Family Travel

5 min read

Epic Weekend in St Augustine: Family Guide!

Plan your epic weekend in St. Augustine with our family guide! Enjoy history, beaches, and pirate adventures in Florida's walkable city. Ideal for travelers seeking a mix of fun and culture.

Tobi Miles
July 1, 2022
Epic Weekend in St Augustine: Family Guide!

St Augustine in Florida is a quaint, magical city which is perfect for a weekend getaway! It's small enough to walk around yet large enough to enjoy great deal of things to do, from family entertainment to nature, history & culture!

As you are aware Florida contains alot of Mammoth cities such as Orlando, Miami and Tampa.

These are great cities in their own right, but don't have the charm and walkability of St Augustine.  St Augustine was actually voted "Floridas most walkable city"by Town & Tourist Readers.

So in this Family Friendly long weekend itinerary, I have included a 3 day Itinerary of my favourite things to see and tours to go on in St Augustine.

You could easily extend this to 4 days or even a 1 week Itinerary, as I have included options so you can choose what suits you best! This is the Ideal Family Weekend Itinerary in St Augustine, but you can also adapt it for couples, girls getaways  or even solo travellers!

Best Time to Visit St. Augustine

The best time to visit St. Augustine is between March and May. At this time of year you will find less people, comfy temperatures, in addition to affordable hotel and airfare rates.

Visiting in St. Augustine's spring means you'll escape Floridas notorious humidity, but still not encounter the colder temperatures.

The average at this time of year is in the (50s-60s)(10'C- 15'C), so you will need a jacket but you won't attract as much rain as during the summer.

Insider Tip:

Bring an Umbrella just to be on the safe side.

Spring Events in St Augustine:

At this time of year you will find a series of great culinary events to dive right into, ideal for foodies!

Summer in St Augustine:

During the summer time, St Augustine attracts large crowds & prices skyrocket! Average summer temperatures are between the 70's and 90's (21'C-32'C).

There is also more rain this time of year & humidity so bring lots of water, sunscreen and an umbrella.

Insider Tip:

Due to it being the end of the school season, lots of families flock to St book you hotels & flights well in advance.


Summer Events in St Augustine:

  • Music by the Sea

Music Bay the sea festival runs from mid may to mid September annually. It features, music, great foods and live entertainment from local Bands.

  • Summer Craft Fair
  • Lion Bridge 5k

Autumn in St Augustine:

During the Autumn months of September-November, temperatures range between high 50s and high 80s (10'C-27'C).  You will find little rain but these months do fall within Hurricane Season!

Insider Tip:

To avoid losing money via Hurricane related vacation changes or cancelations, book a trip which offers refundable accommodation/airfare.

Autumn Events in St Augustine:

There are a few great festivals & events during the Autumn season:

Winter in St Augustine - Budget!

Winter in St Augustine offers less people and very low prices. Your unlikely to see snow as temperatures are between (40s-70s) (4'C-21'c). Rainfall is lowest this time of year, so you can leave the umbrella at home.

Winter Events in St Augustine:

  • Nights of Lights (November-January)
  • Colonial Night Watch (December

Traveling to St Augustine:

St. Augustine is located in northeast Florida, on the Atlantic coast, between Jacksonville and Daytona. Easy access can be achieved via Orlando or Jacksonville airports.

St Augustine - Closest Airports Table:

(Table Copyright, if you wish to embed in your website simply copy and credit it us with a link)

As you can see from the Table above, Jacksonville is the closest airport so I would recommend renting a car from there. This will allow you to cruise to St Augustine in less than one hour.

An alternative is the St. Augustine airport shuttle ,  which costs $60 & $5 for each extra person. The shuttle runs between 7Am-7pm each day. They also run a "Door to Door Service" for  $75 and $5 for each extra person.

St Augustine Long Weekend Itinerary:

Day 1: Colonial Quarter & Pirates!

After arriving in St Augustine, you will want to take a journey back in time to the Colonial Roots. Head down to the Colonial Quarter and wander through the meandering cobblestoned streets, you will understand why St. Augustine is the oldest city in the United States!

St. George Street

St. George Street is the main walkway through St Augustine. Walking along here you will get a real feel for the city and it's checkered past of European Colonialists and Pirates!

Insider Tip:

If you have a family, why not get your kids an eye patch from one of the quaint shops along this street...this will really help excite the imagination of your entire family. This is also a popular area for souvenirs on the way back.

Colonial Quarter St Augustine. The multiple flags represent the vast number of European Colonials which occupied St Augustine.

History of St Augustine:

The Europeans established a settlement and port here in 1565,  55 years before the Pilgrams landed at Plymouth Rock and 42 years before the English setup their colony in Jamestown, Virginia and 43 years before the Spanish Settled in Santa Fe, New Mexico.

