To travel between Trinidad and Tobago, you can either choose by air which is just a 15 minute flight on Caribbean Airlines or by sea on the Inter Island Ferry which takes 2.5 hours. I have no preference to either option but if you get motion sickness, I suggest you go by plane as sometimes the waters may be very rough. If you’re cost conscious boat tickets are much cheaper.
To travel to specific places in Trinidad, check out Getting Around and Getting To tags. Also, check out these two articles for general traveling information: Getting Around T&T and Getting Around 101.
I expect people who are reading this are similar to me in that they’re not going to spend whole day in their rooms and just really looking for a place to sleep at night and their leave excess gear when they’re out on trips. As such, I recommend checking out airbnb to find the right match.
Being from Trinidad, I’ve just mostly stayed at beach houses in the various parts of the island which may not be the best idea if you want to experience all of Trinidad. Anywhere along the east-west corridor from Port of Spain to Arima should be fine though as driving to the main attractions would only take about 2 hours max. If you want suggestions on where to stay based on activities you would like to do, please feel free to ask.
One of the places I can recommend though (as I’ve visited friends who’ve stayed here) is Stanmore Place which is located in Port of Spain. Very convenient location and my friends had good reviews of the place.
Spent a couple vacations in Tobago but mostly stayed in private homes. If you’re looking just to relax on the beach, stay around Crown Point as Store Bay and Pigeon Point are two of the best beaches there.