Discover St. Augustine's Old-World Charm

Lost Girl Jen shares her favorite spots in the nation's oldest city.

By: Jennifer Baggett Brennan

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At the same time that my fellow Lost Girls and I uprooted our NYC lives to take a yearlong trip around the world, my parents decided to retire to St. Augustine, FL. Although it was sad to lose my childhood home, after living out of a backpack for 365 days with my 2 best friends, I discovered that I could carve out my own sense of home almost anywhere. Even in the most unlikely of places, like our volunteer hut in Kenya or the camper van that we drove up Australia’s east coast.

And after numerous trips to St Augustine (including a few, month-long sabbaticals to pen The Lost Girls book), the city truly feels like home -- so much so that my now-husband, Kevin, and I just got married there in June, which afforded us the unique opportunity to experience the town as tourists alongside our closest family and friends.

As the oldest city in the United States, St. Augustine is rich on history, culture and old-world charm. With top tourist attractions like Flagler College, Fort Matanzas and the Fountain of Youth, coupled with pristine beaches, world-class golf courses and innumerable art galleries, restaurants and shops, this is one city worth exploring.

To help inspire your trip, here are my top St. Augustine picks:

1. Where to Slumber

Photo by: TOM REID

TOM REID

Painted against a backdrop of horse-drawn carriages, bubbling fountains and soaring palm trees, this 1888 historic hotel is an iconic landmark that blends old-world style with modern-day luxury. Boasting a regal lobby adorned with Moroccan frescos, exotic tapestries and sparkling chandeliers, 138 well-appointed guestrooms and a stylish antique car collection, the Casa Monica is the kind of place where men will feel inspired to sip bourbon at the handsome lobby bar while ladies can play the elegant Old Hollywood starlet, lounging poolside atop plush black-and-white striped cushions.

Start your morning with an espresso and homemade pastry under a canopy of clouds at the property’s sidewalk café, and then peruse the 2 adjoining art galleries, featuring renowned collections of paintings, sculptures and jewelry. When night falls, delight in one of acclaimed chef Harlan Walden’s internationally-inspired dishes -- like the Kessler signature calamari or Bahamian lobster tail with crab risotto -- at the opulent 95 Cordova restaurant. Then retire to the glamorous Cobalt Lounge to mix and mingle with a stylish crowd, while sipping top-shelf martinis and swaying to the silky beats of top local jazz bands. No matter how you choose to indulge, rest assured that you’ll be treated like royalty.

2. Where to Dine

Photo by: Rob/Harris Productions

Rob/Harris Productions

Located on the lively and historic St. George Street, the Columbia is one of my favorite places to take first-time visitors to St. Augustine. Part of a distinguished line of family- owned restaurants (the original location founded in 1905 by Cuban immigrant Casimiro Hernandez Sr.), the Columbia effortlessly blends the vibe of a beloved neighborhood establishment with a chic international supper club, complete with Spanish-style fountains, sun-drenched patios fringed with palms, a 2,200-bottle wine room and handmade cigars for purchase.

Renowned for its enticing fusion of Spanish and Cuban cuisines, this downtown hot spot lures guests with its award-winning Original “1905” Salad, paella a la Valenciana, authentic flan and overflowing pitchers of sangrias, including one specialty recipe infused with Torres brandy, Torres orange liqueur and sparkling Cristalino Spanish cava. Whether you’re popping in for tapas and a glass of private label wine, lingering over a café con leche after a languid 3-course meal, or celebrating with a large party in the property’s newly designed sky-lit courtyard, the Columbia is sure the charm you.

3. Where to Sip

A venerable Irish pub situated along the downtown waterfront, Meehan’s is the ideal spot to relax with a frosty pint of Guinness and unwind after a long day of sightseeing. Whether you prefer to sidle up to the stylish wooden bar in the main room and indulge in a glass of Midleton, unwind on the second-story balcony while soaking in sparkling views of the Matanzas Bay, or kick back with friends in the large open-air café and tropical bar in the backyard, Meehan’s convivial staff will ensure that you feel just like family -- and that you never leave their “home” hungry or thirsty. “We now have the most Irish whiskeys of any bar outside of Ireland -- over 50 total,” hails owner John Meehan.

In addition to a robust menu of libations, Meehan’s also boasts a diverse selection of traditional Irish pub fare like corned beef and cabbage, and shepherd’s pie along with regional seafood favorites and signature dishes like mahi-mahi and the Galway seafood medley. Top all this off with an eclectic lineup of live music 4 nights a week, and you very well may want to set up camp at Meehan’s for the duration of your St. Augustine stay --as my wedding guests can certainly attest!

4. What to Do and See

No visit to St. Augustine would be complete without a grand spin around the city perched on a tufted cushion aboard one of the area’s ubiquitous horse-drawn carriages. My favorite operator is Avalon Carriage Service, which offers an array of personally guided tours of historic downtown St. Augustine and a variety of unique (and very trusty) steeds. Whether you opt to climb aboard a vis-à-vis style sleigh, antique carriage or even a horse-drawn hay wagon or trolley, Avalon’s friendly drivers will transport you down narrow cobblestone streets -- and back in time -- for a 2 1/2- mile narrated journey past such historic sites and landmarks as the Cathedral Basilica, Lightner Museum, Flagler College, Castillo de San Marcos, the Florida National Guard headquarters and Bridge of Lions. For those celebrating a special event or visiting with a group, Avalon can design custom packages to meet all your needs.

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Discover St. Augustine's Old-World Charm

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1. Where to Slumber

2. Where to Dine

3. Where to Sip

4. What to Do and See