I travel regularly but mostly within Europe.
I have enjoyed reading the posts in this thread, and would agree with you SMa, that the six days I spend in Varadero on a DIY holiday a few years' ago, felt very much like a gilded cage, and I 'escaped' regularly and visited the local towns and also some excursions, having spent a wonderful week wandering freely all over Havana and met all sorts of folk and seen more than most visitors do. At that time there were only two state agencies, Cubanatour and Havanatour, and I used the latter. They were good for their time and the political situation, but visitors from outside Cuba bring their own perceptions of 'must-do's' and 'must-haves' which are often far from even the wildest dreams of native Cubans. I really enjoyed Cuba but fear returning, because it has 'taken off' as a popular destination. Now you may well define that as my being snobby, but what I mean is that if large crowds of different nationalities 'find' a place, the local infrastructure has to change to accommodate them, and this can lead to a sense of unreality and the 'gilded cage' mentality - all inclusive, loads of food and drink and plenty of free time - all of which are very far from the reality for the native Cubans, who remain positive and cheerful despite what has almost become a two-tier system ......... them (the visitors who have everything) and us (the locals who have to be grateful for what they can get).
But it happens closer to home to. I'm speaking from experience when I say, look at the resorts of Mallorca. Palma Nova and Magaluf are nearly exclusively British, and Arenal and Playa de Palma are heavily weighted towards the Germans. There are other resorts like this too, on other parts of the island. As regards the Adriatic, Bellaria is 'little Alsace on Sea', and just a few miles south is Rimini 'little Germany on Sea'. Traditional British resorts have tended to be Cattolica and Pesaro - further south, and on the Venitian coast, Lido di Jesolo was previously visited by the British.
Here in Alsace, the Danes are the first visitors of the summer, as their schools break up earlier than ours, then the ever-present Germans - all year visitors, given their proximity to here - and we see increasing numbers of Swiss, Belgians (for whom Alsace is enroute to the paradise of the hot south) and Italians (many many of whom have camping cars, just like the Germans). Brits are relatively few, but are well-respected by the local communities (after all they and the Americans liberated Alsace in 1945), and many tourist signs and information leaflets are written in German, English and Italian. Thankfully there's no problems with the currency now that we all use the Euro (I've seen many a German trying to insist on paying in Deutschmarks, and sometimes succeeding but at a lamentably low rate!!) but the tourist infrastructure of roads, hotels, wineries offering tastings, souvenir shops etc has snowballed. Luckily we still have protected Sunday opening hours - bakeries in the morning and only souvenir shops and restaurants and cafés all day; no supermarkets or grocery stores.
My choice when I'm on holiday is to explore and visit the country I am a guest in. I suppose I don't consider it so baldly as 'helping the local economy', but the reason I travel is to enjoy experiencing local food, drink, customs and sights. I like moving around amongst the locals - a headscarf and dark glasses give me a head start in Moroccan and Turkish markets - taking public transport where possible and trying 'local' things, rather than enjoying the familiarity of a particular brand of beer or hamburger, though I am aware of the downside of this - the runs, and other ailments! I find that a smile helps to make communication easier, and also to speak slowly in English if the local tongue is beyond me ... mind you the words toilet/yes/no/please/thank you/hello/goodbye (not necessarily in that order) get things off to a good start.
I still have to learn that the pace of life in some of the countries that I visit is not the same as back home. I think one of the most difficult lessons to learn, especially in a foreign country, is that things are not done 'right' or 'wrong' when compared to one's home country but simply differently and it's up to us to make the effort to stretch our thinking and tolerance level. Many times I fail to do this and end up grumbling darkly, but it is a good lesson to learn and to try to apply as often as possible!
After all, in all things as well as travel, an optimist may be as mistaken as a pessimist, but at least s/he is happy! Happy Landings!