A 24-Hour Itinerary in St. Augustine With Kids

Pirates, a massive fort, trolley rides and plenty of adventure for a family with two boys.

St. Augustine is getting ready to celebrate its 450th birthday in a month. Driving into town, the excitement is palpable. Yellow and red banners hang from the balconies of centuries-old buildings, music pours from quaint patios off St. George Street, crowds are bustling to see what the buzz is all about, and among them is our family of four.

Day 1

We checked into the St. George Inn, a lovely bed & breakfast with arguably the best location in town. We reached our private staircase from St. George Street, the main corridor through St. Augustine's historic district and pedestrian-only. Our second-floor room was one of four units on the wrap-around front porch, with inviting rocking chairs looking out over the massive Castillo and the sailboats moored on the Matanzas River. Our room, which had a spiral staircase to a third-floor bedroom, would later be my five-year-old's favorite part of the trip. (Note: The adjacent Mill Top Tavern did play live music late at night, so notify the innkeeper if you want a more quiet room.) From $169, includes a European-style breakfast.

The St. George Inn in St. Augustine

We started our morning at the Castillo de San Marcos. Built in the late 1600s by the Queen of Spain after a series of pirate attacks including Sir Francis Drake's infamous raid, the fort has since withstood pirates, hurricanes and war. Its resilience is due to its unique construction material: coquina, tiny sea shells cemented together by Mother Nature and found on the shores of St. Augustine. At 11:30 am, Colonial Spanish soldiers loaded their cannons and fired out to sea, a fun and festive re-enactment. Even the locals in their motorboats and kayaks rode close to shore to get in on the action. $10 for adults; kids 15 and under free.

We walked across the street to Meehan's Irish Pub on the bayfront for burgers and pints of Harp and Guinness. When our two-year-old dropped his plate of chicken fingers on the floor, the chef diverted disaster by promptly sending out another order, noting he had kids, too.

To prolong our break from the August heat, we stopped inside the Pirate & Treasure Museum. The boys were in pirate heaven. We could have spent an hour reading through the rare materials and looking at the artifacts (like the world's first Wanted Poster and biographies of famous pirates), but our boys were happiest hanging out on "The Deck," where they fired their own cannons, raised the Jolly Roger Flag and steered the ship. They also admired the "real pirate treasure" and seeing Captain Hook's "real hook" from the movie "Peter Pan." $12.99 adults; $6.99 ages 5-12; kids 4 and under free.

While the boys rested back in the room, I meandered down St. George Street. This narrow stretch only a few blocks long packs in more than 100 restaurants and shops selling everything from tchotchkes and souvenirs to high-end clothing, organic-cotton hammocks, ceramic pots and Panama hats. Tourists stayed cool with Hyppo Gourmet Ice Pops, ice cream from Kilwins and sangria in shaded courtyard bars. Others took time to learn about some of the street's landmarks, like the Oldest Wooden Schoolhouse.

St. George Street St. Augustine

For our afternoon adventure, we stopped by a kiosk and got our tickets, in the form of stickers, for the Old Town Trolley Tour. The trolley, as well as Red Train tours, make more than 20 stops throughout town, plus a shuttle to the beach, lighthouse and alligator farm. It's the perfect way to see all the sites in town, especially on a hot day with children in tow. From the trolley, we learned a bit of history from the informative guide, while seeing sites such as the National Guard Headquarters, Flagler College, the Lightner Museum, gorgeous churches and the Casa Monica Hotel. We took stop No. 12 at the St. Augustine Distillery, which has been making national headlines lately for its craft gin, vodka and now rum, which will be introduced this fall. Free tours are offered at the distillery every 30 minutes. Next door to the distillery, which also has a small museum and gift shop, is the Ice Plant Bar. Here, hipsters, foodies and tourists cluster around the vintage bar inside an old ice plant for hand-crafted cocktails and farm-to-table cuisine served by staff sporting suspenders and newsie caps. I ordered the Day Tripper with gin, mixed with a refreshing blend of lemon, lavender, soda and mint, while my husband opted for the Darjeeling with gin, chili lemongrass syrup, lemon and lillet. We bribed the kids with a promised trip to Whetstone Chocolates afterward, where they, too, provide tours and offer samples. Three-day trolley ticket $25.74 for adults; kids 6-12 $10.30; kids 5 and under free.

Old Town Trolley Tours in St. Augustine

We headed to Aviles Street, the oldest street in the United States, for dinner. Its narrow, brick path is home to several outdoor cafes and high-end galleries and shops. It's much more quiet and quaint than St. George, though both streets are certainly worth some time exploring. Cellar 6, which had more of a trendy bar vibe than restaurant, did not have a children's menu, but the brie came out with a generous portion of crackers and fruit which satisfied the kids. If we had not had the children with us, I would have loved to have taken a romantic carriage ride after a leisurely dinner, but instead, we turned in for another busy day in the morning.

Sidewalk cafes on Aviles Street

Day 2

Sunday morning before 8 am, we had the streets and the courtyards all to ourselves. The attractions don't open until 9 am, so we stopped by Our Lady of La Leche Shrine, an absolutely breathtaking chapel originally built in 1603. Covered in ivy and harbored by trees, this tiny building is a holy sanctuary. Inside, dozens of candles flickered in the breeze from the open windows, and all was quiet. Visiting the shrine was a peaceful way to start the morning, and special to me as it's a shine dedicated to motherhood. (We mothers can use all the prayers we can get.) Free admission.

Our Lady of La Leche Shrine in St. Augustine

From there, it was just a few blocks to the Fountain of Youth. Everyone but my skeptical five-year-old took a sip from the legendary fountain that's more fiction than fact, but when in St. Augustine it's a must-do. Also on property are a replica of the native Seloy Indian Village, a lookout tower on the river and easily a dozen roaming peacocks. Historic demonstrations are held throughout the day if you want to spend more time. $15 for adults; children 6-12 $9; children 5 and under free.

We said goodbye to downtown St. Augustine and crossed the Bridge of Lions toward the beach. Our first stop, The Alligator Farm and Zoological Parkwas pleasantly surprising. I thought it might be more kitschy roadside attraction, but it was actually a well-executed zoo, complete with exotic birds, monkeys and more alligators than we have ever seen in our lives. Wooden boardwalks led us through the exhibits and in the canopy of trees above us, the more daring guests ziplined over the alligator pits. $22.95 adults; $11.95 children ages 3-11; zipline courses are $35-$65; must be 10 and up.

Huge American Alligators at the St. Augustine Alligator Farm

Our last stop was just across the street at the St. Augustine Lighthouse. The St. Augustine Lighthouse was built in 1871 and stands 164-feet tall. My son and husband climbed the 219 steps to the top for panoramic views of the city, from the majestic, terra-cotta towers of Flagler College on the mainland to the ocean beyond. (Note: For children under 44 inches tall, there is a great pirate ship playground on site.) A 360-view of America's first city and the triumph of making it to the top, was the perfect ending to our 24-hour adventure in St. Augustine. $9.95 adults; children 44"-tall to age 12 $7.99.

St. Augustine Lighthouse