Riding highway 101 from Del Mar up to the north end of Carlsbad and back is very pleasant. You can also take the bike path inland from Del Mar, more or less, to Poway.

Mt. Soledad has [a hill]. Go further inland for more hills. For convenience (close to work), I typically ride 1k feet/10 mi around Poway without specifically looking for hills. But Poway is comparatively far from downtown.

For a 5-8 mile run, i'd run along the embarcadero - you are really close to it, can take it south to the convention center, then run back north and around harbor island, that gets you somewhere in the 7 neighborhood I think. It's a very pretty run. Nicest in the early morning, when there aren't a ton of people walking around.

For the 16-20 mile run, what are you looking for? Trails? Scenery? Hills? We have all of those in different places in SD. If you are looking to do your long run from the hotel, you could run to Balboa park, then take a bunch of the different trails on the east side of the park.

For hilly rides you can leave the hotel from, i'd probably ride Point Loma. You can find all kinds of insane short hills, although the stop signs get annoying. Ride out to the Cabrillo National Monument - if you pay (or get there before they open the gates), you can ride down to the tide pools. Moment Bicycles does a Tuesday/Thursday morning ride from their shop in Liberty Station to the tide pools if you want to go with a group.

Finally, i'd note for you that Palomar mountain is a pretty long drive from downtown - at least an hour, i'd speculate (it's ~50 minutes from my house, and i'm about 15 minutes north of downtown). If you want to ride something mountainous that is closer (like ~20 minute drive from downtown), check out the Great Western Loop - lots of climbing, fairly quiet country roads, usually lots of cyclists around.

Just head towards the water from your hotel and you will find a sidewalk that winds along the waterfront to downtown. Great run route. For cycling, head up Point Loma to Cabrillo National Monument. Pay the $5 or whatever and make a right when you go through the gate. You'll find a wonderful hill repeat with great water views. 5 minutes up, 2 minutes down. Great interval training. On the other side is a nice dirt trail for hill repeats. Bring you wetsuit and do an open water swim in LaJolla Cove.

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Simplify, Train, Live

We are form Kelowna, been in San Diego for the last 2 months (go every year) and are just heading home.

Run routes:
As others have suggested. Plus anywhere along the coast. We ran Mission Bay loop mainly as thats where we were based.

Bike:
Soledad Mountain is good for hill repeats. Can be a little busy near the bottom on the shallower side, the steeper side I had not done much but it gets pretty steep. We jumped into some group rides with Moment Bicycles, mainly their SUnday rides and they do all sorts of different routes but they have their ride maps up on their site so check those out. Palomar is a great climb, totally continuous with no let up but never too steep. A bit of a jaunt to get out there but worth it. There was some ice and snow at the very top a few weeks back but you could get to the store without hitting any. Just be careful of the melting run off that freezes again in little streams. The coastal route down through La Jolla, down Torrey Pines and into Encinitas is nice. The ride from UCC Cyclery goes through the countryside a bit more and the Orange Orchards, which is also a great ride. Their group goes on Saturdays and splits into easy through to fast in a few big groups. Fiesta ISland can be a bit sand if you are precious with your ride.

Swim:
We swim at Mission Valley YMCA. Nice people, great outdoor pool. Scott at Masters is great and they are triathlete friendly. The gym and cardio room there is pretty sweet too. One of the things I miss most when I go.

There is a big tri club, Moment Bikes has a brochure on their activities of which there seem to be many. We never went though.

Hope that helps.

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https://www.pbandjcoaching.com
https://www.thisbigroadtrip.com

There's a half marathon downtown on the 12th. It's a pretty good loop course that starts and stops in the Gaslamp, down near the Convention Center.

As others mentioned, you can run along the coast downtown and loop the Embarcaderos and Harbor Island. Pretty easy to get in 15 miles with an out and back. Balboa Park is pretty close if you can deal with a few stoplights. Just head up Laurel. Check out the Strava or Garmin Connect heatmaps.

For biking, you can head out to Pt. Loma and hit the tidepool repeats (great pavement). You're staying fairly close to Moment Bicycles in Liberty Station. They have shop rides. The best riding is farther north on the coast up past Del Mar or out to east county for hills. You can also get to Coronado by heading south towards IB and taking the Bayshore Bikeway. Flat ride.

I'm not much help with swimming.

For swimming groups:
If you're an early riser and do not mind driving from your hotel, there's the La Jolla Cove/Shores First Light Swimmers group that meet up to swim between 1/2 mile to ~1.2 miles at 0630 every Wednesdays and Fridays.
Peninsula YMCA is close to your hotel, it's scy but you'll probably find the outdoor pool setting enjoyable especially coming from snow.
The masters swim at YMCA mission valley has a good mix of swimmers and multisport folk too, they have multiple hour sessions that start from 0530 to 0830.

And as everyone already mentioned, join in the Moment group on Tuesdays and Thursdays for tidepool hill repeats. It's typically early enough that the park never charges you for entrance, and you get to dictate how much you want to hammer or cruise as it's practically a no-drop.

I'd avoid National city. That area can be a little sketchy.
Check to see if Coronado has their pool set up for LC or short course this time of year. You might need to call them.

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Karen ST Concierge

x2. The pool is in a real hood. Particularly watch out for the territorial mobs from the adjacent golf course. If you're flashing the wrong color jammers in the pool you could end up in real trouble.

Come on. I know we're gentrified triathletes, but we don't need to tremble at the word "National City."

Hi Seth. Where in snowy British Columbia are you? This winter, it could be darn near anywhere. I am in the F. Valley and go down to Carlsbad each year for a tri-cation. If you can, and the weather is not bad, y'all owe it to yourself to go to Nytro and to ride Palomar.

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http://www.fitspeek.com the Fraser Valley's fitness, wellness, and endurance sports podcast

I assume you are attending the AAOS? So do I. I live in Scotland so I am escaping the cold as well. I am planning to do some rides and runs as well.
PM me on Facebook if you want?
Alexander Siegmeth