Updated: May 21
How to Have the Best Time in this Historic Eccentric City
In Saint Augustine the first of everything meets the trendiest of new ideas in a beautiful way. Here's everything you need to know to make your visit fit your needs 💖
Saint Augustine is uniquely located in the Upper East Side of Florida. Known for it's history, time has preserved much of this city for us to enjoy and learn from. Man has restored quite a bit. It may be old, but it never gets old!
This location makes it easy to travel to from many other places. Close to I -95 and I-10, road trip access is a straight shot. Being a 45-minute drive from Jacksonville makes it close to the hub, and airport. An hour North of Daytona, the International Airport and Speedway are just a drive away. Access to this area is easy, making it a favorable experience!
The Oldest City in America - discovered before Plymouth Rock, Spanish colonists sat down for a meal of shellfish, alligator, tortoise and wild turkey with members of Florida’s Timucua tribe 50 years before Columbus. Cobblestone streets, historical landmarks and pristine beaches set the stage for tons of art, a funky upbeat vibe, and tons of things to see and do. And we love to visit!
Founded in 1565 by Spanish explorers, it is the oldest continuously-inhabited European-established settlement in the United States. Here you’ll find “the oldest” everything, wooden schoolhouse, house, jail, port, and first Catholic Mission, you may also visit the State’s oldest attraction aka the Fountain of Youth.
What’s fun about this very walkable old town area is that its extremely interactive. Tours, trolley's, free tastings, samples, pirates, colonialism, are oozing from the city gates. It’s a city that caters to the tourist, but you won’t feel like a tourist, you feel like you are a part of the party. During the day there is a constant movement of explorers, all on a mission to discover something new. At night everyone is eating, drinking, and enjoying this place, and if you are fortunate enough to catch this during the holiday season, their Night of Light’s event will spark Christmas Spirit in the weariest corners of your mind.
Yes! The Night of Lights is one of the biggest in the country, with over 3 million lights lit for the festivities, more info below...
We have visited St. Augustine MANY times during the years. From the 5th Grade annual field trip to the oldest city to explore the Fort, aka Castillo De San Marcos, and the Flagler College, to road trips up for Christmas pictures, and even a professional conference, I will share my personal favorites and our family go to’s.
First question: Is Saint Augustine Affordable?
As a single mother of 4, we would drive the 2.5-hour car ride rather than stay the night. Lodging is where the costs add up. There is so much to see and do for free, or almost free. I will start with those activities first. Really just walking in and out of the streets and seeing all the landmarks is great. We would come up just to explore. However, as the children get older and are willing to pitch in, I have found more bang for my buck so to speak by choosing one “splurge” activity each time we visit. Over time these add up to some great memories that provide awesome context. I will also share our favorite splurge items. However, I can’t emphasize enough how easy this city is to explore on foot. The great thing is to park (preferably at the Visitor’s Center where parking is free) and wander the whole place.
Let’s dive into a good plan!
First: What are your goals? Each trip has a different set of needs. Do you need peace? Quiet? Dancing? Adventure? History? Exploring? You can find it all here. But knowing myself, when I return home, I want to feel satisfied with my time away. So, I plan accordingly by self-check ins and some planning for how to best suit my needs.
Best Things to do:
Castillo De San Marco is the #1 attraction here. Visit the monumental fort made of coquina rock, which changed hands many times, but was never breeched! As a National Park you enter for $15.00/ per person 15 and older. Children under 15 are free with a paying adult, or get in free with your America The Beautiful Parks Pass. There are some free days through out the year (usually in line with the federal holidays so check the website below if that’s your preference. This is an awesome experience. Full of history and beautiful views.
Tickets are $32.59/ per person when purchased online, and provide 1 day of unlimited re-boarding 22 Old Town Trolley Stops. These trolley’s are a great alternative to walking. The farthest stops are the Oldest Jail, and the Oldest House, which are a couple of miles apart. If you stop at the Visitor’s Center you can get your tickets, park for free and then continuously hop on and off. This is great to me if you don’t want to walk, and get there early. Ride times are between 10:00 – 4:30 and trolley’s run every 15 minutes.
