Expert Advice

Escaping to Florida’s Oldest City To Celebrate (Plus What To Do and Where To Eat in St. Augustine)

One Owner reminisces on a recent winter getaway

Kassi P.
Aerial shot of St. Augustine, Florida, lit up for its annual Nights of Lights.

Christmas and the holidays is truly one of the best times to visit St. Augustine, thanks to the annual Nights of Lights, which takes place from mid-November to the end of January. However, our most recent winter getaway to Florida's oldest city was memorable because of the holidays and because my husband and I were celebrating our first wedding anniversary.

So it was a perfect winter escape.

Aerial shot of St. Augustine, Florida, lit up for its annual Nights of Lights.    

Where To Stay

When we've visited St. Augustine previously, we tended to stay closer to the city. However, this time, we opted to stay near the beach. Thankfully, the Hilton portfolio of brands has a beautiful property right on the water – the Embassy Suites by Hilton St. Augustine Oceanfront

We've wanted to stay at this property since it opened a couple of years ago and luckily were able to book our stay fully on Hilton Honors™ points – staying in a studio room with a balcony. 

Between the beautiful rooms and the outdoor areas, it was a perfect place to relax and decompress for a few days. And since it's an Embassy Suites, you also enjoy perks, including complimentary breakfast and happy hour. It doesn't get much better than that. 

All I know is we will be making another trip to this property — especially when it's warmer so we can enjoy the pool and outdoor areas a bit more.

What To Do

Even though we definitely could've spent our entire trip nearby the hotel, we did venture out to the city of St. Augustine for a little bit of fun. 

Here are a few of our favorites. 

My first recommendation is a meal at Harry's Seafood Bar & Grille. If you've ever visited St. Augustine, you likely already know how popular this restaurant is. (Think: with a line almost always out the door.) Lucky for us, we got a table fairly quickly on their outdoor patio – and on Christmas Eve, too! 

Hilton Grand Vacations Owners taking a selfie at Harry's Restaurant on St. Augustine, Florida, winter getaway.    

The food at Harry's is a blend between Cajun, Creole and Southern cuisine – with a lot of (you guessed it) seafood. However, for non-seafood lovers (like myself), there are plenty of incredible dishes from which to choose.  

As a bonus, when you sit outdoors – you'll enjoy live entertainment, a fantastic atmosphere and a nearly perfect way to spend an evening.  

Next on our list: St. Augustine Distillery. It's not a visit to St. Augustine for us without visiting the distillery. On this trip, we bypassed the tour, but if you have time, taking the free distillery tour is worth it, especially if it's your first time. It's so cool to get a behind-the-scenes look at how distillers make beverages, and you get a small tasting along the way, too. 

We decided to have brunch at their restaurant and bar, Ice Plant Bar, to switch it up. I have to say, holy moly, their brunch was amazing. Not only is the food incredible, but they also specialize in delicious craft cocktails. 

Finally, make sure to soak up all of the incredible lights as part of St. Augustine's Nights of Lights. The entire city lights up in a beautiful holiday display. St. Augustine is a walkable city, making it convenient to appreciate the lights as you stroll through the various areas around town. Still, you can also climb aboard a trolly ride or cozy up for a horse-drawn carriage tour.  

Regardless of what you choose, it is quite a sight. If you can't make it during the holiday season, don't worry — the lights are typically up through January. 

Read "8 Reasons to Re-Imagine Your Holidays With Hilton Grand Vacations" for more holiday travel inspiration. 


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Hilton Grand Vacations Owner, Kassi P.

Kassi P.

Kassi is a three-time Explorer and Owner since 2018, when she and her husband, then in their late 20's, decided vacation ownership was the next step in building a life filled with travel. As Orlando locals, they enjoy staycations and exploring The City Beautiful, but have never actually stayed at their home resort, Hilton Grand Vacations at Tuscany Village.  

When she's not using her ClubPoints in Florida, this urban traveler has a love of international travel and a sweet spot for her second home — New York City, which is where she got engaged while staying at West 57th Street by Hilton Club. When asked about her long run in the Explorer program, Kassi says, "It's my goal to inspire someone to create new memories, get out and travel and make the most out of vacation ownership."

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