In the end, Armando Colaco's boys found their opponents, who are 65 places above them at 88th in FIFA rankings, too good at the Hasely Crawford Stadium.
Trinidad and Tobago, who led 1-0 at half time, scored through Stern John (19th) and Darryl Roberts (47th and 85th).
The first goal of the 'Soca Warriors' came off a penalty from veteran striker John in the 19th minute while Roberts added two more in the 47th and 85th minute respectively.
Both the teams started cautiously with the home side trying to keep possession even as the Indians adopted a more direct approach.
India conceded the first goal in the 19th minute when Raju Gaikwad brought down Darryl Roberts on the right side of the box. Stern gleefully converted from the spot.
Stung by the early reverse, India tried hard to regroup and their best chance of the opening half came on the half-hour mark when Syed Rahim Nabi beat the rival defence on the left, cut in but his right-footer just curled wide of the goal.
T & T doubled their lead immediately after the resumption when Darryl Roberts making it 2-0 in the 47th minute. The goal raised fears that India could be in danger of falling apart, but the visitors combined well as they went all out to reduce the margin.
First a Nabi header off a Raju Gaikwad throw-in in the 53rd minute went inches above the crossbar and then a couple of minutes later, T & T goalkeeper Marvin Phillips blocked Sunil Chhetri's effort and Nabi shot over off the rebound.
India had another chance in the 73rd minute but Jeje Lalpekhlua could not get past an alert Phillips.
India conceded a late goal in the 85th minute when T & T caught the Indian defence on the wrong foot and Roberts fired the ball past Indian goalkeeper Subrata Pal.
India had lost just one match out of four before today after Colaco took over the reigns of the team. They had drawn Maldives, beaten Qatar and lost once and drawn another against United Arab Emirates.
Colaco put up a brave face after the drubbing and said it was a learning experience for his boys.
"Trinidad & Tobago are a much better team and they showed it why. It was a learning experience from my boys. But I'm proud of the manner my boys came back and fought.
We take this experience to Guyana and hope for a better result," he said after the match.
India play their second match of the Caribbean tour against Guyana on August 24.
India: Subrata Pal, Samir Naik (Peter Carvalho -- 83rd), Gouramangi Singh, Raju Gaikwad, Debabrata Roy, Steven Dias (Lalrindika Ralte -- 83rd), Climax Lawrence (C) (Rocus Lamre -- 88th), Mehtab Hussain, Rahim Nabi (Valeriano Rebello -- 83rd), Sunil Chhetri (Sushil Singh -- 83rd), Jeje Lalpeklua.
