The Can Am Spyder is an interesting vehicle. Although I haven't had the pleasure of trying one, they look like they'd be easy to handle. Their dealer network may not be as large as other manufacturers, if that's a concern for you.
There are plenty of kits to turn many different motorcycles into a trike. Harley has foregone the aftermarket and now has a trike in their model line-up. Has the option of a side-car rig been mentioned? If you're going to use a trailer, a side-car offers more room for stuff.
Many community colleges offer the Beginners Motorcycle Safty Federation course (BRC). Often, after passing the course, you don't need to take the road portion of a motorcycle test at your DMV. You'll get a break on insurance, too, so taking the course pays for its self. Private instruction is available , as well. Stop by any motorcycle shop and I'm sure they can help.
MSFMy Gal and I have towed motorcycles (in an enclosed trailer), set up base camp and explored on the bikes. Mainly, we ride the bikes because we enjoy riding the bikes. It's not for transportation purposes. We used to motorcycle camp, because we love riding our bikes, but it was getting difficult to sleep on the ground.
If you're thinking about a flat-bed trailer for the trike, about a 5x10 oughta do it, with a little room to spare. I would think a 5x8 would be too small, considering tie-down points, but I guess it really depends on the trike.
Keep us posted.
'13 F250XL SC gas 4x4 8', Camper & Plow packages, StableLoads, LT285/65R-18 Goodyear Wrangler A/T Adventure, 18x9 Ultra Motorsports "Phantom" wheels
'12 Wolf Creek 850 TC Coleman Polar Cub 9.2k A/C, 90 watt solar, dual propane & batteries, Maggie Rack