Due to it's prime location on the Atlantic coast and gateway to Mexico, St Augustine was a popular shipping lane & trading port. With the Spanish explorers bringing gold & silver from Mexico via the gulf stream on the St Augustine coast.

The Trade route was very dangerous due to many Pirates and the French Explorers who has a base at Fort Caroline just 40 miles north of St Augustine.

Over the next 300 years, many European powers fought for control of this vital trade root and land. Today this has given St Augustine a variety of Colonial cultural influences, perfect to explore!

The oldest House in St Augustine (González–Alvarez):

Be sure to check out the oldest surviving house in St Augustine, the González–Alvarez House, dating back to 1723. The oldest store is also a popular attraction.

Oldest House in St Augustine, González–Alvarez dates back to 1723.

Castillo de San Marcos Fort

Castillo De San Marcos Fort is the perfect landmark to relive the famous Colonial Battles. of St Augustine.

As the Spanish Colonies brought Gold, Silver and other riches to St Augustine. The Pirates came to attack & Pillage!

The fort has survived hundreds of years of cannon ball attacks and it can be seen by observing the rocky stone walls. Grab your entry ticket and take a walk along the famous drawbridge into the fort.

Castillo De San Marcos Fort St Augustine Florida.

(St Augustine Weekend Getaway family guide)


Pirate Battle Reenactment:

Watch the uniformed Spanish fire a Canon out of the Fort, as the Pirate Boats head towards the bay. This is an exciting and fun demonstration of how an attack on St Augustine would have looked!

Insider Tip:

Keep an eye out for the girl with mermaid tail under the fort. Shes not part of the official reenactment but still fun to see and maybe grab a photo with!

The Moat:

You can still see the outline of the dried up moat from the fort. It was kept dry and filled with animals if attacked by sea and flooded if attacked by land.


Head to the storerooms beneath the fort to check the historical displays. For example, their is some graffiti on the walls which was written by soldiers, prisoners and local people which is from over 300 years ago!

Insider Tip:

The Park Rangers here are very friendly & knowledgeable, so feel free to ask them any questions or watch one of their demos. 300 years of graffiti etched into the coquina walls by soldiers, inmates, and townspeople.

St. Augustine Pirate & Treasure Museum

Head to the St. Augustine Pirate & Treasure Museum to get a infamous perspective on the battles, from pirates of course...arghhh!

Pirate Museum Highlights:

  • Blackbeards Firearms
  • Blackbeards Gold
  • Sir Francis Drake Story/Relics
  • Original Treasure Chests
  • Authentic Jolly Roger Pirates Flag!
  • Journals outlining many pirate stories from the ages!

St Augustine Pirate/Treasure Museum. Source: St Augusstine Museum.

(St Augustine Weekend Getaway family guide)


As St Augustine was burned & ransacked by Pirates two major times in it's early life:

Sir Francis Drake - Secret Pirate?

Sir Francis drake was a great explorer, admiral and to the Spanish, a Pirate! His Exploits caused him to be knighted by the Queen. However, he was known for his raids against many Spanish ships and of course he burnt down Spanish St Augustine in 1586.

Fun Fact:

The Spanish nicknamed Sir Francis Drake, El Draque' or the Dragon. Some Spanish were so afraid of him, they rumoured he practiced witchcraft!

Picture of the notorious Sir Francis Drake, the Knighted "Pirate".

(St Augustine Weekend Getaway family guide)

1668 Pirate Attack!

In 1668 St Augustine was attacked again by Robert Searles (John Davis) as a response to an attack to an English Colony in the Bahamas. Thus the Spanish Queen ordered the fort to be built, Castillo de San Marcos, in 1672.

Fun Fact:

The owner, originally created his Pirate Museum in Key West before moving it to St Augustine in 2005.

Day 2: Beaches & Adventure

After battling with Pirate & Spanish Soldiers on Day 1, it's time for some exploration and adventure on St Augustines Coast.

St Augustine Beach Things to Do Weekend Getaway.

(St Augustine Weekend Getaway family guide)

Anastasia Island:

Head to Anastasia Island, for some gorgeous beaches and coastal attractions. Highlights Include:

Farmers Market:

Head down to the Farmers Market on Saturday Morning. It's just 20 mins walk from the lighthouse, at St. Augustine Amphitheatre. Every Saturday you can check out the fresh foods, live music and hand made items.

Insider Tip:

This is a great place to have breakfast before heading to the St Augustine Lighthouse.

St Augustines Lighthouse:

Our family headed to St Augustines Lighthouse first, you can climb to the top and get a breath taking view of Matanzas Bay.

The lighthouse Museum, give you real insight into the history of the lighthouse and the lighthouse keepers daily life!  In additional there is boat building displays,

maritime shipwrecks

and even world war 2 relics.

st-augustine Lighthouse florida Weekend Getaway Families

Feeling Hungry?

