Family Friendly Halloween Fun In St. Augustine, Florida

It’s Halloween in the oldest known city in the nation! Guaranteed there is easy to find spooky, haunted fun on offer! But what If scary isn’t what you’re looking for or you need something a bit more PG to entertain the kids? Well, I’m here to help! Today I’m sharing a few ideas for anyone seeking a laidback, easy as spooktactular Halloween sure to entertain both the kids and adults!
Here are a few simple ideas to ensure a fun, laidback Halloween in
St. Augustine, Florida for the whole family.
1) Set a festive mood.
As a family who travels fulltime, we often find ourselves in a new city every few weeks. This can sometimes feel a bit disorienting. We enjoy our travel lifestyle, but this side effect can occassionally be a bit confusing to our bodies when we move around so often that we forget which city we’re in.
Creating excitement around activities that relate to the season or holiday helps keep us grounded and aware of what time of year it is, no matter where we are on the map. Setting a festive mood also helps my family get revved up to go out and explore our surroundings even more. We like to learn how different cultures celebrate different seasons and holidays. The unique traditions and markers that give a place it’s identity.


For this occassion, my kids decided to set the stage with a few homemade craft projects to get ready for a day of fun and of course the anticipation of a day full of lollies!
Basically, whatever it is that’s going to make it feel festive, go for it! Take a minute to decorate your space, get dressed up, or simply buy some sweets for those potentional trick-or-treaters (or for yourself). Whatever it is that will help set a festive mood to get into a fun, festive headspace, go for it!

Make it a family affair and join in to create a sense of excitement! But, if this feels overwhelming (or you’re short on time), remeber it’s OK to keep it simple!
To be honest, I’m not a huge fan of costumes for myself. But i still managed to grab my favorite black tank-dress from my closet and borrow my daughters sparkly cat-ear headband. And Voila! In less than five minutes I was transformed into a kitty, ready to hit the town! Have fun with it!

2) Hop the Beach Bus Shuttle into historic downtown.
Many of the streets in historic downtown cannot accommodate the size of larger vehicles like ours. We discovered this the hard way on day one of our St. Augustine visit. Not going to lie, it was a bit stressful trying to navigate several of the roads in our F-350 super duty longbed dually. I would compare this experience only to the nail-biter we endured in our truck, navigating the streets of Little Italy during World Cup kick-off in Boston. You remeber – When Italy faced off with England… Yeah. Nutzo! is the only way I’d describe those shinanagins and I’m not too keen to replay that adventure anytime soon! Ok, so St. Augustine wasn’t as bad, but I definitely experienced flashbacks on a few of the roads.
If you insist on bringing your own vehicle, there is street parking and pay to park lots spattered around town. But my advice would be to learn from our mistake and hop the Beach Bus Shuttle in to town instead if you are staying along it’s route.

We stayed out on Anastasia Island and discovered this to be an incredibly convenient and fun way to see the sights. Bonus, our driver was super friendly and knowledgable which only added to the experience.
The Shuttle stops at several popular beach hotels, St. Augustine Beach (A Street), St. Augustine Lighthouse, and even the Aligator Farm. It’s also complementary when you purchase tickets for the Old Town Trolley tour. Check the Old Town Trolley Tours website for Beach Bus Shuttle pickup times and locations. And remember to tip your driver!
#3) Grab a walking map and your passes for the hop-on hop-off trolley.
When the shuttle arrives downtown, it conveniently drops off at Trolley stop #14. Once you arrive, follow the crowd over to the Old Town Trolley kiosk. Show the merchant your proof of purchase (either online or from the hotel you purchased your tickets from) to pick up your passes for the old town trolley as well as a walking map of downtown.
Then make your way down the block to The Koukaburra for a coffee and an Aussie hand pie.


While the kids are occupied with their morning snack, mark out the most important places to visit on your route first. There’s a lot to see and do downtown and little legs (at least in our family) move slowly, so having a general direction / plan to work from helps curb aimless, endless walking (and inevidable complaining) while keeping littles engaged and excited about their adventure. Better yet, give them their own map to highlight. I don’t know about you, but my kids always love this involvement and treat it like a treasure hunt.
To get a head start, check out this interactive map of downtown to start plotting your Halloween route!
4) Go Trick-or-Treating!
Once everyone is refueled, hit the streets on foot. Sightsee, shop the boutiques, chat with the shop owners and trick-or-treat your heart out!
Every year St. Augustine shops on St. George Street host a community safe trick-or-treating event for visitors. Fun for all ages! And be sure to check out Ximenez-fatio House on Aviles Street, the oldest street in St. Augustine, which also hosts their own annual community safe trick-or-treating and fall festival event.


