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, winter is 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. However, each of these spots would be a magical place to pop the question any time of year. 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. In the meantime, here are 7 of the best places to propose in St. Augustine, plus our specially curated package:

Lighthouse in St. Augustine

1. At the Top of a Lighthouse

Start your forever with all of Anastasia Island at your feet. If they take your breath away, what better place to ask them to marry you than at the top of 219 stairs?

Newly engaged couple cheers wine glasses

2. In the Deep End of the Pool

Take the plunge and propose in the deep end of the pool at Cafe Alcazar. Don’t worry, 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 until you get a table, or better yet, ask your other half to marry you while sitting on the benches before you reach the restaurant. Bonus: the cafe often has a live musician, giving you a perfect soundtrack!

Couple holding hands on the beach in St. Augustine, FL

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 them.

Proposal at sunset in St. Augustine

4. 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. One of the best places to propose in St. Augustine is at the peak of the rustic bridge, then take a picture of the two of you. Best. Selfie. Ever.

St. Augustine Seawall

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).

Man proposing at sunset in one of the best places to propose in St. Augustine

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.

Sunset in St. Augustine

7. At Your Favorite St. Augustine Bed and Breakfast

We believe our romantic bed and breakfast is one of the best best places to propose in St. Augustine and we love 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 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 photographs 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!

Man proposing at a restaurant in St. Augustine

Pop the Question With Our Custom Package

Not only can we help with proposal location ideas, but our St. Augustine bed and breakfast also offers a custom package ready to help you with all the romantic details you need to get engaged in a beautiful way.

Our Pop the Question Package includes:

  • Up to 1 hour of event planning with our in-house coordinator. Our event planner will help customize your proposal location and can also help you plan your entire evening, whether you’d like an amazing dinner at one of St. Augustine’s special occasion restaurants, a romantic carriage ride for two, a bouquet of red roses, or even a photographer to capture the special moment. (Prices of these items are not included in the package, but we are happy to help you make the arrangements).
  • One hour in our story-book gazebo, beautifully decorated with sheer white curtains, lovely bows, a “Marry Me” marquee sign, and greenery accents. Or, if you’d prefer something a little more secluded, an hour under our flower-covered pergola at the Sanchez House. (Gazebo and pergola subject to availability).
  • Two songs of your choice, which we can play during the proposal, or immediately afterwards. The second song can be nice for a first dance as an engaged couple!
  • Bottle of chilled bubbly. (Served in your room, or in the gazebo or pergola).
  • Complete set up and tear down of your proposal location, so you don’t have to worry about anything (except finding the right person).
    $199 for Inn Guests | $299 for Non-Guests

Call our office at 904-824-4301 to start planning your perfect proposal today!

BONUS: Book your Bayfront Marin House ceremony within 1 year of your proposal date, and save $100 on your wedding package. You must purchase the proposal package to receive the discounted wedding package. Offer subject to availability, and may be discontinued at any time.

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