- Maui, the second-largest Hawaiian island, is a popular vacation destination for the wealthy.
- Business Insider spoke with Maui-based real-estate agent Josh Jerman to get the inside scoop on how to enjoy the island, town by town.
- Visit Business Insider’s homepage for more stories.
Maui, Hawaii, is known for many things: its white sand beaches, its plethora of snorkeling 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 vacationers.
In 2017, Business Insider’s Melia Robinson reported that billionaires were transforming Hawaii into a techie paradise. Peter Thiel, the founder of Paypal, dropped $27 million on a 1.7-acre Maui property in 2011. 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 3 million visitors for the first time since the island began tracking tourism numbers in 1990.
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. To get the inside scoop on how to enjoy the island, town by town, Business Insider spoke with Josh Jerman, a Maui-based real-estate broker at Hawaii Life. Jerman, a Maui native, has been selling real estate on the island for 15 years. Currently, he has $58 million worth of active listings.
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.
Maui: An Intro
Maui, the second-largest Hawaiian island, is home to around 166,000 people.
It's part of the Hawaiian island chain, which sits in the Pacific Ocean and is made up of eight major islands: Niihau, Kauai, Oahu, Molokai, Lanai, Kahoolawe, Maui, and, of course, Hawaii.
The island is made up of five regions: West Maui, Central Maui, Upcountry Maui, South Maui, and East Maui. It is considered a top luxury destination for vacation goers and welcomes around three million visitors a year.
Source: Maui Now, The Hawaiian Islands
Best dining: For a good meal, Jerman suggests heading over to Wailea. Wailea is a small town made up of just over 5,600 people. His favorite place there is called The Restaurant at Hotel Wailea.
"The Restaurant overlooks Wailea and has an intimate setting with outstanding sunset views and a creative menu with locally sourced ingredients," he wrote in an email to Business Insider.
According to the website, the restaurant's menu aims to reflect Hawaii's history and culture. Customers can enjoy everything from fresh oysters to glazed duck breast.
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.
Jerman's favorite place to go in Lahaina is Fleetwood's on Front St. — 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," Jerman told Business Insider.
Best retreat spot: According to Jerman, the best place to kick back and relax is Hana. Hana is small town located on the eastern end of Maui. It's home to around 1,200 people.
"Hana, which is located on the east end of Maui, has tropical forests, waterfalls, and red, black, and white sand beaches" Jerman said.
When there, he 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. Many properties in Kihei have oceanfront access or are across from a beach.
"Kihei has a diverse range of real estate, and an abundance of it, from $200,000 on up, with dozens of options in the $300,000 to $700,000 range," he told Business Insider.
The median home value in Kihei is $729,517.
Source: Zillow
Best of real estate: Now, if you just want to look at some gorgeous real estate, head over to Makena — a town about 10 miles 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 was recently taken off the MLS but is still for sale for $12 million.
