Maui may not have the same colorful fall foliage you find on the mainland – aloha, mainland! – but those seeking warmth when autumn kicks in are sure to find plenty of it on the lush shores of the Valley Isle.

While it’s a shame for some that school is back in session – lookin’ at you, high schoolers – September on Maui is synonymous with thinner crowds, crisper colors and cooler air. If you find yourself lucky enough to be heading to the land of aloha this time of year, these local activities are a memorable way to shake off those post-summertime blues on one of the world’s loveliest islands…


Maui Travel Guide to Glorious Activities


Molokini Crater + Coastal Clean Up + Gannon’s

Take advantage of the fact that your body’s alarm clock is likely as confused as a mai tai in Montreal, and set your alarm early for a sunrise snorkel tour at Molokini Crater with the folks at Kai Kanani. Departing around 6am from the shores of south Maui, the tour includes breakfast, a second snorkeling stop at the locally famed Turtle Town, and even a post-snorkel bloody mary or mimosa (chee!).

After returning to shore, we also encourage you to give back by participating in Maui’s International Coastal Clean Up at Po’olenalena Beach Park, a volunteer event on Maui’s south side that blends cleaning with camaraderie. Because ecotourism offers new levels of insight and support, this is your opportunity to experience the meaning of malama ‘aina – in essence, taking care of the land – and the role it plays in the local way of life.

Finally, head to the south end of Makena’s Maluaka Beach for a well-deserved dip before rewarding yourself at Gannon’s in Wailea. Helmed by one of Hawaii’s most respected chefs, Bev Gannon, dinner here is one of the most exquisite on Maui thanks to striking views of Pu’u O’Lai, entertainment from local musicians, and a raw bar that’s beyond delicious.

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Mokapu Beach + Maui Blues & Jazz Festival

Wailea’s beaches are the epitome of Maui’s finest: pristine sand, translucent water, swaying palms and skies that aren’t even surprised at their own above average amount of rainbows. Every beach from Keawakapu to Makena is downright stellar, but Mokapu Beach – a small, white sand cove fronting The Andaz Maui Wailea Resort – soothes the soul with its views of Molokini and Kaho’olawe. Lunch can be found at The Shops at Wailea, where you might battle between a Bib Burger at Pint + Cork and a shrimp salad at Longhi’s, followed by a touch of souvenir shopping before enjoying a night out.

When you’re ready, head to the stunning Four Seasons Resort Maui for the Maui Blues & Jazz Festival, where Hall-of-Famers pair up with Na Hoku winners and local talent to impress even the most skeptical jazz and blues connoisseurs. A 5 station gourmet dinner prepped by the island’s leading chefs adds an extra touch of harmony to this much-loved musical event.

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Maui Dreams Dive + The Mill House

Frogfish, sea stars, Hawaiian Green Sea Turtles… most abound on a tour with Maui Dreams Dive Co., where you can take an ‘underwater scooter’ to cruise swiftly along the ocean floor. The staff at this nearly 20 year old outfit work diligently to preserve our oceans, but it’s their fun, carefree attitudes, combined with their knowledge of the Pacific, that renders trips with them a delight.

After resting up under the shade of a palm or the covers of your hotel room, head to the centrally-located Waikapu Valley. The mountains here appear accordion-ed with green, and a coolness descends as you approach; both are celebrated at The Mill House, a lovely restaurant tucked into it all at the Maui Tropical Plantation. Winner of the Silver ‘Aipono Award for Maui’s Best Restaurant of 2017, as well as Gold for Maui’s Most Innovative Menu, this farm-to-fork venue takes novelty to new heights by drawing menu inspirations from the plantation’s diverse range of crops. Dine outside – the air may have a hint of September chill (it’s your time to shine, Canadians), but the views will win you over.

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Ocean Vodka Organic Farm & Distillery + Olinda Forest

Most of that fall warmth will be discovered – and savored – along Maui’s leeward coast, but that doesn’t mean you shouldn’t take a day (or more) to explore Upcountry. Verdant and tranquil, the towns of Kula, Makawao, and Pukalani present a quieter side of Hawaii. Farms in the region also make good use of the island’s volcanic soil, including Ocean Vodka Organic Farm & Distillery.

Daily tours take guests into the sugarcane fields, where their award-winning spirits are made, as well as through their 6,000 square foot solar-powered warehouse and bottling center. End it all with tasting samples in the Martini Garden, where you can enjoy a libation made with fresh grown Maui herbs. Then, shake off that daytime buzz with a leisurely stroll along the Waihou Springs Trail. Otherwise known as the Olinda Forest, this 1.8 mile looping path through 186 acres of pines is beautifully enhanced by the scent of eucalyptus.

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Turnbull Fine Art + Feast at Lele

We get it… watching someone at work is seldom a bucket list essential. When you’re visiting Maui, however, glass blowing and carving become a new form of entertainment in Maui’s cowboy digs of Makawao Town. To watch master sculptors in action, head to Turnbull Fine Art in Kahakuloa; here, a husband and wife team invite you to peer in on their creations-in-the-making before touring their two-acre garden of sculptures.

