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How To Move to Hawaii for Two Months

April 7, 2021

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Deciding to move to the beautiful islands of Hawaii is one of the best decisions you could ever make. The paradise on earth offers you the chance to not only explore black sand beaches and beach cave hideaways, you’ll also get the chance to snorkel with sea life, watch surfers surf the sunset waves, and even visit volcanoes at the highest point of the island. Hawaii also has a rich culture that’s been celebrated throughout many years in history and there will always be opportunities for you to dive in and learn about the local way of life. 

When I first announced that I would be packing up my life and moving to Hawaii for two months, I received quite a few questions on how I was able to do it in terms of logistics and finances. Many people believe that Hawaii is one of the most expensive destinations to travel to, and while I did have to plan out my finances so I could afford this move, if you budget the right away and keep an eye out on deals and discounts, you can easily do this move yourself. Whether you’ve day dreamed about moving here for years or just want to temporarily relocate like I did, this post will walk through all of the expenses and what to think about before coming.

Palm trees in Hawaii

Airfare

Buying your ticket will be one of the biggest expenses you’ll have to budget for when traveling to Hawaii. To lower your overall cost, you can either keep an eye out for flight deals on apps like Hopper and Kayak, or do as I did and use all the airline points I collected over time. Because I had so many points saved up from my Chase Sapphire Preferred credit card, I was able to pay for 2 round trip tickets for myself and my boyfriend without any out-of-pocket expense on my end.

If you are interested in using the points method, right now Chase is offering a signup bonus of 80,000 points (a $1,000 value) for the Chase Sapphire Preferred credit card if you spend $4,000 within the first three months. I don’t recommend this method to those who are unable to pay off their credit card every month, but if you can pay it off without incurring interest, I highly recommend this method!

Housing

Housing, depending on the length of your stay, will also be an expense to look out for. If you plan to stay in Hawaii for less than a month, Airbnb or VRBO will be your two best options to look into. However, if you plan on staying for a month or longer, I’d recommend you check out Furnished Finder. It’s a website geared towards travel nurses, but other traveling professionals are able to use it as well.

Transportation

If you’ve ever been on vacation before, another massive expense you’ve probably experienced before is your rental car. Unfortunately, renting a car on the island will cost you around the same as your monthly rent. My suggestion to help lower your cost, is to either rent local or use Discount Hawaii Car Rental.

If you’re wanting to rent a Jeep, one of the best places on the Big Island to rent from is called Big Island Jeep Rental. They have a huge selection of different Jeep models and their customer service is second to none. If the type of car you rent is of no concern, then Discount Hawaii Car Rental is your best bet. They not only offer the best pricing options, they also partner with rental companies such as Alamo, Avis, Budget, Dollar, Enterprise, Payless and Thrifty.

Groceries

Shopping for food is very expensive in Hawaii, but if you know how to shop smart and look for the right deals, you can eat pretty well on a budget. Use Costco to stalk up on the basics (chicken, rice, milk, butter) then go to local grocery stores like Choicemart and KTA for the other necessities. Some of the best locations to buy local food is off of street vendors who are selling local fruits and veggies like papayas, avocados, and mangos, on the sides of the roads. Another option is visiting the local farmers markets that offer a wide selection of produce at a reasonable price. You’ll get a wide variety of food options as well as a chance to enjoy unique market experiences in Hawaii that help to support local farmers and artisans.

Activities

As I stated earlier, there are so many things to keep you busy on the Island and as long as you don’t live the resort/vacation tourist lifestyle everyday, most of the activities on the island can be free. Many of the island’s activities like snorkeling, hiking, and sunbathing are all free but you might have to purchase snorkeling and other water gear to get a closer experience with sea life. If you don’t mind spending some money though, Hawaii is known for the best sunset boat rides, deep sea diving experiences, ATV tours, and luaus that teach you about culture while serving fresh meals. There’s plenty more I didn’t mention, but a quick search on a travel site will give you the best reviews of visitors who’ve had great experiences doing many different things.

Job

One of the most important things to note about everything I mentioned above, is that I am fortunate enough to work completely remote right now. Because I’m earning an income while living here, I’m able to offset the costs. It’s also important to mention that because I work a corporate job (headquartered in Chicago) I still live my work life on central time, even though I’m now based in Hawaii. This means I start working at 3 a.m. local time (8 a.m. CT) and go to bed around 6 p.m. While this was a bit difficult to adjust to, it actually worked out perfectly because I’m typically done working by noon, and have the rest of the day to explore as much as I want to. 

I know a move like this can seem daunting, but it’s possible and I’m here to show you that with a little effort working through your budget and a whole lot of patience, you too can move to the islands and experience everything Hawaii has to offer you.

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  1. How wonderful for you! I am an educator and have summers off and my husband can work anywhere. You got me starting thinking about how we could plan to do this one summer. If you have any tips on reasonable long term lodging or summer seasonal jobs, I would love to hear more!

  2. Jen Nilsson says:

    Good for you! I hope more and more people will do this as remote work becomes the norm. I’m so pleased to read about your adventures. Congrats!

  3. sydney says:

    Moving to Hawaii sounds like a dream! I loved it when I visited

  4. Sarah says:

    This is super inspiring!! I would love to do something like this. So glad it worked out for you, you gave such helpful tips!!

  5. Diane says:

    I love this SO much! I’m all about making the most out of life, and living it to its fullest. And there’s ALWAYS a way to make it happen. Thanks for sharing your adventure! My plan is to move to France, and every single day I’m working to make that happen 🙂

  6. Karen says:

    What a wonderful adventure to undertake. Good for you for taking the risk. Your daily schedule sounds crazy but you get the best part of the day to explore.

  7. Krista says:

    Great post! I’d love to live in Hawaii for a few months! Seems like bliss!

  8. Natalie Yeats says:

    I would love to live in Hawaii even for a short amount of time. I am a travel nurse and I have seriously considered doing an assignment there.

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