Anonymous wrote:Why "May or October"? Why not go on your actual anniversary? Otherwise, it's just a trip?
At any rate, for a milestone anniversary trip with only 6 days I'd either go to Paris or an intimate beach resort in the Caribbean (like The Caves in Jamaica or AnseChastanet on St Lucia). I'd prefer Hawaii over the Caribbean, but not from the East Coast with only 6 days. Bermuda is convenient with nonstops from DC now, but I wouldn't go in May or October because of how cold the Atlantic Ocean will be (maybe the very end of May would be ok?).
OP here and I’m loving the suggestions, they are definitely giving me some ideas to look into! I said May or October because as I mentioned, we have kids, and we already will have other trips planned with them. I try to space them out because of work.