CincySpyder tows a teardrop. Several of us tow pop-ups. Mine is an Aspen Sentry. Your biggest limitation is weight...the Spyder's towing capacity is only 400 pounds. Throw a filled cooler into your teardrop, and you are pretty close to that with even the lightest teardrop, or even with many popups. Another difficulty is rearview vision. The wider, taller teardrop makes that virtually impossible. The popup bike campers are nice in that respect, since they are low enough to see over and not as wide. As for an Airstream, even the very smallest weighs far more than the Spyder's towing capacity...and more than the Spyder, as a matter of fact. What you wish isn't totally impossible, but it does have its difficulties and challenges. Choose wisely!