Montreal is lovely, and I understand the Pointe Claire neighborhood is fairly English, besides being charming.

If you're considering Australia and NZ Vancouver isn't that far ... what about the Caribbean or Central America? Bermuda? Costa Rica or Panama? Also easy flights to Eastern North America. For Canada I'd recommend just outside a major city. Montreal is great but there will always be a language issue (although that may not be a problem for you). Bureaucracy in Quebec is worse than average and it is mostly in French.

Toronto has everything one could want culturally and in terms of services, is very multicultural but English speaking. It has direct and easy flights to pretty much everywhere on the planet. Well under an hour to DC, NYC, Boston, etc. Real estate is expensive but not quite as nuts as Vancouver. Traffic is a mess and driving unpleasant though (like any very large city I guess). I don't find it a particularly beautiful city, but beauty is in the eye of the beholder and Lake Ontario is wonderful.

Halifax is the only city of sufficient size for you on the east coast. Robo is better placed to fill you in there. I love Halifax, the ocean is fabulous, it is an easy drive to New England. Great music scene. Flights overseas are more difficult, sometimes you have to fly to Toronto to get to Europe. That would drive me nuts.

I really dislike Calgary (perhaps too far west for you) but if you're willing to live in a smaller city like Banff or Canmore (spectacular towns in the Rockies) it is an easy commute to Calgary for services. Weather more of an issue there though.

Ottawa is the fourth biggest city in the country (~1m). I believe it has the best standard of living of any major city. It has amenities and cultural opportunities of a larger city because it is the capital city. It is lovely and a very outdoorsy sporty city. Architecture sucks but is improving. Ottawa has the most highly educated population in the country (due to professionals coming to work in Federal Government or high tech industry). Culturally interesting because it borders Quebec and has a large diplomatic community. It is a bit conservative socially. Boring and bland suburbs, but some good urban neighbourhoods and less than a 30 minute from downtown to remote woodlands and forests. Three gorgeous rivers, a canal, less than an hour to destinations towns like Mont Tremblant and Montebello. 60 minute drive to the border (New York State), plenty of direct flights to major US cities plus Heathrow and Frankfurt. Under two hour drive to Montreal. Predominantly English speaking but functionally quite bilingual.

My choice would be Montreal. my friends live in Pointe Claire and it is very Anglophone and as a bonus it is very close to the airport. It is cosmopolitan and has a wonderful arts scene. It is much more affordable than Toronto but more importantly the traffic will not drive you quite as crazy as Toronto. It is very difficult to get around in Toronto.

There is no getting around the fact the winters are harsh and I believe you should make contingency plans to spend much of the winter in a warmer location. On the plus side it has a lot of great lively cultures, an opera, a couple of symphonies, a ballet, one of the worlds largest botanical gardens, and a thriving local television and film industry that adds a lot of culture to the city.

in Canada you don't have a lot of choice for 1,000,000+ cities. If you would prefer a 300,000+ city you could start exploring some of the small or midsize cities in southern Ontario. Some of them will feel very Connecticut-y.

The downside of Montreal is that it does feel odd to be a linguistic minority in a city and you can feel isolated or apart from the true life of the city which is Francophone. This is one reason I no longer live there, but I believe it is very possible to have an awesome life in Montreal speaking only English.

West Coast my choice hands-down would be Kelowna. Love the okanagan and would prefer not to live on the west coast active fault line.

Is 1914 historic enough for you?

http://www.centris.ca/en/houses~for-sale~beaconsfield/26922115?view=Summary&uc=3

There's also Ottawa. I always forget about Ottawa because it can be a bit staid and boring. The winters are unbearably cold and summers are enormously hot. however it is a lovely clean and well organized city full of tech workers and bureaucrats. The river is beautiful and it is very handy to the Gatineaus which are gorgeous pristine wilderness.

Now if you're feeling like you want more of a Maine thing you can always come down here to Halifax and hang out with me. This 2.5 acre oceanfront estate property in my sister's neighbourhood is available for about 2.5m - they were unsuccessful in selling the condo development they wanted to start up on it. Apparently the historic estate house is salvageable. We are a poor and small city but we do have a symphony and a very active theatre scene.

http://www.solterre.com/finntigh-mara-gallery/

Thank you so much!

