Eleanor Naylor grinning at the beach in Saint Augustine, Florida wearing swim suit and hair in space buns

The BEST 4 Day Family Vacation in Saint Augustine, Florida

Explore the charming atmosphere of Saint Augustine with your family on a 4 day getaway. You’ll experience the unique historical atmosphere with exciting activities and enjoy plenty of time relaxing on the beaches.

Where to Stay in Saint Augustine

To experience the best relaxation, I recommend staying a little south of historic Saint Augustine. We stayed in Butler Beach, which is about 20 minutes from downtown, but you still have plenty of restaurants and shopping nearby.

Our Airbnb had its own pool, but was not directly on the beach. It sat about a block from the nearest beach access point, however, during our stay the two closest access points were closed for remodel. That’s when we learned we could drive our vehicle on the beach for $10/day. Most drive-on access points recommend vehicles with 4WD as the sand can be soft. The home had 5 bedrooms, 3.5 baths and can comfortably sleep up to 15. We had a total of 8 people (5 adults and 3 children). There is also an outdoor elevator. Overall, the home clean, comfortable, and perfect for our large group. Definitely take a look if you’re considering Saint Augustine for your family vacation.

Brittney Naylor and daughter in wicker swing on porch of their airbnb in Saint Augustine Florida

Things to Do in Saint Augustine

Let’s face it, when you take a beach vacation most of the time you’re probably going to spend your days enjoying the beach (or pool), but Saint Augustine has many more activities to enjoy!

St. Augustine’s Alligator Farm

On our first full day in Saint Augustine the temperature was a bit chilly, so we opted to skip the beach until it warmed up. If you know Eleanor, you know she LOVES alligators, so it only made sense that we went to the Alligator Farm. The St. Augustine Alligator Farm Zoological Park is one of Florida’s oldest continuously running attractions, having opened in 1893. It has 24 species of crocodilians, and also a variety of other reptiles, mammals and birds, as well as, exhibits, animal performances and educational demonstrations.

Three children sitting on fake alligator at the Alligator Farm in Saint Augustine, Florida

Castillo de San Marcos National Monument

Built by the Spanish in St. Augustine to defend Florida and the Atlantic trade route, Castillo de San Marcos National Monument preserves the oldest masonry fortification in the continental United States and interprets more than 450 years of cultural intersections. If you went to primary school in Florida, chances are you’ve visited this fort on a school field trip.

Old Town Trolley Saint Augustine

One of the most effective ways to explore historic St. Augustine is with the Old Town Trolley. There are 22 stops and you can hop on and off as many times as you would like in one day. While we did not have a chance to do the trolley tour during this trip, John and I have used the trolley many years ago. Parking can be tricky in downtown Saint Augustine, so using the trolley to get around is the perfect solution. You also receive admission to the old jail or can take a ghost your at night.

Enjoy the Beach

Clearly you can’t visit a beach town and not spend a few days at the beach. And that’s exactly what we did. We spent half of our trip at the beach, which also happened to be the two warmest days. As I mentioned earlier, we drove on the beach and parked. This made it easy to transport all of our beach items. Don’t forget to apply your sunscreen, create some shade with a canopy or umbrella, and keep hydrated.

Places to Eat at in Saint Augustine

There’s no shortage of great places to eat when it comes to the Saint Augustine area. You’ll likely discover many seafood options, great desserts, traditional, and more.

Sunset Grille

Of course, whenever we travel to a destination, I scroll TripAdvisor reviews for places to eat. Sunset Grille was on top of the list in Saint Augustine. Conveniently, it was only 3 miles from our Airbnb, too. Their menu offers an array of options, from burgers, to seafood to chicken. Certainly there’s something for everyone to enjoy. Nine times out of ten, I’m probably going to get the fried shrimp and IT DID NOT DISAPPOINT. John enjoyed his fish sandwich and the kids gobbled up their corndog nuggets and fried shrimp.

Mayday Ice Cream

How do you cool off from a hot day in the sun? Ice cream, of course and that’s exactly what we did on our first day at the beach. Not only does Mayday creates all of their ice creams in Florida, the staff were extremely kind. They offer a plethora of flavors and even provide sprinkles for FREE!

Holding ice cream waffle cone in front of blue painted cone on the wall at Mayday ice cream in Saint Augustine
Two girls eating ice cream at Mayday Ice Cream in Saint Augustine

Mango Mangos

Mango Mango’s is a small restaurant that offers amazing flavors of the Caribbean. You’ll find tacos, fish, burgers, and more on their menu. John and I ate here many years ago and really enjoyed it. The ambiance can be loud and it may be difficult to get seating for a large party, but you can always call ahead. Overall, I would still recommend Mango Mango’s as the quality of food and service were great.

Crabby’s Beachside

Crabby’s Beachside is new to Saint Augustine, but they have numerous locations across Florida.They have a large outdoor patio upstairs for dining, corn-hole out front, and it’s across from a main public beach access point. It’s no surprise I ordered fried shrimp again, but we also ordered to fried calamari for an appetizer. I’m such a sucker for some delicious calamari. John ordered the crab cake, along with hush puppies, and onion rings. The staff were incredibly nice and accommodating for our large group, too.

Two girls with their hands up in the air sitting in large chair outside at Crabby's Beachside in Saint Augustine

Saltwater Cowboys

Additionally, there was one restaurant we did not have a chance to go to, but it was highly rated on TripAdvisor. You’ll find Saltwater Cowboys perched above wildlife-laden salt marshes flanking the Intracoastal Waterway. Saltwater Cowboys is also one of the oldest restaurants in Saint Augustine. They serve fresh seafood, BBQ ribs, chicken, steaks, gator tail, frog legs, and more. The restaurant is located just over a mile from our Airbnb, if you were looking to stay in that area.


Finally, a trip to St. Augustine, Florida offers families the perfect combination of outdoor recreation, history, and relaxation. With the beach, a variety of museums, and historic sites, the possibilities are endless. And with the city’s laid-back atmosphere, parents and children can enjoy a much-needed break from the everyday hustle and bustle. So come experience everything St. Augustine has to offer and create memories to last a lifetime. Take the chance to relax and rejuvenate in the “Nation’s Oldest City”, and discover why it has become a favorite destination for family vacations.

Looking for another great family beach location? Check out Gulf Shores, Alabama!

Or do you have a favorite beach town you’ve visited with family? Let me know down below.

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4 Day Itinerary Saint Augustine for Families

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The Comments

  • simplyjolayne
    April 1, 2023

    Your family is adorable. We have so many amazing memories from traveling with our girls when they were little.

    • Brittney
      → simplyjolayne
      April 1, 2023

      Thank you. Looking forward to traveling more with our daughter as she gets older!

  • Nancy
    April 1, 2023

    Love this, it’s been on my bucket list for a few years, especially want to go at Christmas 💕

    • Brittney
      → Nancy
      April 1, 2023

      Yes! I’ve heard so many great things about the lights and decorations in Saint Augustine at Christmas time! Would love to go one December!

  • Tracy
    April 3, 2023

    I was just in St. Augustine for the first time! Wasn’t it great? I did the trolley tour as well and thought it was a great overview of the city. Cute little town.

    • Brittney
      → Tracy
      April 3, 2023

      Yes! I love that the Old Town Trolley Tours also provide some history for you too!