I've Lived on Maui for 11 Years: My Honest Thoughts on Island Life

Eleven years ago my husband Rob and I sold everything we owned in New York and moved to Maui. We thought we would stay six months, maybe a year, and we are still here. In the decade since, I have helped a lot of other people make the same move, so this is the honest version of what island life is really like: the good, the hard, and the things nobody prepared me for. The short answer is that Maui rewards people who come for the place itself and are willing to build a life here, and it is hard on people expecting an upgraded version of somewhere else.

Why did you move to Maui in the first place?

Honestly, it had nothing to do with Maui at first. Our original plan was Europe, but Rob took a job that required staying in the US, so we needed a new plan, and Maui sounded like the most exciting faraway place we could think of. Neither of us knew much about it. I had never been, and Rob had been once at age six. We were not chasing a lifelong dream; we were living in New York City, ready for a slower pace, more time outside, and work-life balance that did not disappear the minute we checked email at dinner. We looked at the other islands. Oahu felt like another big city, Kauai a little too small, the Big Island not quite right. Maui landed in the middle with the right mix of everything. So we packed a couple of duffel bags, a few weeks after getting married, and made the move.

What made you stay?

We never really sat down and decided. We got here, settled into life, and after a while could not picture living anywhere else. There is a saying you will hear from local people that the island either accepts you or it rejects you. It sounds a little out there, but after living here I understand it. Some people move to Maui, have a genuinely hard time, and realize it is not the right place, and there is nothing wrong with that. For us, things fell into place. We made good friends, found a rental in Paia we loved, and that made it easy to picture a future here.

What caught you off guard?

The hardest thing I did not expect was how far away family and friends would feel. New York to Maui is not a quick trip, so you miss the little things, coffee with someone or dropping by. The upside is that when people visit, they stay for days, so we ended up spending better quality time together here than we ever did back east. I was also figuring out a whole new career. I had spent years at big international law firms, and there is little of that here, nor did I want it. What got me excited was our own home-buying experience; going through it made me want to get into real estate, and I have been doing it ever since. And friendships took time. A lot of people here want to know you are planning to stay before they invest in one, which I completely understand when people are always coming and going.

What do you actually miss about the mainland?

Even after 11 years somewhere this beautiful, homesickness sneaks up on me, in exactly two ways. One is walking. I miss being able to walk for blocks with nowhere in particular to go, wandering for hours and stopping wherever I wanted. Outside a few resort areas and older towns, most of Maui is built around driving. The other is food, especially early on, when it felt like the choice was a resort dinner or plate lunch and not much in between. That has changed a lot, with great food trucks and casual local restaurants now, Hawaiian and Filipino alongside Thai, fusion, vegan, even Southern barbecue. Missing a couple of things does not mean I regret moving here. Every place comes with trade-offs, and these are minor, but it is better to know them before you decide.

What would you tell someone considering the move?

We flew by the seat of our pants, and it is not what I would recommend. Even with all our research, moving somewhere we barely knew felt like a leap. So when people ask, I tell them to spend real time in different parts of the island before deciding where to live. Do not assume you have found your spot after one trip, because every part of Maui is so different in price, community, and daily life. That is exactly what happened to us, even though we never planned it: we started in Paia on the North Shore, bought a home in Kihei on the South Side, and after a while realized how much we missed the North Shore, so we moved back and have been here ever since.

I would also come with realistic expectations and a willingness to get involved. Put yourself out there, find ways to give back, and come in knowing this island has a real community and a hard recent history. The 2023 fires changed lives here. You are moving into a place that was whole long before you showed up, and it is still healing. Respecting that matters.

The honest bottom line

Looking back, I just wish we had known a little more about what life on Maui was really like before we made the move. That is honestly why I do this. I would rather help you get to the right answer, even if that answer is "not yet" or "not here," than watch you learn it the hard way like we almost did. If you are thinking about the move and have questions about what island life is actually like, reach out. I am always happy to talk it through and help you figure out if Maui is the right fit.