Exploring the oldest city in the United States

Celebrating nearly 500 years as the oldest continuously occupied European settlement in the United Sates, don’t be fooled by the age of this vibrant city. This abuela (grandmother) of american cities will surprise you with amazing restaurants, a vibrant city core, miles of beaches, a touch of sinfulness, and historic sites to explore that will turn back time.

As a getaway destination, there is more than a few days needed to experience the scope of St. Augustine’s richness. As a couple’s romantic destination, a girlfriend’s weekend retreat or a family beach vacation, a simple walk over the Bridge of Lions will tease excitement of what historic St. Augustine has to offer.  

Where to Eat in St. Augustine

Good question? Would you like the old city or the more modern? Would you like seafood (fresh catches right from the ocean), farm to table freshness, or have a specific taste preference? I’m certain St. Augustine can satisfy it.

Consider these great restaurants from our recent visit:

• Catch 27 – deliciously delivering fresh seafood made from scratch with the freshest of locally sourced ingredients – what a treat! Try their cheese board as an appetiser with smoked blue cheese and drunken cherries, and any cocktail that features the distinctive St. Augustine gin.
• Present Moments Café – completely Vegan, fresh and organic. Many fresh appetizer, entrée and juice options to offer quite the diverse selection. Note: the Taco’s of Life were tasty enough to encourage this meat-eater to want to try another entrée another day!
• Collage Restaurant – Top rated, upscale fine dining using fresh local seafood, steaks, lamb and veal. Prepare for a first-class dining experience

Cocktails anyone? A great drink experience and the places to see or be seen:

• Prohibition Kitchen – a vintage gastropub with great craft cocktails and live music (most nights) in the speakeasy era of flappers, moonshine and jazz! One of the hottest spots for dinner or a drink after strolling St. George St shopping and exploring. [Note: Prohibition Kitchen is an uber-popular spot in St. Augustine. GoGirlfriend recommends making reservations for seating as soon as you arrive to make sure you get a seat to share this great vibrant venue.]
• Odd Birds Craft Cocktail Lounge – craft cocktails and small bites in a unique, eclectic atmosphere. The intimate courtyard lets you share in the vibe of the talented craft creations.
• Colonial Oak Park – an intimate outdoor music venue under the shades of a very old oak tree. Part of the Colonial Quarter, with live music every Thursday – Sunday.
• St. Augustine Distillery – make your own craft cocktails! Built within a century-old Ice Plant (how else did they have ice 100 years ago?), St. Augustine Distillery offers free tours and free tastings of their small batch gin, bourbon, rum and vodka. Their store offers all manors of these spirits and the elements to make your own cocktails. Consider your lunch stop at the Ice Plant Bar upstairs for some great food in the structure of the old Ice House. Since you’re already sinning, check out what else to do on “Sin Corner” (see below) before you get in your car and leave.

Special Treat: Combining the excellent spirits of the St. Augustine Distillery, and delicious fresh, local ingredients crafted by the Catch 27 Restaurant team, bar-meister Greg Goldstein (Bar Manager - Catch 27) has created a special recipe, exclusively available at Catch 27 for the upcoming season, to share with us – The Farmer’s Market Swizzle.

The Farmer’ s Market Swizzle (exclusively at Catch 27):

• 2 oz St. Augustine Distillery Gin
• ¾ oz Strawberry oleo yaupon tea syrup
• ½ oz fresh lemon juice
• ½ oz Dog Day Garden’s Honey-Lemon Shrub

Shaken with crushed ice & poured into a highball glass. Topped with Angostura bitters, citrus datil and salt-dipped lemon, and red veined sorrel. Looks like a delightful locally-grown creation – only at Catch 27!

Where to Sleep in St. Augustine

Remember this is one of the oldest cities in America sitting smack along the Atlantic shoreline. Decision time – historic boutique luxury or beachside surf and sand accommodations?

Historic Boutique Hotels

• The Collector Inn – 9 historic buildings within the historic district restored to offer 32 guest suites an experience to spellbind the historian, storytellers and explorers. It’s wrought-iron railings, fountains, period restorations and cobblestone courtyards deliver a romantic experience within the luxury of 1 of 11 Best Historic Inns in America. For availability, contact the Collector Inn and check out their outstanding TripAdvisor reviews rating.
• Marker 8 Hotel – completely renovated and restored, this bayside hotel offers a refreshing nautical theme to it’s décor. Perched at the base of the Bridge of Lions and directly across the bay from the old city of St. Augustine, the evening sunset views and the night lights of the bridge and the old city are a romantic treat. For availability, contact the Marker 8 Hotel and check out their TripAdvisor reviews rating.         
• St. George Inn – located at the gates to the historic city, the historic St. George’s inn offers 25 rooms and suites with balcony views of the historic Castillo de San Marcos and easy access to the core activities and shopping of St. George St. For availability, contact the St. George’s Inn and check out their TripAdvisor reviews rating.
• Other Historic Inns - St. Augustine has a collection of 24 historic inns that provide luxury accommodations for the perfect romantic couples or relaxed girls getaways.

