Looking to launch & test an e-commerce business across the Caribbean

I have a vintage hat e-commerce business. I’ve had some (mixed) success targeting foreigners and expats in hot and sunny countries.

EG: Bali, Singapore, and Dubai.

I want to test the waters by targeting expats and foreigners across The Caribbean. I have a few questions.

1. I assume that there are vintage stores or markets like this across the Caribbean? Are there specific areas known for selling vintage clothing?

2. Are there any websites or groups that could be worth promoting or advertising on? Sites and groups where expat residents of the Caribbean would visit?

3. Are there some local businesses I could approach and partner with? (I have partnered with some sneaker stores, surfing shops, skateboarding shops, and streetwear shops in other countries.)

Any advice or direction is much appreciated. I am writing this from my Reddit business account for Cheap Cool Caps. Thanks!

The business is: www.cheapcoolcaps.com

If you see anything you like though, go for it!