St. Augustine, Florida: Where Old World Charm Meets New Fun

Published July 19th, 2023

Images via Anna Hobbs

At 458 years of age, St. Augustine prides itself on being the oldest city in the U.S. It also wants you to know that it’s full of fun. Tucked into the northeast corner of Florida’s historic east coast, it would be easy to miss if you were barrelling down I 95 headed to a theme park or to collapse under the scorching sun.

The travel brochure promised beautiful weather, great music, fascinating history, fabulous food and drink, pristine beaches and outdoor fun. We decided a visit was in order, on the theory that stops along the way can create a vacation’s best memories.

Here are a few of the highlights from a weekend stopover last spring.

1) Old Town Trolley Tour

The 90-minute trolley tour through the historic district with 22 hop-on-hop-off stops is a delightful way to get a feel for the area and your bearings. The tour guide kept us entertained with historical anecdotes, fun facts and stories behind the attractions along the way.

2) Explore and shop historic downtown

The oldest part of the city, with buildings that date to the 1700s is fully walkable and bursting at the seams with rich history and stunning Spanish and Moorish revival architecture. Plenty of art galleries, vintage and antique shops, clothing boutiques, jewellery and souvenir stores make for shopping nirvana. Not to overlook – Flagler College and the unconventional Lightner Museum, built by railway magnate Henry Flagler. We loved the vibrant scene any time of day, but it really comes to life after dark.

3) Treat Your Taste Buds

Locals take their spirits seriously. At St. Augustine Distillery you can tour and taste award-winning bourbon, made from Florida corn and wheat and aged in charred American oak barrels. San Sebastian Winery has been producing dessert and sparkling wines for more than 25 years. Stop by any day of the week for a free tour and tasting. When it comes to mealtime, the biggest challenge is choosing from dozens of eateries. For a spectacular dinner, check out Lena, an outdoor Argentinian -style open grill experience.

4) Castillo de San Marcos

The oldest masonry fort in the US and the oldest structure in the city was built to protect and defend Spain’s claims to Florida following pirate raids in the late 1500s. A short walk from downtown, it is now a national monument and one of the city’s most popular attractions. Rangers brought history to live, leading tours through rooms, once home to soldiers and prisoners.

5) Lincolnville Museum and Cultural Center

Discover the city’s rich history of the Black experience in this exceptional museum. The building that was once the first black public high school in the city is filled with stories of locals who made a difference alongside stories of mistreatment and slavery. Floyd Phillips, the affable museum president told us, “As far as I’m concerned, if you haven’t been to Lincolnville, you haven’t been to St. Augustine.”

6). Ponce de León Fountain of Youth Archeological Park marks the area where the Spanish conquistador first landed in 1513. It’s the ideal place for a picnic lunch overlooking the Matanzas River and Saint Augustine Creek. Our guide told us that “not seeing Ponce de Leon Fountain of Youth Park is like visiting New York City for the first time and missing the Statue of Liberty. Re-enactments with cannon firing demonstrations are performed multiple times every day by authentically costumed 16th century story tellers.

Where to stay:

The Homewood Suites by Hilton is a 10-minute walk to the centre of town. Spacious, contemporary suites with well-equipped kitchens. Free breakfast and friendly staff. www.homewooduitesstaugustine.com

For more information: floridahistoriccoast.com