Since it's a personal trip you'll have the luxury (for the most part) of picking which airports you'll want to transit.
On my trip, I generally picked airports I knew would have a decent FBO with fuel, services + facilities. 100% of them had tie downs, etc. Most of them had courtesy cars / vans, some had rentals. These days with the Internet and sites like SkyVector.com, 100LL.com, AirNav, etc., it's pretty easy see what services will be available at any given airport or FBO.
Insurance: you'll need out-of-province travel medical insurance plus aircraft rental / liability insurance (assuming you'll be renting). Unfortunately most out-of-province medical insurance specifically exclude coverage on flights other than as a passenger on common carriers. The best bet for insurance is to contact COPA or AOPA depending on where you'll be renting from.