There are a handful of Maui towns that you can’t miss when you are exploring this island.  Maui is loved by all and people from all over the world flock to spend a week or two living in paradise.

On Maui you can find adventure, romance, luxury and solitude all wrapped into one.  Okay I’ll stop teasing you, here are 5 of the cutest and most photogenic Maui towns.

5 adorable Maui towns

5 Maui Towns you Can’t Miss

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View of Lahaina town in Maui from a distance


You can’t explore West Maui without stopping in the town of Lahaina.  Perched right on the water is this old whaling village that was once the capitol of Hawaii.  

Lahaina town is filled with history as you walk around town you’ll find remains of the old fort, the courthouse, and the old Lahaina jail.

As you cruise Front Street, the main drag you’ll find plenty of shops, restaurants, bars and art galleries to keep you busy.  

This is my favorite ‘Maui Towns’ and where I’ve called home for the past 10 years.  Be sure NOT to miss Lahaina town while you’re exploring Maui.

Fleetwoods on Front Street one of the best restaurants in Lahaina
Lahaina town Travel guide
Mala restaurant one of the best Restaurants in Lahaina

Top Activities in Lahaina  🐳

Upcountry Maui


Makawao town is located in Upcountry Maui and is rich in Paniolo history.  “Paniolo’s” or the Hawaiian Cowboy have roamed these areas since the 1800’s as most of the land is dedicated to ranches and agriculture.  

Makawao much like Lahaina is filled with art galleries, boutique shops and a few restaurants.  Be sure to stop at the Komoda Bakery for a sweet treat as you explore this Maui town.  

If you’re up for a ‘boozy’ trip, Ocean Vodka, Pau Vodka, and Maui’s only winery are all located in the area around Makawao.

Lavender farm on Maui
Pau Vodka distillery tasting room Upcountry Maui
I'm Jess Traveling at Wai'anapanapa State Park on the road to Hana


If you’re looking for the ideal Hawaiian town then make sure you spend a few days in Hana on your island vacation.  What she lacks in size, she makes up for in beauty and grace.

A red sand beach only accessed by scaling a cliff is in Hana and that’s only one of her many mysteries.  Ten minutes before you reach Hana town on the road to Hana is ‘Waina’apapa State Park’ which contains one of the most beautiful beaches in Maui, a stunning black sand beach.

Twenty minutes past Hana town you’ll reach the Kipahulu entrance to Haleakala National Park.  Inside the park you can explore the seven sacred pools or embark on one of my favorite hikes on Maui, the Pipiwai Trail.

The Pipiwai trail takes you through a long bamboo forest, past ancient banyan trees and finally ends at the glorious Waimoku Falls.

Spend your afternoons lazing at a picture perfect Hawaiian beach or cliff jumping at the Venus Pools.  However you choose to spend your days, Hana is a MUST VISIT of Maui towns.

Beautiful banyan tree on the Pipiwai trail inside Haleakala National Park Maui
Waimoku Falls with I'm Jess Traveling-2
Beach chairs on a beach with a palm tree on Maui
Town of Paia Maui


Paia town is the first of the Maui towns that I lived in when I first moved to Maui.  Decorated with cafes, restaurants, and boutique clothing shops you can easily find yourself imaging living here.

The colorful buildings pop in the sunlight and you’ll quickly fall in love with yet another Maui town.  Must eat restaurants here include Flatbread Pizza Company, Vana Sushi, Cafe Des Amis, and of course Mama’s Fish House.

Charley’s Saloon is also worth checking out if you want to grab a beer and hide from the heat for bit.  Did I mention that Charley’s is owned by Mr. Willy Nelson himself?!?!

For a longer and more detailed list check out the best places to eat in Paia & Haiku.

Baldwin Beach in Paia Maui
Ho'okipa Outlook in Paia Maui
Flatbread Pizza Company in Paia, Hi on the road to Hana
Road to I'ao Valley State Park near Wailuku, HI


Wailuku is one of the oldest Maui towns located Central Maui.  Situated on the foothills of the lush West Maui mountains you’ll find old historic buildings, churches and your governments buildings like your courthouses.

Every first Friday of the month Wailuku town holds a late night pop up “market” where they’ll be food trucks and locals selling hard crafted jewelry and art.

Wailuku is also home to I’ao Valley State Monument and one of the wettest places on Earth.  Get an old town feel and sample authentic Hawaiian cuisine as you roam the town.

Girl hiking the Waihee Ridge in Maui, HI

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    Maui's most photogenic towns  with I'm Jess Traveling
    Maui's most photogenic towns  with I'm Jess Traveling
    Maui's most photogenic towns  with I'm Jess Traveling
    5 Photogenic Maui Towns you Must Visit5 Photogenic Maui Towns you Must Visit5 Photogenic Maui Towns you Must Visit