St Augustine is Florida’s oldest continuously inhabited settlement. In fact, it is St Augustine is the USA’s oldest continuously inhabited settlement! This beautiful town has been here in some form or other since way back in 1565. Naturally, this gives it tons of history, bags of personality and a unique charm. If you are planning a trip to this area, here are 20 fun things to do in St Augustine.

Oh, and just in case you don’t know…because I didn’t…the town is pronounced St OR-gus-teen rather than St or-GUST-in.

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1 – Step Back in Time at Lightner Museum

The Lightner Museum is housed in the former Alcazar Hotel, The Spanish Renaissance revival building was built in 1887 by Henry Flagler (the railway tycoon that put St Augustine on the map in a big way) and was one of the two main hotels in the town. The museum shut in the 1930s and was bought by Lightner who opened it as a hobbies museum, leaving his collections to the city along with the building. It is one of those eclectic private collections full of beautiful and interesting things.

Some highlights include:

• A room stuffed with glittering crystal tableware. It calls to mind many fabulous dinner dances with the gentle clink of glass and a live band playing.
• The giant pool at the back of the building that was once the largest public pool in the USA. This notoriously leaky swimming pool has to be drained and now plays host to brunch every weekend.
• The original hotel steam room. This was known as the Senate due to its neat marble seats. The hammam is accompanied by a room for of alarmingly Victorian water therapy contraptions. The thought of those freezing jets still gives you shivers.

2 – Cute, Creative Cocktails at Tipsy Duck Parlour

The Tipsy Duck Parlor is attached to a bathroom shop which can be a little confusing but once you enter the room, you will be in no doubt you’re in the right spot. One wall is stocked with rubber docks and the duck leg bar stools really add to the mallard mood. Behind the bar, you’ll see shelves of flavoured syrups. Customers can create their own cocktails (or mocktails) by blending up to three of these with soda or hard seltzer. Options range from the fruity (passionfruit or strawberry) to the unusual (butter rum, lavender and habanero). You can also pick from their range of curated cocktails, all of which are based on wine. The Tipsy Duck comes served in a bathtub which is fun but it is not the best tasting of the bunch. The Fizzy Duck and Duck Bubbles both come on dry ice, bubbling merrily and taste great.

3 – Get Your Sea Legs at St Augustine Pirate & Treasure Museum

The Pirate Museum is brilliantly done. It has a great blend of interactive exhibits, loads of information and some genuine pirate paraphernalia. Honestly, you could be tempted to think this will be gimmicky, or just for kids, but this museum pulls no punches. You will hear the grizzly details of pirates’ lives, their plundering and sticky ends. There is loads of information about the areas of the world these pirates operated in and the treasure hunters that are still uncovering their booty. There is actual pirate treasure and even a real Jolly Rodger (skull and crossbones flag) which is one of only two that survive in the world. The last room is dedicated to pirates of stage and screen. Be prepared to covet your own piece of cursed Aztec gold…or at least a prop from the Pirates of the Caribbean film.

The Pirate Museum stays open a little later than many of the other attractions in town so it is good to hit up once everything else starts to close.

4 – Try to Escape from the Old Jail Museum

The Old Jail is unexpectedly pretty. Passing by, you might never know it was a jail but head inside and you will see it in a whole new light. This jail was built in 1891 by request of Henry Flagler who didn’t want the jail right in the centre of town. It served as the town’s jail and prison for 62 years, only closing in the 1950s.

The Old Jail experience is guided by an enthusiastic tour guide who is a font of knowledge and will keep you totally engaged. The tour is mostly light-hearted but there are some poignant moments that are dealt with sensitively. Visitors discover jail life, where prisoners ate, slept and died as well as the lives of the sheriff and his family.

Just next door, you’ll also find the St Augustine Museum which is a cool little museum which gives you a great overview of the city’s history. You can also visit The Oldest Store Museum Experience which takes visitors back in time to 1908, complete with old products, machines and antiques from the time.

