Snowbird condo areas to consider

Do you have a favorite place to vacation or spend winters at? Now that we’ve grown up (aka - our kids are out of college), we’re looking to spend Jan - Mar (perhaps more) away from winter. We’re not sure where - or if we want to buy or rent.

Criteria we need:

Great BIG water view (ocean, etc)
Sailing community
Terrific snorkeling/diving
Decent Wifi - esp since hubby still does projects when we travel
Diverse, welcoming community (locals included)
< 500K if we were to buy (2/2 condo)
English is a primary language (I can handle French, H knows some Spanish, but English would be oodles easier)


Mountain island vs flat - not as committed to this one with my health issues, but it’s still our preference
Same or very similar time zone to the east coast of US (within an hour or two)
Not impossible to reach
Bulk of food (produce, meat) can be grown in the country vs all or almost all needing to be shipped in

At our extremes, we love Hawaii (except Oahu - too crowded), but it’s distance from literally everywhere and higher cost makes us pause. In all other aspects it’s perfect. We enjoyed Grand Bahama (except for it being flat and not being able to grow produce), but not Nassau (too crowded). Bahamas are off the list as is Grand Cayman and similar places. There are areas of FL we enjoy visiting, but snorkeling/diving leaves a bit to be desired. It’s not being highly considered. HI is higher.

We hope to start investigating potential places this winter. In the past St Maarten topped our list, but now we’re not really sure after the hurricane(s) hit last year. USVI and BVI were also in our Top 3 to investigate, but now? It’s also made us think more of renting vs buying, but rentals can be difficult to come by at a decent price.

Any suggestions?

Well…I would suggest going to different places, as opposed to buying.

Places where you probably could rent…

  1. Some place in the carribean...maybe Aruba, St. John, or the like.
  2. Hawai’i
  3. New Zealand...but pick your location wisely as the seasons are opposite.
  4. Key West

Renting is definitely a thought. The reason we originally thought “buy” (and still aren’t sure between the two options) is because buying can be an investment, and an investment that could help pay for itself if we rented it when we weren’t using it (definitely our plan).

Renting is pure “cost out.” It has the advantage of seeing more of the world, but the disadvantage of cost.

H wants us to live on a sailboat, but he’s the sailor. I’m not and am wary of how well I could adjust to it. I love scuba/snorkeling/power boats. The couple of times I’ve been on a sailboat haven’t gone well with my head adjusting to the way they tip. Sailboats aren’t an investment either. They’re a “cost out” too.

For the next couple of years we plan to rent to “test” areas for fit, so the rent vs buy decision doesn’t have to be made for a little bit.

Not sure about the costs but have you considered Bermuda? The snorkeling is amazing and easy to access right off the beaches because the reefs are so close.

I’m sure you considered this, but since you alluded to health issue, make sure you thoroughly check out quality and access to medical care wherever you look! Not fun, but my in-laws searched for a perfect (for them) second home a few years ago and became super excited about one … until they realized the nearest hospital with specialists was an hour away.

Turks and Caicos? No mountains but it is a British colony, uses the US dollar for currency, has the same voltage as us, and it considered one of the top 3 dive sites in the world. Still not very crowded either.

Not sure about produce growing there. No earthquakes or volcanoes to worry about.

St. John would be perfect.

St. Kitts and Nevis checks many of the boxes except for the sustainable food part. They import most everything. That would be true for most of the Caribbean.

Volcanic islands, former English colony, flights transfer in Puerto Rico, friendly for ex-pats, low taxes.

I got excited thinking about Snowbird condos in Utah.

Bermuda limits which properties can be purchased by non-Bermudians.

What showmom858 said.

Personally. I wouldn’t want to be in Bermuda during their winter months as it could be quite chilly. It does have great snorkeling and renting during the winter months is considerably less expensive than in season, so might be perfect for you.

H and I are planning on wintering in different places after he retires. I have no desire to own a second home. My mom is in Florida and though we likely will inherit her place, I have no desire to keep it.

Bermuda is 600 miles off the coast of North Carolina and although it is in the gulf stream it is not warm in the winter months like islands to the south.

@Creekland my inlaws lived on a sailboat several different times. The first was with their children for 12 months. The next was for 2 years in the Mediterranean. The third was for several years with a journey from Australia to the west coast of the US. As they aged they swapped the sail boat for a power boat which they lived on for 2 years. They still have that powerboat and have done periods of 6 months living on board. They always kept a land based home. With the first two trips they rented their house out and had an apartment as my FIL sometimes had to come back for business. My MIL is a saint. The other trips they left there home empty but with a caretaker.
My H talks of buying a boat but I doubt he will pull the trigger. He has been around boats enough to know that you have to spend a good amount to get something reliable especially if you go for a power boat. We feed his boat hunger by every few years doing a bareboat sailing charter. We started out with monohulls and this last trip did a catamaran. On the monohull I feel sick unless I take Bonine daily. The catamaran is pretty stable and I find I don’t get as sick unless the sea is rough. A bareboat charter is a great way to get the experience of living an extended period of time on a boat. On our last trip we met a German couple who had been out in French Polynesia for 4 months on a bareboat charter. He was 88 and she was in her 70’s. This was there 4th trip to French Polynesia. They were headed home and had another sailing trip planned to La Paz Mexico. Obviously charter rentals are expensive but it’s a great way to decide how you like being on a boat.

+1 to St. John

Bermuda is too likely cold for us for winter. Someday I want to get there in general though, but our goal is to escape winter so we’re ideally looking for 70-80 degree temps and their average high in Feb is 69. Then there’s what the others said about buying.

