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I feel you pain with putting up with miserable winters. Our winters are cold and snowy, but I think you're winters are more depressing with all the gloomy skies plus cold and damp nasty mist blowing around.
You left out the most important part which will effect everything. What is your budget? How much can you afford or how much are you willing to spend? Since you are working, I assume you are not independently wealthy. Even most millionaires have a tolerance for how much they are willing to spend. After you determine your budget, it can be determined if you can afford it and the best choices given your budget. I don't think its too helpful to throw out several extremely high rent areas as choices without knowing if they are viable options, given the budget constraints.
How are you going to handle the car? Renting a car on a long term, like four months would cost many thousand of dollars. It might be more practical to buy a used car in Hawaii and sell the used car before departing. It costs about a grand to ship the car each way, which is probably much cheaper than renting a car four months. Maybe if you lived in an area like Waikiki, you could walk most of the time and only occasionally rent a car. Florida is a lot cheaper than Hawaii, plus you can drive there in a few days, which is an answer to the car problem.
I haven't been to Thailand, but if driving is like Vietnam, it is impossible for you to drive there. You might be able to drive a scooter, but that's your limit there. Most transportation would be by taxi, which is probably cheap if its similar to Vietnam. I don't know if you could drive in those other countries. Decades ago my dad drove our family down to southern Mexico. Today, theres a lot of crime in Mexico as an offshoot to the drug trade. I recommend forgetting about Mexico.
The Big Island is much cheaper than Oahu, but maybe you would find Oahu more appealing if you're easily bored. I grew up in a different time than today's generation. My nephews say they are bored a lot. When I was growing up, if I ever said I was bored, my parents always found some work around the house for me to do. I learned to never say that I was bored, never.
Be careful with the rentals that say that they have Internet. I stayed at two places that had Internet. One was filtered so that only email and web browsing worked. A VPN connection back to the office did not work. The other place had an Internet connection where the VPN connection worked, but the Internet connection itself was down half of my stay there. You may need a back up Internet connection.
So, let's start with your budget and how you plan to deal with the car situation.
Thanks for the input DavePhan. I don't really have a budget. I do very well financially but I'm a pretty frugal. I figure if my living expenses wherever I go are close to what my living expenses are in Seattle, I'm good with that. I would say I want as low cost as I can get but I have to like it & be comfortable. I was just in Costa Rica and rented a car and driving was not bad, except in their largest city San Jose where it was downright scary. Car rentals are very expensive though because of the insurance, and the car situation there would be a very difficult one because renting would be cost prohibitive. Thailand is really cheap to live and eat, but it gets old not speaking the local language and 3rd world countries start to wear on me after a while (as Costa Rica did - a lot of things are more run down and more dingy then you are used to). Plus the time zone difference running a business from Thailand is a killer. Overall I'm a very big fan of Thailand though (nice culture, awesome food, nice people), especially the north around Chiang Mai. I didn't like the beach areas as most do, as they are too hot and humid and touristy. Hawaii has better beaches IMO. Thailand is so dirt cheap, you can rent a really nice house for like $300/mo in Chiang Mai. You can even find 1 bedrooms for $150/mo ($150/mo is not a typo). And you can have a nice meal for $2-$3.
I think the extent crime affects tourists in Mexico is really over hyped. The drug cartels are only going after each other, they don't target tourists. I was just in Mexico before Costa Rica, and I felt safer in their bus stations then the U.S (very clean modern bus stations with no scruffy homeless or thugs hanging around like U.S. bus stations would have). I actually think a lot of U.S. cities like Detroit, Miami, New Orleans, etc.. are more dangerous for tourists then most of Mexico. I never felt unsafe or threatened at all in Mexico. There are parts of Mexico that are even safer then other areas, the Yucatan Peninsula is really, really safe (Cancun, Playa Del Carmen, Tulum, etc...), as are nice colonial cities like Oaxaca, Merida and Puebla. The cartel violence is more in the U.S. border cities. That is one of the nice things about international travel, you get to separate the U.S. media hype from the truth you see with your own eyes.
You have a good point about the car situation. Renting is pretty expensive. But if you shopped around it might not be too crazy for 3 mos. Hawaii is nowhere near as high as international, the killer renting in internationally is the insurance because your U.S. car policy doesn't cover and you need the zero deductible coverage to be safe, and that is 50% of the cost of the rental at least. Also Oahu I hear has decent buses and may have zip cars that you could just use when you needed them. You could also pick up an Island Cruiser for a couple of grand, but buying and selling a car every year just for 3 mos usage would be too much of a pain.
Florida is a lot cheaper then Hawaii but I just don't personally like Florida very much. I would take Hawaii in heartbeat vs. Florida. The only place I could probably stand is Key West and that's a little too small of an area. Also, the better areas of Florida are probably not even that cheap during the high season Dec-March.
