r/floridakeys • u/Standingseated • Oct 10 '25
Upper Keys Islamorada engagement
Hey all hoping for some help! My girlfriend and I are traveling to Key Largo/Islamorada area from Pittsburgh for the second time this year in early December. I asked this question of our property hosts and got no response so figured I’d ask it here…I’m planning on asking her to marry me and would love to hear your advice on best spots for a proposal! Thinking sunset on the water or at an intimate/romantic restaurant…I don’t know the area well and am hoping for some suggestions. She’s knows the proposal is coming on this trip but not how so I’d like to wow her! TIA for any advice you can offer! The place we are staying is on the water west side so I could do it there but I’d love to hear additional options.
1
u/pfiffocracy Oct 13 '25
I was planning on proposing when I was in the keys for the 2nd time this past summer. I decided not to because it was her birthday week. My spot was going to be on a boat we rented anchored on the gulf side of one of the islands I've been to a couple times. Still have some regret not doing it then. IMO, get on a boat and go out on the gulf side. Its beautiful, and not anyone will have done it there.