I don't live in SD but my daughter has been there for a year (moved from Boston). She absolutely loves it and says she'll never live "up north" again. She is lobbying hard for my wife and I to move to the area and we are considering it down the road. From the research I've done, I'd most likely want to live to the north of SD, say around Oceanside or similar. Maybe even a bit inland. It is definitely an expensive area to live and lots of traffic. I think public transport has good potential depending on what route you need to take.

I can say after spending the last two winters in Florida, I am NOT looking forward to next winter in Wisconsin. Once you experience a warm winter, it is hard to want to give it up . . .

I've already determined I'd be cycling for my commuting if it's feasible which I would hope in a sunny all year round. Do they have a good cycling infrastructure is one question I'd be curious to know. Toronto doesn't have a great one but we have been bolstering it over the past few years. I've never had a problem riding in traffic myself anyway. Motorist here I think are familiar with seeing cyclist on the roads so they are somewhat mindful.

There are no hills here really though. Thats one thing I'm not a big fan of. Sure there are some "hills" but no real major ascents unless you go an hour or two out of the city. The race scene in southern Ontario is also very good. We have so many racers and races to chose from. Milton (45 minutes West) just got a velodrom for Pan Am games so thats something that is also of interest.

From what I've gathered SD is like the alternative mecca in the US for triathletes. Is that safe to say? High quality coaching, swim squads, group rides are in abundance? Expert bike fitters and wind tunnels?

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"Train so you have no regrets @ the finish line"

I spent a couple of weeks visiting friends there a couple of times.
They live in downtown San Diego.

Weather better of course ( visited around Christmas and it was 60-70 both years), housing probably much worse than your current environment, the driving can be preposterous depending upon your work commute. If you can afford to live downtown, lots of stuff is walkable, but I didn't try getting in a cycling workout, there are some beautiful routes close to there but only did those after my visits, not trying to do them in the course of a work/weekday.

I live in Northern California so I might be kind of used to the traffic and housing costs, but started working from home so I never drive in traffic except for traveling now. The areas of San Diego I was in seemed to be less diverse than San Francisco/San Jose, YMMV.

Well lets take each one at a time;

Things I love about Toronto:
Tons of international flights daily / Same for SD
2 Airports / about 5 major airports within 100 miles
Multicultural / Same, maybe even more so being right on the border
Commerce Center of Canada (everything is here) / Same for SD
Dense downtown area easily walked / Same for SD
Inner city transit and suburban area transit (TTC & Go Transit/ Some transit, but you need a car anywhere in CA)
Tons of races in the summer (20 or so)/ More races within driving distance than just about anywhere, and all year long
Condos have great amenities (I have 25M Pool, Sauna, Gym, Hot tub, Billiard tables, Movie theater for 25, party room, spa, hair stylist, basketball court, BBQ Common)/ Lot of those kinds of places
Waterfront trail for 100km+/ Waterfront everywhere
Food from anywhere in the world you can dream up and imagine/ Every restaurant you can imagine
Festivals and cultural events every weekend in the summer (Nuit Blanche, Doors Open, Luminato, etc)/ Lots of that stuff in SD

Things I hate about Toronto:
Snow and winter / No such thing in SD, winter has died
Transit mentioned above sucks/ You still need a car here
Driving here stinks / Driving is easy around here and pretty safe for cyclists, not like Florida
Housing Market is high (1BR 700sq/ft condo downtown is roughly $350,000)/ Then you will not have sticker shock here, probably about the same or worse.

Thanks Monty I appreciate the insights. I'm really thinking it makes sens but I'm not the only one affected by it so I have to cover many of the preliminary questions. Curious what are health insurance rates like in California for 2 sub 40 year old health freaks? Not an exact quote but having never lived in the US and needing any I have no idea what to expect. Car insurance is like $250-$300 a month here so would it be similar to that?

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"Train so you have no regrets @ the finish line"

Health insurance rates will vary, and since the new ACA law it is a lot easier and cheaper to get for people without. You car insurance should be way cheaper, unless you have a ton of points on your driving record(tickets and accidents). I pay about $600 a year for a new truck, a little less for the older mini van. That seems like a lot for auto insurance, is it that way for everyone?

Not sure where you are going to work, but i would recommend if possible to look for something in the north county. That would be like La Jolla and north all the way to Carlsbad. Lots of great cities on the coast in-between, and in many different price ranges. It really is the birthplace of triathlon as we know it in this area, and continues to be. You have a ton of shops and great group workouts originating from the north county, and it is less densely populated than the city. Sad to say It is catching up however, but along the coast it is still reasonably quiet..

Work would be from a home office with flights twice a month or so to The Bay Area. That was an opportunity for hills if I bring my bike which isn't out of the question or leave a bike at the office.

I have to admit to being a city person. I like living in the heart of downtown. Cycling is rarely ever great in the dense urban jungle so bike lanes and aware drivers is a bonus. Unless bike theft is super high I'd love to cycle at lunch, grab some groceries, maybe stop at a cafe and have lunch. Is it easy to get from the core of the city to the areas you mention by bike? Would you consider it safe enough to do regularly?

