96 Hours in America’s Oldest City: St. Augustine, Florida

If you are looking for a U.S. destination steeped in history, boasting great restaurants, adorable boutique shopping, world-class fishing, a small town feel and sandy beaches, the charming St. Augustine, FL is the place you will want to explore on a long weekend getaway.

St. Augustine, located on the Atlantic coast of Florida, was established in 1565 and is touted as America’s oldest city. Famed for its discovery in 1513 by Spanish explorer Ponce de Leon and then later occupied by the British before being ceded to the United States in the early 1800’s, St. Augustine is a walkable city with spectacular old-world architecture.

Getting There

Located off of I-95 and less than 1 hour south of Jacksonville and just under 2 hours Northeast of Orlando, St. Augustine is an easy to get to. 

Best Time to Go

St. Augustine Night of Lights Festival runs from November – January

St Augustine is truly a year round destination with hot summers and mild winters. During our January visit it was sunny and in the mid-sixties in the afternoon. Great weather for exploring the town or taking a stroll along the beach. For those interested in swimming in the Atlantic, I would recommend coming during the summer months. But note, summer is the busiest season with the largest number of tourists. If you enjoy viewing a world class dazzling holiday light display, then mid-November to January are the months to visit. With over 3 million lights, the St. Augustine’s Nights of Lights Festival will dazzle you! National Geographic named the Nights of Light Festival as one of the top ten places to see holiday lights.  

Getting Around

Walking or a hop on hop off Trolley Tours is the best way to get around St. Augustine’s historic district.  But a car is a good idea if you want to venture further out to the beaches, lighthouse, or Alligator Farm.

History Fort Matanzas, in St. Augustine

Things to See and Do  

There is so much to see and do in and around St. Augustine from the historical Castillo San Marcos Fort built by the Spanish in the late 1600’s to protect the city from pirate marauders to the Fountain of Youth Archaeological Park and plenty of places in between. There are Ghost & Graveyard Tours, Walking Tours of the historical district, romantic carriage rides, Food Tours, Pub Crawls, Ripley’s Believe it or Not Museum and the Pirate & Treasure Museum. Prefer the water? Perhaps a Fishing Charter, a water tour, or climb 316 steps to the top of the lighthouse for a spectacular 360-degree view or maybe a dip in the ocean to cool off during those hot summer months. If you are a beachcomber you might find some shark teeth over at Vilano Beach. If you do find yourself at Vilano Beach check out Crusin’ Tikis, where you can rent out a floating tiki bar and bartender for your group. The kids might enjoy the wildlife at the Alligator Farm while the adults can imbibe in a tasting at the San Sebastian Winery or if they prefer they can sip handcrafted spirits at the St. Augustine Distillery. There is something for everyone in St. Augustine whether it’s a family vacation, honeymoon, babymoon. Romantic escape, girls getaway, guys getaway or any type of trip you can dream up.

St. Augustine’s San Sebastian Winery

Places to Stay

Looking to be close to the historic district with a room with views of the Bay? Consider the Hilton St. Augustine Historic Bayfront Hotel. 

The Hilton Bayfront

Prefer something a little more grand and some spa pampering on the side? The Spanish Baroque Revival designed Casa Monica Resort & Spa, conveniently located in the center of downtown, is my recommendation.

Embassy Suites Oceanfront Resort, St. Augustine

If you are a beach lover the place to stay is the Embassy Suites Oceanfront Resort. This hotel is right on the beach, has a swimming pool and fire pits at night to keep you warm and is a short 10-minute car ride to the historic center.

In 2021 there are 5 new hotels that are slated to open in St. Augustine, which will provide additional options for those visiting the area.

For those that like an oceanfront family golf and spa resort and don’t mind travelling a bit, the Hammock Beach Resort, less than 30 min South of St. Augustine is the spot! For accommodations can choose from a hotel room, to an oceanview suite or if you have a larger crowd you can select a 2 or 3 bedroom villa.  There is an indoor pool and an outdoor pool as well a lazy river and waterslide. There is a kids club, 6 dining venues that cater to ever taste, tennis, bicycling, fitness center, and of course a spa and golf course.    

The Conch House Resort & Restaurant in St. Augustine, Fl.

Where to eat?

There are so many great restaurants that cater to everyone’s pallet in and around St. Augustine. For breakfast, the Australian cuisine Kookaburra Coffee Shop hits the spot, as does the Maple Street Biscuit Company with their flaky biscuit offerings. Craving some mouthwatering Tapas and Sangria or a Cubano sandwich or the mouth watering 1905 salad for lunch? Then The Columbia Restaurant is your spot. It is the oldest restaurant in Florida and there is a reason it has stayed in business all these years. Maybe you’re in the mood for Italian food, Pizzalley’s on St. George is our selection. If you’re thinking about Peruvian Cuisine then make reservations at The Llama restaurant. Does your party likes Southern fare surrounded by kitschy decor, The Floridian is one of the best restaurants in St. Augustine for that type of cuisine. Want a Caribbean seafood restaurant with a water view? The Conch House comes highly recommended. As you can see there is no shortage of eateries in St. Augustine.

The Columbia Restaurant in St. Augustine.

Ready to visit St. Augustine?

When you’re ready to travel, contact your LBAC Travel Advisor to assist in planning your next vacation, whether that is to St. Augustine or anywhere around the world.    

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