At the port of St. Thomas, I'd give the $250 to the lovely Mrs. Jones, (Vita) and I have no doubt that she'd find some jewelery of some kind to spend it on. For me,,,,,,I can't think of anything that I personally would want, except to see her smile.
Depending on the country I would pick up their national football (soccer) jersey. I have quite the collection of them now. At last count it was twelve. The real ones are not cheap and the least expensive one I've found is $60.
We would also hit a local restaurant and try some native foods.
Betty: Would figure out a way to save the rest of the money.
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I would use it to take a cooking class in Venice Italy. Or I would go to Pirtan Donna (Rome store) and do minor damage. Stupid exchange rate!!! Can I have $250 Euros instead. Oh I could get a couple pair of shoes in Livorno Italy. Was I suppose to just pick one????
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Fav island would be Sint Maarten, and I would spend it on ittle somethings for my loved ones. Bling, I dont get in St Thomas, its always more expensive than Sint Maarten and Antigua. I got a beautiful bracelet from Sam and it was a full 185$ more in St Thomas than it was in Sint Maarten. It was the exact same bracelet, in the same "Store", meaning name of the store.
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Delft, I with you on the Dutch side of St Martin. The jewelry prices are much better there than in St. Thomas. Rob and I also like to hit the city markets wherever we travel. In the Charleston, South Carolina city market I got some great buys in jewelry made by local crafts people. I also like to look for artwork and chatchkas (nick-nacks).