Thanks for the input DavePhan. I don't really have a budget. I do very well financially but I'm a pretty frugal. I figure if my living expenses wherever I go are close to what my living expenses are in Seattle, I'm good with that. I would say I want as low cost as I can get but I have to like it & be comfortable. I was just in Costa Rica and rented a car and driving was not bad, except in their largest city San Jose where it was downright scary. Car rentals are very expensive though because of the insurance, and the car situation there would be a very difficult one because renting would be cost prohibitive. Thailand is really cheap to live and eat, but it gets old not speaking the local language and 3rd world countries start to wear on me after a while (as Costa Rica did - a lot of things are more run down and more dingy then you are used to). Plus the time zone difference running a business from Thailand is a killer. Overall I'm a very big fan of Thailand though (nice culture, awesome food, nice people), especially the north around Chiang Mai. I didn't like the beach areas as most do, as they are too hot and humid and touristy. Hawaii has better beaches IMO. Thailand is so dirt cheap, you can rent a really nice house for like $300/mo in Chiang Mai. You can even find 1 bedrooms for $150/mo ($150/mo is not a typo). And you can have a nice meal for $2-$3.
I think the extent crime affects tourists in Mexico is really over hyped. The drug cartels are only going after each other, they don't target tourists. I was just in Mexico before Costa Rica, and I felt safer in their bus stations then the U.S (very clean modern bus stations with no scruffy homeless or thugs hanging around like U.S. bus stations would have). I actually think a lot of U.S. cities like Detroit, Miami, New Orleans, etc.. are more dangerous for tourists then most of Mexico. I never felt unsafe or threatened at all in Mexico. There are parts of Mexico that are even safer then other areas, the Yucatan Peninsula is really, really safe (Cancun, Playa Del Carmen, Tulum, etc...), as are nice colonial cities like Oaxaca, Merida and Puebla. The cartel violence is more in the U.S. border cities. That is one of the nice things about international travel, you get to separate the U.S. media hype from the truth you see with your own eyes.
You have a good point about the car situation. Renting is pretty expensive. But if you shopped around it might not be too crazy for 3 mos. Hawaii is nowhere near as high as international, the killer renting in internationally is the insurance because your U.S. car policy doesn't cover and you need the zero deductible coverage to be safe, and that is 50% of the cost of the rental at least. Also Oahu I hear has decent buses and may have zip cars that you could just use when you needed them.
I agree with your about foreign travel in Asia, at least as I can compare it to Vietnam. I felt very safe in Vietnam when visiting there many times. Americans are treated like kings there. If anyone threatens an American, the criminal is treated very harshly by the justice system there, totally unlike the American justice system that simply lets criminals go to commit a lifetime of crimes over and over.
We rented with VRBO for a bit over a grand per week in Hawaii. Four months of that would be about $16K if we stayed that long. The car would be another grand a month. So, the total for the rental and car is about $20K for 4 months. This does not include air travel, food, gas, and a lot of other expenses. Maybe there is cheaper way to sublet without having to sign a 6 month or 12 month lease.
To ship your car over there is another grand. To ship it back is yet another grand. You might be able to buy a used car there and sell it before you go. You don't want to go to low in price, otherwise you might get a piece of junk that breaks down a lot. If you stay in Waikiki, you could probably walk a lot.
I know what is like to live below my means. I been doing that for over 20 years. It's the key to building up your net worth. I don't know if there is a way to reduce the cost much below $25K for a 4 month stay in Hawaii. If you have a relatively high income, and you have been living below your means for many years, then you could easily afford to spend $25K to $30K a year staying in Hawaii over the winter.
I don't know if there are any viable ways around the relatively high cost. You need to avoid crime ridden areas and you don't want to live in a bug infested condo or house that has to be rented on a month to month basis, rather than a daily basis. Maybe someone can suggest how to winter in Hawaii for less money unless you think spending $25K to $30K is reasonable and affordable.
Florida is a lot cheaper then Hawaii but I just don't personally like Florida very much. I would take Hawaii in heartbeat vs. Florida. The only place I could probably stand is Key West and that's a little too small of an area. Also, the better areas of Florida are probably not even that cheap during the high season Dec-March.
I know what you mean about the lower Florida keys. I've taken extended vacations several times there, staying in Little Torch Key and Big Pine Key, mile marks 28 and 31. We would drive to either Key West or Marathon or hang out at the house on the canal. It's a pretty laid back lifestyle there. A lot of drinking and fishing. I rarely drink. so I did fishing.
The cost is absolutely lower in Florida, plus you can drive there. It will take you awhile from Seattle. It takes 3 days to drive to the lower keys from here. I've driven there three times. The climate is very nice in the winter months. Other times I've visited central Florida, flying and renting a car, also in the winter. Florida is supposed to be pretty miserable from May through September though.
However, the climate and beauty of Hawaii is hands down better than Florida. But there's a high price to pay for the difference.
We rented with VRBO for a bit over a grand per week in Hawaii. Four months of that would be about $16K if we stayed that long. The car would be another grand a month. So, the total for the rental and car is about $20K for 4 months. This does not include air travel, food, gas, and a lot of other expenses. Maybe there is cheaper way to sublet without having to sign a 6 month or 12 month lease.
