Discovering St. FloridaAugustine,

America’s Oldest City Offers Historic Treasures and Modern Delights

By Kirsten Harrington Photographs Courtesy Of Florida’s Historic Coast and Kirsten Harrington

Founded in 1565 by Spanish settlers, St. Augustine boasts the title of America’s first continuously occupied city. This historical gem lies in the northeastern corner of Florida, perched along the Atlantic Ocean. Much of its ancient charm remains, with narrow brick-lined streets, Spanish colonial houses, and, of course, the mighty Castillo de San Marcos. Today, millions of visitors are drawn every year by award-winning restaurants, boutiques, and interactive attractions. Stunning architecture and nearby sandy beaches make St. Augustine a prime tourist destination. Here are just a few of the highlights of one of Florida’s must-see cities:

Step Back In Time

Think history lessons are only contained in dusty, old schoolbooks? Think again. St. Augustine has so many interactive ways to learn about the past, from climbing 219 steps of the St. Augustine Lighthouse to keep watch over the harbour, to feeling the weight of a bar of gold in the Pirate & Treasure Museum

At the Fountain of Youth, there is more to experience than sipping from the springs. Roam the grounds of this archaeological park to see replicas of native Timucuan canoes and huts and learn how blacksmiths shaped colonial nails from glowing hot steel. Adding up the time to see all the exhibits and feed the peacocks, you could easily spend several hours here.

The centrepiece of St. Augustine is the Castillo de San Marcos built by the Spanish in 1695 to defend the city and coastline from pirates and attacks by the British. It is the biggest and best-preserved masonry fort in the U.S. and the views over the city and surrounding waterways are spectacular. Costumed historians give various demonstrations, from canon firing to native American weaving. During my visit, a fascinating talk on the tools and herbs that were used to treat wounded soldiers made me thankful for modern medicine.

Take A Tour

Whether you are a chocolate lover, craft cocktail fan, or history buff, taking a tour is one of the best ways to experience St. Augustine. At Whetstone Chocolates, you will learn how chocolate is made, from cocoa pod to finished product. And, yes, there are plenty of samples along the way. Did you know this artisan chocolatier created melt-resistant chocolate for the U.S. military during Desert Storm? Try one of their best-selling seashell-shaped chocolates which come in a variety of flavours.

Just around the corner, you will find the St. Augustine Distillery, the most visited craft distillery in the U.S. Even a teetotaller like me enjoyed the free, self-guided tour, located in a restored ice plant. You will learn how Florida sugar cane is transformed into vodka, and how various botanicals like juniper berries and star anise are used to flavour gin. There are samples for those who wish to taste, along with recipes for craft cocktails. Ice Plant Bar is also located in this historic building and a cool drink made with custom-shaped ice is a delicious way to cool off.

Hopping on and off the Old Town Trolley is a convenient way to get around, and the drivers share tales of the city along the way. For a scary good time, consider booking a Ghosts & Gravestones tour to hear about St. Augustine’s haunted past.

One of the most dazzling times to visit is during the Night of Lights (November 18, 2023 – January 31, 2024) when the buildings and streets are illuminated with millions of tiny white lights. Experience the magic from a trolley, carriage ride or on a boat in the harbour. Walk across The Bridge of Lions and look back, soaking in the sight of the twinkling city.

STAYING IN HISTORIC ST. AUGUSTINE

One day is not nearly enough time to experience everything this ancient city has to offer. Plan to stay two or three days and book a room at the St. George Inn This luxury boutique hotel in the heart of the historic district is walking distance to everything. Large, comfortable rooms, views over the city and a peaceful fountain courtyard to enjoy complimentary breakfast are just a few of the reasons to stay. Bin 39 Wine Bar serves an extensive selection of award-winning wines by the glass, and sipping a glass of bubbly in the courtyard is the perfect way to end the day.

Step out the door to St. George Street, the pedestrian-only thoroughfare that runs through the city. Explore the shops, galleries, restaurants, and historic venues on this picturesque palm-lined street. Sample Florida honey at Stubbees Local Honey & Apothecary and enjoy a cool drink under a shady 300-year-old oak tree at The Colonial Oak Music Park. This welcoming outdoor venue offers free music several nights a week.

Duck down the side alleys and peek into courtyards. This is how I discovered one of my favourite places, Saint Photios Greek Orthodox Shrine. The non-descript white door on busy St. George Street gives no hint of the colourful frescoes, decorative mosaics, and marble altar that lie within this petite memorial to the first Greek settlers in America.

Savor The Flavors

When hunger strikes, you will find everything from casual pizza and tacos to fine dining and elevated cocktails. Early risers can fuel up on caffeine at The Kookaburra, an Aussie-American espresso bar near the cathedral. Try a Hot Aussie (latte with vanilla and cream) and one of their “Brekkie Pies” – savoury pastries with meat, eggs, and cheese. Ancient City Brunch Bar serves “Bruncharcuterie” – delicious house made empanadas, French toast, and pastries on artfully displayed boards.

For fresh fish, reserve a table in the beautiful garden at Catch 27 where seafood from local waters is showcased in pasta dishes, salads, and entrées. The Floridian is another standout, serving small plates and innovative main dishes like the brisket posole verde.

Craving sweets? Head to Peace Pie on Aviles Street for unique ice cream sandwiches made with layers of pie filling. Family-owned Zeno’s Boardwalk Sweet Shop is the place for saltwater taffy. With more than 100 flavours, you are sure to find your favourite. They make great gifts – if you can resist temptation.

Beautiful Buildings

From the 28 stained glass windows in Trinity Parish to the ornate red and timber interior of the Cathedral Basilica, the oldest Catholic Parish in the United States. St. Augustine’s churches are some of the oldest and most beautiful in the country. Many are open to the public and some offer tours on certain days. Be sure to take a look.

Your trip would not be complete without a glimpse into the wonders built by Henry Flagler, oil tycoon and railroad pioneer responsible for building the Ponce de Leon Hotel. Now the home of Flagler College, this iconic property was once an opulent retreat for wealthy northerners. This well-preserved Spanish Renaissance masterpiece contains dozens of Tiffany stained glass windows, a Thomas Edison clock and intricate mosaic tilework.

Across the street, you will find The Lightner Museum, which was once another Flagler-inspired Gilded Age resort called the Hotel Alcazar. The Villa Zorayda completes the trio of eye-catching properties on this corner. A self-guided tour of this Moorish-style property is a delightful surprise.

Whether you are looking for an active family vacation or romantic weekend getaway, this charming ancient city offers something for everyone, making it one of Florida’s star attractions. UA