*I recommend walking if you are able, as the stroll itself is so rewarding, however if you can’t, or you want to hear the history, it is worth the experience! Get there early to make the most of this offer.
Between Thanksgiving and New Years Eve, and the wee start of the new year, something spectacular happens here. This city lights up millions of white Christmas lights, and if you can catch the opening night it is quite an event. Anyone searching for the Spirit of Christmas needs to experience the thoughtful design of Saint Augustine made new.
~ Hop on Hop off Trolley is free on select nights
~ The beautiful City Square becomes a winter wonderland with all of the old magnificent trees strung with lights and a huge Christmas Tree in the middle.
~ Christmas carolers and every kind of treat are lined up for your enjoyment.
~ Christmas Parade to help get your festivities right!
~ Weekend nights it snows from the roof tops on Spanish Street! Snow starts at 6:30 pm, give or take a few minutes.
The Plaza De La Constitucion - Aka "The Square"
This is the hub, where the courtyard in the middle provides space for events.
On the night you visit, event or no, it's a magnificent stroll under the trees in the midst of old relics and art. Enjoy the space and wander around. Cathedrals and galleries all around for your pleasure, not to mention good things to eat! There's sure to be street musicians and music coming from some of the parties, the Governor's House hosts some impressive parties as well.
Walk down St. George Street by the old city gates and check out their little shops and décor. Sample, explore, take your time… this is purely leisurely enjoyment. This will lead you right the City Square, you can even have a picnic there if you’re not eating at any of the local options. There are several boutiques and galleries to see. Walk by the Bay and see why they call this the “Bay of Dolphins”. Explore the historical hotels, college, basilica, and churches. Even just wandering in and out of the places is fun. There are random cannon balls and other monuments everywhere, with plaques to read explaining the history. There is an amazing park: the SWING project. This is located 10 W. Castillo Dr., St. Augustine, FL, 32084. Currently it is undergoing repairs and scheduled to reopen in Spring of 2022.
Tree enthusiasts will appreciate the “Old Senator” as they’ve named the oldest tree - This is one of those things that adds culture and uniqueness to the tours through St. Augustine. Yes, it’s just a tree but it has also got a cool backstory. It’s unique as it has a palm tree growing through the center of it and it’s heart shaped. It’s also over 650 years old. Legend has it if you kiss someone under the tree, you’ll be with them forever. I have tried this, and I’ll let you know if it’s accurate 💓.
This is one of the stops on the on/off trolley tour and they’ll stop under the tree, it is near the Fountain of Youth in a Motel Parking lot. It’s a little farther to walk, but if you’re a walking person it’s in range.
Old Town, St. Augustine
Learn about life in colonial St Augustine. The real first colonial village in America. St Augustine's history, blacksmithing, how to fire a cannon to stop the British…. All the relevant topics to create the vision for your children. A glimpse into daily life for the first settlers.
The Oldest Wooden School House
I say this because if you come here with kids, or happen to be a teacher, this really puts perspective into how far we have come. Take the stroll through the past and see for yourself. You kids will appreciate it!
Sunday – Thursday 10AM – 5PM Friday – Saturday 10AM – 7PM
Closed Christmas Day
Tuition To Enter
Children 6-12 $4.95 Children 5 and under FREE
Out back there is a bell that they would ring when it was time to begin, and there is something about the history and time that ties you in to it's timeless existence when you ring it yourself!
Originally the fancy Gilded Age Alcazar hotel, it was built in 1888 by railroad tycoon Henry Flagler. The museum will transport you to extravagance with its stunning entrance, and one of the country’s best collections of 19th-century art.
Senior (65+)/ Military Price: $14.00
College Student: $14.00
Youth (12-17): $10.00 Child (11 and under): Free
The Bridge of Lions
A double-leaf bascule bridge (aka, a drawbridge) spans the Intracoastal Waterway in St. Augustine, which connects downtown St. Augustine to Anastasia Island across Matanzas Bay. A pair of marble lions guard the bridge. It’s a mile long walk across the drawbridge, and beautiful. No tolls / fees assessed to cross bridge by car or foot. Bridge provides amazing views of city, fort, bay, sunset, lights and crosses over intracoastal waterway. Worth the stroll, be aware of the homeless. Gorgeous on a nice night.
