Top Things to Do on Maui: A Day by Day Itinerary

This lovely post was contributed by Maui Guide, a handful of Maui residents who decided to share their love of Maui with the world! With each post, they hope to leave visitors better educated and prepared for their visit to the islands.

Visits to Maui tend to be marked by a mix of exhilaration and poignancy—there’s endless fun to be had with a limited time to do them. Here are ten intoxicating ways to spend your Maui days—and where to eat along the way:

La Perouse Bay + Keawakapu Sunset + 5 Palms

Driving out to La Perouse Bay is an experience in itself: the glossy lawns of Wailea’s resorts give way to kiawe fields and mile-long expanses of alabaster sand. Skirt past Makena State Park until the road grows narrower; here, quiet announces itself in the form of axis deer flirting beside the road and the occasional pueo darting behind the clouds. The barren landscape of La Persouse Bay is Insta-worthy in every possible way, but the real treasure to be found is seeing the backside of Molokini Crater and Pu’u O’lai from its direction. There are a few companies that take you on Molokini snorkeling tours on the backside, which is pretty impressive.  It requires an exhilarating ride out from Kihei Boat Ramp on Redline Rafting. We’ve always had fun on those trips.  

Or stay and Snorkel in the pebbly cove at La Perouse—or walk through the lava fields—before driving your way back towards Keawakapu Beach on the edge of Kihei, where you can laze on the grass in front of the Mana Kai for a sunset that might linger for life. 

Appetite stirred, grab a stool at 5 Palms (on-site), where you’ll struggle to make a choice between Molokai Potato Gnocchi and Grilled Prawns.

Hula Festival + Lahaina Historic Walking Tour + Kimo’s

Hawaii is more than just the origin of kite surfing and the shaka sign: Hula is rumored to have gotten its start in Maui County, when Laka—the goddess of hula—shared her evocative dancing from a sacred hill in Kaana. Molokai may be just a ferry or plane ride away from Maui’s shores, but no need to travel more to experience the hula it birthed: Every August, the grounds beneath Hawaii’s largest banyan tree sees the Emma Farden Sharpe Hula Festival—a day of traditional and modern hula performances, exhibits, and workshops in the name of one of Hawaii’s greatest kumu hula. Mark your calendars!

Gain an even stronger understanding of the islands’ storied past on a walking tour of the state’s former capital, where you’ll find Hawaii’s first stone church, a 19^th century prison, and a cemetery filled with Melville’s ghosts. 

Score an ocean-side seat at Kimo’s for dinner—the island institution, with its Bikini Blonde-battered fish and chips and ahi poke towers, is one part tiki bar and three parts sheer elegance.

Kaupo + Ka’eleku Cave + Milagros

With its long, sunlit days, Maui is made for taking the scenic route; and while few roads in the world are as picturesque as the trek to Hana, taking the “back way” in presents its own brand of wows. Wrapping around the rear of Haleakala, the journey takes you through the ancient fishing village of Kaupo, past grazing cattle, and along jutted paths reminiscent of the rural Down Under. 

Once you’ve reached Hana, check out Ka’eleku Cave, where the depths of the town’s renowned lava tube can be accessed with a guide (and powerful flashlights). 

Circle back to civilization by heading towards Ke’anae (and stop at roadside waterfalls and vast lookouts on the way) before settling in for a late-night meal at Paia’s Milagros. Savor a plate of Portobello Mushroom and Spinach Quesadillas from a seat outside: People-watching in the “Windsurfing Capital of the World” is a huge part of the town’s charm.

Haleakala Sunrise + MauiWine + Kula Bistro

1.5 million annual visitors ascend the steep, switchback slopes of Haleakala to see the sunrise from its summit. There’s a solid reason why: Daybreak from the rim of Maui’s largest volcano puts sear-marks on your soul with its indelible unfolding of dazzling shades. Leave driving in the dark to the folks at Skyline Hawaii, who will take you on a memorable tour of the 10,023-foot volcano and its surrounding environs. 

Breath restored, imbibe in a flight of island-crafted wine at Maui’s only winery; the glimpse inside King’s Cottage—where the last king of Hawaii is said to have reveled—is worth the trip alone.

End it all chowing down at Kula Bistro, where you’ll find homey faves like Vodka Pomodoro next to local eats (hello, Kalua Pork Eggrolls).

Baldwin Beach + Mystery Maui + Aria’s Restaurant

Baldwin Beach is hailed as the “North Shore’s Big Beach.”  Long stretches of gorgeous sand and turquoise waters await a much smaller crowd than you’ll find at south or west Maui beaches.  Check the wind before going, which is largely why less people visit, as well as the surf.  Just like Makena’s Big Beach, this spot gets serious swell that can be dangerous for those new to waves.  

Sunbathe and swim before dusting off the sand to play a chief investigator at Mystery Maui. Located in Wailuku, this fresh take on island nightlife has become a favorite of kama’aina and their kids, because what’s more fun than discovering hidden clues and solving clever (sometimes hilarious) puzzles? 

