Celebrating the Holidays in St. Augustine

St. Augustine is known as the Oldest City in America. And during the Holidays, the city displays over 3 million shimmering Christmas lights throughout! Jeff and I are only a couples hours away from St. Augustine so we decided to spend a few days there for my birthday. Being a December baby, I’ve always had a special love for the Holidays and couldn’t imagine a better place to be than a city filled with lights, charm and history!


Nights of Lights usually begins with their Light Up! Night ceremony on the first Saturday of the Holiday season. Due to precautions made necessary by the Coronavirus pandemic, the ceremony wasn’t held this year. The city of St. Augustine has been celebrating Nights of Lights for over 27 years, and surely, they wanted to keep up the tradition up this year.

The Nights of Lights Sign in front of the Hilton Hotel

Where to Stay

Casa Monica Resort & Spa, Autograph Collection

Located right in the heart of the downtown district, Casa Monica is a historic hotel with an elegant Moroccan theme. Built in 1888, the hotel is home to high-end restaurant, a rooftop pool and sundeck. Plus it’s walking distance from Castillo de San Marcos, Flagler College, The Fountain of Youth, Ripley’s Believe It or Not, and a short drive from the St. Augustine Lighthouse and more.

For a more detailed look at Casa Monica Resort & Spa, check out my post here!


Also, be sure to check out St. Augustine’s Bed and Breakfast options if you want more of a unique stay!

Hilton Hotel by the Bay of St. Augustine

Where to Eat

Columbia Restaurant

St. Augustine offers a lot of great food. But if you want to experience the old spanish ambience at the one of Florida’s Oldest restaurants, check out Columbia. We decided to dine in for a light lunch and enjoyed their bread and butter (a local told us it’s her favorite) and their famous 1905 salad! If you go, grab one of their Sangria Pitchers for a sweet boozy beverage!

And of course, if possible take a look around this gorgeous historic restaurant! Columbia is especially beautiful during the holidays!

Columbia Restaurant in St. Augustine

One of the highly recommended places to eat was Harry’s! We sat outside even during the holidays because of how cozy and lively the outside patio is. They offer warmers to keep you toasty from the bay breeze. At Harry’s Seafood, you’ll find specialties in cajun flavors.

Where to Drink

The restaurant and bars close earlier in St. Augustine, so make sure to prepare if you plan to hop around for drinks.

  • Tini Martini Bar: Known for their over the top decorated balcony, Tini Martini Bar is located at the Casablanca Inn. Facing the bay, this bar serves delicious Christmas treats like peppermint flavored martinis and white chocolate espresso drinks. My personal favorite when it’s chilly out is a nice Old Fashioned. They also serve the classics and their twist on the signature menu.
  • No Name Bar: If you’re looking for a bar that is more low key but a hell of a lot of fun, check out No Name Bar. We met a couple at another spot and they highly suggested this place. On the weekends, they offer live music and drink prices you can’t refuse. And during the holidays, you’ll see appearances from the Grinch and even santa himself!

If cocktails aren’t your thing, check out a few of these wineries and distilleries! Some even offer tours!

The Grinch at No Name Bar


San Sebastian Winery
What goes better during the colder seasons other than wine? San Sebastian Winery offers complimentary Winery tours and wine tasting are offered 7 days a week. And upstairs, you’ll find their “The Cellar Upstairs Bar and Restaurant” which offers their wine with live music on their rooftop! Which is a favorite spot for locals!

Carrera Wine Cellar
Maestro Winery


To warm things up, head over to the St. Augustine Distillery! This distillery produces Florida’s most awarded spirits plus offers a complimentary tour and tasting! If you have any free time, it’s definitely a short drive from the heart of downtown. The tour can be done at your own pace! And they offer free tasting of their mixers featuring their spirits. And if you’re in the mood for food, check out the Ice Plant Bar for locally sourced dishes & seasonal cocktails.

Other Distilleries to check out:

  • City Gate Spirits
  • Scoville Vodka
  • Sailbird Distilling Company

Historic Tours

Here is a list of tours to check out while your in St. Augustine during any time of the year!

Buy Your Tickets Online and Save 10% Off or check out https://www.trolleytours.com/st-augustine for all trolley tours!

  • Castillo de San Marcos National Monument
  • Old Town Trolley Famous Nights of Lights Tour
  • Old Jail After Dark
  • Ripley’s Red Train
  • Ghosts & Gravestones Tour
  • St. Augustine Eco Tours
  • Scenic Cruise Tours
  • Florida Water Tours
  • St. Augustine Sailing

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