BlackEleven pretty much covered it. I like to cruise St Catherine's, lunch at Ruebens deli (RIP Ben's) and down Peel St and stop in at Sleemans Pub for a couple of pints.
Walk by the Sun Life building (the crown jewels were stored there during WWII) and Mary Queen of the World. Down to Windsor Station/Bell Centre where my dad worked and down de la Gauchetiere.
Walk through Square Victoria and check out the old financial district towards Old Montreal. Walk into some of the banks. Pints at Place Jaques Cartier and a walk up St. Pauls street.
Dinner on St Lawrence (Don't forget to bring your booze as most places won't sell any) and patio hop the main all night.
St Viateur bagels are a must. Check out the fireworks at La Ronde (Six Flags) every second Sat or so. Spend the day there if you like coasters. The casino is a must too.
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