll be electrified by South Maui’s Wailea (though they are also known for memorable Wailea luaus. But no matter where you stay—or where you to choose to spend your day—know this: Every part of Maui is nothing short of amazing.
