Five of Historic Saint Augustine, Florida’s Best Kept Secrets

Five of Historic Saint Augustine, Florida’s Best Kept Secrets

Please note: This post contains affiliate links, which means I may receive a small commission if you make a purchase, at no extra cost to you.

In Saint Augustine, Florida antiquity allures visitors while the modern establishments entertain and nourish. We headed to St. Aug. with no set itinerary, but found ourselves seduced by its historic spell.  To newbies, the city may be overwhelming.  If you are just visiting for a short stay, these are my recommendations for the perfect St. Augustine, Florida weekend trip.


Saint Augustine Florida

A Quick Introduction to St. Aug., Florida:

In a trance-like gait we wandered neighborhoods, lusting over old Victorians.  We stopped to admire parks with artistically and poignantly dedicated monuments and reached over to stroke local furry celebrities parading down the cobblestoned roads.

St. Augustine, Florida boasts of the Fountain of Youth—home to some possessive peacocks—the oldest wooden schoolhouse in the United States, and B&Bs bursting with guests who have never left. An old fort greets you on one side adjacent to a cheesy yet swashbuckling fun pirate museum. I even earned my piece of the treasure at the end of the tour.


Downtown Saint Aug Florida


Across town, stumble into old graveyards, hidden parks, and the past waiting to be discovered. Ride bikes down cobblestone roads, peruse native literature and used books, try some local spirits (literally and figuratively), and dine to some live music before a ghost tour. A few days stay is hardly enough. Make your time in St. Augustine, Florida as tourist or local as you wish.


discover Saint Augustine Florida


St. Augustine is my reprieve from endless stucco and paper towns. Take my phone away as I Zillow old Victorians and try to peep over walls.



Sound appealing?  Be sure to visit these five local places to create the perfect St. Augustine, Florida weekend trip:

5 Hidden gems in St. Augustine Florida



1. Lunching on an asparagus sandwich at Café Alcazar’s historic swimming pool

Imagine having lunch in the world’s largest indoor swimming pool of its time. Housed in the historic Lightner Museum (my husband was disappointed when he realized it was not the “Lighter” Museum), Café Alcazar sits in the deep end of the former Hotel Alcazar’s indoor pool. Henry Flagler built this extravagantly gorgeous hotel and casino in 1888 with the pool spanning around 120 feet long and ranging from 3 to 12 feet deep. With over three stories and an impressive façade, the café feels like everyday lunch is actually a beautiful art or wedding reception. Today tourists and locals can enjoy a fine dining meets casual lunch experience while listening to serene instrumental music. Munch on unique sandwich selections, fresh fish, and homemade specialty sides. The chic vibe is anything but pretentious with fantastic service and a historical atmosphere unlike any other.   Sneak up to the second floor–pretending to use the restroom–to spy a gorgeous overview of the impressive landmark and get a feeling for the true scope of the pool. Be sure to read the history placards with old pictures of the pool on your way out the back door.


2. Roasting marshmallows and spending a romantic, cozy night at The St. Francis Inn

A gentle swing on the porch. A cup of tea in the sitting room. Witchy cat eyes staring back at you from the trees.  One of my all-time favorite B&B’s, this Irish inn offers social hours with local wine, beer, and liquor as well as an array of desserts. My favorite: s’mores by the incandescent courtyard fire.  Let staff know in advance, and they will cater to dietary needs.  We found ourselves ensconced by history older than our grandparent’s grandparents with floors hiding secrets of trysts and neighboring buildings with centuries of foreign settlers and inhabitants.  If you book far enough in advance you can pick your room, each with a special name and design.  With the friendliest staff and sweetest breakfast–french toast casserole anyone?–the Inn completes a perfect vacation.


3. Sipping on handcrafted cocktails at the Ice Plant Bar

Only in St. Augustine, Florida can you find yourself sipping handcrafted cocktails in a speakeasy meets steampunk warehouse at the Ice Plant Bar. With drinks and ice made with precision, we celebrated a quiet afternoon picking at fresh cut tuna smothered in capers and nuts.  The building dates back to 1927 where workers broke down ice for shrimp boats and local use.  The original crane sits above the bar, topping off that factory-feel.