5 – Enjoy Some Southern Seafood at Catch 27

The best spot for seafood in town is Catch 27. The menu is crammed with fresh fish and southern flavours, all served with flair and class. The cocktail list has very grown up flavours, no sugar bombs here. The Wanderlust conjures up the joys of a tropical Thai island and the Swedish punch spiked Suite 302 keeps your tastebuds intrigued to the last sip.

The vibe at Catch 27 is somewhere between fine dining and a lovely meal in a friend’s garden with service that comes at a slower rate than the usual in the USA. Nobody is rushed outso you can take your time to enjoy the food. Sit outside if you can for a jovial atmosphere. The dishes are quite large so if you want to make it to dessert (and the creme brulee is worth it) then pace yourself. The Catch 27 take on shrimp and grits has plenty of fans so it may well be one to try.

6 – Drink From the Fountain of Youth

Juan Ponce de Leon was a Spanish explorer (conquistador) who travelled across the Atlantic with Christopher Colombus’ second expedition. He spent years searching (successfully) for gold and (unsuccessfully) for the mythical fountain of youth. Eventually, he head north through the Bahamas, landing in a new place that he called La Florida (the land of flowers). This was just down the coast from St Augustine. From there, he began continued his search for the precious metals and precious waters. Rumour was, the spring he found in St Augustine was thought to be that Fountain of Youth. But sadly, its not true and was probably just a good place to fill his cantina.

The water that flows from the ground at the Ponce de Leon Fountain of Youth Archaeological may not have magical properties but it is always worth a sip just in case. (Yes, it does have that slightly swampy Florida taste). There is so much more to this park than just the well though. There are historical demonstrations of blacksmithing, canon firing and you can climb the watchtower for a nice view over to the ocean. You will also find reproductions of the native Timucuan village the Spanish would have discovered here, and the first church they erected. Finally, there are the famous residents of the park. Big, beautiful peacocks strut the paths, calling out to the peahens and showing off their stunning plumage.

7 – Grab Some Grub at Grilled Cheese Gallery

The humble grilled cheese (or cheese toasty if you’re British) is a thing of beauty.; comfort food at its best. At Grilled Cheese Gallery, they believe this ooey, gooey treat should be celebrated and elevated. They have created some seriously delicious combos which are surprisingly filling. The Duchess has lobster and four kinds of cheese. The Asian Cowboy features short rib and kimchee. The Country Boy is a combo of pulled pork, mac and cheese which is a marvellously, messy mashup. Every sandwich comes with a little side of tomato soup to dip into. Oh, and they have a selection of gravy-laden poutines too! It is enough to send you into a happy lunch coma. But there are plenty more fun things to do in St Augustine so push through!

8 – Savour a Sip at San Sebastian Winery

We love a winery that isn’t stuffy or bound up in pretension. San Sebastian Winery is just the kind of spot which lets you enjoy your love of wine without feeling like you haven’t studied enough beforehand. Plus, their selection of wines is local and rather lovely. You will especially enjoy it if you have a sweet tooth. Your experience is described as a self-guided tasting. Guests pass through three rooms with tasting areas. The staff will pour a little of each wine in turn into your little plastic glass and leave you to savour it without any scary “So tell me what you can taste” moments. There are about nine tastes to try ranging from crisp whites to sun sweetened port. It all adds up to a couple of glasses so make sure your designated driver (if you have one) only has a couple of the sips they will like most.

If you want to continue the experience, there is a paid tasting area and the sommelier will curate a tasting for you. We opted for the sweet wines as we have very much enjoyed the semi-sweet offering offered already and it did not disappoint.

9 – Lick a Hyppo Ice Lolly

Ice lollies (popsicles) are taken up a notch at Hyppo. This gourmet iced confectionary spot combines fresh fruit, real booze and delicious creamy ingredients to create the most delectable desserts. There is a huge selection which will make choosing rather difficult. Are you a blackberry ginger fan, a tangerine cream gal or a peanut butter pie guy? Well, you are all covered. For grown ups, there is is the over 21’s selection which are like frozen cocktails (yes, the prosecco pear is genuinely bubbly wine). But for something really grown up, the espresso will put some pep in your step.

