St. Augustine, Florida – A Visit to Spain without Leaving the United States

Ziplining - Courtesy Florida's Historic Coast
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There’s always a reason to visit St. Augustine, the oldest city in the continental US. For history buffs, there’s the lure of explorer Juan Ponce de Léon and his quest for the Fountain of Youth or the “new” Castillo de San Marcos, which has stood guard for nearly 350 years. For foodies, there’s a seemingly unending array of cuisines with pubs, confections and food and libation tours to keep you sated. And the outdoor attractions add another layer to the beautiful city with four miles of beaches, top-rated golf courses nearby, and fun family-oriented activities like ziplining over the Zoo at Crocodile Crossing at the St. Augustine Alligator Farm or climbing the 219 steps to the top of the St. Augustine Lighthouse and touring the adjacent Maritime Museum. But that’s only the beginning. 

St. Augustine Alligator Farm ©Meryl Pearlstein
St. Augustine Lighthouse and Maritime Museum ©Meryl Pearlstein

You’ll need days and days to cover the museums, learn about the city’s very original and Spanish Colonial architecture, and maybe dabble in the ghost lore that lingers at every turn. Perhaps that shudder that you sense is the ghost of Pedro Menéndez de Avilés himself, the Spanish admiral who established the city in 1565.

Tonevendor Vinyl ©Meryl Pearlstein

But, it’s really in the winter that the city truly sparkles. And I mean really sparkles. St. Augustine’s popular bright lights spectacular Nights of Lights carries through until the end of January. Millions of tiny white lights adorn palm trees, the Bridge of Lions, building facades, boat masts and marinas, creating a magical world of white light for the festive holiday season. Some of the hotels and restaurants also take the holiday into their own hands with outrageous holiday decorations and colors. You’ll want to stick around to see the city at night as well as during the day.

St. Augustine lights towards the marina ©Meryl Pearlstein

Where Should You Go to See the Lights?

Overlooking the Plaza de la Constitución, the new Casa Reina has a rooftop that you should immediately book to score prime viewing of the city and the water. And the guacamole, tacos, and perfect margaritas will add to the festive mood.

Lightner Museum at night ©Meryl Pearlstein

Ride St. Augustine’s Old Town Trolley Tours for a daytime view as well as their Famous Nights of Lights Tour that skirts the city taking you in a hop-on, hop-off fashion to major attractions. Spend some time by the Lightner Museum which seems to glow blue at night particularly when you look at it through an iPhone. Once home to Henry Flagler’s Gilded-Age Hotel Alcazar, the museum is a repository for the collection of collections amassed by Otto C. Lightner started in 1948. Across from it is gorgeous Flagler College, originally the Hotel Ponce de Leon and also built by Henry Flagler. You can book a private tour, and you should if only to see the most amazing collection of Tiffany glass in actual use in the United States. Stick around for the bells – they’re not what you’d expect from a Gilded Age building. On the hour, they play a variety of songs ranging from a classical prelude to “New York, New York” and other popular tunes.  If the music has gotten you thinking, there’s a pretty amazing vinyl shop, Tonevendor, across the street, where every album is carefully wrapped in plastic and sorted by categories you probably didn’t even realize existed.

Old Town Trolley Tours ©Meryl Pearlstein
Flagler College ©Meryl Pearlstein

Walking Tours are another way to catch the views and fill your stomach and head at the same time. The St. Augustine Experiences Tours  have been created by foodie savant Alex Drywa to offer a variety of themes ranging from brews and pralines to chocolate brunch. You can create a tour to match your particular interests. If you feel like having a wine, chocolate and beer combo tour, just ask. I particularly loved the Not Just a Chocolate Tour which kicked off at the Ancient City Brunch Bar and then meandered through several chocolate and pastry shops, the Hyppo popsicle shop, and a frozen custard emporium. Photographers will be enlightened with history and camera techniques by Patricia Bean on her Saint Augustine Photo Tour, particularly relevant when you try to capture the city’s bright lights on your iPhone. A perfect way to add an endnote to any of these tours is a stop at the St. Augustine Distillery, where some of the country’s best small-batch bourbons and gins are made. You’ll learn about the history of the distillery and sample cocktails made from their spirits. 

If you prefer to create your own magical visit, you can walk along the Bayfront and view the amazing light displays at the Hilton St. Augustine, Bayfront and more. For the pause that refreshes, visit the buzzy Cobalt Lounge in the gorgeous Casa Monica resort near Aviles Street, the oldest street in the city.

Daytime Activities

Plan for a stay that’s at least four-days long if you want to experience the full range of activities available. Here are some of my favorites.

