I am a Canadian and I currently live in the Philippines. You will spend your entire budget just getting here so let's rule that out.
You seem to be focused on the weed thing so you will want to rule out Cuba. You will spend the rest of your life in jail if you are caught with weed there!
I lived in Colombia for 3 years. I was happy that so many foreigners were scared to go there. Prices go up with tourists! I never had a problem and I was out to the bars every night!
It is legal to carry around a few joints and 1gram of coke! That could have changes so just Google it.
People there are the friendliest people I have ever met anywhere.
I am going to suggest a trip of a life time to you and if can get by all the bullshit hype about Colombia.
Take a bus to Buffalo. Grab a Jet Blue fight to Calli, Colombia. They have some very cheap flights. Rent a room in a hostel near downtown area where all the Salsa Bars are. I will give you more specific directions if you are interested.
I partied every day there. Went to all kinds of places (use your imagination) and never had a problem.
My daily schedule:
Breakfast nice buns and fantastic coffee- $2
Visit to a special place for a morning companion - $12
Visit small store on the street for a beer .75 a beer
Lunch at my favorite Argentinian Restaurant for lovely steak and baked potato $6
Workout at gym $3 a session
Take Salsa lesson $5 a session
Buy fantastic bbq chicken next to my drinking hole $2
Back to drinking hole - beers and extras! $20
Visit to a special place for a evening companion - $12
Room in hostel $15 a day
Total expense - $77 a day!
Rinse and repeat!
Note: you can get some pretty good weed for a few dollars. Fairy dust for $4 a gram
Hint: do not wear gold.! do not tip! Be friendly with people. You will meet some of the nicest people in the world in Colombia and you will not break your budget.
Are you good looking and want free sex. Let me know because I have a friend who has all kinds of girls working on webcams in Calli. It is legal there and he is an affiliate for Reality Kings. He is always looking for guys to match up with his girls.
Now if all this is too much for you why not try Andres Island, Colombia. English is the 1st language. Look in the Toronto Star and you will get a cheap trip there. Weed is legal there but remember only for a little bit. I really like that place and I am sure you will too. After you go there you will see that Colombia is not as dangerous as the newspapers makes it out to be.

Food and drinks are all included!