If your guy wants a treat, see this guy. Cuban tobacco, choice of wrappers, rolled at the shop by nice Cuban ladies. A really unique place to visit.
http://www.correnticigars.com/contact.php
Otherwise, I would look for Macanudo HAmpton Courts, which are very nice, not Cuban, but won't break the bank, either, and are sold in tubes that keep them fresh.
Or, try Yitz's, just west of Avenue Rd. on Eglington. Bis selection, reasonably priced.
Hope that helps!