Wealthy weekender's guide: Where to eat, stay, and party in Maui, Hawaii

big and bougie hawaii 4x3 big and bougie hawaii 4x3
Maui, Hawaii.
Richard Theis/EyeEm/Getty; M Swiet Productions/Getty Images; Shayanne Gal/Business Insider

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 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 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 , a Maui-based real-estate broker at . Jerman, a Maui native, has been selling real estate on the island for . Currently, he has .

2020欧洲杯体育平台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

best of hawaii
Shayanne Gal/Business Insider

2020欧洲杯体育平台Maui, the , is home to around . 

2020欧洲杯体育平台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: ,

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.

best dining hawaii
Shayanne Gal/Business Insider

"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.

A post shared by The Restaurant at Hotel Wailea (@therestauranthw) on Nov 29, 2019 at 10:40am PST

According to the , 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.

best nightlife hawaii
Shayanne Gal/Business Insider

Jerman's favorite place to go in Lahaina is Fleetwood's on Front St. — a restaurant and bar owned by musician Mick Fleetwood.


A post shared by Fleetwood's on Front St. (@fleetwoodsonfrontst) on Sep 17, 2019 at 3:10pm PDT

2020欧洲杯体育平台"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.

best retreat spot hawaii
Shayanne Gal/Business Insider

"Hana, which is located on the east end of Maui, has tropical forests, waterfalls, and red, black, and white sand beaches" Jerman said.


A post shared by Travaasa Experiential Resorts (@travaasa) on Jun 13, 2019 at 9:29am PDT2020欧洲杯体育平台

2020欧洲杯体育平台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.

best investment hawaii
Shayanne Gal/Business Insider

"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.

Ingmar Wesemann/Getty Images

The median home value in Kihei is $729,517.


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.

best real estate porn hawaii
Shayanne Gal/Business Insider

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.

Travis Rowan, Living Maui Media

SEE ALSO: A Louisiana couple bought an 80-year-old general store for $55,000 and turned it into their dream home. Here's how they did it — and what it looks like now.

DON'T MISS: Here's how much space $1,000 in rent will get you in 11 major US cities

More: Features Big and Bougie Hawaii Travel
Chevron icon It indicates an expandable section or menu, or sometimes previous / next navigation options.