Once you’ve solved the mystery, head to Aria’s Restaurant. This lively bar and restaurant serves island favorites like tempura Mahi fish tacos, braised chocolate chipotle lamb shank and Asian braised pork belly.  YUUUUM!

Mendes Ranch + Bailey House Museum + The Mill House

Little did the Mendes family know that their relocation to Maui from Portugal would result in a huge boon for Hawaii. Once a working ranch, the family owned and operated outfit now offers morning and afternoon Maui horseback rides across its gorgeous, windswept acreage, where visitors are granted panoramic views of the central coastline. 

Saddle off, peer back in time at the ever-enchanting Bailey House Museum in Wailuku, where you’ll find artifacts from the bomb-pitted island of Kaho’olawe and photos of Maui’s first missionaries. 

The warm—let’s be frank, tropical—weather is ideal for al fresco dining, which is just one part of the pleasure that is dining at The Mill House. Nestled on Maui Tropical Plantation in the green velvet that is Waikapu Valley—and boasting killer views of the West Maui Mountains—this farm-to-fork venue changes its menus twice daily to reflect what’s freshest around the island. Come early for a craft cocktail at their horseshoe bar, where relics from Maui’s sugarcane era are paired with exceptional drink choices.

Molokini Snorkel + Peace Park + Pint and Cork

The Kai Kanani has earned a reputation as one of the most cherished boating companies on the island. Let them show you their twist on early-morning luxury with a catamaran cruise out from Makena to Molokini—the teeny, crescent-shaped crater 15 minutes by boat off Maui’s southern most coast. Here, you’ll find droves of marine wonders in every possible color; riding back to the Maluaka Beach in the sunshine is almost as fun as diving under. 

Join south side residents at Kihei’s Peace Park, where the grassy slope gives you the perfect perch to watch the sun sink between the outer islands. 

For dinner, check out one of Wailea’s most happening spots, Pint and Cork. Coined a gastropub and “neighborhood gathering place,” this sleek but still chill place possesses an epic collection of draught beers and plates ranging from warm mushroom salad to pork adobo moco.

Surfing Goat Dairy Farm + Lumeria + Mama’s Fish House

Surfboards are no rare sight in the Hawaiian Islands, but they take on a whole new lure when they’re used as a fence to pen in baby goats. Get the chance to see several scampering about at Surfing Goat Dairy Farm in lower Kula, where the savannah-like conditions are well-used to breed, feed, and milk more than a hundred Billys and their kids. Cheese making demonstrations follow alfalfa feedingsstraight from your hand, while their display of goat cheese truffles—including an ultra-creamy Rum Raisin—will prompt even the most virtuous eaters to cheat on their beach-break diet. 

Beat the heat by heading next to Lumeria in Makawao, a wellness resort that offers daily yoga and meditation classes. Not up for instruction? Spend an hour or two finding your inner om by touring their lush grounds. 

Then, be quick enough to catch sunset above Kuau Cove at the world-renowned Mama’s Fish House. The second most popular table in the U.S. (according to OpenTable), this lovely, romantic venue plates seafood so fresh the time, place, and fisherman is listed on the menu.

Twin Falls + Ho’okipa + Makawao Third Friday

True, summertime evokes backyard barbeques before dense rainforests for most, but this is Hawaii, after all: We may be part of the United States, but we’re still an exotic, tropical island. Meaning, our jungles are made all the more enticing with otherworldly plants and tumbling waterfalls. Experience one of Maui’s most beautiful and accessible at Twin Falls, a pair of cascades on the way to Hana. 

On your way back, hit up Ho’okipa Beach Park. The waves may be flat this time of year, but the vistas of Maui’s rugged coastline are perennial. 

Conceived by the Maui County Office of Economic Development, Maui Friday Town Parties were created to highlight our small towns’ art and food scenes and historic charm. Should your North Shore day fall on a Fri-nally, head back upcountry for Makawao’s iteration of the island-wide endeavor. The paniolo-themed block party features local artisans, live entertainment, fun for the keiki, and a pop-up food court. 

Outrigger Canoeing + The Shops at Wailea + Ferraro’s

Canoeing has a long history in Hawaii—it is, after all, how the archipelago was discovered. Experience this enormous part of the islands’ history at the uber-pristine Wailea Beach, where skilled guides will take you and your crew on an outrigger around South Maui’s fabled coastline. Along the way, you’ll be given facts about Maui and its people and culture. (Bonus points: the waters here are home base for some of our magnificent honu.) 

Dust the sand off your feet—or not—before sauntering through the boutiques and bars at The Shops at Wailea (two gems not to miss: SoHa Living and Mahina). 

Then, splurge with class at the Four Seasons’ Ferraro’s Bar e Ristorante, where live violin music is paired with roasted racks of lamb and chanterelles. Soak up the view of the Pacific, where the sun may be setting on summer but is guaranteed to return to this special place domani. Or, rather, ‘apopo. 

Much Mahalo to the folks at Maui Guide for sharing these amazing itinerary options. I know I’m inspired for my next Island hop! Head on over to Maui Guide and show them some Aloha!

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