Retiring overseas is an exciting lifestyle for some. Making sure that it's the right choice for you depends on various factors. For example: how easy is it to adjust in the country that you're planning to move to and/or how good is the support system (medical, friends, contacts etc.).
Financial planning is important, you can get a general picture of the cost of living by using online calculators. Internet access is easily available with various websites about retiring abroad. If you've never lived abroad, the hardest time is probably the first year: language; new place; different types of food etc. After that, you pretty much have a good idea if this is for you or not, financially.
It is wise to have an exit plan just in case you want to move back home. But don't spend your days focussing on your exit plan. Try to switch your new frame of mind to surviving and thriving in your new location, so that it's not super-easy for you to return 'home' at the first bumps in your expat road.
If you're worried about making new friends, there are usually a lot of international support groups like women's associations, professional associations, language schools and volunteer organizations in many countries that help to meet people - especially if your chosen locale is popular with other expats - particularly those who are also retirees abroad.
It is also a good idea to meet the local population to find potential new friends or to find out about local culture, and to help you to assimilate more quickly. Whether or not you have made the right decision about moving: you have to weigh the pro's and con's, the way you would if you were moving within your home country. Family separation issues are to be considered for example. A lot of this depends on the country or continent you're moving to. If you're moving to a developing country there are different issues to face than if you're moving into a first world country.
Talking and sharing feelings to other people in the same position often helps to get a clearer picture. In addition to local, face-to-face meetings and groups, remember to gather information online (especially stories of other people's experiences), to help to give you a better picture of what to expect. Both before and after your move, be proactive in searching for people in the same situation as you, so you can find the support you need as quickly as possible and so that you can live a wonderful life in your new expat location, by the beach in the Caribbean!
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