7 Places to Propose in St. Augustine
Bayfront Marin House
St. Augustine, Florida

7 Places to Propose in St. Augustine

Are you planning to get engaged in St. Augustine in the near future? Between Christmas, New Year’s Eve, and Valentine’s Day, the next few months are considered ring season here in St. Auggie!

We’re ringing in the engagement season with our own list of perfect places to propose in the Ancient City. Every couple is different, so give us a call if you want to discuss a few ideas of your own. We have an engagement coordinator who can help you put together the perfect plan to pop the question. (It’s true–it’s a real thing!) In the meantime, here are some thoughts to get you started:


St. Augustine Lighthouse1. At the top of our gorgeous lighthouse, with all of Anastasia Island at your feet. If she takes your breath away, what better place to ask her to marry you than at the top of 219 stairs?

2. Take the plunge! And propose in the deep end of the pool at Cafe Alcazar. Relax…you don’t need to pack a wetsuit. The pool is now empty and has been converted into one of the best lunch spots in town. Wait til you get a table, or better yet, ask her while sitting on the benches before you reach the restaurant. Bonus: the cafe often has a live musician–giving you a perfect soundtrack!

3. Under one of St. Augustine’s “love trees”. There are a couple of them in town…but the two most famous ones are the one on Riberia in front of the Love Tree Cafe (across from Mojo’s BBQ), and one on Bridge Street in front of the school (about a block and half from the inn). Don’t know what a lovetree is? It’s two trees–in these cases, a palm and an oak–grown together into one. Both trees are thriving, and it’s said that if you kiss in front of one of them, you’ll be together forever as well. Insider’s tip: the tree at the cafe is more picturesque, but the one on Bridge Street is quieter–pick the one that suits your personality, and stroll past it (or ask us to help you coordinate a carriage ride that will go right in front of it!) while telling your love the story of how you can’t live without her.

man proposing in St. Augustine

4. Picture Perfect in the Lightner Courtyard. You may know where the Lightner Museum is, but have you spent any time in the courtyard in front of the entrance? It’s a beautiful space, with lush plants and flowers, soft classic music, and a pond full of friendly koi. (Insider tip: Take a quarter with you when you go, because there is fish food at the base of the bridge). Speaking of the bridge, it spans the pond, and connects the two sides of the courtyard, and it’s a perfect spot to connect two lives together. Propose at the peak of the rustic bridge, then take a picture of the two of you. Best. Selfie. Ever.

5. On the seawall. What is more romantic than the water behind you, perfect sailboats bobbing on the bay, and the Oldest City in front of you? Proposing on the seawall is a gorgeous place to start your lives together–sit on one of the benches, drop to one knee in front of our inn, or walk underneath the pergolas near the Bridge of Lions (there’s actually a little jutting out area that is perfect for two).

6. On an upswing on the Bridge of Lions. Speaking of the Bridge of Lions, what about proposing in front of it while the drawbridge is raised? It’s good luck to kiss when the bridge is up, and it ensures that traffic will be quiet when you choose to whisper sweet nothings to each other. The bridge goes up on the hour and the half hour, as well as when boats request access. Insider’s tip: using the scheduled opening is much easier for planning.

romantic suite at St. Augustine inn7. At your favorite St. Augustine bed and breakfast. We <3 love <3 being a part of proposals!! Pop the question in your room (maybe by hiding a ring on the tray when we deliver breakfast in bed), in our gazebo, or sitting on our upstairs deck in the swing. We’re here to help any way we can–just call us at 904.824.4301 to start planning your engagement of a lifetime!

No matter where you decide to pop the question, consider hiring a photographer to capture the magical moment. We’ve worked with several photographers on engagement photos–they can be surprisingly sneaky when they have to be! They can “shadow” you or just wait for you at the spot of your choosing, then unobtrusively take some beautiful shots as you drop to one knee. After sealing the deal with a kiss, you can go to a few spots around town to take some posed pics as well as the spontaneous shots during the proposal itself.

St. Augustine is the backdrop for so many romantic proposals, elopements and wedding celebrations–why not start your fairy tale in the Oldest City…we’ll be happy to help you plan it!

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