A Night Out in St. Augustine

America’s First City

When most people think of our nation’s humble beginnings, the first thought that comes to mind is the Puritan pilgrimage from Britain that lead to the first Thanksgiving at Plymouth Rock in 1620. However, the nation’s first city was actually established about fifty years earlier than the Plymouth Colony, and in a much warmer climate. America’s first and oldest occupied city is actually St. Augustine, settled in 1565 by Spanish explorers on the northeast shores of Florida and establishing the region as Florida’s First Coast. The city was named after Saint Augustine of Hippo, the patron saint of brewers who turned away from a life of partying and debauchery for a more divine path of sacrifice and prayer. Over the last four centuries, the city has become a chronicle of the southern peninsula’s affair with explorers, swashbuckling pirates, and rich Spanish culture. The city is must-see for any tourist looking to veer off the beaten path and dive into Florida’s hidden treasures.

St. Augustine is a city veiled in romance and adventure that takes each visitor on a journey through multi-cultural influences in everything from food to architecture. There are plenty of shops, breweries, restaurants, and trolley tours that will give you in insider’s view of the entire city. If you prefer to travel on foot, you’ll feel like you’re walking through time as you take in the French, Italian, Greek, and English architectural stylings, forts guarded by canons, and towering cathedrals around every corner. If you’re looking for a spot to take a postcard-worthy selfie, you’ll want to take a stroll along the main street to witness the iconic Bridge of Lions that stretches over the Matanzas Bay and bids access to the neighboring Anastasia Island. With bits of history bursting from every building, there is never a dull moment in America’s First City.

Gardens at The Collector

Photo by Amira Shomr

Spend the night at The Collector Luxury Inn & Gardens

Tucked away between the swaying trees on Cordova Street is The Collector Luxury Inn & Gardens where you’ll begin your stay in the gorgeous city of St. Augustine. The inn showcases a collection of nine 18th century cottage homes furnished with vintage fireplaces and charming architectural detail that offers an inviting hideaway to settle in for the night. Guests will not feel stuck in past as the inn combines history with luxury comforts like soothing fountains, elegant gardens, and hidden alcoves to sneak away with your special someone. The inn also boasts its very own private bar The Well where guests can spend all night sipping on original cocktails crafted with style, allowing guests to drink the night away without ever leaving the grounds. Take a drink to go and enjoy the cool breeze on the large wrap-around decks adorned with rocking chairs sat in by literary greats like Mark Twain, or sit outside in the courtyard next to cozy fire pits to experience the moonlit gardens under the stars.

If you’re ready to get out on the town, The Collector is just a stone’s throw away from all the enticing sites you crave in the heart of the city. Flagler College and the famous Lightner Museum are within walking distance, as well as a menagerie of art galleries, craft shops, and local cafes just waiting to be explored. You’ll also get a breathtaking view of the marina that hosts the Black Raven Pirate Ship that you can board for a dinner theater extravaganza along the bay. If you’d rather not stray too far from the inn, try guest favorites like Dog Rose Brewing and Café Alcazar for taste of the local scene that is just around the corner. Whether you choose to hit the town or enjoy a night of relaxation and pampering, The Collector Inn will guarantee an unforgettable night in St. Augustine.

Casa Maya


Photo by Casa Maya Facebook

Dinner at Casa Maya 

When dinner time rolls around and you’re looking for the freshest bite in the city, treat your taste buds to the incredible cuisine at Casa Maya Mexican Seafood Grille & Tequila Bar. The relaxed atmosphere of the two-story home will make you feel right at home with the option to dine anywhere from the veranda, living room, dining room, or outdoor garden. Your senses will be electrified with scents of sizzling seafood delivered daily from local fisheries, locally grown seasonal herbs and veggies, and the tantalizing aroma of homemade authentic Mexican dishes. Try an incredible melody shrimp tacos and house hot sauce, or spice things up with succulent octopus ceviche. If you’re looking for something above sea level, take a chance on savory pork carnitas served with crisp plantains, or dig into Aztec pork sautéed in a homemade roasted almost chipotle sauce. There’s no wrong choice when it comes to this delectable menu.

Casa Maya’s dedication to high quality ingredients and delivering a flavor overload in every bite will put this grille on the top of your must-visit list every time you visit St. Augustine. Before you wrap up your meal and head to your next adventure, be sure to leave a little room to try one of the restaurant’s signature craft cocktails made with wild flavor combinations. Try a jalapeno-infused tequila and Chile ancho liquor in the Smoke & Fire, or keep it classic with the house Casa Mayarita for a citrusy spin on the quintessential margarita. Keep an eye out for the drink of the day as these limited-time cocktails often include spirits from the local St. Augustine Distillery. It’s 5 o’clock somewhere, and there’s no better place to quench your thirst than Casa Maya.