I just spent a few hours looking at Ottawa; very charming! I like being near a U.

I saw your link and was like, no, I don't want to spend that much, and it is too big, .....and then I opened it and ahhhhh! Wow!

I kind of like the idea of having to learn French beyond my rusty HS tourist french, and I am thinking more urban and walkable and smaller (like 3br not 6+).

westmount? Is chichi, Anglophone, and right downtown. Here's a fixer upper for you.

http://www.centris.ca/en/houses~for-sale~westmount/19822195?view=Summary&uc=9

I second Robo's vote for Kelowna in BC, gorgeous but rather boring and little cultural diversity. Ottawa and Montreal have essentially identical climates: cold winters, typically lots of snow, although much less in recent years. Not as cold as large swaths of the northern central US states though. Toronto is warmer because of lake effect. I won't be spending January and February here once the kids are off to Uni.

A few nice Ottawa listings here: http://www.dreamproperties.com/

Or let me find you a gorgeous piece of land with 45 minutes of Ottawa on a lake in the Gatineau Hills, build your own place!

One last Ottawa pro: we have the world's hottest leader here! ;)

One of my closest friends married a man from Ottawa, has lived there for many years (originally from a northeastern state), and loves it. She had an extremely serious medical condition last year, requiring major surgery,and had great success with the healthcare system there, as well. I believe she has dual citizenship, as she did vote in the recent election here.

Mtn, thanks for bringing this up. DH and I have had this discussion and I have seen it on other academics' blogs where they say they will give it a year or two and then seriously decide. We have MIL but we have no children, just cats.

Based on my years left until retirement, as I have previously posted, the next few years are a good time to move if I am going to do that. I'm definitely keeping my options open and making myself look as good as possible on my curriculum vita.

Back when I first met DH, I had applied and interviewed for a job in Australia that would have been a 3-5 year commitment. Being that far from my mother who was in her 80's was a consideration. When DH said he would go my reaction was "Woah! This guy is serious!" I wound up not getting that position, but never say never. Certainly those colleagues are still doing that work but also probably approaching retirement age.

I find the weather in Ottawa is like 5% worse than Montreal although they're on the same parallel pretty much.

There's also NDG
http://en.profusionimmo.ca/propriete/details/MT17654619

Or the old port

http://equipeburdman.com/en/inscription?code=21025536!

If you decide you could do small town living there are the eastern townships.

http://www.centris.ca/en/houses~for-sale~lac-brome/13741918/photos

I often visit my daughter in Moncton New Brunswick and look up real estate around here for fun. This one is pretty close to my dream house. http://www.luxuryhomes.com/lh/listing/Canada/New_Brunswick/Fundy_Bay/81_Harbour_View_Lane(04)

The Eastern Townships are gorgeous. We got wonderfully lost going through there about 15 years ago, on the way from Montreal to New England for my college reunion.

Mtnrd, since you're planning ahead, I'd spend some time in each season driving from Toronto via Ottawa to Montreal, meandering a ways out around each, and see what you think. Maybe do some rentals to get a feel for each area.

I moved from the U.S. east coast to Alberta almost 25 years ago and have never regretted moving here, despite the winters and Stephen Harper : ) . Besides, the winters make spring and autumn that much sweeter!

Gscience, I consider it an unlikely scenario , but not a preposterous scenario, that we may want to move, and hence I want to do some due diligence in advance. I know a few independently wealthy people who own homes in NZ, and I can see why, having been there a few times myself, but I am probably kidding myself that I could live that far away. But it seems to me that a fair amount of savvy Americans view it as the best choice if you have no constraints and are just picking a wonderful place to live.

Sochi, We were in Vancouver, Calgary, Banff and Canmore last summer. Of those, the only place I'd want to live is Vancouver. But I worry about buying into a bubble, and I'd rather not be a flight away from family.

