Winter month, where?
 

My husband and I unexpectedly (long story) find ourselves retiring at the same time. We talked about going away for the winter when we retire and it looks like next winter will be it! I think it will be for a month this first year. We live in the Great White North and would like to spend January or February some place warm. On the water would be great.
Can anyone who has done this recommend a place in the US or Mexico or Caribbean or elsewhere? We would most likely like to rent a home or condo, through VRBO or homeaway. Any great ideas? Prices need to be moderate (do NOT ask me what that means). Thanks!!!!

Here are a couple of things to think

Instead of thinking automatically of Jan and Feb because they Are the coldest, what is the most miserable month where you are? For most people in New England, it is March when they want to cut their wrists if it snows again. For Southern transplants, it is April, because April should be almost summer.

Second, how warm do you want to be? What is a too hot? Florida is too hot for many people by Easter, but Georgia and the Carolina's are just getting nice. You can golf there all winter. Ditto the FL Panhandle, and the Alabama and Mississippi coasts.

We have spent winters in Florida, both as condo owners and as visitors. We now spend the winter in Richmond, VA, mostly for family reasons, but it is enough warmer than NE (mid 50's quite often) that our various ailments don't hurt. No beach, lots of great food, history, and culture. Our Toronto friends say it looks just like home except that the rare snow generally melts by mid afternoon.

Explore yourselves and try to think hard about what you really want. Above all, take the opportunity to rent in several states and areas before you even dream about buying. In addition to the real estate issues, formidable, there are huge tax and inheritance issues to consider.

Are you driving your own vehicle from home or are you flying and renting a car whenever you need one?
I drove from Oregon to Yuma AZ for a gathering of geocachers the second week of February. After the event I went across Southern AZ with a night north of Tucson. The next day I headed east into NM and ended up in Silver City.
If you are looking for access to the ocean you can go into Mexico to Puerto Penasco which is on the Gulf of Baja south of Organ Pipe Cactus NM.
My advice would be to spend 3 or 4 nights in a place and then move to another. After about 4 places, go back to the place you liked the best.

Puerto Rico....it's warmer than anywhere in the continental U.S. No passport as it's part of the U.S. but a totally different culture than you're used to. If nothing else, it will give you a pretty good idea as to whether you'd like retiring to somewhere like that. I'm sure you have a fairly good idea what it would be like living in the southern U.S., or at least can make a pretty educated guess. But spending a month in Puerto Rico would take you way out of your comfort zone and that would really help you make some decisions about what you're willing or not willing to consider for the future.

Long story for us too - similar only I'm retired and hubby has a few years to go yet but his job allows him to work from anywhere. So we're also searching out places. We're spending the month of Feb in FL next winter. I found a waterfront condo on vacationrentals.com in the New Smyrna Beach area. Moderately priced compared to the gulf side. We plan on looking around for other areas while we're there.

We also live in the great white north, and for the past 8 years we do a week or so every January in the Riviera Maya area of Mexico - sheer heaven. The air is in the 80's, the water is azure blue, warm, and swarming with fish, the food is inexpensive and fabulous, and the locals are friendly. Lots of Americans, Canadians, Argentines and Europeans. Look at Tulum, Playa del Carmen, Akumal and Puerto Morelos. Go to locogringo.com for lots of info.

My Minnesota friends say that the first thing to decide is desert or Florida :-) I know you said water would be great, so while I'd always recommend Tucson and vicinity because it's beautiful and there's lots to do, I assume you've ruled out the Southwest. In Florida, I suggest Sarasota and its surrounding area. The gulf side beaches are gorgeous, and there's lots to do within a reasonable driving radius. Weather won't be too hot, either.

One thing you want to take into account is it is more expensive to go to PR, Mexico, Hawaii, etc because of air fare and car rental. We paid almost $1000.00 a month for car rental. Add that to airfare and it's a lot more expensive than staying in the continental U.S.

Wow! Great advice. So helpful. To clarify, we are not looking to buy anything in the future or move to any of these places. Just snowbird a bit. I will look into your suggestions. I also posted on the Europe site but I think staying in North America is going to be better for us.

Puerto Vallarta, Mexico. That's my true love. Look at www.vallarta-getaways.com under "Unique Old Town rentals" to see the kinds of places you could rent.

No need to rent a car in PV. Busses, taxis, and walking can get you where you want to go. At least the way I vacation in Mexico (and I go there often) it is most definitely NOT "more expensive than staying in the continental US".