Summary: We went for less than a week, I was not overly impressed - I doubt I will be returning anytime soon.
Trinidad: Port of Spain was a boring city, My travel partner has never been to a 3rd world country so she had fun exploring the markets, bars etc.
We checked out Pitch Lake in La Brea, Was an interesting experience, Imagine an entire lake made of pure tar. We spent sometime cruising the countryside, people are mostly friendly and respectful of foreign cultures, I felt safe (and often revered & respected) with my kippah & tsitsit.
After a day in Trinidad we decided to spend shabbat in Tobago as it's quieter there, We took an overnight ferry for $5 and put up our hammocks in the crew mess hall.
We spent shabbos (I sent my partner fishing with the locals - while I cooked the rest of the shabbos food) in Fish Tobago guesthouse which was nice, but the former owner who was acting as boss left a very a sour taste in our mouth, I do not recommend this place to others.
Sunday we rented a car and drove up to the northern tip of the island, we picked up hitchhikers on the way so we can learn about the local culture - we ended up stopping at several family/town festivals which were very nice and educational.
Towards the evening we snuck into a nicer resort to use the pool and relax. Then we started scouting a place to sleep, I found traces of larger animals in the Jungles so we kept looking and ended up on the top of a hill overlooking charlotteville, we put up our hammocks and went to sleep (it was too windy up there for me to fall asleep but at least I didn't miss netz/vasikin)
Monday we drove back south through the mountain back roads, was wondeful, we found a few isolated beaches, bays, and fishing villages. We made it down to the southern tip/crown point with enough daylight to go Jet Skiing and Glass Bottom Boating/snorkling (nice tropical waters with a very diverse marine biosphere)
That night we ended up waiting 9 hours in line for the ferry (huge lines as one of the ferries was out of service) In the morning we decided to just take a flight back so we don't miss our flights back.
I skipped a bunch of details as I doubt anyone will end up in Trinidad anyway but feel free to ask questions.
The view from one of the hilltops on the way back from the northern tip of Tobago
Pigeon Point (shot from the glass bottom boat)
Me practicing freediving (I swam up under the glass bottom boat to scare the chreft out of the other people on the boat, it worked)
The famous nylon pool
This is what the asphalt in Pitch Lake looks like (my friend ended up falling in, it cost us $40 and 2 hours to clean her up)
Pitch Lake Wiki The Pitch Lake is the largest natural deposit of asphalt in the world, located at La Brea in southwest Trinidad