Travel Guide: Digital Nomad in Hawaii

Like many great stories, my journey as a Digital Nomad in Hawaii starts with love. I met my boyfriend my first week in Bali at a co-working space. 10 months and 14 countries together later, we were ready to settle in somewhere for longer than a couple of weeks. My boyfriend is Australian and I’m American so we started researching mutual territory that checked all our boxes: agreeable time zone, strong WIFI, warm weather, a town that offered opportunities to make friends, and preferably somewhere affordable with surf.

After much deliberation and research, we settled on being Digital Nomads in Hawaii. It met most of our criteria, except for the fact that it’s one of the most expensive places to live in the world! That was the biggest disadvantage and deterrent. We both have stable jobs, I work as a full-time Digital Media Strategist and my boyfriend owns his own e-Commerce company. Even still, we were going to need to scrape pennies together to afford a furnished, short-term, walkable rental in Hawaii no matter which island we chose to live on.

So, how does a Digital Nomad in Hawaii choose which island to live on? I spent more time researching this subject than I did on researching where to settle down. Here is what I learned:

  • Oahu: I ended up choosing this island because I wanted to be near Honolulu for the airport, WIFI, and co-working spaces. Also because it had surf, hiking, and a naturally beautiful landscape. Plus there was plenty going on for nightlife. I’m not a partier but I do enjoy going out for dinner and drinks and being social and a lot of the other islands seemed to close their doors when the sun went down. Most importantly because it’s home to Kailua: the only town I could find in Hawaii that didn’t require a car.
    • Kailua: I can’t imagine a better place for a Digital Nomad in Hawaii! I’ve been here for one month and find it to have everything I need. While Kailua is one of the most expensive places to live in Hawaii it has everything you need to feel comfortable. ChadLou’s is an adorable café in town with excellent coffee, strong WIFI, and comfortable (enough) chairs and tables to use as desks. This is a popular workspace, which also makes it a great place to meet other local Digital Nomads in Hawaii. It’s a small town with a big central shopping center so most residential areas of town are within walking distance to everything you need: grocery stores, restaurants, library, cafes, gyms and workout studios, and best of all a Target! Our AirBnB came with a couple of bikes, which we’ve found to be essential (another thing I asked for specifically!) It also has one of the most beautiful beaches in the world, bars, and breweries and is a short bus ride to Honolulu (30 minutes and only $2.50!)
    • Waikiki: Many locals don’t like Oahu because it’s “too touristy” but I didn’t find this to be true once we left Waikiki. I believe this one little area of the island is the reason for Oahu’s reputation. Granted I am technically a tourist! Waikiki is very busy, corny and it’s basically an outdoor shopping mall. While it’s not my kind of place to live it was fun to visit, surf and go out here.
    • HonoluluDigital Nomads in Hawaii can find a few co-working spaces here. It’s a bit touristy and busy but fairly affordable as far as housing and the city is friendly to those of us who don’t wish to purchase a car.
    • North Shore: Outside Honolulu is quite rural and there are plenty of farms. There’s a beautiful coastal road from Honolulu that will take you to the North Shore where you’ll find yourself in a surfer’s paradise. There are a few little markets, pop-ups, grocery stores, and food trucks up here for your casual dining pleasure. There’s a beautiful little bike trail and everyone seems to walk around barefoot. If you’re going to stay on the North Shore you’ll definitely need a car. You’ll also need to drive a fair ways if you enjoy working in cafes or co-working spaces.
    • Haleiwa is pretty touristy but not in a neon sign, shopping mall, and street vendor kind of way. It’s cute, with little boutique shops and restaurants that are geared towards tourists. I would say this is a livable area and offers coffee shops that could double as an office. However, even here you’ll need a car.
    • West Coast: This area of the island is a sacred place for locals. Tourists are urged to steer clear of the beaches here so I wouldn’t recommend living on this side as a visitor.
  • The Big Island, Maui, Kauai: From what I’ve learned these islands are beautiful, remote, require a car, and don’t have much to offer as far as nightlife. If going out for dinner and drinks doesn’t concern you and you’re willing to invest in a car for your stay these are perfectly viable options and likely offer that special, mystical quality nowhere in the world offers but Hawaii.

As a Digital Nomad in Hawaii, I highly recommend ensuring you have the funds to make it work. It’s an expensive flight here no matter where you are in the world and an expensive flight home if it ends up breaking the bank.

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