Marriage Proposal Planning Guide: Proposing in St. Augustine

If there is one thing COVID-19 has taught us, it is that no matter what craziness is going on in the world, love is not canceled. Lovebirds are finding creative ways to keep the romance alive and create milestone moments. Today, we wanted to talk about one of the biggest relationship milestone moments: marriage proposal planning! Whether you want to plan the proposal down to the smallest moment, or simply pop the question when the time feels right, it’s a good idea to do a little bit of research beforehand. A great place to start is our recently posted engagement ring shopping guide. Once you have the perfect ring, the next step is to pick a time and a place to pop the question. We may be biased, but we think that our very own city of St. Augustine, Florida is the perfect place to plan a proposal. We’ve created a foolproof marriage proposal planning guide for St. Augustine!

Plan a Marriage Proposal Destination Getaway in Historic St. Augustine

When many couples start to think about the perfect proposal, being swept away to a romantic destination often comes to mind. Planning a marriage proposal in a far-flung international location might not be an option for the immediate future, but there are some fantastic destinations within the U.S. that are available to those looking to get away to pop the question. According to Hotwire.com, “domestic travel, especially quick, local getaways for 2 to 3 days, are a great way to test the travel waters again and get a much-needed change of scenery while staying close to home.”

Small towns like St. Augustine, Florida are an ideal option for those who want to stay away from the large crowds that are often found in big cities. Recently voted one of the 2020 USA Today 10 Best Historic Small Towns, St. Augustine is big on charm, yet small when it comes to population.

Compared to other parts of Florida, the St. Augustine area has had a relatively low number of COVID-19 cases, and the city is taking precautions to protect residents and visitors alike. We recommend checking out the Florida’s Historic Coast or VisitStAugustine.com websites for updates. 

Aerial photo of St. Augustine by That Moment Productions

Selecting the Perfect Location in St. Augustine for a Proposal

Once you decide that St. Augustine is the perfect city to plan your marriage proposal, the next step is to decide on a date and a location. With social distancing being an important factor to consider right now, we’re sharing a few of our favorite outdoor proposal locations in St. Augustine.

Nicci and Joe’s Engagement during Nights of Lights in St. Augustine, Photo by Angelita Esparar

Proposal Location 1: Proposing in Downtown St. Augustine During Nights of Lights

During the months of November through January, St. Augustine hosts its annual Nights of Lights celebration. With the city adorned in over two million twinkling white lights, it’s one of the most popular times of year to plan a proposal!  

If you want to be in the heart of Nights of Lights, we suggest going for a casual stroll through the historic district of St. Augustine. If the weather is cooler, perhaps pass by our neighbors, The Kookaburra, for a Mocha Nut Latte, or Kilwin’s for a hot chocolate. The fresh air and pit stops should calm the nerves before getting down to business and popping the question. 

When it’s time to get down on one knee, the Castillo De San Marcos or the Plaza De La Constitucion are locations that allow you to social distance from others while sharing an intimate moment. St. Augustine’s iconic fort on the bayfront, the Castillo De San Marcos, has a large lawn that would make for a perfect proposal spot away from some of the larger crowds. The Plaza De La Constitucion, located right in front of The Treasury on the Plaza, has a beautiful gazebo that feels like it is straight out of a Hallmark holiday movie!

Katie and John’s proposal photos

Proposal Location 2: Propose at Sunrise on the Scenic Shores of St. Augustine Beach 

St. Augustine is known for more than just our historic district; we’re also known for our beaches! Being located on Florida’s east coast, we are known for our gorgeous sunrises. Surprise your partner with a sunrise trip to the beach. Grab a cup of coffee and some Aussie Pies from The Kook Beachside, a blanket, and cozy up to watch the most beautiful scenic view you’ve ever seen together. (They’ll forgive you for waking them up at the crack of dawn once they see the sunrise–and the ring–we promise!) 

Brittany Jones, wedding planner and owner of Uncorked Occasions, has a few tips for planning a sunrise proposal. When you plan a proposal at St. Augustine Beach, ask yourself, “Is there a memory you can recreate? What about a favorite song, treat, or item you can bring with you or have set up in advance? Is there something special you can bring home? One example would be using the beach sand from the proposal site in a unity ceremony at your wedding.”

Preston and Anastasia’s St. Augustine Beach Proposal, Photo by Josh Haltam photography

Looking for even more St. Augustine proposal ideas? Check out this post! 

More Tips for Planning A Proposal in St. Augustine

When marriage proposal planning in St. Augustine, there are important factors to keep in mind. As planner Brittany Jones, shares, “it’s tourist season year-round in downtown St. Augustine, and there are many events that take place, including our Nights of Lights, parades, races, etc. You want to know what you’re getting yourself into with regard to parking, busy streets, and obstacles. I recommend choosing a proposal location or two outdoors (plan A and B), and then make a plan C indoors for inclement weather.”

After you pop the question and your partner is sporting their new bling, it’s time to celebrate! Jones shared her tip for a sweet engagement celebration: “I recommend picking somewhere within walking distance and setting up a bottle of bubbly, some flowers, and maybe even inviting a few surprise guests to be there upon your arrival. Make it a moment and a memory worth sharing for a lifetime.”

To make your proposal even more special, consider hiring a photographer to capture the moment. We’ve got a great list of St. Augustine wedding photographers on The Treasury on the Plaza website. Your partner will admire your attention to detail and thoughtfulness for planning the ultimate proposal, and capturing this special moment for posterity. You can also use the images for a social media wedding announcement and save the date cards, which is a win-win.

Finish the night at one of St. Augustine’s amazing restaurants. There so many delicious options right in the downtown historic district where you can enjoy the taste of St. Augustine. A few of our favorites are Harry’s, The Floridian, Catch 27, Collage, and Preserved…although there are so many culinary delights that it’s hard to choose! Many of these restaurants also have outdoor dining available, so you can keep the celebrations as safe as possible!

Harry’s is one of the many restaurants in St. Augustine with outdoor dining

It’s no secret that 2020 has delayed many special events. However, your marriage proposal doesn’t need to be one of them. With some creative thinking, social distancing measures can actually work in your favor! Because let’s face it, who likes to be interrupted and distracted by strangers during one of the most important questions of your life? Social distancing has forced us to spread out from others, but it also allows us to feel a sense of privacy, even in a busy place. Use these measures to your advantage! Your partner will be so impressed by your marriage proposal planning efforts, and be even more excited to say “yes” to spending forever with you!

The Treasury on the Plaza is here to help from the moment you say “yes!” to the day you say “I do!” Make sure to visit us again when it’s time to find the perfect wedding venue.

Want to learn ALL THE THINGS about planning the perfect wedding? Make sure to check out our Ultimate Wedding Planning Guide!

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Proposal photos by Nicole Piper Photography and Angelita Esparar Photography