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"Train so you have no regrets @ the finish line"

Is it easy to get from the core of the city to the areas you mention by bike? Would you consider it safe enough to do regularly? //

NO

Now to be fair i never lived in the city, and only rode that direction a few times when i had to. But SD is a really spread out county, and to ride to even the southern part of north county, well that would be your ride there and back, and pretty busy roads. You can go south or inland from the city, but even then you are riding through the worst SD has to offer to get to the good stuff. If you like city living, then fine, you can just drive to where the good rides start. I believe that is what most do that live there. I see a lot of cars pulling up and parking in Encinitas on the weekend, probably for that exact reason.

''Housing Market is high (1BR 700sq/ft condo downtown is roughly $350,000) ''


Yesterday my son signed a contract on the same size condo with a nice balcony in downtown SD for $325,000, with maintenance of $250 per month. It has all the amenities, meeting/party room, pool room, spa, etc, but the pool isn't 25 yds. The only reason his was that expensive is because he had a very specific, small neighborhood that he wanted to stay in. I'm in New York and when Matt asked about the price, I told him that if that condo was in NYC it would be over a million without the balcony. San Diego is beautiful. The North County (San Diego County) is more beautiful. The scary thing is that California is in a very serious drought and although San Diego County did build a desalination plant that is about to come on line, it is at the end of the pipe for water and no one can say for sure which way the weather will go.

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''Sweeney - you can both crush your AG *and* cruise in dead last!! 😂 '' Murphy's Law

I've lived in both Toronto and San Diego.
Now I live in NYC.

But he is what you will enjoy about San Diego:
Best weather ever. Proximity to other great cities and races.
San Diego has quite a few cool neighborhoods, think the Annex or Kensington 20 years ago.
The city is still relatively cheap to live.
Very cool people.

What you may miss
Free healthcare. Public transit may not compare, but the TTC does suck - admit it.
You will miss the Leafs, but come football season, you get the Chargers. You also get to see the Padres instead of the Jays.

Imagine, a drive up the coast to LA or through the desert to Vegas.

Cost of living is lower in San Diego, but if you are going to miss that Toronto elitism - you know what I'm talking about, you may not dig on the west coast cool laid back drama free lifestyle.
San Diego has its share of multiculturalism as well, you may get the best Mexican food ever.

I loved San Diego. There were things I liked about Toronto. If I had a choice, id experience San Diego as long as I could.

cshowe80 - why don't you come here to San Diego with your SO for a few days and first check out the area? You can see for yourself and put some value on what's most important in your criteria. I'm a real estate agent, mostly specializing in La Jolla and the beach communities like Mission, PB, Point Loma, and around. Its not downtown living, but plenty of great urban feel for your cycling and outdoor lifestyle. Lots of quality choices for 1bed for $350K, and of course upwards from there. I'd look forward to spending a few hours with you driving around some of the neighborhoods and showing housing prices, neighborhood vibe, lifestyle interests, etc. Its what I do for a lot of out-of-town interested buyers ...I often feel I'm a tour-guide and beach communities pimp first, and real estate expert second. PM me if further interested.

San Diego is a great city. I'd move there in a heartbeat if I could.
-SD

Interesting how the top of your list for things you like about Toronto are two items that are focused on getting you out of Toronto. I've found that I take far less vacations since moving to San Diego, you already live where people go on vacation.

But if that's really important to you, the city itself is not great for international travel. It's not terrible, but SD is the largest metro area in the US that is not the hub of any major carrier. We're vastly overshadowed by LA when it comes to available routes, but LAX is over a 2 hour drive which is not at all worth it in my book. It's not the end of the world though, you'll just end up doing a lot of short connections to LA if you travel extensively.

To some of your other specific points, I think to most people a move from Toronto to SD is a no brainer but you mention that love the city and it's worth mentioning that downtown SD is probably pretty lackluster compared to Toronto. The Toronto metro area pop. is 2x that of SD metro, SD is by no means a backwater but I'm sure it lacks some of the depth of cultural diversity that you might find in an even bigger city. One thing for sure that kind of sucks about SD is that it's not a city that has a lot of hometown pride. Granted, people who are from here love it, but it's a city of transplants and that is sometimes reflected in embarrassing ways. Go to any given Padre's game and you're likely to see more away fans than home. Depending on your age, there is a weird vibe here due to the transient nature of the population. People move here from the midwest or new england for college or for their 20s to escape the weather, but many eventually return home to settle down somewhere with more affordable home prices. It's a city that's sometimes entirely overrun with tourists, or with the entire state of Arizona from June-August. Combined with the near unchanging weather it life has this tendency here to turn into this mid-70's-and-sunshine-blur of people coming and going with less rooted and meaningful relationships both to eachother and to the passing of time.

Not that I would call this a very scientific measure of a city, but I've always found it kind of interesting that after 3 or 4 different series and something like 15 seasons of travel shows Anthony Bourdain has never done a single show in San Diego. I think is because of for all it's perks, San Diego itself seems to lack a true sense of authenticity on par with other major cities. We're just too diluted.

Now, none of this is to say that I wouldn't move to San Diego in your position and that I don't agree with all of the other great things people are saying about San Diego in this thread. I love this city and I don't disagree with the others, but playing devil's advocate I think it's important that you don't get an entirely one-sided story.

Go spend a week in Coronado. Eat at Miguel's. Go to the Del and hang out. Check out the beach. Run round the island. I suspect you'll be convinced.

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