Downtown Hanalei, a beautiful town on the North Shore of the island of Kauai, Hawaii. (Editorial credit: bluestork / Shutterstock.com)

9 Prettiest Downtown Strips In Hawaii

No matter where you go and what you do on the Hawaiian islands, it will be an experience like no other. But suppose you’re seeking an unconventional Hawaiian experience that truly captures the aloha spirit and the warmth of the Hawaiian people. In that case, you won’t find it in the tourist traps of Honolulu. You’ll find it in the lesser-known and more scenic parts of Hawaii. Here are 9 of the prettiest downtown strips in Hawaii that will entice you to put your worries away and let the spirit of the Hawaiian islands ease you into relaxation.

Hawi

Shops of Hawi, Hawaii
Shops of Hawi, Hawaii. (Bob Linsdell, CC BY 3.0, via Wikimedia Commons)

If you’re on the Big Island and want to get away from touristy activities, a visit to the beautiful little town of Hawi will do you good. The local shops, restaurants, and scenic coastline in Hawi will put you at ease with a combination of retail therapy, nature therapy, and delicious bites. Local businesses such as the Sunshine Trading Company and the Hawi Farmers Market are great spots to find unique gifts, artwork, and sample local produce.

You can also enjoy 100% Kona Coffee at the Kohala Coffee Mill, or stuff your face with locally sourced dishes at the acclaimed Bamboo Restaurant, one of the oldest on the island. Finally, you can take in the stunning scenery of this beautiful town with a drive on Kohala Mountain Road or a hike to the Pololu Valley Lookout.

Kaunakakai

Aerial view of Kaunakakai and its Hawaiian Coast
Aerial view of Kaunakakai and its Hawaiian Coast

The island of Molokai is mainly known for its isolation, as well as cattle ranching and pineapple farming; however, its largest town, Kaunakakai, offers an authentic Hawaiian experience fostered by its tight-knit community and hospitality. The town’s main street, Ala Malama Avenue, will put you at ease with its nostalgic and relaxing atmosphere and is home to local businesses like Imports Gift Shop, where you can find unique items from around the world, as well as Hawaiian products and local art.

The town centre of Kaunakakai is home to a number of local food trucks and restaurants, including the Kanemitsu Bakery, home of the irresistible Hot Bread. And if you’re truly committed to hiding away from the mainstream tourist traps in Hawaii, Hotel Molokai is the place for you. Located on the shores of Kamiloloa Beach, the hotel's Polynesian village of bungalows will redefine your definition of an island paradise. The warm waters of Kamiloloa Beach will wash your worries away, and you can also say hi to the aquatic wildlife while snorkeling at the adjacent Molokai’s South Shore Reef.

Lanai City

Overlooking Lanai City, Hawaii.
Overlooking Lanai City, Hawaii.

Lanai City is another great destination if you’re seeking to unplug yourself from the world. Hulopoe Bay is considered one of the most beautiful beaches in the world, where you can swim in pristine waters surrounded by a gorgeous tropical backdrop. If you visit Hulopoe Bay during the winter months, you might spot a humpback whale or two. Lanai City is also the starting point of the Munro Trail, which takes you on a challenging 20 km forest trail to Lanai's high peak through ironwoods, eucalyptus, ohia lehua, and even pine trees, which gives the area a bit more of a rustic, mainland feel.

Downtown Lanai City is also home to popular local restaurants like Ganotisi’s Pacific Rim Cuisine and Pele’s Other Garden Deli, where you can enjoy dishes inspired by local ingredients. Once you’re done filling your belly, you can stroll through Dole Park, which is Lanai's take on a town square. This green space is rimmed with local shops and art galleries, as well as the Lanai Culture and Heritage Center, where you can learn about the history of the island of Lanai and its culture.

Makawao

The town of Makawao is on the slope of Haleakala volcano in Maui. Editorial credit: EQRoy / Shutterstock.com
The town of Makawao is on the slope of Haleakala volcano in Maui. (Editorial credit: EQRoy / Shutterstock.com)

Located on the slopes of Maui's Haleakala volcano, Makawao is a desired destination for artists and rodeo lovers. It is filled with working artists and was once named one of the top 25 arts destinations in the United States. You'll be treated to the fine craftsmanship of glassblowers, wood sculptors, and painters at galleries such as Powell Studios and Makai Glass Maui. If you're interested in art classes, the Hui No'eau Visual Arts Center offers a wide range of options, as well as self-guided tours and gallery exhibits.

Makawao is also home to paniolos, Hawaiian cowboys who have been wrangling cattle since the late 19th century. If you are in Makawao during Independence Day, you can catch its paniolos competing at the annual Makawao Rodeo. The rodeo features the usual events like calf roping, bareback bronco riding, and barrel racing, but they come with a few Hawaiian twists. Aside from art and cowboys, you can't leave Makawao without eating its famous cream puffs from the iconic T. Komoda Store. Just look for the long line at the door and you'll know you're in the right place.

Wailuku

Aerial View of the City of Wailuku on the Island of Maui in Hawaii
Aerial View of the City of Wailuku on the Island of Maui in Hawaii.

