Moving from California to Hawaii was always in the back of my mind. Whenever I visited, I’d catch myself thinking, “Could I do it? Could I actually move here?” And then I’d leave, and the thought would fade—until late 2022. That’s when my wife, Jill, and I were invited to speak at an event on the Big Island. Long story short, we fell in love, and that kicked off a chain of events that ended with us living in Hawaii.

This article gives a high-level look at our experience and some things to think about if you’re considering moving from California to Hawaii—or anywhere, really. It’s not a step-by-step manual, but more of a starting point to get you thinking. For an more in depth guide, head over to our comprehensive page: Essential Tips for Moving to Hawaii

The Allure of Island Living

My wife and I are both outdoor enthusiasts. We’re avid hikers and backpackers, and for me, a lot of my outdoor time growing up in Southern California revolved around the ocean. So Hawaii just made sense—it’s a paradise for outdoor activities with constant perfect weather and mild temperatures. Hawaii has everything I had but it’s a little better (or maybe different) and you can basically get outside every day.

Key Differences Between California and Hawaii

That’s not to say the move didn’t come with some adjustments. The one that hit me the hardest? The cost of living. It’s just more expensive here, plain and simple. When you’re living on an island thousands of miles from the mainland, getting goods here costs more—and that trickles down to everything else. So, you embrace a minimalist lifestyle. It’s actually more relaxing and definitely healthier.

The lifestyle change, though, has been amazing. People here tend to be more minimalist, and life happens outdoors. The pace is slower, and people are warm and welcoming. But those are things to think about before making the move. Downsizing was huge for us—we came from a big house with four kids in San Diego, so we had a lot to sort through. Ultimately, we shipped a 6x6x6 container of items we couldn’t part with and still ended up selling things after we arrived.

Planning Your Move to Hawaii

Downsizing and Decluttering

One of the first things we did was downsize—big time. Coming from a larger home with four kids, we had accumulated a lot of stuff. We sold, donated, and gave away anything that didn’t make the cut. In the end, we fit what we truly couldn’t part with into a 6x6x6 container. Honestly, we still brought too much and ended up selling more after we got here. Since our first move we migrated over to Oahu and took even less with us. We furnished our 1 bedroom place in Kailua in about 3 days using Facebook Marketplace and Target as our sources.

Shipping Your Car to Hawaii

Shipping our cars was surprisingly straightforward. We used Pasha, and the process was simple. It cost us about $2,000 per car, which felt steep at first but turned out to be worth it. Once the cars arrived, registering them in Hawaii was easy—and way cheaper than registering cars in California. Getting Hawaii driver’s licenses was simple, too. If you’re thinking about bringing a car, I’d say go for it. I almost forgot! The Hawaii DMV is awesome. Without going down a rabbit hole, I’ll just say the cliche of DMV staff doesn’t apply to Hawaii.

Outdoor Activities: Surfing, Paddling, and Diving

Surfing and Standup Paddling Adventures

I didn’t ship any boards when we moved because the cost didn’t make sense for me. Instead, I bought standup paddleboards through Facebook Marketplace at a great price and picked up my surfboards new. To be honest, used surfboards here aren’t much cheaper than new ones, so I just went for it. Expect to spend between $500–$700 for a solid epoxy board off the rack.

Exploring Freediving and Snorkeling

Diving here is unreal. Warm water, no wetsuit required, and visibility that’s just incredible. The sea life is next-level, so I made sure to invest in high-quality gear, especially a good mask. It’s made all the difference.

Hiking, Cycling, and Exploring Hawaii’s Landscapes

Hiking Adventures

Hiking in Hawaii is amazing—there’s just so much variety. You’ve got dry volcanic trails with rugged terrain, and then you’ve got lush rainforest hikes that lead to waterfalls. One of my absolute favorites is the Lanikai Pillbox Trail in Kailua. We hike that mountain 2–3 times a week, and it’s the perfect mix of challenge and scenery.

Cycling Opportunities

Cycling, on the other hand, is more of a challenge here. A lot of roads don’t have bike lanes, and in my opinion, it’s just not worth the risk. I’ve stuck to neighborhood rides on a beach cruiser, which has worked out fine, but hiking has definitely taken the top spot for me when it comes to staying active.

Adjusting to Hawaii’s Weather and Rain Patterns

Warm Yet Rainy Climate

The weather was one of the biggest adjustments for me. Coming from Southern California’s dry climate, I wasn’t used to the rain. Here, it rains almost every day—even if it’s just for a few minutes. Sometimes it rains for days. I’ve learned to keep a lightweight rain jacket handy, and honestly, you just get used to it. The rain is part of what makes Hawaii so lush and beautiful.

Practical Tips for Settling into Island Life

Finding a Home in Kealakekua and Moving to Kailua

We started off by buying a home in Kealakekua on the Big Island, and we loved it. The beauty, the slower pace, and the recreational opportunities were incredible. But after a while, we realized we wanted a bit more activity and culture, so we decided to move to Kailua on Oahu. It’s been a great fit—still laid-back, but with more access to restaurants, shops, and events. Once you’re here, it’s much easier to move around. Island to island moves are an entire different situation. Let me know if you want advice on that. It was easier and there are a few tricks to that. A couple of things that come to mind, I was able to pack both our cars with the exception of the driver seat when we shipped the cars. Also, we moved over with those black plastic crates with yellow tops on the airplane. 3 each and carry on luggage. Talk about reducing again!

Building a New Routine

Getting into a rhythm has been key. We’ve connections in the community, and embraced the sustainability mindset here—things like shopping local and doing more outdoor type activities makes it all worthwhile.

Final Thoughts

Moving to Hawaii from California was one of the best decisions we’ve made, but it’s definitely not for everyone. Downsizing, shipping cars, and adapting to a slower, more minimalist lifestyle can be a big adjustment. But if you’re ready for the challenge, the rewards—like year-round outdoor activities and stunning natural beauty—are totally worth it.

FAQs

1. What is the cheapest way to move to Hawaii from California?
Sell most of your stuff and ship essentials in a small container. Use checked luggage for immediate needs.

2. How long does it take to ship a car to Hawaii?
About 2–3 weeks, depending on where you’re shipping from.

3. What’s the biggest adjustment when moving to Hawaii?
Higher costs, more rain, and a slower lifestyle.

4. Are water sports gear and equipment easy to find in Hawaii?
Yes, but new gear is often worth the cost since used items aren’t always much cheaper.

5. How do I find local hiking trails and outdoor activities?
Check online groups, apps, and visitor centers—they’re great resources for exploring.