-- Last Updated: Mar-05-13 11:01 AM EST --
... but I'm sure it could be done. If you plan to go with a buddy, I'd plan on tying in your gear and using the biggest float bags you can. Two people can re-enter a float-bag equipped boat pretty easily, but then there's always the question about re-entering in the kind of waves that would cause you to tip over in the first place.
Also, tandem paddling with gear will be tough in rough water. Clarion is right about tandem paddling in steep waves. There's a segment in one of Bill Mason's old movies showing tandem canoe paddling in some really rough conditions, with both paddlers kneeling in the center of the boat, one person immediately behind the other. In steep waves you need to keep both ends of the boat light, and the two paddlers can move to the center IF there's not much gear on board. Tandem whitewater-specific canoes put the paddlers very close together in the same way, but with a saddle instead of just kneeling.
Since you describe mostly calm conditions, I think almost any tandem canoe designed for your load (16 to 17 feet is probably big enough if it's a general-purpose boat with some gear-hauling ability) with float bags will do the trick.