10 – Hop On (and Hop Off) the Tram

If you are short on time, enjoy a leisurely mode of transport or aren’t able to walk for long periods, the hop on, hop off Old Town Trolley Tours tram service is ideal. It is especially good if you are planning to park your car up at the Old Jail (where parking is much easier) and then hit some of the attractions in the town. As you travel around St Augustine to most of our fun things to do list you will have a live commentary from the driver with lots of interesting town history. Sit near a speaker if you are particularly keen to hear this. As you board, you’ll be given a map and you can plan your day according to the tram’s route or just pick it up as and when you need a rest.

11 – Ease Your Cocoa Cravings at Whetstone Chocolate

The story of Whetstone is an intriguing one. This family run company has done it all from tiny artisan producer to giant warehous4es and back again. The tour begins with a little tasting so the group can relax and enjoy the story of the company. It eases the desperation you feel on the way into a chocolate shop when you know there might be samples. There is a short explanation about how chocolate is made, and then the group is escorted through the factory with exciting machines but sadly, no obvious Oompa Loompas.

In all there are 6 – 9 nibbles which is pretty good. To the European palate this chocolate is going to taste a little unusual as American chocolate has an acidic quality that is added in. If you are going to pick anything up from the shop at the end of the tour (and we recommend that you do) opt for for something with a fun flavour. There are so many options and it is a great excuse to try something new.

If you’ve got more time in Florida, check out The Perfect Day in Crystal River

12 – Walk the Bridge of Lions

In the 1920s, a bridge was built between St Augustine and Anastasia Island. Cars become popular and they needed a way to get their vehicles to the lovely new homes on the island. This blocked the shipping lane and so the bridge was designed with a centre that could be opened up. The drawbridge still goes up almost every half an hour from 07:00 – 18:00 so there is good chance you’ll catch it up at some point. Just don’t book a cab to cross to the island around these times or you’ll have some waiting fees! At the start of the bridge you will find two lions, copies of the Roman Medici lions. These have been the subject of many, many a selfie.

13 – Get Spooky on a Ghost Tour

St Augustine has almost 500 years of history so it’s to be expected there there a few spirits haunting it. The coolest way to learn about these ghouls is with one of the many ghost tours. The original Ghost Tours of St Augustine runs a tour every night. The guide is fun, engaging and has plenty of personal haunting stories alongside the more well known local legends. From Henry Flagler’s third wife to the jilted bride in the graveyard, each story is intriguing and a little scary if you think about them too hard. Whether you believe it or not, it is always cool to hear a well-told tale in the location it is based and to have your spooky senses tickled a little.

14 – Dinner and Drinks at Prohibition Kitchen

Located right at the centre of St George Street, St Augustine’s short pedestrianised road, Prohibition Kitchen is the coolest place in town for dinner, or drinks…or both. Their boozy milkshakes are legendary and their drinks selection features a huge number of rums, bourbons and tequilas. There’s even a “Create Your Own Old Fashioned” section of the menu if you really know what you like. Instead you’ll find some grown up drinks and a great selection of food options. Particularly recommended is their devilled eggs dish. These change regularly so ask what the special is when you visit. Plus, if you time your visit right, there is likely to be live music too.

15 – Pop Into Flagler College

There aren’t too many places in the world that you can freely wander into a university but luckily, the lobby of Flagler College is open to the public.

Henry Flagler, the railway magnate, built this fine Spanish Renaissance Revival building in 1888 as an invite-only hotel called the Ponce de Leon (what else?). IUt was a masterpiece of architecture being one of the first poured concrete buildings of its kind. It paved the way for famous buildings created by the same architects, John Carrére and Thomas Hastings, like the New York Public Library. Edison lit the building with 4000 lightbulbs and the whole thing was steam heated. It was all rather modern. The hotel remained open for 79 years, briefly taken over by the coast guard during WWII but then finishing life as a hotel in 1967. The next year, it became the centrepiece of the newly established liberal arts university, Flagler College.

As you pass the fountain, take a look up the grand solarium. This glass dome was the favourite spot of one of Flagler’s wives who used its giant circle as the perfect spot for her Ouija board sessions. Then, as you enter the lobby, keep your head skywards to admire the magnificent ceiling, bedecked in beautiful murals.