To ship your car over there is another grand. To ship it back is yet another grand. You might be able to buy a used car there and sell it before you go. You don't want to go to low in price, otherwise you might get a piece of junk that breaks down a lot. If you stay in Waikiki, you could probably walk a lot.
I know what is like to live below my means. I been doing that for over 20 years. It's the key to building up your net worth. I don't know if there is a way to reduce the cost much below $25K for a 4 month stay in Hawaii.
You should be able to get a short-tem sublet (check craigslist) or VRBO negotiated to $2,500 - $3,000 per month. Availability will be your biggest challenge.
An advantage of living in the Waikiki area will be that you don't have to have a car, it is a nice to have. The Bus is suitable for side trips on a as needed basis.
$2,500-$3,000/mo is way more then I want to pay for a furnished studio. Not worth in IMO. If I can't find something a lot cheaper I will just say screw Hawaii & head somewhere else. I spent 3 weeks vacationing in Thailand last year and only spent a little over $2,000 total on everything including my plane ticket. I averaged about $25-$35 a night for my lodging in Costa Rica. I was spending about $15 a night on a nice spotlessly clean B&B room in Thailand with AC.
You should be able to get a short-tem sublet (check craigslist) or VRBO negotiated to $2,500 - $3,000 per month. Availability will be your biggest challenge.
An advantage of living in the Waikiki area will be that you don't have to have a car, it is a nice to have. The Bus is suitable for side trips on a as needed basis.
That monthly price sounds much more affordable, about $12K instead of $16K for 4 months, which is good new for me because I'm thinking of eventually snowbirding in Hawaii as I get closer to retirement or during retirement. The prices on Craigslist look a lot cheaper on the the Big Island. Although a car is needed, which would add to the cost. Although a higher priced VRBO or hotel would be needed for the first week to get the longer term sublet setup to avoid getting into a sight unseen situation with the longer term rental. I've had good luck with the VRBO rentals, except for the Internet. I just need to check to make sure that the Internet isn't filtered so that a VPN connection to work functions and get a backup hot-spot portable Internet connection.
I'm not sure how to handle the long term rental for the car. A 4 month car rental could be about $4K. It would probably be cheaper to drive from Minnesota to LA and ship the car both ways. I could stay at the brother in law's place in southern California while I waited a week for the car to get shipped across. The airfare would be a lot cheaper from southern California than from Minneapolis too. That scenario would probably be more viable when I'm retired, since I'll have plenty of time to drive across the county at that point in my life.
I've stayed in Vietnam for a lot less too. I stayed at the New World Hotel the first time in Vietnam, which is the same hotel the US presidents stay at, although not on the top floors, which are more luxurious. That was for $86 per night. The other trips, I stayed at hotels for $10 to $15 per night that where in nice areas, clean, and had AC. It's possible to snowbird in a beautiful area near the ocean in Nha Trang for about $10 to $15 per night. But Vietnam is a third world county so you live your life differently than in the US. You have to be extremely careful what you eat and drink to avoid getting seriously sick for a week.
I suspected that the high cost of Hawaii might be a problem for the OP, that's why knowing the budget right off the start is so important and absolutely critical to answering the questions. To some people, including myself, that monthly rate is within are ability to pay those prices. However, that does not mean we are willing to spend that much money and part with that much cash. That's a totally different situation than not having enough money.
Maybe the OP should check out the Big Island, since the prices are lower there. Or, check out Florida, where the prices are even lower, plus you can drive to Florida and eliminate the car rental or car shipping costs. The weather in Florida during the deep winter months is very nice most of the time. Once and awhile there are cold snaps in Florida for up to a few days to a week, but they are pretty rare. Florida is not as nice as Hawaii, but it's drastically better than the pacific northwest or upper midwest during the deep winter months, and a whole lot cheaper!
Yeah I would definitely check into FL or the Big Island unless I can find something less. To me it's probably not worth the high cost of housing. Costa Rica, Panama, Thailand are also options, vastly cheaper then the Oahu. Thailand is really not that bad, it's kind of in between 3rd world and developing, so are Costa Rica and Panama. There are parts of Costa Rica like Tamarindo Beach on the Pacific Coast that are pretty upscale full of American expats and does not have the 3rd world feel at all and are vastly cheaper for a monthly furnished rental. I think Mexico would also be a lot cheaper on the Caribbean coast or Baja or Pacific Coast if you wanted beach. I think Hawaii has a nicer combo of beaches/mountains/ambiance/amenities then any or these other options, but there is a point to where it becomes cost prohibitive with at $3,000/mo for a studio. But I personally don't need a penthouse suite, I'm guessing if I really beat the bushes on airbnb.com and Craigslist I could find something for a lot less then $2,500-$3,000 for a furnished studio for 1 person on Oahu or other islands .
hmmm, Kailua, last 15 or so days has been day and night rain, which might make you feel like you are back in the PacNW.
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