Don’t forget to tour the St. Augustine Distillery next door for some rum, gin, whiskey, and vodka sampling.  Tasting and tours are free.  Stamp in with the time clock, sip a few samples with mixers, tipsily shop away, and rinse your hands in the bathtub-esque sink.  Factory warehouses with an old-fashioned flair call to me like the history nerd and gentle bacchanalian that I am.



4. Listening to live music while munching on southern deviled eggs at Prohibition Kitchen

I especially crave taverny pubs in historic places and St. Augustine is no exception.  Located on the famous St. George Street, in the heart of it all, Prohibition Kitchen serves up craft burgers and sandwiches with a vintage, southern flair.  Sip on hand-spun milkshakes to live music after a day full of exploring or wind down by designing your own Old Fashioned, even picking your bitters.  We loved watching a couple dance along to the music, sashaying out the door prohibition-style.  Reminiscent of flappers and illicit hedonism, Prohibition Kitchen brings you back to a different era.


Cocktails at Prohibition Kitchen


5. Beer tasting at Dog Rose Brewing Company

Dog Rose Brewing opened in the fall of 2017 and is a short walk from the center of historic downtown.  They offer a hoppier selection of brews and their stomping grounds are pristine.  Taste a flight while watching your beer brew or play a round of darts and table shuffleboard.  The colors and artwork remind me of Saturday yoga at the brewery, and I could sit here all afternoon people-watching out their gorgeous wall of windows.

Nearby, you could also check out: Bog Brewing Company or get your wine on at the San Sebastian Winery.


Pin The Perfect St. Augustine Weekend Trip To Your Boards:

5 Must Sees for St. Augustine Florida



To further help you plan the perfect St. Augustine, Florida weekend trip or get in the spirit (that joke never gets old) take a peek at these travel guides and local books:






  1. Jana
    April 13, 2018 / 12:09 pm

    Thanks for the wonderful tips! My boyfriend and I are heading to St. Augustine this weekend and I found your blog from Instagram. I’m so glad I did! I’m definitely going to suggest we check out some of the places you mentioned. In your opinion what is the best part of town to stay in that allows you to walk around the most without needing an Uber? Thanks so much for your suggestions!

    • April 13, 2018 / 8:00 pm

      Hey Jana! Thank you so much! I did see your IG follow request too ; ) Staying anywhere in historic St. Augustine should be OK. Everywhere mentioned above is within walking distance of each other (you could look for places around there, St. George St., etc). All of the historic downtown is walkable and many places also let you borrow bikes. If you are headed to the beach or state park, though, you might need to Uber. Our first visit to St. Aug, we were on the other side of the bridge (not downtown) and had to drive. There are plenty of lots and a parking garage. You have to pay a full day fee for the garage, but it is attached to the visitor’s center/bathrooms. Also check out the local trolleys–you can get tickets and hop on/off at favorite spots. I know The Ice Bar and winery are definitely on a trolley route.

    • April 15, 2018 / 4:22 pm

      Hope you are having a great vacation! I want to hear all about it, especially if you found some place that we should check out.

      • Jana
        May 11, 2018 / 6:50 pm

        We had a wonderful and relaxing weekend in Saint Augustine! The April weather was perfectly sunny and warm enough for day and nighttime sight seeing. We ended up staying a couple miles from the downtown area and Ubering downtown. We explored the Castillo de San Marcos, walked through picturesque historic downtown, ate at several restaurants and stepped out to immerse in the nightlife on Friday and Saturday. We learned that the bartenders are heavy handed in St. Augustine, just a little added bonus. One of our favorite restaurants was Brunch, where we had eggs Benedict and shrimp and grits and rich cups of freshly brewed coffee. I always judge a breakfast spot by the quality of their coffee, and Brunch did not disappoint! Your tips were helpful and gave me insight on what to expect before heading there, thanks so much!!

        • Christine
          May 12, 2018 / 9:47 am

          That sounds like the perfect weekend! Only once have we stayed further outside the city–on the water–and that was really nice too. The bartenders ARE heavy-handed, lol! I love their generosity ; ) I’m going to check out Brunch the next time we are up–because I do love brunch. Thanks for the suggestion. Thank you for the compliment too; please keep in touch via IG, for sure.

Leave a Reply

Your email address will not be published. Required fields are marked *