Photo by Michael’s Tasting Room Facebook

Wine at Michael’s Tasting Room

Now that you’ve wet your whistle at Casa Maya, you can head just next door to their neighbors at Michael’s Tasting Room. The award-winning restaurant has been nationally recognized on The Food Network for its culinary elegance and has been awarded The Wine Spectator’s Award of Excellence for over eleven years in a row. The intimate setting of the wine room blooms through the building’s history from its humble beginnings as the Buchanti House built in 1764. The historical landmark was transformed and now offers a romantic candle-lit atmosphere for celebratory dinner dates, casual tapas, and world-class wine tasting guided by the restaurant’s knowledgeable staff. The beautiful dining room also showcases local St. Augustine artistry and distinguishes Michael’s as complete luxurious experience for the accomplished foodie.

The cuisine at Michael’s never stays the same, and you’ll always find a new reason to visit and browse the ever-changing menu seasonally. From steaks to coastal Spanish-inspired dishes, Chef Michael gets his inspiration from utilizing the finest local ingredients and marrying them together in a medley of rustic yet refined dishes. Along with the incredible cuisine, the restaurant’s exclusive wine cellar boasts over one-hundred local and imported wines from France, Germany, Spain, Italy, Argentina, and more. The cellar is a main attraction for private events and wine tasting parties that are sure to give everyone a taste of the finer things in life. Whether you’re just stopping in for a glass in the evening, are celebrating with your favorite bottle and friends, or want to try every wine in a region, the options are endless and the wine runneth over at Michael’s Tasting Room.


Photo by The Hyppo Facebook

Cool down at The Hyppo Gourmet Ice Pops

After strolling through the streets to walk off the incredible meals you’ve had, you’ve probably worked up a sweat and need an indulgent way to cool down. Just a few blocks over from Michael’s, you’ll smell the sweet aromas wafting from The Hyppo Gourmet Ice Pops. This whimsical pop shop uses simple, natural ingredients combined with fresh fruit to make over four-hundred and fifty flavors- and counting! Inspired by the Mexican-style frozen dessert known as paletas, these sweet goodies are not your ordinary freezer section pops. Like traditional paletas, The Hyppo’s ice pops combine unique flavors for a mouthwatering experience. The key to the delicious ice pops is using the freshest seasonal fruits available, allowing the shop to change their flavors every season and try new combinations for a satisfyingly cool treat.

The ice pops are made and packaged right in the shop with just the basics: cane sugar, fresh fruit, and cream. The wholesomeness of the ingredients makes all the difference, from the moment you tear open the wrapper to the very first bite of pure goodness. While the shop only carries about one-hundred flavors at a time, there is no shortage on new flavors to try. Guests can peruse an eccentric array of ice pops like mango habanero, chipotle peach, or pineapple jalapeno to ditch the boring vanilla and chocolate status quo. For a more adventurous palate, the shop offers exquisite combinations like watermelon basil, espresso horchata, and champagne to entice your taste buds. While you’re enjoying your frozen snack, browse the shop’s collection of merchandise and take a t-shirt home to profess your newfound love for your new favorite summer treat.

St. Augustine Distillery

Photo by St. Augustine Distillery Facebook

Tour the St. Augustine Distillery

You’ve checked out of the incredible Collector Inn and you’ve tasted every worthy dish this side of the Matanzas Bay, but you’ve got one last stop to make before saying farewell to the romantic city, and that is the St. Augustine Distillery. Take home a little piece of the historic city with spirits crafted from Florida’s finest crops and passionately distilled by a local community of artisans with a dedication to perfection in every sip. Using local sugar cane, wheat, corn, and citrus, the distillery celebrates farmers and Florida heritage through the carefully crafted whiskey, rum, vodka, and gin they sell and ship all across the state.

If you’ve got some extra time to spare, take advantage of the distillery’s tours that take a step behind the craft and reveal the location’s history as a reinvention of the Historic FP&L Ice Plant. Built in 1907, the site belongs to the National Register of Historic Places and was home to St. Augustine’s first power and ice complex before being restored and molded into the distillery it is today. With the privilege of preservation and perseverance, the St. Augustine Distillery is helping move the plant into the future with ingenuity, innovation, and community pride. The company is currently working on creating the first bourbon fully developed in Florida, and continues to provide quality spirits to local businesses, restaurants, and patrons alike. Grab a bottle of your favorite spirit to enjoy at home and reminisce on your whirlwind trip through America’s oldest city. You’ll be taking home a taste of history!

Define your own unforgettable moments in history and experience the timeless excitement waiting for you in the heart of historic St. Augustine.