Beachfront Accommodations

• Beachfront accommodations run the gamut from plush luxury to simple and functional. For a broad spectrum of choices between St. Augustine and the prestigious Ponte Vedra, there’s an vacation rental assortment at Florida’s Historic Coast and through Visit St. Augustine.
• Online searches: Condo’s, apartments and beachfront cottages on Airbnb and VRBO
• Standard Hotel options: Want the ease of moving into a hotel while still having beach access? Consider the range of beach hotel options from the Best Western to the Hampton Inn and Suites, Hilton Garden Inn to Ascend’s Castillo Real among many others.

Where to Play in St. Augustine

Florida’s Historic coast offers a wide array of options from family beachside or historic exploring to relaxing beachside walking, to couples/girlfriend getaway time spent together. A few days will not be enough to dig deep into this vibrant community.

St. Augustine Historic and local culture

St. George St, downtown St. Augustine – visit the St. George historic district for the great shops, restaurants, nightlife and central hub of the community. From the central park area at the foot of the Lions Bridge, walk left and right through the maze of shops, museums and restaurants. The grand Lightner Museum, the stately Cathedral Basilica of St. Augustine to the fortress Castillo San Marcos are just a few of the historic must-sees within this colonial quarter. For the kids, add a visit to the Black Raven Pirate Ship for a hearty bit of pirating. [Note: our recommendation is to park across the Bay and walk the 10 minutes over the beautiful Lions Bridge for the ease of parking gridlock on weekends and high season. You’ll enjoy the night views of the city from the bridge].

Ponce De Leon’s Fountain of Youth Archaeological Park – what’s a visit to St. Augustine without a drink from the fabled Fountain of Youth? Where Ponce De Leon landed in 1513 sits the legendary Spring of Eternal Hope flowing for centuries (that kid inside of you wants a sip) mythologically rumored to hold the key to eternal youth – kinda crazy if you missed it, right? The Archaeological site also houses structures, exhibits and excavations to educate and entertain you. [Note: The trolley tour has a major departure stop just up the street with an Old Jail, Oldest Store Museum, Snack shop and Spice & Tea Exchange. This is a great parking and departure stop to avoid the downtown congestion along the hop-on, hop-off trolley tour route the mile or so into the city. Consider stops at Ripleys, the Castillo or sin corner …]

“Sin Corner” – doesn’t that sound delicious? Well, it is! All within a block just outside the main historic downtown St. Augustine, the St. Augustine Distillery (with samplings), the San Sebastien Winery (with samplings) and Whetstone Chocolates (with samplings) are all in close proximity for a delightful afternoon of tasting and sinning. Just note that smack in the middle also sits the St. Augustine Police Department … do you think that was planned?

Live Theater - The performing arts are an important part of St. Augustine’s culture.  The community Limelight Theatre has a full calendar of theatrical performance throughout the year. The theatre is in a 10,000-sq. ft., 125-seat facility producing shows on two stages.

Nights of Lights - Imagine walking across the Bridge of Lions and panning your horizon to 3 million lights wrapping historic St. Augustine. A timeless Spanish tradition that spans back the era of this historic city, through the beauty, scope and breathless twinkling views, this Christmas tradition takes the age-old tradition and explodes the event with it’s modern Night of Lights wonder.

And so much more … best resource is through Florida’s Historic Coast – Things to Do.

And consider we haven’t even begun with the Historic Coast beaches – the best beach to walk for miles, the best beach-house-gazing walk, the active hotspot to be scene, and the inactive secluded beach gem to just be one with the sand and surf.

St. Augustine getaway opportunities? There’s so much that you can do as a couple’s getaway, a girlfriend’s weekend catching up, and some restaurants with re-creatable recipes with local ingredients you can take home and continue to enjoy. You’ll have to stay tuned for our upcoming posts.

Have you enjoyed St. Augustine as a getaway destination? Was it the Night of Lights, the history and culture or the beaches that drew you there? We’d love to hear your experiences. Drop a comment below or connect with us on Facebook and Twitter.