I’ve been fortunate to live in various parts of Hawaii, on The Big Island and Oahu. Each place has its own unique vibe, character, and beauty. If you’re wondering what it’s like living in hawaii, head over to a great write up about living in Hawaii. The content of the article outlines some of the things to consider if you’re planning on moving to Hawaii or want to learn a little more about some of the social aspects of Hawaii. While everyone has their own preferences, I thought I’d share my personal experiences living across different parts of the islands. Currently, I’m living in Kailua on Oahu, but I’ve also lived in Kealakekua on the west side of The Big Island, where I still own a home. Here are my favorite places, for different reasons, in the Hawaiian Islands. No order of preference, just my take on each place, where it is and why I like it.
1. Honolulu (Oahu) – The Best for City Living
Image is in public domain. An aerial view of downtown Honolulu, Hawaiʻi taken on April 7, 2007. In the foreground is Aloha Tower, a clock tower and lighthouse greeting visitors to Honolulu Harbor since 1926. In the center of the photo is First Hawaiʻian Center, the tallest building and oldest bank in Hawaiʻi. In the lower right is the Falls of Clyde, the only surviving iron-hulled, four-masted full rigged ship, and the only surviving sail-driven oil tanker in the world. The Falls of Clyde is now a museum ship in Honolulu Harbor.
Let’s start with Honolulu, this is a big city and the closest you’ll get to big city living on any of the islands. Honolulu is the perfect mix of urban conveniences and natural beauty. If you love being close to action—restaurants, shopping, nightlife—while having easy access to beaches like Waikiki, Honolulu is for you.
2004_0215AF by Marufish is licensed under CC BY-SA 2.0. Image may have been resized or cropped from original
Living here, you get access to everything. From world-class healthcare to concerts featuring famous artists, an art scene and nightlife, Honolulu has it all. The city is incredibly diverse, with people from all over the world calling it home, which makes for an enriching cultural experience. However, it’s important to note that with all of this comes a high cost of living, particularly when it comes to real estate.
While I don’t live in Honolulu, I can appreciate the balance it offers for someone who wants the convenience of city life but still enjoys Hawaii’s outdoor lifestyle. It takes me about 30 minutes to get to “Town” which is what locals call Honolulu. Then, depending on what I’m trying to do, maybe another 10-30 minutes to find a place to park. Local knowledge and luck are involved with the parking. I love heading into town for dinner, maybe a concert or to surf Waikiki when there’s a big enough swell to spread the crowd out.
2. Kailua (Oahu) – The Best for a Relaxed Beach Town Vibe
Lani Kai Beach and the Mokes. Sounds like a band, right?
369 Lanikai Beach by Matt Sims is licensed under CC BY 2.0. Image may have been resized or cropped from original
This is where I currently live, and I absolutely love it. Kailua, on Oahu’s windward side, has a more laid-back atmosphere than Honolulu, but it’s still close enough that you can drive into the city when needed (about 30 minutes). One of the best things about living in Kailua is the beaches. Kailua Beach and Lanikai Beach are not just beautiful—they’re world-famous. I spend a lot of time outdoors here, from standup paddling to hiking in the nearby mountains. You can even surf a few spots over in Kailua when the swell direction is right. The spot I live nearby, Castles, does best on a South/Southeast swell. I’m always checking for the quick surf potential. The “town” part of Kailua, referred to as “Kailua Town” has a Target, several grocery stores including a Whole Foods. Plus, plenty of restaurants, retail stores, and all the amenities of a town without the crowds of Honolulu.
The town itself has a tight-knit community feel. It’s family-friendly, and while it has grown over the years, it still retains that small-town charm. One downside is that, like much of Hawaii, Kailua’s housing market is competitive, and prices are high. But if you’re looking for a peaceful, beach-centric lifestyle, this place is hard to beat.
3. Haleiwa (Oahu) – The Best for a Laid-Back North Shore Lifestyle
Tourists love taking pictures next to this popular sign.
Haleiwa Sign by 86265563@N00 is licensed under CC BY 2.0. Image may have been resized or cropped from original.
If you’re a fan of Hawaii’s surf culture or simply want to live in a place where life moves at a slower pace, Haleiwa on Oahu’s North Shore might be for you. While I haven’t lived there full-time, I’ve spent enough time in Haleiwa to appreciate its rustic charm. The town feels like a world away from the hustle of Honolulu, but it’s still accessible.
The North Shore is famous for its big wave surf spots like Waimea Bay and Pipeline, and even if you’re not into surfing, you’ll love the relaxed, community-oriented vibe. Haleiwa has great local shops, food trucks, and farmers markets, making it perfect for those who want a more rural, yet connected, lifestyle. One thing to keep in mind is that, being a popular tourist destination, the area can get crowded during the winter surf season. If you want to visit one of the famous beaches or surf breaks, get there early.
