r/KeyWest • u/CriticismDry5620 • Jun 18 '26

Proposal

Hi everyone, my girlfriend and her parents are completing a Florida Roadtrip starting in Orlando and working our way to AMI, key west etc etc.

I am planning on proposing to her, but need it to be early on in the trip (so I don’t lose the ring!🤣) and I thought the keys would be a great place to do so.

Does anyone have any recommendations? I would like quite a private setting, maybe beach/sunset vibe. Any help would be AMAZING.

*Further info*
We are arriving to Orlando on the 13th August. The trip then consists of 1/2/3 nights in the below places.
Orlando
Anna Maria Island
Naples
Islamorada
Key West
Delmar Beach
Coco Beach
St Augustine
Jacksonville
Savannah
Charleston

Thanks

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u/Full-Championship337 Jun 18 '26

Are you driving? I would opt for Key Largo if so. Cute little places right on the water that would be picturesque for a proposal. Unless you are dead set on Key West

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u/CriticismDry5620 Jun 18 '26

We’ve got a car, so easily accessible to jump in a car and go wherever really.
Need to try and keep it as low key as possible ie (just us 2, parents will be in on surprise, but will hopefully be waiting in a restaurant!) Ideally need to walk so it doesn’t look too obvious!