I worked on the Tourism Toronto account for a little while from the marketing side. One of our assignments was to get people from Boston, NYC and Washington to come up here for a weekend. My first question was, if you lived in one of those cities why in the world would you want to visit Toronto? It's like saying to a Torontonian, enjoy a weekend away in Hamilton. Why?!?
I do think Toronto's problem/strength is we're a city of neighbourhoods not a city of big tourist attractions. Which means you really need to go to the different neighbourhoods and walk around them and just soak up the vibe rather than, go see the Empire State Building, go see the Eifel Tower, go see Big Ben. We just don't have those tourist things. I'm fine with it.
That is the exact problem. Toronto is great for residents, but for tourists it's not a big draw to go spend a weekend. Why would you spend a weekend here if you live in Chicago, or Boston or New York? Yes we may be cleaner, our crime rate is lower, but those are not that important to tourists. Mostly it's business travel or special events like TIFF or Caribana or Taste of Danforth that brings in local people and folks from neighbouring towns and nearby cities to town.
Being a city of neighbourhoods is not an attraction either. All cities have neighbourhoods. While ours are quaint, they are not big city neighbourhoods like you would see in Paris, London, Boston. Our neighbourhoods are really just former high streets of the villages they used to be part of. In most other cities, neighbourhoods are blocks of activities, cafes, restaurants, parks. Ours are basically just a few blocks of retail along a main road. Would any tourist really make the treck to visit Greektown, Y&E, or Chinatown? There isn't anything special there that distinguishes it from similar neighbourhoods in Boston or New York. Having traveled to many cities in US and Europe, our neighbourhood high streets are pretty run-down and are architecturally ugly. Even Bloor St, while much improved after the reno, doesn't compare to Chicago's Mag Mile. Bloor's trees are 50% dead and the side-walk is starting to be dug up. This is the best Toronto offers at the moment.
Most tourists to Toronto, come for business travel, or to visit family. I've hosted many family members here. Their most favourite places are Niagara Falls (falls themselves, not the town), and Niagara-on-the-Lake and trips to wineries. In terms of parks, Toronto Islands is the best park we have but it's only great for day-trips and not a casual 1-2hr stroll. Most of my family/friends love Distillery District, due to the rich architecture and the cool spaces and retail it offers. CN Tower and downtown are nice for one day, but it's not a major draw as many cities have towers or observation decks on tall buildings.
As a resident in Toronto, I've made many weekend trips to Chicago, Boston, Ottawa, New York, Montreal. Each city has a unique feel. Chicago has amazing architecture and a pleasant waterfront (although I feel there is not much to do there but walk around and visit museums). New York has Manhattan, the dense urban jungle with so many things to do. Central Park is amazing, the Broadway shows, Fifth Ave. Boston, has the New England charm and history. Ottawa although somewhat boring, does have the parliament buildings and decent museums. Montreal has the Mont-Royal park, the old port, and the French flair. Compared to these cities, Toronto is fairly bland. We have a bit of everything but we don't excel at anything in particular. Yes we have diversity and lots of restaurants. So does Montreal, and I'd argue their food tastes better.
Having said that. I think Toronto is getting better. Once all the projects get built, we will have great new/improved areas such as the Waterfront and the PanAM district.