Well this one is going to be brief as you may have already purchased your flights. But keep reading for some important tips.
While looking for accommodations you should start looking at flights. Caribbean Airlines typically opens up flights roughtly a year in advance, whereas most airlines open up flights approximately 11 months in advance. Coming from hubs like Miami, NYC and DC you can find very affordable one way flights under $200 each way. This is a nice time to save some money, but if you have to choose between housing or flights to tackle first I will always say housing! Many major airlines fly to Trinidad and Tobago. Check out United, American Airlines and JetBlue to name a few. I often by my tickets in one-ways, however don't put off that return flight for too long! While the flights start out low, they climb steadily as the seasons change. One advantage of purchasing one-ways is that you buy yourself some time to decide if you want to go to Tobago or not. It can be a hassle (and expensive) to change your flights later in the year when you realize you didn't want to miss out on Tobago.
Tobago on Ash Wednesday
Flights normally open up a couple of weeks after the initial round of flights to Trinidad are released. Frequently check Caribbean Airlines site. The cost is about $50 round trip from POS to TAB. Each year, I waste my tickets, but it is better than not having any at all. The only other option would be the ferry which has had major issues in the 2018 Carnival season. Would you rather a 20 minute flight or a 3 hour, possibly rough, ferry ride? Or even worse, no flight and no ferry? This year there was quite a line of people at the airport hoping to fly standby. I'd suggest staying in Tobago for at least one night then buying your Tobago return flight to POS with enough time to allow you to get into POS and settle for your flight back to your home. Alternatively, you could hop to another nearby island to cool down after a jam packed carnival season. For Carnival 2016 I decided to stop and see family in Barbados for a few days. Tickets to Barbados and back home were quite affordable, so it provided a great respite from the action in Trinidad and the snow and cold in New York.
POS to Tobago (TAB) flights are open NOW! Don't walk, run and get your tickets. I'd aim for a morning/early afternoon flight on Ash Wednesday, March 6th. This will allow you to get settled in Tobago and to get to Candy Coated Wine Down nice and EARLY. This will also allow you some time to explore Tobago.
Look out for the highly anticipated Part IV COSTUMES!