If history, culture, and tranquility are what you need, Wailuku is the downtown for you. The heart of this historic downtown is Market Street. It’s known for its wooden storefronts and family businesses such as highly-acclaimed SixtyTwo MarcKet, a restaurant serving locally-sourced seasonal cuisine, and the long-standing family business, Takamiy Market Inc, which offers bentos and other daily take-out specials. While on Market Street, stop by the Iao Theatre and admire the restored Art Deco building, which is a hub for community events and live performances.

If you happen to be in Wailuku on the first Friday of the month, you can’t miss Wailuku First Friday, a monthly street market that celebrates all things local with food trucks, artisanal craft vendors, and live music. To cap off your stay in the historic heart of Maui, enjoy the peaceful atmosphere of Kepaniwai Park Heritage Gardens, featuring a Japanese temple and themed lush garden walks.

Hilo

Hilo Bay street view. (Editorial credit: JBula_62 / Shutterstock.com)
Hilo Bay street view. (Editorial credit: JBula_62 / Shutterstock.com)

Hilo is rich in culture, history, and architecture. Historic buildings like the Hata Building and the Palace Theatre have unique architecture, with the latter featuring a neo-classical Beaux-Arts design that dates back to 1925. The Palace hosts a range of programming, including movies, concerts and other community events. You can also discover the Big Island’s culture and heritage at the East Hawai’i Cultural Center, which includes an art gallery and performance space, or you can learn about the impact of the devastating tsunamis that devastated Hilo in 1946 and 1960 at the Pacific Tsunami Museum.

But if you want to take in all that this historic downtown center has to offer, you have to venture along Kamehameha Avenue on the shores of HIlo Bay. Here you can browse shops with centuries-old wooden storefronts to find unique art, and fill your belly at restaurants like the Puka Puka Kitchen and Pineapples Island Fresh Cuisine, just around the corner on Keawe Street.

Old Koloa Town

Koloa Village is a community of shops, services, restaurants, and residences in the heart of Old Koloa Town, Kauai.
Koloa Village in the heart of Old Koloa Town, Kauai. (Editorial credit: bluestork / Shutterstock.com)

Old Koloa Town on the island of Kauai will take you back in time with its well-restored buildings, historic centers, and trails. The best way to start your exploration of this historic town is through the Koloa Heritage Trail. The 10-mile self-guided tour will lead you to sites like the Old Koloa Sugar Mill, as well as geological points of interest, like the 5 million-year-old Pu’uwanawana Volcanic Cone and the Makawehi & Pa’a Dunes.

To learn more about the town’s sugar plantation history, stop by the Koloa History Center to get in-depth knowledge on how the plantations shaped the community and culture of this town and Kauai Island. If you’re visiting in July, be sure to join in the festivities at Koloa Plantation Days, where community events include a culinary market, a family fun run, and a Polynesian revue with fire dancing.

Hanalei

Hawaiian canoe on the Hanalei pier.
Hawaiian canoe on the Hanalei pier. (Image credit steheap via AdobeStock.)

At the opposite end of Kauai in Hanalei Bay, this sleepy town is surrounded by stunning waterfront views and evergreen tropical forests. You can surf and paddle the warm, pristine waters, or simply enjoy a relaxing dip. If you prefer fishing or need a place to enjoy a stunning sunset with a loved one, head over to Hanalei Pier, one of the town’s main historic landmarks made famous in the 1957 classic film, South Pacific.

Another noteworthy landmark in Hanalei is the early 19th-century Wai’oli Hui’ia Church, featuring well-crafted stained glass windows and well-preserved architecture, surrounded by a picturesque tropical backdrop. Finally, end your with tapas and a glass of wine at Bar Acuda, or sample local produce at the Hanalei Farmer’s Market.

Holualoa

Holualoa, Hawaii: A photo of the entrance at the Hula Daddy coffee plantation shop.
Hula Daddy coffee plantation shop in Holualoa. (Editorial Credit: Chris Allan via Shutterstock.)

If you love a combination of coffee and art with your nature, Holualoa is the spot for you. The best time to visit this tropical bohemian haven is in November during the Holualoa Village Coffee Art Stroll, part of the Kona Coffee Cultural Festival. This annual event brings together farmers and artists, where you can taste a range of brews and browse the wealth of local talent. There are a number of galleries along the main strip of Mamalahoa Highway to suit every artistic taste.

In addition to its creative side, Holualoa is primarily a great launching point for coffee-themed adventures. You can sip and savor to your heart's content at Heavenly Hawaiian Farm Tours & Konalani Coffee Bar and Hula Daddy. And when it’s time to get the jitters out of your system, you can get lost in nature at find your zen with a Cloud Forest Sanctuary Jungle Tour or a walk through Kaloko-Honokohau National Historic Park.

Downtown does not always have to mean urban concrete jungle. The beautiful towns of Hawaii will change your perception of how a holiday should be spent. You don’t have to absorb hustle and bustle or weave your way through tourist traps. You can ease into nature’s peace and tranquility, the craftsmanship of local artists, and the true meaning of a stroll down a main street. So, the next time you’re in Hawaii, you know where you need to go to enjoy beauty and life’s simpler things.

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