*Just keep in mind that because Halloween falls on a different day each year events may be held on different days, typically on weekends, so make sure to check Google, or visitor and event websites before you go so that the you don’t miss these special organized community events!*
For more ideas, or if your group can handle something more intense than PG (check tour age restrictions), there are plenty of spooky experiences on offer in a city with such rich history and stories to tell! Check out Ancient City Tours for seasonal experiences like Ghosts and Gravestones Frightseeing, or the Old Jail afterdark paranormal investigation. A Night Among Ghosts even offers a paranormal overnight experience at Ximenez-Fatio House Museum!
5) Hop the trolley for a history lesson of historic downtown.
By this time little legs are ready for a break, so now would be a good time to make your way to a trolley stop location and hop-on for a little history lesson and break from walking until you’re ready to hop-off at your next location.




6) Grab a bite to eat.
After a full morning of walking and exploring this fun city we were all pretty starving. Brunch at Ice Plant fit the bill! With their fresh, delicious, farm to table menu, and casual, friendly atmosphere, it was exactly what we were hoping for.


I highly reccomend the Brown Butter Dutch Baby or the Broken Yolk Sandwich! Both delicious choices. Ice Plant specializes in hand crafted cocktails using fresh squeezed juices, house made syrups, and artisinal spirits. My Bloody Mary was made with vodka from the distillery downstairs!
Another fun fact, they carve their variety of ice daily from large blocks of slow frozen filtered water. The result being clear, hard ice, free from imperfections.
I adore places that pay such close attention to every detail of their craft. It definitely comes through in the end result.



7) Take the #1 whiskey tour in North America.
When everyone is refueled from brunch, stick around and head downstairs to the distillery for the #1 whiskey tour in North America. Chat with knowledgable staff and sample some of their fantastic offerings like their award winning gin, vodka, and bourbon.
Set in a restored 1907 ice plant, St Augustine Distillery is a working distillery with historic roots, who share a strong commitment to sustainability, community, and passion to their craft.
Such a fun experience!



8) Explore some more!
Ice Plant and St. Augustine Distillery, conveniently located in a shared wharehouse, are even more conveniently a pick up location for the trolley. So, when you’re fully saturated and sastisfied hop back on the trolley (or continue on foot if you’re keen) to continue the history lesson and highlights you made to your map earlier in the day.
Among the many things to do and see here in St. Augustine, Castillo de San Marcos is an absolute must during your visit! This incredible fort, built by the Spanish to defend the Atlantic trade route has a rich history spanning more than 450 years!
Just remember to bring your National Parks Pass or Verterans ID for free admission. Otherwise, there is an entrance fee.


9) Treat yourself!
Because our kids are basically hobbits who seem to constantly be eating and because they have been fantastic explorers for us today, (plus this is a treat filled holiday, and they specifically called out icecream on their map!) we absolutely had to make a stop at Whetstone Chocolates for some icecream before wrapping up our Halloween adventures downtown.
San Sebastian Winery is just around the corner from Whetstone if you’ve got it in you to keep going and want to check them out too. Otherwise, you can snag the trolley near by and head back toward the center of town to catch the Beach Bus Shuttle before it’s last call return route.



What a fun day! We created wonderful memories,
scratched the surface of history in this amazing city
and went to bed excited to explore even more tomorrow!
10) Continue the party at home.
By this time my crew was ready to head home for some down time before the little party my kids put together for us earlier in the morning. We turned on some spooky tunes, examined our trick-or-treat loot, and decorated a cookie graveyard before calling it a night.




Wow, what a fun day, full day! We kept it super simple, but still created wonderful memories, scratched the surface of history in this amazing city and went to bed excited to explore even more tomorrow!
I hope your Halloween adventure in this historic city is just as fun as you explore all that St. Augustine has to offer!
Cheers!