16 – Treat Yourself to Tastings at St Augustine Distillery

St Augustine Distillery has been brewing spirits (liquor) in an old ice plant since 2013. It’s fitting that they chose somewhere that produced commercial ice, as they now produce some whiskey to pour over it.

Visitors come and try, not only the delicious liquor but also the perfect cocktail mixes they have created to do with each one. There are five or six tastings featuring rum, vodka and bourbon. The coolest thig is that after your last tipple, you can request to taste anything on the shop shelves. We rarely buy anything as souvenirs but we did take home a bottle of the passionfruit laden Tiki mix (just add rum and bubbly water). However, the Florida Mule is most people’s favourite and it was a close run thing for us!

17 – Experience a Touch of Exotic at the Villa Zorayda Museum

Local rich guy Franklin Smith built himself the most fabulous mansion. During construction a brand new method of mixing concrete and the local coquina stone was developed, making the large scale house possible in the humid Florida climate. Henry Flagler loved the place so much that he asked to buy it for his wife, but Frankin refused and taught Flagler how to use his techniques. (The Ponce de Leon and Alcazar Hotels were made with this method).

These days, Villa Zorayda is a slice of the exotic which is hinted at by the beautiful Moorish revival exterior. Grab an audioguide on your way in to bring the unusual collection and designs to life. The interior of the house is designed as a Moroccan Riad. Inside is a wild collection of genuine antiquities, commissioned pieces and cool gilded-age innovations. Marvel at the stunning stucco walls and intricate tiling. You may well forget you are in Florida entirely!

18 – Take in the View From St Augustine Lighthouse and Maritime Museum

The St Augustine Lighthouse is located on Anastasia Island and the current tower has been warning ships since 1874. There’s some wonderful views you really earn by climbing the 219 steps to the top of the 50m (165ft) tower. Luckily, there are plenty of landings to stop and catch your breath. Not only that, but each landing has some fun and interesting information boards that are worth stopping to read. For example, you will hear the story of the 15 women of the Junior Service League of St. Augustine that fought to retain and restore the lighthouse.

Surrounding the lighthouse are several museum buildings that discuss general maritime history, the troubles of navigating the local waters and marine archaeology. There are some cool first person accounts of nearby shipwrecks. Plus, you get to see how the lighthouse keeper and his family used to live. It’s all so interesting and you can spend a couple of hours here with a quick drink in the cafe.

19 – Try Some Practically Perfect Pizza

Another St George’s Street hot spot is Pizza Time. This has been ranked as the USA’s second-best pizza by Tripadvisor. In this place the pizza is already prepared, just pick a slice (or three) and they will warm it up. The slices are big, you will need two hands) but priced accordingly (it is not NY £0.99 territory). The ingredients are premium (a whole burrata on your slice for example) and the sauce is clearly handmade and done with love. Now, second best pizza in the USA is a big claim. You would have to eat a lot of pizza to compare it, but I’ll let you be the judge.

20 – Get Your Golden Girls on at The Local

There are plenty of guesthouses in St Augustine. Many have long histories, which is coo…BUT…our votes for the coolest accommodation in St Augustine has to be The Local! If you love 1980s Miami, pastel coral, poops of pink and palm leaf motifs galore, you will adore it here.

This motel has embraced its retro vibes and run with them creating an extremely instaworthy spot with modern touches. The Local is contactless which means guests use their phones to enter their rooms and gain access to the pool and tea and coffee station. It is perfect for Millennials! Of course, free car parking is included but guests can also rent bikes to get around as there is a dedicated station just outside the front door. The Local is located on Anastasia Island, not in the Historic District. So you will have to factor in the 30 minute walk to the main attractions, or the cost of taxis ($9-$11).

Final Thoughts

St Augustine is a fantastic place to take a weekend break. There is something about historical spots in the USA. Sometimes they can have an abundance of twee, or a disturbing presence of familiar chains. However, St Augustine is a thriving town with an abundance of historical, fascinating sights and a flourishing independent business scene. Whether you have one day, or four, you will fill it and have an amazing time.

If you are wondering what a successful day in St Augustine looks like, here it is:

Rosie xx