Sounds like you will fit in beautifully. We always travel with one rollaboard each (RSteve's brand), plus one tote bag (to put cameras, netbook, travel pillows, carry on toilet articles clear bag, and other miscellaneous stuff in. When boarding the plane, I will put my travel purse in the tote bag, too, so the combined bags count as my 'personal item.'
When de-planing and moving on foot, the tote tag straps are secured over the handle on the rollaboard, so we still have one hand totally free. To me a tote bag is similar to a daypack....when on tour, we put a sweater (if chilly) or rain jacket , umbrella (if rain chance), hat, sunscreen, sunglasses, camera, etc. in the tote and often leave it on the bus when doing day tours.
We are not big shoppers, but if you might be making purchases, it's a good idea to have a small tucked away foldable tote. On the flight home, we typically check the rollaboards, just so we don't have to keep up with them in airports and during connections.
Oh, and I should have added, the tote bag's straps are long enough that it is carryed on my shoulder when going up stairs or entering the bus, etc.
If doing weekend trips, we try to get share one rollaboard or use smaller duffel bags instead.
Have a great time on your tour!!