I'm a 30 year old online poker pro, which means I can live almost anywhere. Financially Hawaii isn't a good pick, since my wage doesn't go up to compensate for the increased cost of living. But I was born there, and my parents lived there for like seven years. Now that my dad is retired, we're thinking of moving there along with my girlfriend for something like six months. I need some advice on where I might want to live.


My dad loves the Big Island, and his number 1 spot to live in Hawaii would be Hilo. He's 65 but is in very good shape, so he would be outside hiking, etc pretty much daily. I'm not sure if it would be a good fit for my gf and I. We aren't really that into nightlife, but Hilo seems like it might be a little too laid back. I imagine it would also be tough for her to get a job in Hilo since it's pretty small. She has work experience in the health foods industry but doesn't have a college degree. She's never worked in tourism or agriculture. Kailua-Kona would be another option, but I'm not sure how it compares to Hilo. Expense is of course an issue in Hawaii, and I'm looking for a two bedroom place for under 2k. Needing a car would also be a big drawback on the Big Island.


Honolulu has obvious advantages. No need for a car, easier employment for my gf, access to everything. But it might be a little too hussle-bussle for us. I've also heard it's very expensive, but I assume in such a big city there are some reasonable places.


Maui is also and option, but it seems very expensive and from what I've heard, it's getting pretty overrun, almost like a new Honolulu.

Any thoughts or suggestions on places I should consider?

I lived in Honolulu for a summer and have been back many times. Great city. It is like a mini-San Francisco or other large US city. There are plenty of places you could live outside of the Honolulu-Waikiki area where you could live a much more 'small town' slow pace of life, and drive into the city for work, shopping or whatever.

I believe Hilo is the rainiest city in the U.S. Kona is sunnier and your GF would have a much better shot at getting a job since that side of the island is where all the tourist facilities are. The people in Hilo can also be somewhat xenophobic. I'd choose Kona. The big island sounds like the best fit for your dad because of its size and extremely diverse terrain. He won't run out of things to do.

My wife would be better to answer these questions, she has more knowledge about it than me. When she gots off of work, in like 6 or 7 hours, I will have her post something.

Off the top my head though Hilo is nice, although I would not reccommend it if you are a light sleeper. In many, if not most, areas of the big island there are coqui frogs, which make these really loud ass noises at night. You may need ear plugs.
http://www.youtube.com/watch?v=k0Ic_3uGzCE
I live in honolulu. Its ok, I just hate that its hot all the time. IDK im weird though I guess because I'm always hot and my wife says she's FREEZING sometimes and im like wtf. Im not sure if you can find a 2 bedroom place for under 2k here...again my wife would know the answer to this. I live in one of the "nicer" condos and I believe in my building some of the 1 bedrooms are renting for like $1800/month. Im not even sure if that includes our mainttenance fee which is like $515 per month. And that maintenance fee is for 1 bedrooms, the 2 bedrooms have a higher maintenance fee. My wife might know some stuff about Maui.

mauiiiiiiiiiii

I'm sure lots of people who've been there forever think Maui is getting too overdeveloped, but let's not exaggerate, its' got a long LONG way to go before it even begins to approach what Honolulu has become.

Depends upon what you like to do I guess, but were it me it'd be a no-brainer, I'd choose Maui for sure. Kauai is amazing, too, but I think I'd go stir-crazy there after a while. 'Course, I'd have no problem hanging there for six months.

No matter which island you settle on, my advice--bring extra $$$$$$!!

check out Craigs list
http://honolulu.craigslist.org/apa/

you can rent for cheaper than $2K.

Since you'll only be here for 6 months, I'd stay in Oahu. There's more things, more jobs, more places to eat, better bus routes if you aren't going to have a car. The further out you get from Honolulu, the cheaper it'll be for rent. Oahu still has lots of nice places for hikes and beaches. Keep in mind we are an Island so even if you don't stay in Honolulu, the commute still isn't that bad by bus. Just don't stay in Waianae, Ewa, or Waipahu. We do have a lot of traffic though morning/afternoon.

Try Kailua area since there's nice beaches and some hiking trails. Might be a little on the expensive side but you never know.

Big Island is ok. Not much to do. More country. Cheap rent. Probably no jobs.
Maui is almost or more expensive than Oahu for some things. Not sure about rent.
Outer islands in general are just more country than Oahu and it will probably be harder to get a job. You can always take a mini trip to the outerislands and its cheap for flight anyways.

I have lived in Hawaii for 39 years in all three of the places you mentioned, 19 years on O'ahu, 16 years in Kona, and 4 years in Hilo.

Hilo is definitely the cheapest, and excellent hiking for Dad at the Volcanoes National Park and Waipio Valley. I have seen it rain 26 inches in 24 hours there, but aside from that, it really isn't quite as wet as they make it out to be, depends on the year and how high up the mountain you go, but sometimes it's so muggy you wish it would just rain instead. It's kind of hard to get work in Hilo especially in health food stores because the farmers markets pretty much serve that function.

