5 reasons to visit Maui, the second-largest of Hawaii’s islands (2024)

Maui is known for many things: its white sand beaches, its plethora of snorkelling spots, and its waterfalls are just a few. But the island – the second-largest of Hawaii's islands – is also known around the world as a destination for ultra-wealthy holidaymakers.

In 2011, Peter Thiel, the founder of PayPal, dropped US$27 million on a 1.7-acre Maui property. Meanwhile, celebrities like Oprah and Woody Harrelson have been known to snap up second homes on the island.

It's also an increasingly popular spot for tourists. In 2019, according to the US News and World Report, Maui welcomed three million visitors for the first time since the island began tracking tourism numbers in 1990.

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Fortunately, if you're one of those tourists, there are plenty of spots where you can find a great night out or a delicious meal – you just have to know where to look. We got the inside scoop from Josh Jerman, a Maui-based real-estate broker. From the places with the best dishes to the area with the biggest homes, Jerman's tips will help guide you on the perfect trip through one of America's most beloved islands.

Best eats

For a good meal, Jerman suggests heading over to Wailea, a small town made up of just over 5,600 people. His favourite place there is called The Restaurant at Hotel Wailea, where the menu aims to reflect Hawaii's history and culture.

“The Restaurant overlooks Wailea and has an intimate setting with outstanding sunset views and a creative menu with locally sourced ingredients,” he said.

Best nightlife

If you're looking for a fun night out, Jerman says Lahaina is the place to go. Lahaina is home to Front Street, which is filled with restaurants, shops and bars along the water. Especially noteworthy is Fleetwood's – a restaurant and bar owned by musician Mick Fleetwood.

“Fleetwood's is happening and Mick Fleetwood often plays along with surprise guests such as Sammy Hagar and Steven Tyler. The rooftop lounge is the coolest late night scene, open to starry skies, a lively bar, and live music,” said Jerman.

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Best retreat

According to Jerman, the best place to kick back and relax is Hana, a small town located on the eastern end of Maui and home to around 1,200 people – as well as tropical forests, waterfalls, and red, black, and white sand beaches.

When there, Jerman recommends staying at the Travaasa Hana, a luxury resort that offers everything from a deep tissue massage to trail rides.

Best investment

If you want to buy a house in Maui but aren't looking to shell out millions, Jerman suggests looking in Kihei, where many properties have oceanfront access or are across from a beach.

The median home value in Kihei is US$729,517. “Kihei has a diverse range of real estate, and an abundance of it, from US$200,000 on up, with dozens of options in the US$300,000 to US$700,000 range,” said Jerman.

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Best of real estate

Now, if you just want to look at some gorgeous real estate, head over to Makena – a town about 15km away from Kihei. The home in the image below sits off of Makena Road and is across the street from the beach. According to Jerman, it is for sale for US$12 million.

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This article originally appeared on Business Insider