The truth is like a lion. You don't have to defend it. Let it loose; it will defend itself. - St. Augustine
Saint Augustine is a walkable City, charming with it's cobble stone pathways and store fronts to wander... Keep Walking....
And if you like to have some adult beverages along the way....
Free Distilleries – There is more than one place where you can have a free tour with tasting. Free samples are a highlight along this journey, although the lines may be a deterrent. We have found these places very worth the stop!
City Gate Spirits, which is located on A1A between Orange Street and Fort Alley is so centrally located and offers a quick tour with 10 mini shots of samples given to eligible participants (you must be of age). They have a booze valet (which we used) where you can make a purchase and pick it up another time (or day) to keep from carrying it around all night.
St. Augustine Distillery is a bit further out off that main square (but still close enough to walk or catch a trolley to) and offers a larger tour with lots of tasting options.
While we’ve done both and enjoyed both, I couldn’t do them both in the same day!
Free Winery Tours – San Sebastian Winery is also a plant you can tour, tasting along the way. I always enjoy the behind-the-scenes peek and of course, history.
Is there any good music?
Many places have a live band playing. Lot's of classic rock or funky jazz. Dos Gatos is a small bar with a DJ at night that has some good music if you'd like a little adult dancing. Good drinks and fun spot.
Honestly, we've heard some pretty good street music and danced right on Aviles Street by the Peace Pie. If you are in the mood for fun, fun is everywhere to be had.
Ok... so what if we want to eat here?
Places to eat:
All the rage is about Harry’s and Prohibition Kitchen (clink links above for website/ menus) for some awesome food and atmosphere. We strongly recommend both. Also, the Pizza Time pizzeria on St. George Street, which is diagonally across from Prohibition Kitchen and always has a long line, boasts being the 2nd best pizza in the US as determined by Trip Advisor. I am from NY. It’s definitely the best pizza outside of NY. There are snacks and sweets everywhere. Every time we visit, we try some gourmet ice cream and some yummies. They’ve all been delicious.
Things to See/ Do in The Surrounding Area –
These you can’t walk to like the rest of the activities, but if you have a car and sometime are close by.
Historic tower, keeper’s house, look out building and nature trail are all included and provide views of the whole area that you will appreciate. Walking up those steps is $14.95/ adults and $12.95 for kids. Kids under 44 inches -free. They also have Sunset Moonrise $35.00 tickets, which sell out weeks in advance, so order ahead. They have other nightly tours so definitely check their website and get the time you are hoping for.
When you think of rich ecosystem this place is the top tier. Four miles of pristine beach, the coquina quarry that was used to build the fort, marsh lands, trails, grills, Wi-Fi and you can rent paddle boards, bikes and other sporting items. Did I mention camp sites? This is worth the visit just for the trees (tree enthusiast here) and the native wildlife that enjoys paradise daily. Car entry is $8.00.
Take the short ferry over to the “other” fort! Narrated by a Park Ranger, you will gain a lot of insight to the rich history of this area. The small castle on the island stands three stories tall. The second story is an open plaza (albeit small) and within the walled portion of that level the sleeping quarters for the garrison and supply storage. the third level contains the officer’s quarters with a very narrow, steep stairway to the roof top for the 360-degree view.
Plan to arrive early. This tour is a popular attraction. Park spaces and ferry seats fill up fast!
Ferry Departure Times: 9:30, 10:30, 11:30, 1:30, 2:30, 3:30.
The free ferry to the fort carries 34 people on a first come, first served basis weather & staff permitting
State Park Car entry - $8.00.
Don't forget your camera!
This was walking along St. George Street one December. We went up for a few hours, walked around the Fort and checked out the Christmas lights. How cool to make these memories as a family and I love to see my kids all having a great time exploring!