Grab a slice of homemade coconut cream pie from Lorraine’s or a loaf of banana bread from Julia’s – arguably the best on the island – before winding your way back toward Lahaina for the Feast at Lele. The brainchild of Old Lahaina Luau’s creators, this Polynesian feast and show presents the finest food and dancing from the Pacific island nations of New Zealand, Tahiti, Samoa, and of course, Hawaii.

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Parasailing + La Perouse with Redline

Ocean adventures are one of Maui’s biggest draws, partially accounting for the 1.5 million visitors the island sees annually. And while parasailing may have been invented by a Frenchman in the 1960s, it’s become a frequent sight off of Ka’anapali Beach, a glorious stretch of sand in Hawaii’s first master-planned resort community. Safe and surreal, the sport allows you to soar over the sea without, well, having to do much of anything except enjoy the scenery with your eyeballs. Consider it luxury kite-surfing. September is the last month of the year to get your glide on, so relish it while you can.

For those looking for a more immersive ocean experience, Redline Rafting offers daily Molokini snorkeling tours to the lesser visited ‘Forbidden Coast.’ Departing from Kihei boat ramp, their high speed raft gets you places other boats won’t, including the back side of Molokini Crater and La Perouse Bay, where you may just run into a pod of Hawaiian Spinner Dolphins while marveling at the rugged, lava rock-covered beauty of this quieter, understated area of south Maui.

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Molokai Sea Cliffs + Paia

Molokai, the lush, laid back neighbor island off of Maui’s west coast, claims the title of the world’s tallest sea cliffs. Mounting 3,315 feet into the sky, these enormous beauties near Kalaupapa – the island’s former banishment grounds for people diagnosed with leprosy – can only be accessed by a trail not suited for cars. Enter Blue Hawaiian Helicopters, who offer West Maui & Molokai Helicopter Tours with a pilot who doubles as a State-Certified Tour Guide. Brush up on your knowledge of Maui’s history, geography, culture, flora and fauna while taking in views of the West Maui Mountains, Pailolo channel and sea cliffs.

Feet squarely back on ground, drive to the north shore hippie gem of Paia, where low-slung storefronts hold galleries, boutiques, and plenty of funky taverns to people watch to your heart’s desire. After eyeing the goods at Alice in Hulaland, a one-of-a-kind shop that peddles everything from sunglasses to bongs, catch sight of a few pre-winter sets at Ho’okipa Beach Park. Home to some of Maui’s most legendary waves – and the Billabong Pro – this is the spot to kick back and watch local surfers and kite surfers do their thing. After watching sunset from the beach’s headlands, backtrack to Paia, the “Windsurfing Capital of the World,” where you can sip a locally-crafted beer at Rock & Brews before eating what’s been voted Maui’s best pizza at Flatbread.

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Massage + Kohola Brewery

There’s no time like vacation to give your knotted muscles a rest. Treat yo’self to some of the island’s most talented hands at Maui’s Best Massage, or have them come to your hotel or condo room for added convenience. Located in the Island Surf Building in Kihei, this heavenly treatment center focuses on signature massage styles such as Relaxation, Deep Tissue, Lomi Lomi and a Couples or Group massage.

When thirst strikes, head to the heart of Lahaina Town, where independent craft brewery Kohola pours pints that range from a tangy Talk Story to a sweet-but-delicate Lokahi Pilsner. For dinner, book a table at the uber-elegant and award-winning Lahaina Grill; the entrees aren’t cheap, but they’re worth the splurge.

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Kula Botanical Garden + Haleakala Sunset

Founded more than 40 years ago by Helen and Warren McCord, Kula Botanical Garden highlights Maui’s fertile farm country with over 8 acres of wonders, ranging from proteas to orchids. Waterfalls and ponds add to the allure, while the panoramic views of the island are well worth the uphill drive. Grab an early dinner at the rustic, delicious Kula Bistro – where you’ll find signature pasta dishes and tender steaks – before adding layers of clothes for one of Haleakala’s legendary summit sunsets.

Navigating the switchback roads after dark might sound like a job best left to someone else, so let an experienced guide handle the wheel while learning a number of fascinating Hawaiian facts from your Skyline Hawaii guide. Manned by a team of highly experienced guides, this eco-friendly outfit – who donates a portion of proceeds to local conservation efforts – illustrates this sacred spot with humor and skill. Mother Nature does the rest, and she’s on fire.

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Festivals of Aloha + Island Art Party

An annual tradition throughout the islands, the Festivals of Aloha were founded to showcase and celebrate Hawaiian heritage. Royal pageantry, live music, parades and activities for keiki (and the whole family) render it one of the most beloved parts of fall for kama’aina and visitors. Its location alone are deserving of room on your itinerary, as Lahaina’s Banyan Court Park holds the largest banyan tree in the state, as well as an old prison and courthouse.

Back down in oh-so-lovable Kihei Town – don’t you just love a good rhyme? – book a spot at one of Island Art Party’s group painting classes. All of the necessary painting materials are provided –  including a talented (and patient) painting host slash instructor – and they have a bar in case you need a little liquid assistance to create (or tolerate) your tropical masterpiece. Return home with your own personally-painted souvenir to showcase proudly, or give it away as a present to that coworker you’re never sure you like. Either way, you’re bound to have a good time.

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Underwater photography by Peter Rimkus.