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A Comprehensive Guide to Ditching the Snow and Snowbirding to Hawaii

So you’ve had it. The shoveling, freezing cold mornings, frozen windows and springtime mud. You’re just one tropical calendar away from packing it all up for a move to Hawaii for winter. And I can’t say I blame you. I’d trade fleece leggins for a grass skirt any day. Oh, and did somebody say, “pina colada”? 


It’s quite common for Americans living in the northern states to expat to warmer climates. In Florida where I grew up, we call them, “snowbirds”. Northern state residents who live in Florida for 4-6 months a year. They usually have two homes, both with seasonal clothing, and they drive south for the winter.


So how can YOU be a snowbird to Hawaii? This guide will give you all the info you need to move to Hawaii as a snowbird. So you can ditch shoveling snow for building sandcastles and sucking down Pina Coladas.


Move to Hawaii for Winter


How to Move to Hawaii for Winter and Live Your Best Snowbird Life Ever


If you’re serious about trading the snow for the sand then you’re going to have to get planning. This doesn’t have to be difficult, but there are things to consider before your seasonal move to Hawaii for winter. 


Decide on a Budget


Trust me, I’m a daydreamer and a night thinker, but as much as I’d love to sail off into the sunset, there is a real budget to consider. What’s yours? 


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If you have the means to purchase a second home in cash, fantastic! If you’re planning on a mortgage or renting, then you’ll want to consider what you can afford for your cost of living. Cost of living to think of; rent/mortgage, utilities, maintenance (pest management, lawn care, home maintenance), upkeep, travel expenses, food, fuel, spending.


It’s important to research the cost of living in Hawaii as compared to where you currently reside. It could be less, it could be more. Iron out these details and decide what you can afford.


Decide on a Destination for Your Hawaii Snowbird Life


Of course, once you decide a budget for your move to Hawaii for winter, you’ll need to figure out where you want to live. But how does one pick the perfect place in paradise? 


A good way to start is by making a list of your lifestyle choices. Do you love the beach or are you more interested in magical hikes? Are you a city person or a quaint countryside person? Do you want to surf into the sunset or drink cocktails in high-end hotels? 


best islands to visit in hawaii, move to hawaii for winter


If you want to be in a densely populated area, you might consider Honolulu. If you’re more into that beachside life, Paia might be for you. Here is a quick reference of places to consider for your lifestyle type:


  • Kailua-Kona if you’re retired
  • Haleiwa if you want that small town life
  • Miliani Town if you’re bringing the whole family
  • Hanalei if you want to surf into the sunset
  • Honolulu if you want that city life
  • Paia if you want to forget everything beachside


Once you figure out how you want to spend your days in Hawaii, you can then reference your budget and what it costs to live in those areas. Here are some of the most affordable Hawaiian cities.


Will You Rent or Own?


If you’re planning to move to Hawaii for winter then chances are you’re financially comfortable enough to do either. If you want my opinion, homeownership requires regular upkeep. And since you’re already going to dealing with upkeep on your primary residence while you’re away, it only makes sense to not have to do it twice. 


Move to Hawaii for Winter



Not to mention, Hawaii is one of the most expensive places to buy a home in the US. You can rent at a much cheaper rate and not have to worry about the upkeep while you’re away (or there for that matter). Hawaii Business published a great article on whether to rent or buy in Hawaii.


How to Keep Up on Your Primary Residence While You’re Sun Bathing in Paradise 


Are you leaving a home that you own for 4-6 months out of the year? Have you ever stopped doing everything for 4-6 months on your property? Since you won’t be there to monitor your home for damages, maintenance and theft, it’s mindful to make a list of all the things you normally do with your property over the winter months. 


Here are some suggestions:


  • Grounds (ice, snow, bad weather) – Hire a landscaper to tend to the property while you’re away
  • Structure (gutters, windows, hardscaping) – Hire a handyman to check on your structure every two weeks
  • Pest Management (rodents, bugs) – Be sure to have pest management check the residence before you leave and come by while you’re away
  • Theft/Vandalism – Install indoor and outdoor cameras, the Ring system is great
  • Overall – Have a trusted friend/neighbor check on your property and be your eyes and ears while you’re away


Special note: Never tell anyone you don’t know and trust that you will be away from your residence for an extended period of time.


How to Get Around When You’re in Hawaii


If you’re going to move to Hawaii for winter then you’re for sure going to need transportation. You could purchase a vehicle there and garage it during the months that you’re away. But chances are you already have two vehicles.


seaside Road


A better plan would be to put that second vehicle to good use and ship your car to Hawaii. 


Things to Buy and Leave in Your Paradise Home


You’ve nailed down your budget, you’ve decided on a city and set up your living arrangements. Now it’s time to furnish and fill your closets and drawers! Before you hire movers or show up with a suitcase and a bank card for a shopping spree, why not shop in advance? 


table interior


There are great online stores where you can shop for everything you need for yourself and your new paradise home. I love Wayfair for furnishings and decor. Of course, Amazon is a great place to shop for your new warm-weather styles, but you can also shop at Target, Walmart, and pretty much any of your favorite retailers. 


Shopping online for your goods will get you set up without having to pay moving costs. All you’ll have to pack are a few personal items!


How to Get Your Pets to Paradise


dog at the beach


You can’t move anywhere without your furbabies. You’re going to have to travel with your pet. Whether you’re driving to southern California and taking a flight to Hawaii or flying directly from your current home, you’re going to have to fly at some point. It’s best to make that flight as short as possible.


If you have little pets like small dogs or cats, then you can load them into an airline-approved carrier that fits under your seat. If your pets are larger than that, you’re going to have to bite the bullet and prepare them for cargo hold travel. 


dog at the beach


Here are some important considerations when transporting your large pet in the cargo hold:


  • See Your Veterinarian – Make sure all shots are up to date, that your pet is in good health and get an Rx for anxiety
  • Get the Right Carrier – Make sure it’s airline approved and large enough for your pet to reposition themselves
  • Make it Cozy – Add blankets, toys and something with your scent to the crate to help calm your pet
  • Tell the Captain – This is important so the captain can climate control and depressurize the cargo area
  • Make Sure They Eat and Potty – They should be fed (a little) and relieved before a flight
  • Run Them Down – If you get them tired they will sleep on the flight which is optimal
  • Labels and Microchip – Make sure your carrier is well labeled and that your pet has a microchip 


move to hawaii for winter, people at the beach


Tell Your Friends! 


You did it! You’re living the good life in paradise while your friends and family are chumping it up in snowmageddon! Tell your friends and family to come and visit you! After all, what’s the point of a winter escape if you’re going to keep it all to yourself.


In Closing


A move to Hawaii for winter can be a dream come true. Even if you’re not planning for it this year, you should start planning for it long before you do it. By following this guide, you’ll be well on your way to Pina Coladas and sandcastles. 


Christa Thompson

Christa Thompson is the Founder and Chief Editor of The Fairytale Traveler. She started traveling the world in 2003 when she attended a summer abroad study at the University of Cambridge in England. Since then, her wanderlust has been fierce. Her three passions in life are her son, traveling, and being creative. The Fairytale Traveler brand gives Christa the opportunity to do all of these things and to live intentionally every day. "It's never too late to believe in what you love and to pursue your dreams." -Christa Thompson

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