If you are hopeless romantics and/or history buffs, you’ve got to check out St. Augustine, Florida. After you spend a leisurely day here, you may just want to stay. Let’s plan a St Augustine date you won’t soon forget!
Our recommendation is to stay at a quaint bed & breakfast near the square on the night before your romantic getaway to the Oldest City. Our favorite is the Bayfront Marin. Each room is decorated in a uniquely themed colonial style, plus you have a view of the marina and the Bridge of Lions. In the morning, you can have a leisurely breakfast on your balcony (in true St. Augustine style) watching a gorgeous sunrise over the Matanzas Bay. It’s the very beginning of your perfect date in St Augustine.
Start by spending your day exploring historic cobblestone streets, weaving through narrow alleys adorned by colorful buildings. Duck away for some lunch and people-watching from Sangria’s second-story balcony, located right above St. George Street.
You will be taken back to the 16th Century if you whisk your date by the Colonial Quarter where workers wear full era-appropriate gear and demonstrate how to forge a sword and load a musket. This will score you extra points if your partner is a history buff whose love language is quality time and worldly experiences.
Walking through the city gates will immediately transport you through history and time with Spanish architecture, cuisine, and the sense of romantic adventure.
At the corner of Orange St and St. George St, you will find a plaza off the beaten path where you can enjoy ice cream, a glass of wine from Bin 39 or even indulge in a cigar. This is a great way to relax before your next mini couple’s adventure.
I highly recommend booking an Ancient City history tour in the back of a horse drawn carriage. This is the perfect way to spend your mid-afternoon. The carriage will take you along the bay, down the less busy Aviles street and up by the magnificent Lightner Museum and Flagler College buildings. You will learn a good bit of St Augustine history while snuggled together in the back of the carriage.
Bonus: ask to be dropped off at the breathtaking Casa Monica Hotel, where you will be enjoying the rest of your evening and spending the second night in luxury and style.
If you are jazzed to wear your Saturday-night-best and really feel the sparks in St Augustine, we have just the nightlife plan to turn up the charm! The best part: you’re already staying at the jewel of our romantic city, the Casa Monica Resort, and you don’t need to leave your hotel to experience the magic.
Do briefly walk out to take a few photos together on Casa Monica’s iconic stairwell. The building itself is gorgeous with marble columns on the outside and priceless art pieces on display on the inside. It is an icon of luxury and will surely cast a spell on you.
But this is only the beginning of your magical date night in St Augustine, because hidden in plain sight inside the Casa Monica Hotel is an intimate and captivating show that will absolutely blow you away.
Your unsuspecting partner may not be aware of the riveting experience coming next. Surprises are so rare, and you have really got a good one up your sleeve tonight! As the visionary, you will be barely containing all the excitement building up during your dinner at the Cordova Coastal Chophouse & Bar.
“Wow this steak is magical!”
“You sure cast a spell on me.”
“I’m not a mind reader, but I bet this is going to be an unforgettable date night.”
Ok, what’s with all the magic stuff?
We have a surprise for you both — for hidden within the chambers of the opulent Casa Monica Hotel is a boutique speakeasy style showroom set up for a mind-blowing, entertaining show.
Inside the secret room, is the world-renowned master magician and entertainer, Bill Abbott, waiting to inspire and mesmerize you with a bit of old town magic and mind-reading.
When you finish dinner and go to check in, you will be directed to the Cordova Room, where you and the small group who will be enjoying the show with you can partake in a complimentary welcome cocktail and get to know one another. We (Bill and wife, Rebecca) will visit with you and make you feel incredibly welcome and special with a set of interactive mind-bending illusions to give you a small taste of what’s to come.
After a short time, you will be ushered into the showroom: a small boutique with a vintage jazz speakeasy vibe, where your night truly begins. Bill will seduce your minds, dazzle your senses, and masterfully work his craft in delivering an up close and personal, highly interactive and intimate magic experience.
This St Augustine magic show is not like any other. It is a one-of-a-kind VIP experience that involves complex and unbelievable illusions and hypnotic mind reading.
You will leave the theater room fascinated, blown away and thoroughly entertained.
What an amazing way to wrap up your romantic St Augustine, Florida trip!
We just know you’ll be coming back soon!
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