I’ve had trouble finding bourbon on VG in the past. Although Edith used to have some stocked at Mad Dogs, years ago. Anyone know where I can purchase a bottle on the island? I’d not, can I pack a bottle (carry on from SJU or checked from DCA?). Worst case it will be dark rum on the rocks, but thought I’d check. We are land based on VG, so stops in Tortola. Thanks.

Riteway on VG has a decent liquor selection, so I'll bet you can find bourbon there. There is a store to the far left of Mr. Nice Guy that also might have it.

Thanks! I’ve also made do with some aged rum in the past.

You should be able to add a bottle in your checked baggage. My recommendation is to wrap with towel or clothes to cushion. I've never made a connection through Puerto Rico, but there have been statements that items in luggage do disappear.

After you clear security in San Juan, the next thing you encounter is a large duty-free store; in fact, you literally can't miss it, because you have to walk through it in order to go to the gates. Here's a link to the store's liquor offerings (not attesting to when it was last updated), https://sanjuan.shopdutyfree.com/en/liquor, but it shows Jack Daniels and Woodford Reserve as available. Easy enough to just grab a botte there and carry it onto the plane with you.