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I'm traveling alone to Cuba for two weeks (American). Need advice!

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Hi all - I'm a 30yo American male and have decided to head to Cuba for two weeks in January. I've done a lot of research on these forums already so I hope I don't sound too amateur.

Also, just a quick note on my style of travel: I like to travel independently and go off the beaten path if possible. I appreciate good people, good culture, good food, beautiful sites, and serendipitous connections -- pretty much what anyone would enjoy :) I know with Cuba the food won't be exceptional but that's a small price to pay. I've always wanted to go and now I have the opportunity. Would love this forum's advice on the below questions!

- Getting in: The obvious question is how to get in. Two friends of mine have flown through Mexico City to Havana without a problem (Cuba didn't stamp their passports, just gave them a slip of paper). I want to make sure this is still the case.

- Lodging: I prefer to stay in hostels when I travel but have mostly heard of people staying in casas particulares. Is there even a hostel culture in Cuba where I can meet fellow travelers? If so, I found a good one here that I'll probably stay in when in Havana (http://www.hostelz.com/hostel/202558-Rolandos-Backpacker)

- Cultural activities: Any local events or cultural events I should consider looking into? I really enjoyed Thai kickboxing in Thailand, Flamenco festival in Cordoba, etc. Is there anything I should keep an eye out for in Cuba?

- Outdoor activities: On a similar note, are there any outdoor activities I should look in to doing? Would love to tour some cigar factories in the hillsides or similar. Hikes are also fun. I've heard good things about scuba. The less it feels like a formal tour, the better, but I understand if that's not an option

- Cuba destinations: I'm thinking of spending 6-7 days in Havana. I've heard I should also visit Trinidad and Vinales. Are there others I should consider?

- Money: I plan to take about $1200 for two weeks. I'll just have to be careful with my money. Am I way off base?

- Getting around on my own: I know this is a longshot, but I'd love to rent (or borrow from a local) a car or motorcycle to get around the island. Is this even possible?

Thanks all :)

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