✨ Pirates Burned This City to the Ground and Now It's Gorgeous
A romantic wander through St. Augustine with ghost tours, hot toddies, and holiday vibes.
Hello, fabulous!
This week we’re headed to one of America’s oldest cities with cobblestone streets, haunted mansions, pirate lore, and now…millions of twinkling lights.
Back in October, we celebrated our 22nd anniversary with a long weekend in St. Augustine. We stayed in the sweetest little Airbnb right on St George Street, which meant we could wander all the historic alleyways to our heart’s delight. The city felt vibrant, walkable, and deliciously spooky in all the best ways.
But now that December has arrived, I kinda wish I were back under the palm trees, walking along the bayfront with a warm drink, watching the entire city sparkle for the Nights of Lights festival. So grab your hot cocoa and fluffiest throw - we’re heading back to St. Augustine, dreamy-holiday-edition style.
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Hottie Tea Toddy
St. Augustine isn’t just beautiful - it’s the oldest continuously lived-in city in the U.S., founded by the Spanish in 1565. So when the holidays hit and the city lights up, it doesn’t just sparkle - it glows with centuries of charm. Millions of white lights drape over ancient stone walls, sway from palm trees, and shimmer across cobblestone streets like something out of a storybook. Every corner holds a secret or a love letter from another time. So of course that calls for something special and warm in your hands: a drink that feels like a hug, a little history, and a lot of holiday magic all at once.
Enter the Hottie Tea Toddy from local favorite St. Augustine Distillery: a cozy twist on the classic hot toddy that feels like a holiday exhale. It starts with steeped tea, melted honey, fresh lemon, and their Florida Straight Bourbon. Simple, warm, and just herbal enough to feel special, especially when the city’s twinkling and the Florida “cold front” has everyone suddenly reaching for sweaters.
INGREDIENTS
1 tea bag of your choice
1 TBSP (¾ oz) St. Augustine Bourbon Barrel Rested Honey
1.5 oz Florida Straight Bourbon
¼ cup lemon juice
8 oz boiling water
DIRECTIONS
Boil water for your tea. As water is boiling, cover the bottom of a large mug with honey.
Place your tea bag in the mug and add boiling water. Cover mug, and allow to steep.
Uncover, add lemon juice and bourbon, and stir. Enjoy hot.
Dark & Stormy
For another fun St. Augustine-inspired sip, I have to share this one from fellow Substacker Robin. She’s been mixing up cocktails for her Cocktail Solstice Countdown series (they are yummy!), and when I saw this recipe I immediately thought: yesssss - this belongs in a St. Augustine issue, especially with all the pirate vibes. She graciously let me include it here for you. It’s called Dark & Stormy, and it’s so good.
INGREDIENTS
2 oz Dark Rum
½ oz Fresh Lime Juice
5-6 oz Ginger Beer
Garnish: Lime Wheel
DIRECTIONS
Add the above ingredients in order in a highball glass with ice…
Gently Stir
Garnish
Did you know that St. Augustine was once attacked by Sir Francis Drake, the famous English privateer (aka pirate with a license)? In 1586, he burned the city to the ground during a raid, making it one of the first recorded pirate attacks on American soil. The Spanish rebuilt, of course…but maybe that explains the ghost stories?
Collage is this tiny restaurant on the north end of the strip, and I found it through Google Reviews that were almost too glowing to trust. Turns out they were spot on. It was one of the most memorable meals we’ve ever had, and celebrating our anniversary there made it even sweeter.
The restaurant is small - about 15 tables - with humble décor that feels intimate and romantic, and the service was incredible. Every dish was stunning, delicious, and full of little unexpected touches that made it feel like we’d stumbled onto a secret. It’s not one of the places blasted on all the “Top 5” lists , which made the discovery of this hidden gem even better because if more people knew about it, it would be.
We started with Escargot and the Scallop Saltimbocca (scallops wrapped in prosciutto and sage). They brought complimentary grilled garlic, a fun change from bread and butter, then Speed had the Collage Surf and Turf (tenderloin + Maine lobster tail) while I had the Homemade Lobster Ravioli. We finished with our go-to crème brûlée (and forgot the photo, of course!). Total mouthgasm worthy and one of our Top 5 meals EVER. It was a magical little spot! We left full, happy, and a little bit proud we found it.
