Hi Cheryl, Havana is a great city for just wandering around and soaking up the atmosphere - on my first visit I I couldn't get over how it felt like I'd walked onto a film set for a 1950s film!
Re safety advice I can't really add anything to what merseygull has already said - don't do anything you wouldn't do in places like London or Barcelona and you won't go far wrong. And if you aren't sure - get a taxi, they're cheap enough and any bar will call you a licensed yellow cab. Just as here, you do need to be careful about unlicensed ones but only licensed ones are allowed to wait on the ranks and there are enough of them dotted around. Often the easiest way of getting around the old town is in a 'bicitaxi' something akin to a cycle rickshaw. Also try a 'cocotaxi' just once for the experience and make sure you hang on tight! They're little bright yellow adaptions of 2-stroke scooters and can sway alarmingly as they shoot around the traffic but certainly a good cheap way of getting from A to B for short distances - you'll get seasick if you use them for anything longer than a 10mins journey
I do walk around Havana Vieja on my own quite late at night but I understand enough Spanish to know what people are saying about me and I do look Mediterranian enough for most people to assume that I am Cuban until I open my mouth. But one of the things that contributes to the safety on the streets is the fact that Cubans keep late hours - especially in the heat and humidity of summer. The streets are quieter at 2 in the afternoon than they are at 2 in the morning so you'll find people out wlking the streets, sitting on their doorsteps gossiping with the neighbours etc far later than you'll ever see at home in the UK and all that makes the streets feel very safe and also means that in the event of something happening any opportunist thief is going to have a crowd of locals giving chase in an instant.
But as merseygull says - why tempt fate by making yourself a target? The thing to remember is that compared to the locals, all tourists are fabulously wealthy - your holiday is going to be costing pp much more than a Cuban doctor earns in a year. So only take what you really need with you on an evening out - leave the passport in the safe on your room along with your plastic and spare cash, don;t flash lots of large denomination notes around, stick to costume jewellery, use a small bag with a long strap that you can wear across your body or a discrete moneybelt you can wear under a shirt if a man, don't flash a smart phone or obviously expensive cameras around. And shove a 20CUC note in your bra or somewhere about you so that if something does happen you've always got the taxi fare back to the hotel on you. And remember that the policemen in blue uniforms are there especially for tourists and will have reasonable spoken English if you do ever need assistance.
But there really is no need to worry - you won't encounter large crowds of drunken lads (or lasses for that matter) roaming the streets as you do in most UK cities of a weekend evening, no brawling in the streets, no sense of threat in the air even in situations where there are large crowds, nobody approaching you in the streets to sell you drugs, very little evidence of street prostitution (you will see it in other situations but that's a different story). You will encounter some street begging in Havana, especially if you look like a tourist but it is all done with a lighthand and never in a threatening manner. Elderly women dressed in traditional in traditional creole style with the trademark huge cigar will expect a tip if you photograph them but a small denomination coin will suffice and if someone hands you flowers as a 'gift' they will expect a small payment too. So unless you want to hand over some money don't accept anything which is handed to you.
But most of all remember to enjoy yourself! There's lots of info on here and lots of people ready to help with specific questions but most certainly, yes, you will be able to get out and see old Havana (the Vieja district) and you will find it hard to escape the music. Every bar on Obispo (and everywhere else in Vieja!) has a live band playing at some point in the evening so wander around have a drink in each one that takes your fancy and be ready to just put a 1CUC coin in the hat when it comes round after the band has played their set. Buy a CD if you like them, politely refuse if you've already got more Buena Vista cover albums than you can shake a fist at and do not fear trying to barter them down from the 10CUC asking price! They will refuse your offer with a smile if it really is too low but if there's another couple at the table and they also want one, well I've never come across a band that refuses an offer of 15CUCs for 2 CDs
If you have a more specific interest in Cuban music and salsa or son dancing then some venues are better than others and I can make a few suggestions but if you just want an authentic soundtrack to a night out then you'll find it hard to avoid it.
Eating out is a different matter - on the whole food in Cuba is pretty basic and pretty 'samey' once you get away from the better class of hotels but even then the best food in Cuba is usually to be had in the 'paladares'. These are small privately run restaurants in people's homes and they can come and go pretty frequently so the the best way of finding one is by asking around once you are there. Apart from the paladares select somewhere to eat on the basis of the view (there are some restaurants with fantastic views directly on the Malacon) and/or the ambience (a number of the hotels in the restored colonial buildings have lovely open air patios where food is served to non-residents) but expect the food to be nothing special. On the whole I've eaten much better in the family homes I've stayed in than in the hotels - nobody goes to Cuba for the food but it does have so much else to offer that more than compensates!
One of the things that UK visitors do often find strange when walking around in Cuba is that people passing by will often pass comment on you and especially on women, as will the elderly men sat on their doorsteps. This is not harrassment in the sense of being designed to make you feel threatened. On the contrary this tradition of 'piripos' is about wanting to make you feel good. Cuban women have tremendous self-assurance and self-esteem but they would wouldn't they, having grown up in a culture where regardless of the age, shape and size they have been surrounded by people telling them how beautiful they are and how good they look. And this goes for both men and women who think nothing of even stopping someone on the street and commenting on how nicely they are dressed. And they don't mind if you do the same - if I see someone wearing something that I admire and would like to be able to have then I will stop and politely ask them where I might be able to buy something similar and they will take it as a compliment rather than an intrusive personal comment. Every evening out with a group of Cubans starts with kisses on the cheek all round and everybody finding something nice to say about everybody else. It means that a quick drink in a bar before moving on for the evening's dancing etc is never quick but it does create a feelgood factor that gets the evening off to a great start.
And that's a good intro to another tip - most Cubans thinks most tourists are scruffy! They on the otherhand take great pride in their appearance and both men and women will put effort into dressing for a night out and, despite the housing conditions of many people, their clothes will be scrupulously clean and ironed. Wrinkled combats are not something most would ever consider wearing for a night on the town! So while you won't be treated with disrespect for dressing very casually of an evening, you will be treated very warmly and you'll fit in better with local life if you look as if you've 'made an effort' as my mother would say.
SM
