I would go to ancient world, Greece is first on my list but Egypt would be nice, too. I would also like to go to see Atlantis and England of Druids and Merlin. From relatively closer past I would go to visit Michelangelo, Picasso and Marie Curie.
I would go to the period known as the Age of Enlightenment (18th century). In my opinion, that is one of the most fascinating eras in history because of all the changes that were going on -- in science, self-governance, democracy, women's rights, etc. Fascinating era!
I'd start by travelling to next Wednesday night and getting the lotto numbers. Then I'd come back and spend a dollar on that.
As time and humor allowed, from thence forward I would take a trip to the week ahead, buy a copy of The Wall Street Journal come back and start really blowing up my wealth.
For fun I'd take trips into the far future and far past, and if anyone I loved ever got hurt or died, I would go back to the time where that could have prevented it and, if I had to, duct tape them to a tree until the time of that demise was past.