Schooner Freedom ©Meryl Pearlstein

Sunset Sail on Schooner Freedom – on a tall ship, you’ll cruise the waters, sipping Champagne and watching the crew hoist and lower the sails to catch the maximum amount of wind. You’ll also get a lovely view of glittering St. Augustine from the water and the marina.

St. Augustine Experiences ©Meryl Pearlstein

St. Augustine Eco Tours – a beautiful way to spend a day on the water and a chance to learn about the varied flora and fauna in the area as well as the myriad ecosystems, this tour is a mix of slow and fast speed boating in the harbor. Naturalist (and captain) Zach McKenna will point out the dolphins that pop up during the tour as well as the varied bird species. 

Biking at Anastasia State Park – St. Augustine’s beaches are flat, flat, flat, creating a perfect surface for riding a fat-tire bike. You can stop as you wish, dip your toes in the cool water, and search for shark teeth, a favorite pastime here.

Eat, Drink and Be Merry

After all, it’s the holidays, and this is what you should definitely do. Popular restaurants require advance reservations although some do offer walk-in bar seating. I highly recommend these to give you a sense of the range of experiences in St. Augustine.

Barley Republic – A hidden gem sitting behind busy St. George Street, the friendly Barley Republic pub has an outdoor patio (with heat lamps) providing a comparatively quiet place to sip and enjoy the likes of shrimp cocktail, burgers, wedge salad, fried pickles and other pub grub. The beer menu is extensive.

Casa Reina ©Meryl Pearlstein

Casa Reina – Newly opened in time for Light-Up!, the kickoff to Nights of Lights, the bi-level Casa Reina also has an expansive rooftop patio. The menu travels through Mexico with tacos, Mexican cocktails, perfectly seasoned guacamole and St. Augustine seafood done South of the Border-style. This is your go-to if you love tequila and mezcal: Casa Reina has a menu with nearly 70 choices.

Catch 27 ©Meryl Pearlstein
Shrimp at Catch 27 ©Meryl Pearlstein

Catch 27 – Specializing in seafood, Catch 27 has a lovely backyard area adorned with lights. The dishes are American creative with Southern-inspired favorites like the decadent deviled egg BLT with fried oyster and bacon-wrapped dates smeared with St. Augustine’s own heat-generating datil pepper jelly. The catch of the day is always a highlight but non-seafood eaters won’t go hungry either. Book well ahead as the restaurant is very popular. An extensive menu of craft cocktails, both classical and newly created, adds to the romantic outdoor setting.

Urban Asado ©Meryl Pearlstein

Urban Asado  – This is a real highlight and an unusual experience. What was once a leña, or movable food truck and grill, now has a permanent home where outdoor grilling, Argentine-style, is helmed by Chef Matt Brown in what they dub “a chef collaboration.” A combination grilling fabrication/warehouse and restaurant, the Urban Asado space is St. Augustine hip, set against the San Sebastian River with breezes and grill scents wafting over outdoor tables with fireplaces. You’ll feast on appetizers like ceviche and provoleta, followed by grilled vegetables and a mix of carnivore-pleasing chorizo, chicken and steak. The asado-style cooking is based on techniques of roasting and grilling and you can watch as your meal is prepared. Take note, it’s BYOB.

Columbia Restaurant — The Columbia sits in the heart of the historic district, exactly where it should be. Dating from 1905, the restaurant is one of several of the same name that specialize in Cuban and Spanish cuisine. The restaurant itself is worth exploring with many rooms each reflective of Hispanic culture and filled with tiles and fountains. Don’t-miss menu items include the restaurant’s original “1905” salad (prepared tableside), Spanish bean soup, paella a la Valenciana and pompano en papilot. Sangria comes in white and red versions, each delicious, and a perfect accompaniment to Columbia’s white chocolate bread pudding.

Rest Your Weary Head

Courtyard at St. George Inn ©Meryl Pearlstein

For a true sense of the charm and hospitality of St. Augustine, the St. George Inn, located on pedestrian-only St. George Street with some rooms directly facing the Castillo, is a bed and breakfast with a built-in wine bar! Your room is comfortable and may overlook St. George Street, with rocking chairs on the balcony for your idling pleasure. Breakfast is a friendly affair served in the courtyard around a beautiful fountain and rimmed with charming shops selling wind chimes, jerky, espresso, chocolates and ice cream. Mid-day (or later), the Bin 39 wine bar will help you pick out an interesting vintage so you can sit and listen to the live music under the palm trees. Hungry for more information? The Florida’s Historic Coast website has it all.

Along the Bayfront ©Meryl Pearlstein


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