Caribbean and more 
in $150s-$370s RT
Friday is sort of like an honorary weekend, don't you think? A day for taking things easy and looking forward to that R&R around the corner. You deserve it!
Speaking of rest and relaxation, you also deserve a rejuvenating trip down south—preferably to somewhere with warm sand and cool cocktails. That's why we spent our Friday morning putting together this sweet bundle of JetBlue flights all over the Caribbean and Latin America. No need to thank us, ¡de nada!
We've got all your favorites in this one, from Puerto Rico to Cancún. But don't overlook the rarer options either, like Guyana (home of the world's scariest waterfall) and St. Vincent & the Grenadines (our favorite country that sounds like a band name).
So forget TGIF! By the time you finish booking, you'll be saying TGISJFC—Thank God I Subscribe to Jack's Flight Club :-)
Taking off ✈️
Tip Published: Sep 26, 2025
Round trips from Boston (BOS):
- Liberia (LIR) - $374
- Montego Bay (MBJ) - $356
Round trips from Fort Lauderdale (FLL):
- Aguadilla (BQN) - $176
- Cartagena (CTG) - $251
- Grand Cayman (GCM) - $227
- Guatemala City (GUA) - $197
- San Jose, CR (SJO) - $185
- Sint Maarten (SXM) - $275
Round trips from New York (JFK):
- Cancún (CUN) - $279
- Cartagena (CTG) - $313
- Georgetown (GEO) - $342
- Grand Cayman (GCM) - $289
- Guatemala City (GUA) - $173 (up to $208)
- Kingstown (SVD) - $279
- Punta Cana (PUJ) - $283
- San José del Cabo (SJD) - $376
- Tulum (TQO) - $239
Round trips from Newark (EWR):
- Cancún (CUN) - $291
- Punta Cana (PUJ) - $313
- San Juan (SJU) - $152
Round trips from Orlando (MCO):
- Aguadilla (BQN) - $212
- Cancún (CUN) - $279
- Ponce (PSE) - $214
- San Jose, CR (SJO) - $217
Round trips from Tampa (TPA):
- Punta Cana (PUJ) - $329
How to Book
This is a Takeoff-only Flight for Jack's Flight Club Takeoff members only. For step by step instructions on how to book it you'll need to login or upgrade to Takeoff membership.