I’ve wondered about Turks and Caicos, esp since we might give up the mountain idea. Flat islands have difficulty growing much as the islands are too sandy (vs volcanic soil which is rich). The flat ones also seem to be more prone to flooding during hurricanes. However, the beaches there look absolutely stunning.

St John is one we would have loved, but it’s very pricey (likely too pricey) and I’m not sure how much they’ve recovered from the hurricanes.

St Kitts and Nevis I haven’t really looked into. They tend to top some of the violent crime lists which probably turns me off even if it’s not really an issue where ex pats live. I might need to look into it more though. We had a vet who loved St Kitts (and BVI) for vacationing.

We already own rental properties for investments. We’d see this as another investment - just one we could personally use part of the year as we wanted and rent it out the rest of the time. It’s highly likely we’d sell one or two we own to purchase the other - a transfer of investments. I don’t want a pure second home as that’s totally money out too. My in-laws have a vacation cottage. It is nice to go to, but it’s a large expense and means they rarely travel anywhere else. If we purchase a vacation rental we could still go elsewhere knowing it’s earning money to offset our travels - assuming it would be rented if we went somewhere else.

As we’ve traveled we’ve talked with people who are already doing this, albeit so far, not in areas we’re interested in. As long as one runs the numbers and the economy (travel economy) stays relatively strong, it can pay a lot of it’s own cost given time. Some have had it pay for more than the cost making it a relatively ideal investment. Hurricanes are definitely a factor to consider though. Nonetheless, we still plan to start investigating other places. We just need to align our list as we can’t afford to island hop until we find the right place - not without a winning lottery ticket anyway and considering we very rarely buy a ticket, our odds are lower than the already low odds (though our bank account is higher by the amount we don’t spend on tickets so there’s that).

@mom60 H had talked about getting a catamaran for just that reason. I still have doubts. My ideal is watching him sail (any type boat he wants) while I walk the beach or ride (a horse) on it. I wonder how easy it would be for kids/grandkids to visit, etc. It’s super easy with a second bed/bath and reasonably sized living area. When the living area is surrounded by water I’d worry about the younger set.

The pro is definitely being able to go wherever, whenever. Another con is wondering where to store the boat when we aren’t using it. His ideal is our using it the whole year…

We’ve spent the first half of our married life with “my” pony farm, so it only seems fair to spend at least a good part of the second half next to BIG water, but I’m just not so sure I can buy into being on the water all the time.

I was just on St. John and it is recovering well. There is still a ways to go, and the 2 resorts (Westin and Caneel) are not open yet. Westin will reopen in January and Caneel is in a dispute and up in the air as far as the future. The island was wonderful and most restaurants, bars, shops etc are reopened. Flights to St. Thomas are still not back at full volume and there is much rebuilding still going on on both islands. The issue I would have with spending the winter on St. John would be food. It is expensive and everything is brought in (groceries). It is such a wonderful place, though, that it would be my choice in a heartbeat for a place to be for an extended stay. We can’t wait to go back.

I was chatting with someone the other week, and she was telling me she and her husband were looking for a place to spend the winter months, away from Chicago.

They researched, and they were sure the Phoenix area was their destination. So, they did a rental for several months, and were so glad they did! Turns out, Phoenix was not a match for them after all. For them? Nice place to visit. Didn’t want to spend months there.

I vote for renting, to test the waters, so to speak.

@Creekland - I’m not anywhere near a natural sailor but I have come to love my time on the boat trips as long as the water is warm. My H has sailed his whole life and in his younger years worked as a yacht rigger. All the boat responsibfall on him. I am a great chart reader and a great marker sighter but I would have a real problem if he fell off.

Regarding grandchildren visiting. We took our kids at age 3 and 5 to visit the grandparents in Bora Bora. I think they were the only kids we saw the entire trip. They had a monohull at that time. They did find for us a family style motel on land for part of the trip. We also took the kids to see them in the Bahamas. We also did visits to Canada and Alaska and the San Juan Islands in Washington. For most of the visits we flew in and met them somewhere that had a marina. We would go out for about a week and they would return us to same location. We actually had a trip planned for this August to British Columbia with several of the grandkids (now all young adults) but just cancelled today due to my in laws deciding not to do an extensive trip. The kids always loved visiting and while it took work my kids and the cousins are all extremely comfortable in and on the water.

My SIL bought a place in Costa Rica. She lived there for several years but eventually found the summer months uncomfortable. She has rented it off and on. She first used an agent for short term rentals but the agent wasn’t honest. She had some success with long term rentals to ex pats but each time there is a change it’s difficult.

Grenada! Lush, mountains, good soil, lots of sailing. People are wonderful and kind, speak English. It is not touristy, you can purchase a nice safe cinderblock house on top of a hillside overlooking the water. They are a democratic country, clean drinking water, very environmentally friendly. Low crime rate, mostly crimes of opportunity. The population is diverse with native Grenadians, Brits, Canadians, Germans, and Indians. It lies just south of the hurricane alley. Jet Blue offers non stop service from JFK. Caribbean Air offers connecting service through Trinidad. American and Delta also offer connections through Miami and Atlanta. Terra Caribbean - 404 - Page Not found

@Creekland you are already a landlord so you know what this entails.

The very LAST thing I want to do in my retirement is have a second home to manage as a landlord. In other words…I would not want to own a place and rent it out when I am not there. I wouldn’t want the maintenance and other responsibilities that come with being a landlord.

I want to be the person who picks up the keys, pays the rent for a couple of months…and then leaves!!

Friends did the “let’s try it” thing for a few years an realized they liked going to different places. BUT if they really liked a place a lot, of course they could return. I think I like that plan.

Re: Phoenix…we have a kid who lives there…and we will likely go there for January and February at some point. It will sure beat the weather in CT at that time of the year!!