You'll need to split the trip into two years. Eastern stuff (Bermuda+ Great Lakes) if you're quick on deliveries and then Western stuff (Big Boat Series + Transpac) since they run the TP and Bermuda race in opposite years. If you're touring the Great Lakes, you should include the Bayview-Mack as well. Splash in Lake Huron and run the byc-mack, sail down to chicago for the chi-mack the following weekend, then the ugotta regatta in harbor springs is the third weekend. Pull it in Harbor at Irish boat shop and ship it to where ever you need it for the next race. Maybe Key west, BVI and Antigua for the winter and then out to California for the next year?