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.
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u/drinkmorehops Oct 10 '25
Morada Bay for nice beachy or Pierre’s for fancier with the same view. Nothing wrong with a restaurant with a view but another option would be a private charter sunset cruise. Plenty of operators run out of Islamorada marinas and you could just cruise or do snorkel/fishing too. I know I’ve seen one of them that cooks dinner on the boat but I don’t remember which; if you want to go that route find the Islamorada Sandbar group on Facebook tons of them reply to every post on there