It all depends on you and your abilities.
Are you male or female?
Young or older?
Independent or adventuresome or conservative or timid?
What are you looking for in a visit?
Museums, history, culture, beach, bars, shopping?
Do you prefer a bigger hotel or a small boutique hotel?
Do you speak Spanish fluently, a few words, or none at all?
Have you travelled much in the developing world?
I am a 45 year old adventuresome male looking for history and preferring to stay in small b&b's. I travel alone all over the world, developed and developing countries, and have never had a problem. I try to learn a few things about the country before I go, purchasing a travel book and learning a few phrases, but I am fluent in Spanish and English. HOWEVER, what works for me may be totally wrong for you.
PS. This thread will probably be moved to the travel forum before long, and we can continue the conversation there. If you don't want to post private information about yourself, send me or one of the other persons on here a private message, and perhaps we can help you make an informed decision so that you might a wonderful time here in Paradise.