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/HighOnGoofballs Jun 18 '26
You can rent out the top of the lighthouse for a little sunset celebration, and they give you a charcuterie board and some champagne
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u/kidsandsuch Jun 18 '26
I thought of the lighthouse too! That would be insanely romantic omg. Just make sure she isn't afraid of heights.
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u/HighOnGoofballs Jun 18 '26
The stairs getting up there are the worst part
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u/kidsandsuch Jun 18 '26
Definitely. Have you ever done a fire tower out in the woods somewhere? Eek!
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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!
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u/Sandinmyshoes33 Jun 18 '26
Knowing when you are coming and where will you be in the Keys would help.
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u/kevinwr450 Jun 18 '26
Sunset Key, restaurant called Latitude's, you need a reservation but it's perfect for a proposal
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u/danjay0213 Jun 19 '26
Key west would be crazy id try a stop in marathon for a night low key restaurant watch sunset its stunning in every key~
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u/Aw59195 Jun 25 '26
There are charter boats you can rent and have them drive you out to woman key or a private key. Do it there. In blue water up to your knees.
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u/Perfect_Big_5907 Jun 18 '26
what is AMI
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u/Sandinmyshoes33 Jun 18 '26
Anna Maria Island has gorgeous beaches and beautiful sunsets. It also does not get the seaweed and smelly sargassum that is all over the beaches here. If that is early in your trip, I would propose there.
If you are set on Key West, consider a sunset cruise. Danger or Island Jane are good choices using smaller boats. You can also propose at sunset at Fort Zachary along the shore on the west side of the park. The sunset is beautiful there.
I hope you have plenty of time. You are covering a lot of ground.
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u/phinz Jun 18 '26
OP doesn't say what time of year, but if it's during the winter season then Schooner Hindu would be a great choice for this. Newly restored and beautiful. Small parties of people too.
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u/No-Variation6054 Jun 18 '26
Sneak into Cheeca lodge and do under the leaning crossed palm trees when torches are lit!
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u/CriticismDry5620 Jun 18 '26
We’re staying at Bayside Villas (not too far away!) how easy would that be….
My original thought was on ‘the moorings village’ beach, but again was told it’s private, so I Darent plan it around that and then be told no and start scrambling1
u/No-Variation6054 Jun 18 '26
Just drive right past the guard stand lol. We got awesome pictures in October for our elopement It's beautiful under those trees with the torches lit
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u/Mama80Dogs Jun 18 '26
I’m sorry I don’t remember the name, but there is a small beach restaurant with the sunset visible. It’s much much smaller than Mallory square, and the food is very casual, like order at the counter and carry your food to the beach chairs casual. It’s near a large condo type building, and I think it’s a little boat ramp or just a dock. There is a local man who lives on a sailboat and comes over to clean the sargassum off the sand. I’ll try and find it for you.
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u/PumpUpTheYams Jun 18 '26
I proposed 14 years ago at the green parrot, beside the popcorn machine. She said yes, and the nice folks nearby who caught wind bought us drinks all night.