You guys live fancy! I managed to travel Europe for around 50 euros a day on average for 4 month, so I figured around 100 CAD a day is doable. I typically spend about $20-$40 for a place to stay on average, CAD that is, using Hostelworld and AirBnB. Gas is like lets say 15 bucks a day. Food, I pack it myself, and cook in Hostels and so on, so I do it for 20 bucks or less usually per day. And, 25 bucks thats left is for booze and drinking, and that overall should average out nice and easy, as I don't drink daily. And I am talking about CAD. I have done it in Europe, so I doubt major touristy areas in US will be any different.
Especially going through touristy cities, there are plenty of tourists to chat up with, go clubbing with, find cheap accomodation and so on. I am just thinking of riding it nice and slow, around good roads with nice views for most of the day, and head to the hostel/airbnb around dawn, meet up with other tourists, and depending on the vibe, drink up and have a good time. Or, if it doesnt work out, just sleep, wake up the next day and try my luck on a different city, different day. I just plan to do it for as long as I can before I run out of cash, and head back to Toronto. I am thinking of doing it just like I do when travelling, go to a city, try my luck in the bars and clubs, if it works out, stay a few more days, if not, pack up and try a different city a different day. I like Florida, Myrtle Beach and Virginia Beach because they have nice beaches to just lay in the sand, and when at night, they got a pretty good night life.
As many of you guys suggested, my idea seems better off in a car than a bike. But, I feel like the freedom of a two wheeler is different than a cager. I can enjoy the countryside during the long trips, and enjoy nightlife during the night when I reach my main destinations. Plus, I dont have a car.
Normally, when I travel I travel extremely light. Backpack, beach towel, hygiene stuff, 2 pairs of clothes for change, water, food, bike repair kit and a rain jacket. I have a full faced helmet, and a decent mesh jacket. I plan on checking the weather regularly and not riding on the rainy days.
As I said, I will never ride drunk or hung over, will be fully insured medically, and have power bank with me to keep me connected throughout the ride. Safety is paramount for me, so I dont wanna do the trip in any less than 5-7 days, as I wanna enjoy my ride and not be tired in the middle of the trip. If I run out of money, I can estimate when I should turn back.
So, I am definitely gonna follow your suggestions, and head down to Kentucky at my own slow and steady pace through Pennsylvania. I got my uncle down there, so I can stay out there for a bit if anything goes wrong, and head back up to Toronto. If everything goes swell, I am gonna head further down south, and make a loop around Myrtle beach, Virginia beach, and head back to Toronto.
I actually do not care if I make it to Florida or not, I am just looking for a good time, wherever. The journey is more important than the destination anyways. I just go with the flow, so the schedule I posted was tentative on the route I wanna follow. My uni finishes around the end of April, and I got a work that starts at June, so i got around 40 days to kill, and am in no rush to reach anywhere. As nakkers just said, I just wanna ride till I run out of cash for as long as I can, and return back to Toronto.
I feel like where there is a will, there always is a way.