One of my favorite parts of Saint Augustine is seeing my kids be so adventurous and curious. They ask a ton of questions along the way forcing me to dig deeper into the history. Just taking them to a place with so much information makes me feel like a good parent. They can see for themselves the way things used to be. History comes to life, and if you are fortunate enough to catch a reenactment, you will really see things in a new way. Environmentally, this city by the Bay is scenically appealing. Even the trees around are fun to climb. Magnolia Street is beautiful with all of it's hanging Spanish moss. Enjoy the atmosphere and all the details!
As a date, this is just a place away from the world where you can get caught up in some romance and share something magnificent. Saint Augustine does an amazing job creating the atmosphere.
But I do want to stay the night....
The farther you stay from Saint George Street, the less expensive and more availability there is.
The closer you stay, the easier it is to walk, but the cost is higher.... definitely decide what works for you.
We once stayed by the beach, and found some good rates. We Ubered over to the area, and between traffic and miles it was about $50.00.
We also stayed in a quaint Airbnb, and were close to everything. It was small but the room did have a fridge and microwave. In this duplex there were seven separate places, with comfy beds, and hot water! I'd stay again, and recommend. It was nice to be able to walk back and drop off a jacket or change shoes. Even in December, with expected temps in the 60's, it was cool on the bayside, but the buildings blocked the breeze and we were hot!
Many of my friends have camped in the area as well. The State Park has RV's sites as well as tent camping. This is a scenic adventure that is highly in demand, and spots are difficult to score. These are often booked several months in advance, however, those who have done it, share great memories. This is on my bucket list for sure.
Depending on your itinerary, check sites like booking.com and VRBO to determine what you need to make your stay magical. While I love a good day trip I know the expense of staying adds up!
But as you can see there is so much to see and do. If you are coming here from out of area, Saint Augustine could be a four- or five-day excursion to really see the area thoroughly. Every time we go we see and try things that are new, as well as hitting some favorite spots. When we travel, we go prepared for anything. Afternoon shower? I've got umbrellas close by. Someone can't wait over an hour to be seated? There are some snacks in my bag. Even now as the kids are older, I try to plan for everything so I am free to just have a good time while I am there and not be interrupted by anything. Travel time = ultimate quality time. Leave your phone (unless you're taking pictures of the moments) and really dive into the presence of the moment.
If you do walk around early in the morning, you'll notice far less crowds and businesses open later.
The Churches were all pretty full on a Sunday morning, and the shuttle was running.
Tips & Thoughts
* Come prepared for sun and rain, the weather predictions are not always accurate! ☂
* Wear shoes you like to walk in.👟🥿👠
* Parking is the tricky part, go early and find a good (free) spot! There are lot's of metered spaces, as well as $20.00 pull in lots as well.🚓
* Don't forget to be present. This is a one of a kind kind of place, enjoy it. ⏳
* You can spend as much or as little as you like your range of opportunities is vast!💲
* Great places to picnic and great places to dine. You decide.🍷
* Sunrises on the beach are really cool if you are awake :-)☀🌞
* Wait times to be seated can be lengthy! Be prepared. Get there earlier than you need to.
* The area around Historic Saint Augustine is like a regular town, They have a Walmart and almost any other store you could need.🏟
As always, wherever your travels take you, enjoy the road you are on! Be present, as quality time is a gift. Share the journey so others can benefit from your pros and cons! Feel free to share/ comment below your favorite places or ideas for the area as well and may all your travels be blessed.
Thank you for being a part of our ride,
Make the memories, take the pictures, and live your beautiful life with gratitude for the diversity we are immersed in ❤
What places does your family escape to for a quick get - a -way??
We LOVE Saint Augustine at Christmas time, but if you want a big city adventure, click here for a New York Christmas adventure!
For more Florida travels, click here and explore how to road trip around the Sunshine State!
Thank you and please share your thoughts and experiences, we are all on this journey to live and love together. I welcome your travel tips & tricks :-) Thank you for subscribing, let's stay connected!
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