I'm leaning more towards them finishing the first leg in Tobago earlier this morning. Phil appears to have been seen going through security, apparently on his way to Tobago. That sounds like he had been on the ground in Port of Spain already, and I don't see him heading there for leg 2 when leg 1 was just starting.
Monday seems more likely for a leg 2 start, though I don't really like the options out of Piarco tomorrow- it seems a bit sparse.
I'm wondering if they'll do a second leg in T&T or have an extended pit stop to get to better flight options on Tuesday?
My best guess is either connecting through Panama City to South America, or a visit to Barbados or Suriname before moving to Europe. Most other locations (esp. Guyana) are kind of dead ends in terms of moving onward to other regions.
I'm skeptical of them spending more than a leg or two in the Caribbean, so I'm not sure how likely Barbados actually is, but it does have descent connections onward to Europe.
I'm also doubtful they'd double back to the U.S. to connect onward.