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5 of us went in 2020 just before the pandemic started. It's a fun time there's no doubt about that!
I would think the mess that is Canadian airlines will be sorted out by the time Spring Training starts. But maybe that's me being blindly optimistic as we are flying to California in March. Winnipeg to Tampa is a bit of an awkward flight as well, no direct flights, and what is available is has a long-ish layover. Orlando is only an hour from Tampa and has more flights, although expedia currently doesn't list a direct option on the random dates I picked. It's 3400km each way so that's pretty much a 2.5 day drive, definitely something to keep in mind.
Dunedin is an okay place, although we didn't spend too much time in Dunedin itself. The whole area northwest of the bay seems a bit older. I wouldn't say run down, but definitely had an aged appearance. We had an Airbnb in Tarpon Springs which is north of Dunedin a bit, I don't know what is available for hotels in Dunedin, sorry.
The weather is pretty good, but it rains quite often. Showers will pop up from the gulf seemingly out of nowhere. Luckily they are normally pretty quick, rolling through in less than 30 minutes.
I do know that the parking is pretty poor around the ballpark though. It's in a residential area so it's mainly street parking if you can find it. There's a library next door to the ballpark, but they have signs up not to park there during games, but it seemed a lot of people, us included, we're ignoring them. Most, if not all of the Jays games start at 1:00, so it makes it a bit tough to do something else during the day if that's what you want to do. We were golfing before the games and to do both we were up at 6:00 each morning, which still didn’t put us at the ballpark for first pitch.
TD Ballpark is pretty meh but it is a really fun place to watch a game, despite the ballpark being what it is. Shaw Park in Winnipeg is much nicer for comparison. All around the outfield is standing room on the concourse, overlooking both bullpens in left and right. We watched one from out there and one from the seats down the first base line. We went to a game at the Phillies park in Clearwater and it’s really nice. The Yankees are also right in Tampa, but we didn’t go to a game there so I can’t comment on what it is like.
All and all I would definitely go again, but I’d take a bit more time so we weren’t so rushed trying to golf and get to the ballgames.