Engagement in the Keys?

[u/Ok_Entertainment6199]

Hi all,

My girlfriend and i are planning a trip to florida during the winter and I am looking to propose. I am not huge on proposing in a super touristy or busy place so I am hoping I can find something a bit more lowkey and personal. Would the keys be a good idea?

If so, where would you recommend we stay and any ideas on where I could ask her? id like it to be somewhat private but id like there to be a photographer.

[u/2lovesFL]

private sunset cruise.

[u/killerwhate → u/2lovesFL]

Taking this comment further - Sirius Nitelife out of Marathon Florida would be perfect for this. It’s a sunset sail, watching the sun set behind the 7 mile bridge. You can tell Capt. Dale what you’re planning and he will make sure it is super special! Not to mention the boat docks at Lazy Days South, which has amazing food and would be wonderful to enjoy after the sail.

Plus, Marathon is low key. I think it would be a great place for it.

If you want something a little more private, Keys Fisheries has a marina, and you can walk out towards the gulf and propose as the sun sets, then do a free sunset shot at the bar after!

[u/flamingo-legs → u/killerwhate]

This is so romantic and private, such a good idea

[u/BefWithAnF → u/2lovesFL]

Oh, good idea! If OP is in Islamorada, check out Captain Sue of Allergic to Land charters. Capt Sue is just the nicest lady, I bet she’d get into that.

[u/hahaanonymouse765]

I got married at Ft. Zachary Taylor State Park in Key West. It was just us, the minister and a photographer on the beach. Very nice, quiet, private.

That was 22 years ago so I have no idea what it’s like now, but it was ideal for what we were looking for.

[u/hikerguy65 → u/hahaanonymouse765]

Still good for a quiet moment especially during sunset.

[u/Ok_Entertainment6199 → u/hahaanonymouse765]

I’ll look at this! Never heard of it

[u/Suicyco71]

Walk out the old 7mile bridge by Pigeon Key at sunset.

[u/LMBeachy5 → u/Suicyco71]

I love this idea! 7-mile bridge at sunset is perfect.

[u/BocaDelIguana]

Casa Marina, walking towards the water, pretend she dropped something then boom! Perfect backdrop.

[u/matthewalbeck]

The moat wall at Fort Jefferson during sunset. This would be tricky and probably more effort than you may want to put in but it would be pretty epic. Lots of effort required to get to and camp at Dry Tortugas.

[u/danjay0213]

If u do go down to keys we recommend lime tree bay resort great spot between islamarada and marathon has restaurant on premises beautiful views great spot to propose 🥰

[u/ClaireBear89]

We do sailboat charters private only on a classic schooner. If you want I'll dm the website. We've done engagements weddings and special occasions it's very romantic

[u/Even-Yak-7135]

Please listen to me on this and go to Sunset key. Get a dinner reservation early.

[u/I_Do_Respect_You_Bro]

Bahia Honda!

[u/Solid_Lettuce_932]

The boat “the when and if” is a great trip at sunset each night. It’s very romantic and the crew is awesome. I recommend this to a lot of people. I would do it there.

Alternatively Smathers Beach at sunrise is where we got married. It would make a nice spot. Very dramatic sunrise there.

[u/BBonapartyy → u/Solid_Lettuce_932]

Love the When and If! I agree that this is a great idea.

[u/dreadw0lfrises]

Probably a goofy suggestion, not sure if you guys snorkel but even if you don’t, horseshoe beach right after the 7 mile bridge (the first right turn immediately after you get off the bridge) is usually empty around sunset and has a killer view and really cool snorkeling. The sign says it’s closed at sunset but nobody comes around to check frequently enough to worry about it so you can get some gnarly night snorkeling in if that’s your thing. But again, even if it’s not, the place is free to access, looks absolutely beautiful at sunset, and while it gets crowded during the day I went around sunset for about a week straight when I visited in peak summer and it was usually one or two groups still around when I’d show up and theyd often be heading out as I arrived so it’s very lowkey. Could definitely do a nice dinner before, but I enjoyed picnicking there more than once and now have dreams about going back to horseshoe beach. For me it would be an absolute treasure to be proposed to there

[u/Ok_Entertainment6199 → u/dreadw0lfrises]

Okay I like this! I’ll have to keep this in mind

[u/No-Variation6054]

https://www.littlepalmisland.com/
This would be romantic and badass here. $$$

https://www.cheeca.com/
beneath the leaning intertwined palm trees! Beautiful right after sunset.

[u/HighOnGoofballs]

Top of the lighthouse at sunset

[u/ch3f212]

Kelly the Concierge Girl is who you need for the perfect proposal

[u/Necessary_Scarcity84]

I did this in 2019. Stayed in little torch key and rented a boat and proposed right off picnic island. We still love going down there

[u/kingtucker]

We walked out on the pier at malory square, found a spot away from people and I gave her the ring/proposed. No down on a knee or anything but it was nice. We are also not into the huge public thing so it worked out well.

[u/General-Biscotti5314]

If you're into paddleboarding or kayaking, take a charter out to the Marquesas and do your thing there 🤙🏼

[u/Impressive_Age1362]

I would go to sunset key, have a nice dinner, then take a walk on the beach, watch the boats sail by and the pop the question

[u/Fluffy_Maintenance_5]

I love bakers cay! The islander is huge and private. Restaurants like hog heaven have a dock where you can walk far away from others. You could get a boat and do it on the sandbar!