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With stunning beaches, a laid-back vibe, and near perfect weather year-round, moving to Hawaii likely sounds like a dream. But choosing where exactly to put down roots can be overwhelming with six major islands and diverse communities to pick from.

If you’re short on time, here’s a quick answer to your question: Oahu and Maui offer the widest variety of neighborhoods, job opportunities, dining and amenities, making them top picks for many new residents. But island life appeals differently to everyone.

In this comprehensive guide, we’ll cover everything you need to know to decide the best place in Hawaii for you including an overview of the islands and towns, housing market, cost of living, quality of life comparisons, and insider tips from locals.

Getting to Know the Hawaiian Islands


Oahu is the most populous and visited island in Hawaii. Honolulu, the state capital and largest city, is located here. Waikiki Beach draws visitors from around the world with its famous white sand beach and turquoise waters.

Outside of the city, Oahu offers incredible natural sights like the North Shore’s epic waves, Pearl Harbor and the USS Arizona Memorial, the verdant Ko’olau mountain range, and outdoor adventures like snorkeling at Hanauma Bay.


Often called “the best island in the world,” Maui is known for its beautiful beaches, lush forests, scenic roads, and variety of activities. Highlights include watching the sunrise over Haleakala volcano, driving the famous Road to Hana with its bamboo forests and waterfalls, exploring historic Lahaina town, snorkeling at Molokini crater, and relaxing on Ka’anapali or Wailea beaches.

No wonder Maui is many visitors’ favorite island!


With its dramatic cliffs, secluded beaches, tropical rainforests, and cascading waterfalls, Kauai is often called the “Garden Isle.” Popular sights include Waimea Canyon, the breathtaking Napali Coast, Wailua Falls featured in classic movies and TV shows, historic towns like Hanalei, and family-friendly Poipu Beach.

Outdoor lovers can hike trails along the Na Pali Coast, kayak down the Wailua River, or surf at Hanalei Bay.

Hawaii Island

The largest Hawaiian island, the “Big Island” of Hawaii boasts incredible diversity. There are barren lava fields, stark volcanic craters, black sand beaches with sea turtles, charming towns like Kona, historic structures and petroglyphs, coffee and macadamia nut farms, waterfalls in lush valleys, world-class resorts along the Kohala Coast, and more.

Don’t miss seeing an eruption at Kilauea volcano in Hawaii Volcanoes National Park!

Lanai and Molokai

For a more remote Hawaiian experience, consider visiting Lanai or Molokai. With no traffic lights or shopping malls, Lanai offers a slower pace focused on nature and relaxation. Molokai promotes itself as “the most Hawaiian island,” where locals outnumber tourists and ancient Hawaiian traditions carry on.

Here you’ll find empty beaches, soaring seaside cliffs, quiet fishing villages, local farms, and a chance to immerse yourself in Hawaiian culture.

Comparing the Best Places to Live in Hawaii

Housing Market and Cost

Hawaii’s housing market is notoriously expensive, with median home prices over $800,000 statewide as of late 2022. However, prices vary significantly by island and neighborhood. For instance, median single family home prices reached $1.2 million on Oahu but only $575,000 on Hawaii Island as of Q3 2022 according to Hawaii Life.

Employment Opportunities

Honolulu on Oahu offers the widest variety and highest number of jobs in sectors like healthcare, hospitality/tourism, defense/military, and technology. Neighbor islands have fewer opportunities overall but industries like agriculture, astronomy, and renewable energy are growing in areas like Hawaii Island’s Kona coast.

Dining, Shopping and Entertainment

As Hawaii’s economic center, Oahu offers unmatched variety in dining and shopping, especially in Honolulu and Waikiki. For entertainment, Las Vegas-style shows abound in Waikiki while Neighbor Island offerings focus more on local culture and natural landscapes.


In terms of transportation infrastructure, Oahu is generally easiest to get around without a car due to public transit options. Hawaii Island is very spread out making a car a necessity for most residents to access basic amenities and job centers.

Interisland flights operate several times daily to all major islands.

Weather and Outdoor Activities

With year-round warm weather, Hawaii offers endless outdoor recreation. Oahu’s famous North Shore sees massive winter waves for surfing while beaches abound statewide. Volcanoes National Park on Hawaii Island provides a unique landscape for hiking and sightseeing.

Schools and Community

Island Top Public High School 2021 Niche Grade
Oahu Mililani High A+
Maui Baldwin High A-
Hawaii Waiakea High B+

While data shows Oahu with higher rated schools, small tight-knit communities abound on Neighbor Islands providing a strong sense of ‘ohana (family) for many locals and transplants.

Best Communities on Oahu

Oahu is home to some of the most desirable and popular communities in Hawaii. With its vibrant culture, beautiful beaches, and ideal weather, it’s no wonder why so many people flock to live on this island paradise.


Kailua is arguably one of the best places to live on Oahu. Nestled along the windward coast, this laidback beach town offers residents a relaxed lifestyle along with stunning natural scenery. Kailua Beach is renowned for its sparkling turquoise waters and soft, white sand – earning it the distinction as one of the most beautiful beaches in the world.