After taking a beach stroll & scaling the lighthouse grab a bite to eat at one of the following place:

st-augustine Lighthouse florida Weekend Getaway Families.

(St Augustine Weekend Getaway family guide)


Anastasia State Park:

After the lighthouse & lunch head towards Anastasia State Park  , for 1600 acres of beach walks & adventure! At Anastasia State Park you will find long stretches of beaches with walkways over sand dunes & tidal marshes.


  • Camping  (139 campsites close to beach)
  • Hiking - Ancient Dunes Nature Trail.
  • Coastal Wildlife/Bird Watching
  • Biking
  • Fishing
  • Shelling
  • Surfing
  • Swimming
  • Kayaking
  • Star gazing

Insider Tip:

If you have an extra day, dedicate one purely to Anastasia State Park. with so much to do you could camp here for a few days if you wish or just drive in.

Kayaking along the GTM Reserve:

Take a Kayak along the GTM nature reserve which stands for (Guana Tolomato Matanzas National Estuarine).  Take a guided tour through the protected marine areas to have chance of spotting dolphins, sea turtles, migrating birds and even bald Eagles.

How much does Anastasia State Park cost?

Anastasia State Park costs $8 per vehicle for entry and is open from 8AM, 365 days per year. Contact tel: 904-461-2033

How much does Camping cost at Anastasia State Park?

Camping costs $28 per night, plus a $6.70 reservation fee & taxes. This Includes water and electricity.

Best Tour: Airboat Safari on St augustine Coast:

Day 3: Tours

On your last day in St Augustine I suggest trying out one of the unique tours around this great city.

St. Augustine Distillery

The St. Augustine Distillery, is where you can learn about Floridas Spirit making history & Distilling processes.

This is a small scale facility constructed from a renovated 1917 Ice plant. Here you can watch the spirits being handmade and of course try out some samples!

St Augustine Distillery Florida (Weekend Getaway.)

(St Augustine Weekend Getaway family guide)


Are Kids allowed at the St Augustine Distillery?

Surprisingly, Yes! Although the experience is not really aimed at kids they are completely welcome and may even find it quite interesting. But of course, they can't taste the spirits until they are 21 years old!

Wolfs Museum of Mystery

An eerie & unique Museum based on the film "Wolf's Museum of Mystery" a paranormal movie about 2 people which run a museum in St Augustine, with a ghost named Mary and many quirky patrons.

It is actually the personal home of the writer of the movie Wolfgang Von Mertz. Here you can discover lots of unique & rare items from all over the world and lots of Horror movie props of course!

Ghost Tour of St Augustine:

This is a great tour for couples & families alike! A story telling guide accompanies you around the city at night and tells you ghoulish, ghostly tails about various landmarks from the old Jail to the Old drug Store.

Many tour companies offer similar tours throughout the city, this ghost tour is the one our family has a great experience with!

Pirate Ship Black Raven - Best Tour for Families!

My Family had such a fantastic time on the Pirate Ship Black Raven Boat Tour! It's a truly immersive Pirate experience on a real life Pirate Ship! The Kids get to dress up as Pirates an hop on board the cruise.

On Board, costumed Pirates duel it on with a live pirate show! As the performance isn't scripted it's great fun watching the "Pirates" improvise with crowd.

Pirate Tour St Augustine.

(St Augustine Weekend Getaway family guide)

My Favourite part was when another Pirate Ship (Queen Annes Revenge) pulled up alongside and pirates from each ship started to duel!

I think I enjoyed it more then the kids! There is also a live treasure hunt and the price is very reasonable considering all the extras, swords for kids, face painting and full on water pirate show.

Places can sell out pretty fast, so book well in advance. For more details & to book head to Viator.

(The provider Viator also offers free cancellation up to 24 hours in advance so there is no reason not to book.)

Pirate Tour St Augustine.

(St Augustine Weekend Getaway family guide)

Where to Stay in St Augustine?

For a Great Selection of Accommodation in St Augustine, my family always uses, they offer great variety of accommodation and options to book now pay later.

Follow this link, for a special search on the best accommodation in St Augustine.

Need help Planning!?

  • Do you find planning a trip time consuming & even stressful?
  • Would you like a tailored Bucket List vacation?
  • Would you like an experience designed to keep EVERYONE Happy?

If you answered YES, to these questions then you should contact a Travel expert to take care of everything for you!

Taking an organised tour or tailored vacation is great, as they will organize your flights, hotels, car rental, activities &  Insurance!

To find out more check out: Which are the Best travel Tours?

Orlando Tours[/caption]

Want more St Augustine Activities?

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Tobi Miles
Article updated:
March 28, 2024
A nomadic wordsmith savoring the world's flavors and penning stories that turn every journey into an epic.
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