Kona is more expensive than Hilo but cheaper than Honolulu. There's a fairly active hiking club in Kona, but the trails are either rocky or steep, certainly not much for groomed trails, but the real cool thing is you can go to some obscure beach after trekking through some lava field and be the only one there. The problem with Kona is that there's isn't the tradewinds the rest of the State has which makes it kind of hot, and the volcanic haze just sucks in every day from about Noon on. If you stay in Kona the trick to this is to get a place at the right elevation; it's usually nice and cool starting at about 750' ASL, but if you go too high (above 1,500') rain and mold and mildew can start to be a problem. As you head north towards Waikoloa the trades come back, but at times they are almost too strong. It seems like it shouldn't be much of a big deal, but a month straight of 30 MPH winds will start to make you crazy. For my money the best place on the planet is a little town called Puuanahulu, which is halfway between Kona and Waimea. It's got nice breezes, and is cool, and dry. There are some nice trails there too. Rents are especially cheap in Kona now because there's no work there anymore and all the construction workers are pulling out.

O'ahu has the most work, but the traffic can get to be nuts. I still like it, but it's not as cool as it was when I was a kid. Lot's of nice trails and the surf is way better than the Big Island.

I can't add much but I lived in Honolulu for a summer and loved it. Hope I can do it again someday.

Go for Honolulu dude. It's actually not that expensive compared to the East Coast. The selection of food is also so much better. I like Asian food, so maybe my view is biased.

Thank you for this thread.

I'm looking at a 1-3 month stay, starting in a few days. Would appreciate any opinions on locations given this criteria:

Lodging: Preferably under $2k/month, less being better. I don't care about much beyond being clean, safe, and having decent internet access. Hotel, VRBO, short term lease, AirBNB, renting a room from a private party... all of these things are fine, I'm not picky.

Food: Would prefer variety and have a strong preference for local Hawaiian food. No interest in fancy stuff.

Transportation: Would prefer somewhere that doesn't need a car, but am OK with renting one for a few months if it makes things easier. Would prefer to get around with a bicycle or walking, though.

Area: Prefer outdoors activities, the more the better. Waterfalls, hiking, etc. If there is a marina nearby or popular sailing spot, that would be the best. Would love to do as much sailing as possible. No interest in fabricated tourist stuff or nightlife.


From the research I've done so far, it looks like Kauai is going to be my default choice with Maui as a backup. I know I'll need to rent a car in Kauai, that's no problem. I'm also completely down with spending the first month in Kauai, then heading to Maui for the second month or something like that.

I lived on St Thomas in the USVI for about six months, and have no problem with island living or being on island time.

Mainly I'm just looking for a chill place to relax and enjoy nature and the Hawaiian culture, while still having solid internet access when I want it. I'm not at all picky with food/lodging beyond basic cleanliness and healthiness, and have no interest in nightlife, excessive drinking, or that kind of thing.


What do you guys think? What am I missing? Any alternate suggestions? Any suggestions for a better place to spend the first month while I explore?

Also, I figure I can island hop via the little passenger planes to the other islands to check them out. This is what I did in the USVI for visiting Puerto Rico. Safe to assume this is easy & inexpensive? Either Kauai or Maui seem like fine base locations to do this from. Correct me if I'm mistaken, please.

Thanks for any advice!

I am planning a similar trip on/around April 2014, albeit for only 4-6 weeks.

I've traveled extensively in Asia but fell in love with Hawaii when I spent two weeks there (Maui & Kauai) several years ago. I've also spent a week on the big island but prefer the previous two.

Do you have profiles / references on either airbnb or couchsurfing.org? Not suggesting you'd want to couchsurf the entire time, but that might be a good way to find a local who had a spare room to rent. Also craigslist of course.

Obviously renting a car would make things easier, but hitchhiking seems to be prevalent & much more socially-acceptable on the islands versus mainland U.S. states.

Not sure what "local Hawaiian food" would be beyond seafood, maybe Asian influence, or Spam??

If you end up staying for 2-3 months imo you'd be making a mistake in not splitting your time between the two islands. Certainly 4 weeks is enough time to get a nice feel for either place.

Six months in St. Thomas? It'll be interesting to hear how you like Hawaii in comparison. I spent a week on vacation in St. Thomas but wasn't overly impressed, though I did enjoy a dive bar I found near the marina there.

If you do go through with trip would appreciate it if you'd post a follow-up since (as I said) I am planning a similar trip next year.

I found some options on Craigslist. I have a couchsurfing profile, but have not used airbnb, will look into it.

As far as local food, I was thinking of things like kalua pig, lomi lomi, laulau, etc.

Looks like I'll be splitting my time then, almost certainly gonna be there 2-3 months.

I'll post the trip report in my "chopstick goes for a sail" thread over in OOT.

Thanks for the advice!