How We Fund Our Caribbean Trips

People ask us how we take one — sometimes two — Caribbean trips a year. The honest answer is a few systems working quietly together.

The Business Card Strategy

I run a small business and charge everything possible to a travel rewards credit card. The points accumulate through spending we were going to do anyway. The key — and this is non-negotiable — is paying the balance consistently. The interest rate on travel cards will destroy your vacation fund faster than any resort minibar. We treat it like a debit card that happens to generate points.

Ask your accountant if this makes sense for your situation. Ours just shakes his head and books his own vacation.

The Crypto Contribution

I have been known to sit on a porch in Utila or at Margaritaville in St. Thomas and take some profits from crypto via a debit card while watching the ocean. The Caribbean has surprisingly good wifi. Markets do not care that you are watching sea turtles hatch.

This is not a crypto investment strategy. It is just what happens when you are sitting somewhere beautiful and the numbers look right.

The Ground Game

Red Hook grocery store the first night in St. Thomas. Pumpkin Hill Minimarket in Utila. The local store near Pigeon Island in St. Lucia where the rum went down the drain but the people were wonderful.

Hydroflasks from Mongoose Junction in St. John. Morning drinks made in the room. Taxis instead of rental cars in St. Thomas because Margaritaville has them lined up out front all day.

The points get you there. The ground game makes it sustainable once you arrive.

The Honest Bottom Line

None of this requires wealth. It requires consistency, discipline on the credit card balance, and the willingness to buy rum at a grocery store instead of paying resort prices.

Year one our site generated enough to fund another trip. Combined with credit card points that is a week in the Caribbean. That is the whole point.

[CREDIT CARD AFFILIATE LINKS PLACEHOLDER — insert approved affiliate links here]