re: Suggest a trip: Single guy, mid-30's, solo, budget-friendly

I know this is late, and Im also about to update my Cuba post with my itinerary. Cuba can definitely be done on a budget! Casa Particular's are an incredibly cheap option, and most offer a food option that is cooked by the family. Check AirBnb, book your first couple nights there so you can get comfortable and familiarize yourself with the area, then go from there. If you use "collectivos" which are local taxis that accept CUP, as opposed to CUC, you can get around very cheap.

Give me your email and I'll forward you the excel sheet I made including links of all the things to do while you're there. It will include area, price, and notes.

It all depends on what you are trying to do? Are you trying to party? Mojitos are about 2 USD, beer is less than a dollar. Are you trying see the history? Do you want to see the country side? There is amazing hiking a few hours east and west of Cuba. You can hike through Vinales, which is absolutely amazing. 3 hours east of Havana, $24 tour-bus style ride round trip from Havana. The hershey train is less than a few dollars to get outisde of the city and into the country side. You can see most of the stuff in Havana for nearly free. I would suggest spending two nights in old Havana, then moving to Vedado, which is less touristy and more "new world".

Let me know if you have any more specific questions and i'll give you my email.

Also, as far as booking tickets there, definitely go with Cuba Air from cancun. Def the cheapest. DO NOT use AeroMexico. They are an awful company in general.