This post may contain affiliate links and we may earn compensation when you click on the links at no additional cost to you.
If you are looking for a warm, sunny Christmas experience with plenty of Christmas cheer, December is the perfect time to visit Saint Augustine, Florida!
This town is excited for the Holidays to begin! Every street and building is decked out in festive lights every evening. Restaurants start up their tabletop fire pits, and their patio heaters to keep the outdoor seating areas cozy.
And every palm tree is circled with elegant white lights for the evening.
I’ve rarely seen a town so well decorated for the holidays! Even the trolley tours have festive lights and Christmas carols playing. Somehow, the drivers get all their trolley visitors to sing along with every song as they tour into the late hours on the Christmas lights tour! Every few minutes another group of moving carolers go singing by in their trolley!
St Augustine has a wild and wonderful history that you can still see and walk through today. It was founded officially in 1565 by the Spanish who first saw land from their arriving ships on August 28, the Feast Day of Saint Augustine. Landing eleven days later on September 8th, they founded what would become the longest inhabited territory in North America.
The huge Castillo San Marco at the entrance of the harbor is a prominent landmark reminding us of the town’s strategic location and importance. It was the capitol of both the Spanish Florida Territory and then British Florida, and eventually ceded to the United States in 1819.
Today you can still walk the streets of the historic district and imagine the days of pirates ships and Spanish settlers, soldiers and craftsmen. St George Street is for pedestrians only, and is the main road through the heart of the historical district.
The town has done a great job in keeping the historical character in all its downtown buildings. Original buildings have been restored, such as the oldest wooden schoolhouse in the US, and its surrounding buildings.
Newer buildings have been built as replicas. Even the Hilton Hotel has been built to blend in to the historical style of Saint Augustine.
No tall hotels or resorts block the gorgeous views of the marina and ocean here within city limits because, within its old ordinances, is a ruling that no building can be taller than 35 feet! At the time this was instituted, that was the height of it’s tallest building and it was causing consternation with the town. The happy result for us today is that, unlike so many other east coast towns, the views are saved for the public and town to enjoy, with no huge wall of hotels to block it out!
Saint Augustine has some of the most original, artisanal shopping you’ll find in these parts! If you love window shopping, you’ll have plenty to do here!
And what better time to get some unique Christmas gifts taken care of than December at this amazing little alley of Artisans!
Personally, I was quite smitten by all the fountains and sitting areas, and parks… And that there is live music coming from many a doorway at all times of the day.
The Colonial Oak Music Park has free live music in the center of Saint Augustine, and partakes in the free 3 weekend-long Sing Out loud Music Festival in September.
Seeing how this town is such a quaint, historical gem, it’s fitting to stay in one of the many Bed and Breakfasts, or Historical Inns that are sprinkled throughout the town. We stayed in the Southern Wind Inn, on Cordova Street.
Their beautiful foyer was a warm greeting in itself, along with the kind owners who made sure we had everything we needed.
I’m a sucker for the oval or octagonal rooms and covered porches of these old southern houses, so of course I chose the room encompassing the octagonal porch on the right top floor! It’s called the Fern Room with its relaxing pale green decor.
This house has kept it’s vintage charm , but all the modern amenities are added for their guests. This room has a king size bed, a cozy sitting area, as well as a desk and chair. And like all their rooms, it has a private bath.
Hot coffee and tea will be waiting downstairs in the morning for you, and breakfast is served in a lovely dining area, indoors or out.
I especially loved their inviting porches! Upstairs and down. And although it was December, it was warm enough for guests to eat breakfast on the front porch.
Once we arrived at Southern Wind Inn, our car was not needed at all. Everything is within walking distance. Happily, the Inn offers a parking permit for the lot across the street.
These are some of the other festive Bed and Breakfast/Inns that we noticed while walking around town, all decked out for the holidays! There’s plenty to choose from!
The Carriage Way Inn was voted Best Bed and Breakfast, and their holiday Decorations were on point!
There are so many more to choose from! Some of the Bed and Breakfasts are adult only, and others, well, just aren’t suited for rambunctious guests. But there’s accommodations to fit all ages and budgets. Next time I return with our kids, I’ve promised them we’d stay at the Pirate House! It doesn’t look like much from the outside but it’s centrally located, and a bargain price! But it’s only for those who are more “pirate-friendly.” I’ll let you know how it goes!….
In the meantime, Happy Holidays from Saint Augustine!
Bridget T
