How to Book Trinidad’s Carnival Last Second for Free*

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Book Trinidad Carnival Last Second is part of the Rum Rum Caribbean Castaway Trip Report.


“Don’t wait till the air raid sirens to evacuate.” “Early camel gets across the Sahara.” Growing up, those expressions were told to me over and over again. I never listened. Surely my procrastination will catch up to me one day, but thus far it hasn’t (see A Bullfight In Madrid and My Yarra Valley Wine Tour).

It was a Thursday, a day I’ll always remember. Because that was the day that my laziness died. TPOL is a Rolling Stone …

It was the Thursday before Fat Tuesday, and I had nothing to do after an arduous round of golf in Puerto Rico. Anxious from retirement life, I hopped on IG to see what the real world was doing. As I wrote in my Rum Rum Trip Report overview, a friend of mine was in Rio for Carnaval, an adventure I had embarked on well before Alex became TPOL (see Guns & Butter: Rio de Janeiro Travel Guide). Reminded that there’s a life outside of shuffleboard, I started looking at flights.

Step 1: Get to Trinidad

1a: SJU to FLL: 3700 JetBlue + $5.60 versus $144

Obviously, if your flight originates in the Caribbean, you have to fly to Miami to get to the Caribbean.

1b: MIA to POS: 10k Avios + $5.60 versus $187

Avios again to the rescue (see Out of Burma Thanks to Avios).

Step 2: Stay in Miami

Saturday stopover for a Miami Pool Party? Why not?

Hyatt Stay Certificate at the Confidante free versus $580.

Step 1 and Step 2 were the easy parts. The hard part was finding somewhere to stay in Trinidad.

Step 3: Who does points in Port of Spain?

Hyatt: I stayed here last time (see Hyatt Regency Trinidad: A Little Bad, Mostly Good) and was denied entry to the pool after checkout. Would I be welcomed back?

Nope, the hotel was sold out.

Holiday Inn Express: Stay at the airport? Sold out and a terrible option except for the fact that I would be close to the great food (see The Best Airport Food: Trinidad’s POS).

Radisson : Sold out for points. Retail $800.

Hilton: Sold out for points. Retail $700.

Courtyard: Sold out for points. Retail $700.

Refresh, refresh, refresh.

Sold out.

(Refresh, refresh, refresh)^50

Sold out!

Nap 1: At this point, it was 2AM and I decided to give it a rest. I call it a nap because anyone else who plans points trips obsessively knows that rem sleep can’t be found when you’re plotting routes and cumbersome itineraries.

Early Start: 8AM, I’m up without an alarm. If only consumer law was this motivating (visit BachuwaLaw to file a claim against a bad corporation).

This time I find two nights available at Courtyard. I book one with 25k points and one with a 25k stay certificate. Total cost $0.00.

This leaves three more things:

  1. Find a flight out from Trinidad. Everything on Ash Wednesday back to PR via USA was sold out or $1000.
  2. Find a hotel for Sunday.
  3. Find a school to play mas, the term for partaking in the revelry.

#2 was my first priority. I tried throughout Friday to refresh, refresh, refresh cubed. It didn’t work. I tried on mobile, I tried on my laptop, incognito, with my eyes closed. Nothing. I decided to take a break and figured worst case I’d have to find a non brand hotel or an AirBnB. My compulsion not to check lasted for a few minutes. Refreshing again, I saw the same lack of availability and that the non brand hotels were selling out or rising drastically in price. Still, like a predatory crocodile, I slowed my heart rate and patiently waited.

When I landed in FLL and still found nothing, I stayed the course. After enduring a predictable JetBlue delay then Uber Pool misery at 6AM followed by Explorist can’t check in early at the Confidante because I have fake status, I didn’t panic. Instead, like all things that go my way as a result of being an incessant nag, the Hilton opened up for 50k pesos and I booked it. Total cost $0.00.

Total Total Cost: Nothing! Or $11.20, if you’re a negative nerd.

A camel can’t change its humps, nor will I. Not bad for last second.

And now to find a band in Trinidad to play mas the day before Trinidad’s biggest celebration. How hard can that be?

Will TPOL play mas? Or will TPOL sit on the sidelines? Find out soon.

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