We learned the team at Collage is pretty much amazing. They make everything from scratch, use fish from local waters as well as produce from nearby farms, and are led by a female chef (Chef Nicole Parker). On top of that, College has been listed on OpenTable’s “Top 100 Romantic Restaurants in America” multiple times. Totally tracks.
Talk about colorful! The historic Casa Monica Resort & Spa feels like you stepped into a Spanish-Moorish dream. Arched doorways, velvet textures, and just enough moody glam to make you believe you own 14 caftans and a crystal decanter set. Next time we’re in St. Augustine, we’re definitely staying here. We did have lunch at the hotel restaurant, Cordova Coastal Chophouse, and the ambiance was incredible.
Where’s the most moody glam place you’ve ever stayed?
Since it’s that most wonderful time of the year, I have to mention the annual St. Augustine Night of Lights! It’s an annual event during the holidays when the city’s historic downtown is dressed up in millions of tiny white lights draped over the old buildings, palm trees, and downtown streets from Nov 15, 2025 through Jan 11, 2026.
I love the idea of strolling the historic streets while everything glows with millions of tiny white lights, grabbing something warm to drink, and just wandering with no agenda. St. George Street, the Plaza, and the Bayfront are built for that kind of night. Here’s a great Night of Lights drone tour for your viewing pleasure:
🗓 St. Augustine Food + Wine Festival | May 6–10, 2026
Mark your calendars, friends, because this is one of those “okay, we’re definitely going” events. St. Augustine’s wine scene blends historic charm with modern flavor: think cozy tasting rooms, local wines with Floridian flair, and plenty of spots where you can sip a glass al fresco while watching the lights dance over the cobblestone streets.
If you love good food, good wine, and the idea of sipping something fabulous while wandering around a beautiful historic setting (because I totally do), put this on your list. I’ve been eyeing this festival for the tastings alone, and it’s officially on my must-do lineup. Sharing it here in case you want to plan a little trip too. This feels like the kind of weekend you come home from happy and well-fed.
More info → staugustinefoodandwinefestival.com
Ghost Tour
You can’t visit St. Augustine without doing at least one ghost tour. It’s practically a rite of passage. I’ll admit, I’m not really into spooky stuff either, but we found a low-scare, high-fun option that totally worked for us: the Riding with the Ghosts a Golf Cart Ghost Tour in St Augustine at 9:15 pm.
It was the perfect length (just long enough to get into it, not long enough to regret it), the guide was funny and full of historical gems, and seeing the city lit up at night made the whole experience feel more magical than macabre. A great way to end the day…and zero jump scares.
Other attractions we enjoyed
Medieval Torture Museum (this was gross so don’t take little ones)
Walk down Martin Luther King Avenue (Lincolnville)
Would you go on a ghost tour…at night?
To me, St. Augustine style feels like soft gothic meets coastal sparkle - equal parts historic charm and seaside ease. Think black florals, flowy dresses, glowy skin lit by lantern light, and metallic flats that can handle cobblestones. It’s one of those cities where you might pass a centuries-old mansion on your way to a cute beach café, so your outfit kind of needs to live in both worlds: romantic, a little mysterious, but still breezy and walkable.
Here’s my own little collection of holiday sparkle…pieces I love that totally channel the St. Augustine vibe.
1. Replica “By the Fireplace”
2. Mac Duggal High-Neck Gathered Tulle Midi-Dress
3. Bobbies Tara Low-heeled Sandals
4. Zara Beaded Handbag
5. Charlotte Tilbury Matte Revolution Lipstick in Pillow Talk
6. Lucite Petal Leverback Earring - Black Beetle
Would you wear this soft-goth-meets-beach-glam vibe?
Thanks for joining me on this dreamy holiday edition of Daytrips! This was so much fun to put together. I may not be in St. Augustine right now, but writing this helped me relive the magic from my anniversary trip AND from the kind of December I want to create: slow, sparkly, and full of moments that feel like a Hallmark movie.
If you enjoyed this little getaway, give it a like, leave a comment, or send it to a friend who needs a cozy escape.
See you next time under the twinkle lights!
💌 From Sandra’s Desk
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Let’s Discuss
Been to St. Augustine? Or have a holiday town that lives rent-free in your heart? I’m always looking for dreamy destinations to feature. Tell me in the comments or reply to this note. I read every single one. 💖
💬 LET’S DISCUSS: Been to St. Augustine? Or have a holiday town that lives rent-free in your heart?
What an enchanting trip, and a perfect way to celebrate your anniversary! I’m definitely adding St. Augustine to my wishlist of places to see.