The community itself has a small-town vibe with locally-owned boutiques, mom-and-pop restaurants, and friendly neighbors. It’s also family-friendly, with highly-ranked public schools. Outdoor enthusiasts will enjoy the hiking trails, kayaking, kite-surfing, and more.

Hawaii Kai

Hawaii Kai is a wonderful option for those looking for suburban living on Oahu. Tucked along the southeastern shore of the island, it offers exceptional views and easy access to world-class beaches. Residents can enjoy days filled with snorkeling, paddleboarding, or simply relaxing in the sand.

The area has an upscale vibe with custom homes, oceanfront high-rises, and several shopping centers. Families are drawn to Hawaii Kai for its reputation for excellent public and private schools. It’s also just a 20-30 minute drive to downtown Honolulu.


Mililani is consistently ranked as one of the best master-planned communities, not just on Oahu, but across the entire United States. Tucked away in the center of the island, it offers residents suburban living at its finest.

The area is known for its excellent schools, family-friendly neighborhoods, and abundance of amenities. From parks to community centers to shopping malls, Mililani has everything residents need for daily living. It also features reasonably priced homes when compared to other parts of the island.

Outdoor enthusiasts will love the easy access to hiking and biking trails across Oahu.

Best Towns on Maui

Maui is full of charming towns and communities, each with its own unique vibe and appeal. Here are some of the best places to consider living or staying for an extended visit:


Historic Lahaina, situated on Maui’s western shore, is undoubtedly one of the most popular towns for visitors and residents alike. Its walkable streets are lined with art galleries, boutiques, and restaurants, not to mention the beautiful beaches and harbor just minutes away.

The weather is consistently warm and sunny year-round, making Lahaina an idyllic place to soak up the island lifestyle.


Lively Kihei offers six miles of sun-drenched beaches with gorgeous views of Haleakala and the West Maui Mountains. This affordable community has experienced significant growth in recent years, attracting families and individuals looking for an oceanside locale.

Kihei offers numerous condos, vacation rentals, and amenities while still retaining its laid-back, small-town charm.


Paia is a haven for surfers, hippies, and health-conscious residents. Tucked away on Maui’s North Shore, this funky little town has a tangible bohemian vibe and plenty of vegetarian-friendly dining options. The beaches around Paia are world-renowned for surfing and windsurfing.

It’s also the gateway community to the Road to Hana, offering easy access to lush rainforests, cascading waterfalls, and rugged coastlines.


Upcountry Makawao is loved for its cool mountain air, paniolo (Hawaiian cowboy) heritage, and charming shops and boutiques housed in historic plantation-era buildings. Artists and craftspeople have set up galleries sprinkled throughout town.

Makawao hosts a popular monthly art night and is located a short driving distance from Haleakala, wineries, and lavender farms set amid rolling pastureland. The pace of life here feels slowed down and peaceful.


For those seeking luxury living, Kapalua is an exclusive resort community framed by Maui’s western coastline. Picturesque beaches, world-class golf courses, high-end restaurants, and sleek condos define the landscape.

Rich in natural beauty yet outfitted with every modern amenity, Kapalua appeals to discerning residents looking to indulge in the good life against an exquisite tropical backdrop.

No matter your budget, interests, or lifestyle, Maui likely has a community where you can feel right at home. Take time to explore the island’s diverse neighborhoods before choosing your own personal slice of paradise in Hawaii.

Top Spots on Kauai

Kauai is often called the “Garden Isle” thanks to its lush green landscapes and breathtaking natural scenery. From waipio Valley to the Na Pali Coast, there are countless incredible places to explore on this Hawaiian island. Here are some of the top spots to check out on your visit to Kauai:

Waimea Canyon

Known as the “Grand Canyon of the Pacific,” Waimea Canyon is a must-see destination on Kauai. Over 10 miles long and 3,000 feet deep, this massive canyon features vibrant red, orange, green, and brown colors streaked along its cliffs.

Go hiking along one of the trails or take in the panoramic views from an overlook along Waimea Canyon Drive.

Na Pali Coast State Park

The magnificent Na Pali Coast boasts some of Hawaii’s most dramatic scenery with its towering green cliffs rising from the Pacific and secluded beaches tucked between them. You can hike the famous Kalalau Trail for days of adventure or opt for a boat tour sailing along the coastline when weather permits.

Just glimpsing the Na Pali Coast is an unforgettable experience.

Hanalei Bay

On the North Shore, Hanalei Bay offers postcard views of emerald mountains and a crescent-shaped bay. Relax on the golden sands of Hanalei Beach or check out charming shops and restaurants in the surf town itself.

Outdoorsy types should also consider surfing, stand-up paddleboarding, or kayaking in Hanalei Bay when conditions allow.

Kilauea Lighthouse

The historic Kilauea Lighthouse, built in 1913, now shines its beacon over Kilauea Point National Wildlife Refuge. Take a tour of the lighthouse before embarking on easy cliffside trails offering fantastic opportunities for whale watching and birding.

Keep your eyes peeled for humpback whales from December through March along this part of Kauai’s North Shore.

