Luxury Travel: St. Augustine Combines Old World Charms with New Age Amenities

by Catherine Trifiletti

Eat, drink and chill in America’s oldest city.

A quick Google search of St. Augustine’s long and often times tumultuous history can easily make your head spin. Between its initial discovery in 1565 by Pedro Menendez de Aviles of Spain, invasions by pirates and British rule the city itself changed hands of power over 300 times before being established as U.S. territory. A trip to the nation’s oldest city explains why the Floridian gem was sought after with such fervor. There is a special peace that takes hold looking out over Matanzas Bay, one that was undoubtedly felt by the various groups looking to lay claim to the waterfront city. That remarkable connection to the past is what has kept visitors intrigued for years, but we were surprised and excited to see a place, known so prominently for its historical attractions (hello, Fountain of Youth), have a multitude of other offerings to satisfy every kind of traveler beyond history buffs alone (who presumably need no convincing to make the trip). Whether it’s old cobblestone streets that have evolved into bustling dining and cocktail scenes or boat ride offerings, there is no lack of opportunity to eat, imbibe and relax in St. Augustine.


With over 458 restaurants, St. Augustine is becoming more of a culinary destination than just a historical one. Considering the city itself has traded many hands over the years, it is no surprise that the eateries around town represent a varied range of tastes. A tasting tour of the city offered through The Tasting Tours company provides a sampling of the best and brightest dishes St. Augustine has to offer. Knowledgable tour guides from St. Augustine Historical Walking Tours spout off facts and stories about the city’s landmarks while guiding guests through various cafes and restaurants. As long as you’re ok with drinking Greek red wine with your gyro before noon and a sparkly glass of Chardonnay with your pierogi soon after, this tour is for you.

A squeeze of citrus sizzles Athena Restaurant’s Saganaki or flaming cheese dish. (Photo by Catherine Trifiletti)

Dine at picnic tables under a canopy of palm trees for true Florida ambiance at the The Floridian, where local produce takes center stage in dishes like cornmeal crusted fried green tomatoes topped with micro greens and green tomato relish. Other dishes like pickled pepper shrimp provide light sustenance under the beating Southern sun. The Ice Plant Bar is another stand out, where an industrial-meets-rustic setting reflects the city’s evolving farm to table food scene. A whole branzino soaked in a fennel chorizo broth elevates the meaty fish to new heights. Also not to be missed is Casa Monica Resort and Spa’s resident eatery Costa Brava. Chef Fred Mero is cooking up bright Mediterranean style dishes highlighting local cuisine while paying homage to classic coastal ingredients. The Sherry Baked Seabass accompanied by artichoke, bright tomatoes, Castelvetrano olives, lemon and pequillo peppers embodies the concept to a tee.


A copper still at the St. Augustine Distillery. (Photo by Catherine Trifiletti)

Despite its age, the ‘drink local’ trend of microbreweries and distilleries has not skipped over St. Augustine. The aptly named Ancient City Brewing Company began making suds in 2014 with offerings ranging from the clean Galleon Golden Ale to the decadent Castillo Coconut Porter (6.8ABV) that pairs well with any guilt-filled dessert (notes of dark chocolate shine through enough that some might actually choose to skip dessert- no judgement either way). St. Augustine Distillery, also opened in 2014, tapped into the growing beverage scene with small batch vodka, gin, rum and whiskey. The distillery inhabits the century-old Historic FP&L Ice Plant that was once at risk of being torn down to make room for condos, but since the past is so deeply engrained in St. Augustine’s present, distillery pioneers took it upon themselves to restore and repurpose the worn down space and maintain its prized history. Hop on a free tour to learn the distillation process and sample the carefully crafted spirits to get a firsthand taste of the distiller’s handiwork. The distillery offers mini sips of its Florida Mule, which plays on Moscow’s classic version substituting ginger beer for homemade ginger simple syrup. Sangrias Wine & Piano Bar, off the bustling St. George Street, lives up to its name serving seven homemade sangrias with unlikely add-ins like blueberries and pineapple. Try the Grateful Fruit with white wine, white port, orange, grapefruit and fresh basil. For a low key night cap and head to Cellar 6 on Aviles Street.

Guests enjoy drinks at Cellar 6. (Photo by Catherine Trifiletti)


Honeydew basil pop at the hip popsicle shop, The Hyppo. (Photo by Catherine Trifiletti)

The Florida heat is a force to be reckoned with, but St. Augustine offers plenty of cool respite opportunities on the famous pedestrian friendly St. George Street lined with ice cream parlors, restaurants and shops. The Hyppo shop specializes in exotic popsicle flavors like honeydew basil, chipotle peach and gin pear. Take your artisan popsicles along on a boat trip because it would be a tease to visit the bayside city and never see it from the outside looking in. Jump on any of the chartered boat offerings to leisurely coast along the calm waters of Matanzas Bay. If your captain is as accommodating as Jim from Dean Charters, he can drop you off on the doorstep of St. Augustine Lighthouse & Museum built in 1871 that features a newly renovated museum outlining the precision and care that goes into preserving artifacts from ship wrecks. A spiral of 219 steps leads up to a sprawling 360 degree view of the Old City below.If outdoor activities prove too much exertion, look no further than the Poseidon Spa at Casa Monica Resort & Spa, where massages and facials provide a recharge from the hustle of the day’s activities.

A man walks up the spiral staircase making up 219 steps in the St. Augustine Lighthouse. (Photo by Catherine Trifiletti)


The Kessler Collection’s Casa Monica (Photo Courtesy)

There are a number of hotels and inns scattered throughout St. Augustine, but none provide quite the same boutique experience as Casa Monica Resort & Spa. As a member of the Kessler Collection, the hotel feels more like a bohemian art gallery than a mere resting place. Intricately hand-painted archways of crimson and gold expose an immediate connection to the Spanish influence of St. Augustine. Look no further than the lobby to instantly find all your senses piqued. Your eyes can feast on original artwork by landscape artists like Jeanne Claude Roy who showcases bright colors with acrylic paintings of idyllic settings. Many of the pieces are for sale and more are available in the resident Grand Bohemian Art Gallery hosting several other artists handpicked by Richard Kessler himself, who has a carefully curated art collection across his nine luxury hotel properties. The distinct smell of cinnamon and sandalwood permeates throughout the hotel masterfully evoking rest and relaxation. The culprits behind the scent are candles for sale, as is a round up of Casa Monica’s signature ambient playlist (featuring tunes from Moon Boots and Jody Wisternoff) so that you can take your vacation home with you.

Getting There

St. Augustine is located 52 miles from the Jacksonville Airport

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