Ottawa looks super to me! Really like what I see on line

Robo,

Thanks for the invite to Halifax! : ) I was there when I was 10 and not since.

I like your description of Westmount. Also liked the old stone property you sent. By then all three kids will be in college, so I don't want a huge house. I would like something walkable and not suburban or rural. I was really attracted to some of the townhouses in Westmount. It looks like there are very nice properties well under 2mn USD.

http://www.sothebysrealty.com/eng/sales/detail/180-l-968-j246eg/westmount-montreal-westmount-qc-h3y3j2

http://www.sothebysrealty.com/eng/sales/detail/180-l-968-tp4zse/westmount-montreal-westmount-qc-h3y3h9

http://www.sothebysrealty.com/eng/sales/detail/180-l-968-d6wwnl/westmount-montreal-westmount-qc-h3z3l5

or this,nice marriage of new and old

http://www.sothebysrealty.com/eng/sales/detail/180-l-968-qf52ly/ville-marie-montreal-ville-marie-qc-h3y0a3

Anyway, it's a fun little past time / diversion.

PS oh the view from the terrace!

http://sothebysrealty.ca/en/property/ontario/greater-toronto-area-real-estate/toronto/156749/

Thysrealty.ca/en/property/ontario/greater-toronto-area-real-estate/toronto/156749/

Mtnrd, I know you would prefer not to sidetrack another thread with political debate but I am curious as to why you think your quality of life would be better in another country. Or, are you just feeling that you would like to make a major change?

D, It just makes me feel a little better to prepare for the unthinkable. I'm a worst-case-scenario planner. Though we are white, protestant, affluent and not targeted in any way, I feel our President Elect is a loose cannon. I would not want to live in a country that really did bring back internment camps, for example. I also do not think extreme regimes are a safe place to invest all of our assets. We have huge exposure in real estate alone. Is it likely we would choose to leave? no. Is it possible? yes.

Lastly, I am totally ignorant about health care. None of us take so much as an aspirin, and even tho I am part time I get excellent benefits. I have not even thought about how I would obtain health care when I truly retire. (we are not old enough for Medicare; and tbh idk if I would be happy w Medicare? no idea)

I think you're smart to think ahead and plan for all contingencies. Ottawa has a great deal to offer, let me know if you come this way for a look, you are most welcome. Here and at our cottage.

*immediately plans to impersonate mtn so she can spy on Sochi's cottage up close*

You are both very kind, thank you. I appreciate it.

what's the tax situation going to be for an American living in Canada? What health insurance coverage will you be eligible for?

I adore Montreal. My in-laws live in New Brunswick. We are headed up there in a few weeks.

I have been dying to visit Quebec City. Reminds me from photos of Salzburg. Robo, what are your thoughts on Quebec City?

Quebec city is a beautiful place to visit but has only 0.2% or so unilingual Anglophones. I'm not really current on Quebec politics but I believe there is much more nationalist Quebec sentiment in Quebec city as well. My anglo friends get yelled at occasionally in the more Francophone areas of Montreal so I can only imagine what your experience would be living in Quebec city. Unless I was planning to become fully bilingual I would not.

QC is very charming but smaller and to me, very touristy. Go there in the summer for plein aire Cirque du Soleil performances!

Jmc,

The tax or healthcare burden would not drive my decision, because it is not an economic decision, but here's the little that I have read. I know that as long as you are a US citizen, you pay US taxes. But in most parts of the world, if you are a resident, you pay taxes locally. Usually there are foreign tax credits so you don't pay twice. Sales taxes are much higher.

its my understanding that you are eligible for Canadian healthcare after 3months residence.

A lot depends on whether you choose to be a resident, a part time resident, a citizen, etc.

More than you probably want to know, Jmc and MtnRd, but worth keeping in the back of one's head in case things ever become more permanent than expected (though some Americans abroad are hoping that the one silver lining to the election is that this situation might get dealt with).