4. Hawaii Kai (Oahu) – The Best for Suburban Waterfront Living
Living on the canal in Hawaii Kai
Hawaii Kai is another fantastic place to live if you’re looking for a suburban, family-friendly environment with a little more space. This neighborhood, located on the southeastern side of Oahu, offers a quieter lifestyle while still being relatively close to the city.
Hawaii Kai is well-known for its waterfront properties. If you’ve ever dreamed of living in a house with your own dock and access to the ocean, this might be the place for you. The area is popular among families and retirees, thanks to its good schools, parks, and shopping options. While I haven’t lived in Hawaii Kai myself, I’m over there all the time. It’s the Costco I frequent along with being the starting out point for a few of my favorite trails up the steep slopes of the interior mountains. The views are stunning for the residents up in the hills. It’s about 20 minutes away from central Honolulu, definitely worth a visit.
5. Kona (Big Island) – The Best for Sunshine and a Vibrant Lifestyle
West Side of The Big Island of Hawaii
Now, let’s talk about Kona on the Big Island. My house in Kealakekua has a view of downtown Kona, and it’s one of my favorite areas. Kona has some of the best weather in Hawaii—warm and sunny almost all year round, with very little rain compared to the other side of the island.
The town itself has a lively vibe, especially compared to other parts of the Big Island. You’ve got access to beautiful beaches, great snorkeling spots, and a variety of restaurants and bars. There’s a quaint downtown area with shopping and restaurants. Kona is also known for its coffee farms and rich history, making it a great place to live if you enjoy being active outdoors while also having a sense of community. Housing prices are more reasonable than on Oahu, but still higher than in more rural parts of the Big Island.
6. Hilo (Big Island) – The Best for Nature Lovers and Affordable Living
Stunning photo of “Coconut Island” in the town of Hilo, Hawaii. source: https://pixabay.com/en/coconut-island-hilo-hawaii-palm-1975480/ Pixabay image. No attribution required.
I’ve always loved Hilo for its natural beauty and laid-back atmosphere. Hilo has a slower pace than Kona, but for those who enjoy lush rainforests, waterfalls, and a quieter way of life, it’s perfect. Yes, Hilo is rainy—it’s one of the rainiest places in the U.S.—but that rain also creates the stunning tropical scenery that makes this area so special.
Hilo is more affordable than many other parts of Hawaii, especially when it comes to housing. If you’re looking for a home that’s surrounded by nature, without the high price tag, this is the spot. It’s also close to Hawaii Volcanoes National Park, so if you’re into hiking or geology, living here is a dream. Employment opportunities are more limited compared to Kona, but if you’re in healthcare, education, or government work, you’ll find plenty of options.
7. Waikoloa (Big Island) – The Best for Resort-Style Living and Sunshine
Waikoloa Coast, West Side, Big Island Hawaii
Waikoloa, located on the Big Island’s Kohala Coast, is one of the best places for those seeking resort-style living with incredible weather. Like Kona, Waikoloa is almost always sunny, which makes it perfect for those who want to spend their days outdoors.
Waikoloa has beautiful sandy beaches, and a dry climate. This is where we typically headed if we wanted to spend a day at the beach. You’ll find plenty of golf courses, luxury resorts, and high-end shopping centers here. It’s quieter than Kona but still offers access to beaches and outdoor activities. Housing can be expensive, especially if you’re looking at some of the newer developments, but it’s a beautiful area to live in if you want that resort vibe year-round.
8. Captain Cook (Big Island) – The Best for a Rural and Peaceful Lifestyle
The Captain Cook Monument
I have a personal connection to Captain Cook. I lived in Kealakekua, which is nearby, and I still own a home in the area. This part of the Big Island offers a more rural, peaceful way of life, perfect for those who want to be away from the hustle of busier towns like Kona. Captain Cook is known for its coffee farms, scenic views, and small-town atmosphere.
What I love most about this area is the tranquility. It’s quiet, the people are friendly, and you’re surrounded by nature. Plus, you’re still just a short drive from Kona if you need more amenities. The housing here is more affordable than in some of the more tourist-driven areas of the Big Island, making it a great option if you’re looking for a slower, simpler lifestyle in Hawaii.
Conclusion
Living in Hawaii is a dream come true for many, and I’ve been lucky enough to experience different parts of these islands firsthand. From the bustling city life in Honolulu to the peaceful vibes of Captain Cook, each place offers something unique.
My current home in Kailua provides that perfect balance of beach town relaxation with access to the conveniences of city life. Meanwhile, Hilo and Kona on the Big Island offer contrasting lifestyles, with Hilo’s lush beauty and Kona’s sunny, active environment. Whether you’re drawn to the surf culture of Haleiwa or the luxury of Hawaii Kai, Hawaii has a spot for everyone.
At the end of the day, the best place to live in Hawaii is the one that fits your lifestyle and makes you feel at home. And honestly, wherever you choose, you’re living in paradise! Get out there, visit some of the areas in Hawaii. So many different vibes to the different areas.
What do you think?