Does anyone have an idea if it makes sense to just bite the bullet and buy tickets now (the full refund option is not a lot extra on these tickets so would take that as insurance), or if the flight costs might come down significantly in the interim? We are looking at west coast to Caribbean so we have to take a domestic flight first and I’m guessing that’s where the cost load comes in. Google says best pricing for TG flights is early October, but we can’t wait that long to finalize plans for various reasons. However, we can wait as long as June. For those with experience, what do you suggest? We have tended to avoid flying over thanksgiving for a few years now so have not watched price trends over time.
If they fly to where you are going in the Caribbean - always Southwest.
When they run sales, you simply rebook - and get a credit in your account for the difference.
Obviously, if their fare today is higher than anothers, then no - but they are the safest and best airline to work with - and fly to plenty of places in the caribbean.
I regularly re price with them and get credits. You just have to check each week - usually Tuesday or Wed to see if it went down.
I bought a ticket to Vegas the other day for $330 from Nashville…pricey but I had to go. Two days later their sale started and it was $180. Now I have a $150 credit - so it’s great.
Good luck.
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Unfortunately looks like they don’t fly to this island.
Edit: but thanks for reminding me we can do this, I just got some SW credit for our spring break college tour trip 
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Last year we had a wedding on a Caribbean island. I purchased tickets very early and purchased refundable tickets.
They actually never went down, only went up or stayed the same. I felt comfortable that I had that part of the trip scheduled.
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I’m eyeing a similar flight(s) for Feb 2026, west coast to Grenada (West Indies) - my personal experience…book while it’s available. Then simply do not look back - if you do look back, you can (possibly) request a refund of the difference if the fare reduces, but it won’t come in the form of $, but instead credit, with a time limit to use it (exception is Southwest, those credits don’t expire) - I’m sitting on a Delta credit for $350 that will need to be used (purchase, not flight date) by Nov. I can’t even use it for a gift flight for my D. I have no idea if I’ll be able to use it or if it will disappear, but I was given absolutely wrong information by the person who helped me on the phone. 
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With Delta, get the 2nd fare - it’s usually plus $30.
Then you can cancel. While it’s typically a credit good for one year in that case, we had one from my daughter’s trip to Germany. Every time we used and cancelled, the one year re set.
I don’t think by rule it was supposed to, but it did.
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The one I’m looking at is refundable into original payment method for a small extra cost. It’s AA, which we don’t fly often. I’d be fine with a credit for an airline we use regularly.
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Ohhh! I like a good workaround! If Nov gets close I’ll try it. Worse that happens is I lose it.
Thanks! 
Agree - I hardly ever fly Delta unfortunately -
That’s what we flew, AA. Through Miami which seemed to have a lot of planes that flew into various Caribbean islands. Refundable to our credit card
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Yep, we flew them via Miami to Ecuador/Galapagos as well. I have to say, we had a terrible experience at MIA with them that time. Hopefully it will be better this time. The route out is via Charlotte (better timing than via Miami), which I’ve never flown into/through before.
Someone mentioned on a different thread you should buy “refundable” and when prices drop, cancel and buy new lower price.
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Yes, Miami airport is the worst airport my family of flyers has ever encountered and yes, we always seem to be stuck flying via American to the Caribbean - even out of Atlanta when using a package deal. Prefer Delta direct but AA has pretty much locked up the travel services to the Caribbean.
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But interesting what was posted above about southwest services there, will definitely look into that next time - they do seem to have a number of options, SW has a lot of flights out of an airport that is more convenient to us than the one we usually end up using for distance. We’ve not looked much at the Caribbean from the west coast so far but definitely want to explore more. Pity the flights are a schlep.
This is what we will do. Now to remember to watch prices!
Thanks everyone.
Any tips for Sint Maarten, let us know too please
Another option could be - really depending on price - flying to San Juan and then taking another to St Martin which is as low as $250 RT on jet blue (they use silver airways).
That may not work but you never know. Of course it might involve a hotel night too. So maybe not.
We did that going to Europe last year. Flew to Miami on SW. Then on a portuguese airline. Way cheaper than booking from Nashville.
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I don’t think there’s anything direct to San Juan from the Bay Area? Not going to do more than one stop or too long layover (we could have got cheaper via Copa but with an overnight).
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Oh yeah AA has CLT - that’s a great airport.
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If this was separate tickets, I never do this flying internationally because if there is any issue with delays on the first flight, you’re stuck with cancellation issues on the second. And I have had enough missed flights due to delays to be thankful for always booking on one ticket.
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Not according to my business traveler husband. It’s fine if your end destination is Charlotte, but it’s not always so great if you are connecting. My DH spent many nights in Charlotte because of some American Airlines SNAFU…he hated it.
So…if you need a connection, my DH says…no to Charlotte.
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