I moved to Canada from the U.S. more than 20 years ago. Taxes and banking for Americans abroad have become exceedingly complicated in the past few years by FATCA (Foreign Account Tax Compliance Act) and FBAR (Foreign Bank Account Report), enacted after the U.S. went after UBS to catch fat cat tax cheats hiding assets and laundering money in offshore tax havens, but what the legislation is actually doing is complicating life for the 99 percent of Americans living regular lives outside of the U.S. and ignoring the fact that the fat cats can easily hide their assets domestically (Delaware etc). The U.S. is one of only two countries in the world (along with Eritrea) with citizenship-based taxation instead of residence-based taxation.

Americans abroad don't necessarily have to pay taxes, because of double taxation provisions, though there are significant treaty gaps -- what the U.S. deems “foreign earned income” is exempt from U.S. tax but other forms of “foreign” income such as investments are in fact doubly taxed. And the annual tax filing burden can be onerous and expensive -- there are significant (Forbes calls them "frighteningly high") penalties for compliance errors in what is now a very complicated filing system, especially with FBAR, which is filed not with the IRS but with, believe it or not, the Treasure Dept's Financial Crimes department. Under FBAR, an American abroad must list all “foreign” financial assets to which one is signatory if the aggregate is above U.S. $10,000. This includes accounts held jointly with non-Americans (including spouses) and accounts for organizations of which one might be a signing officer, including nonprofits (and your children's swim club). Reporting requirements include all account numbers and bank addresses. There is the concern of data safety as well as a thriving business of unscrupulous accountants and others in the compliance industry gouging the worried and unwary.

So far, Canadian banks have been much more relaxed with customers than those in Europe, Asia, and Mexico. It's more of a "don't ask, don't tell situation", though one of my kids was asked at the bank two years ago, at age 16, when arranging signing authority for an after-school club, about their dual citizenship (that child renounced citizenship after turning 18). In other countries, it's too much bother for the banks to deal with U.S. citizens what with the possibility of 30 percent tax penalties, so checking, savings, retirement, investment accounts, credit cards, loans, mortgages, etc. have been canceled, often without notice and in the case of investment accounts, triggering taxes. All further complicated by the fact that until recently the Patriot Act made it impossible for anyone without a U.S. address to open a bank account in the U.S.; as of this month one can get an account with American Citizens Abroad.

Anyone considering a move abroad should probably read up on FATCA and current tax laws. Some good sources of information are international tax lawyer Phil Hodgen's blog, Victoria Ferauge's blog, the Isaac Brock Society blog.

For health care, yes, usually three months, but all provinces have free emergency medical services.

Yeah, I know a lot of people who have come back to the US because of FATCA, or renounced their US citizenship to stay where they are. Owning property abroad is also a big can of worms for US citizens. (Or I'd be living in Chateaudun right now.)

Lol Robo, you can come anytime, no need to impersonate mtn! I have a couple of close American friends living here who have a hell of a time with US taxes. They never have to pay, but they have to file each year regardless. You just need a good accountant to keep on top of it.

And/or restructure one's portfolio!

Maybe not so relevant if you decide on Canada, but since you're considering other countries, too:

http://www.bbc.com/news/35383435

ETA I forget whether it's mentioned in that article or not, but several people have told me the cost of getting your taxes done as an American overseas is just unbelievable.

writersblock, it can be costly, in great part because one usually needs a Canadian accountant as well as a U.S. accountant, each familiar with each country's tax laws and statues. And some of the U.S. accountants take advantage of the situation and their Canadian/U.S. clients; they are known as "compliance condors". I'm lucky to have a good one who I needed for another reason, but I don't really look forward to maintaining that relationship for another 20-30 years.

IMO, if in the next few years FATCA isn't repealed and/or citizenship-based taxation replaced with residence-based taxation, Canada will join the other countries by cracking down. Kid #2 has an appointment to give up citizenship next year, and so do I.

MtnRd, maybe add a little cabin in Delaware, Wyoming, or Nevada!

I don't think Mtn would fit in very well in Wyoming....

Hey, i fit in fine in Jackson Hole when we went skiing there. : P

Since the world seems to be going to hell in a hand basket, would a location with nearby access to a US Embassy be something to consider, assuming you're not giving up your US citizenship?