With lush gardens, towering waterfalls, epic beaches, and incredible hiking trails, Kauai certainly lives up to its “Garden Isle” nickname. Exploring all it has to offer could take weeks…or even years! Whatever you decide to see, Kauai’s magnificent tropical landscapes are sure to leave you in awe.

Notable Areas on Hawaii Island

Hawaii Island, also known as the Big Island, is the largest and most diverse of the Hawaiian Islands. While the entire island has plenty to offer visitors, there are a few particularly notable areas to highlight.


Kailua-Kona on the western side of the Big Island is one of the most popular tourist destinations. This coastal town is home to fantastic resorts, great shopping and restaurants, historical and cultural sites like the Ahuena Heiau temple, and excellent water sports and ocean activities.

The famous Kona Coffee is also grown in the surrounding areas. Kailua-Kona has a lively yet laidback vibe that makes it a prime base for exploring the island.

Volcanoes National Park

No trip to Hawaii is complete without visiting Volcanoes National Park, home of the active Kilauea volcano and crater. This area has an almost otherworldly landscape with volcanic craters, steam vents, and fields of lava rock.

You can hike across old lava flows, watch the fiery glow from the Halema’uma’u crater at night, and learn all about the science and culture of volcanoes in Hawaii. As the landscape is constantly changing, each visit brings new sights.


The largest population center on Hawaii Island, Hilo on the eastern side has more of a local small town character compared to the resort atmosphere of Kona. With its high annual rainfall, Hilo is lush and tropical and known for sights like the rainbow-hued Boiling Pots area, the large farmer’s market with fresh island produce, and the popular Liliuokalani Park and Gardens along Hilo Bay.

The downtown area also has some interesting historic buildings and a nice selection of indie cafes, shops, and restaurants.

Waipi’o Valley

Waipi’o Valley on the northern Hamakua coast is truly a special place on Hawaii. This large valley dotted with taro fields and waterfalls has an untouched natural beauty and was once home to Hawaiian royalty.

You can hike or take a shuttle down into the valley to admire wild black sand beaches, soaring cliffs, and the winding stream. Exploring Waipi’o offers a glimpse into old Hawaii and just how stunning the islands once were before modern development.

With volcanic landscapes, rainforests, waterfalls, beaches, historical sites, and modern amenities, Hawaii Island has diverse areas to appeal to all interests. These notable regions showcase the island’s raw natural wonders as well as the cultures and history that make Hawaii so unique and beloved.

Living on Lanai and Molokai

The islands of Lanai and Molokai offer a more peaceful and secluded lifestyle compared to bustling Oahu or Maui. With small local populations, lack of traffic, and untouched natural landscapes, these islands provide a sanctuary for those seeking to get away from it all.


Lanai is the smallest publicly accessible Hawaiian island, with only around 3,000 residents. Nicknamed “The Pineapple Island” for its past as a pineapple plantation, Lanai has no traffic lights and feels like stepping back in time.

The two small towns on the island, Lanai City and Kaelepulu, have a charming old Hawaii vibe with plantation-style homes and mom-and-pop restaurants.

With over 90% of the island owned by tech billionaire Larry Ellison, Lanai offers luxury resorts and world-class golf courses catering to upscale travelers. Yet there is also plenty of relatively undiscovered wilderness to explore, from red dirt roads winding through the Garden of the Gods rock formations to secluded Hulopoe Beach, consistently rated one of the best in Hawaii.

For outdoor enthusiasts, Lanai offers superb dolphin watching, premier game fishing, horseback riding through the Cook Island pine trees, and excellent whale watching in season. Deer and turkey hunting are also popular activities for locals and visitors with permits.


Molokai is called the “Most Hawaiian Island” due to the high percentage of native Hawaiians living there, making up over 50% of the population. Molokai is all about embracing the laid-back pace, rural landscape, and unspoiled beaches, with no buildings taller than a coconut tree.

Locals in the main town of Kaunakakai know just about everyone, creating a small-town community feel. Neighboring towns like Kualapuu, a former pineapple plantation village, offer rich Hawaiian history and heritage sites like the Kalaupapa National Historic Park and its sad Hansen’s disease colony.

Visitors to Molokai can enjoy activities like kayaking, fishing, hiking, and cultural tours of historic churches and restored fishponds. Or just relax on gorgeous white sand beaches like Papohaku Beach, one of Hawaii’s longest at over 3 miles, with hardly another soul in sight.

For those seeking solitude amid exquisite natural landscapes rich in Hawaiian heritage and culture, the peaceful islands of Lanai and Molokai offer all that and more.


With dreamy beaches, lush landscapes, and welcoming culture, Hawaii offers so much allure as a place to live. By weighing factors like affordability, job prospects, accessibility, weather, and lifestyle against your own priorities, you can discover the Hawaiian community where you’ll feel most at home.

Oahu and Maui provide endless amenities and opportunities. Kauai channels more small town charm. Hawaii Island captures the frontier spirit. And Lanai and Molokai promise peace and seclusion. Wherever you land, the aloha spirit is sure to work its magic on you in this island paradise.

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