St. Augustine Retirement Guide

See also:
25 Best Places to Retire in Florida
Ultimate List of 55+ Communities in Florida

Famous for being the oldest city in the country, St. Augustine is absolutely the perfect place for anyone who appreciates history. The city is located along the east coast of Florida just about 45 minutes south of Jacksonville, and a little over an hour north of Daytona Beach.

In addition to being a great location for history buffs, St. Augustine is also filled with tons of culture, great shopping, unique places to eat, and two really wonderful retirement communities. If you are passionate about any combination of those things, the Nation’s Oldest City could be a great option for your retirement!

St. Augustine History

St. Augustine was discovered by Spanish explorers all the way back in 1565. From that point, it served as the Spanish capital of “La Florida” for more than 200 years. The famous Spanish explorer Ponce de Leon believed to have found the fountain of youth here.

In the late 1700s, the territory of Florida came under British control. It was then transferred back to Spanish control shortly after and then eventually awarded to the United States in 1819.

Henry Flagler played a key role in the development of St. Augustine into a popular winter retreat for wealthy northerners. In his role as a partner with John D. Rockefeller, Flagler had tremendous connections and did a good deal to develop St. Augustine into the city it is today.

Today, the city still pays tribute to its rich history with an impressive collection of museums and historic buildings that are still standing.

St. Augustine Culture

With a history as rich as you’ll find in St. Augustine, it should come as no surprise that there is also a thriving cultural community here as well. In addition to the many museums and historical monuments you will find throughout the city, there are also a number of cultural events and theaters that have their own historical significance.

You could spend entire days getting lost in the Lightner Museum, the Art Galleries of Saint Augustine, and the Butterfield Garage Art Gallery. There are also plenty of opportunities to take in performances at historic venues like the St. Augustine Amphitheater and the Limelight Theatre.

St. Augustine is also home to the St. Augustine Music Festival which celebrates classical music here every summer.

St. Augustine Lifestyle

In addition to all of the culture and history that St. Augustine is known for, there are also plenty of outdoor activities available for anyone seeking a more active lifestyle.

Many of the old historic monuments like Castillo de San Marcos, Mission of Nombre de Dios, and Fort Matanzas National Monument provide plenty of walking as you explore, which is great for everyone who is counting their steps these days.

And if you are looking for a really serious challenge, the 249 steps to the top of the St. Augustine Lighthouse are another great combination of history and exercise that are sure to get you another badge on your Fitbit!

If you are passionate about wildlife, the St. Augustine Wild Reserve and Anastasia State Park are great places to see everything from alligators and otters to all of the local birds.

St. Augustine Shopping

Shopping in St. Augustine comes in two distinct varieties. There are some excellent options for outlet shopping like the St. Augustine Premium Outlets.

But if you are more interested in finding independent boutique shops in a great setting, St. George Street is the place to be. This great area combines the old historic feel of St. Augustine with lots of great shops and restaurants.

St. Augustine Dining

Like most of the cities in Florida, there is no shortage of great places to eat in St. Augustine. If you are just starting to explore the city, there are three places that you absolutely must try.

First off, The Blue Hen Cafe is the ultimate spot for breakfast, brunch, or lunch. You can tell without much effort that the food here is definitely made from scratch, and it all tastes fantastic. Their specialties are southern breakfast food like sausage biscuits and corned beef hash.

There is no better fit in a former Spanish colony than a Spanish tapas restaurant. Michael’s Tasting Room features a constantly evolving menu of small plates that will allow you to sample a little bit of this and a little bit of that…all while working your way through their fantastic wine list.

St. Augustine Area Communities

Reverie at Trailmark is a 55+ community in St. Augustine. The Lodge is a 4,600 sq. ft. Lakeside Clubhouse that features indoor and outdoor social spaces, six pickleball courts, a resort-style pool and spa, a catering kitchen, and what sounds to me like one of the coolest amenities…an open-air Bier Garten.

There are 11 new single-family home designs, ranging from 1,500 to 3,000 sq. ft. The community features lakeside and preserve homesites. Prices start in the $300k’s.

Final Thoughts

Everything about St. Augustine revolves around the fact that it is the oldest city in the country. But that doesn’t mean you won’t find modern amenities here. This community offers the perfect hybrid that brings the new and the old together in a way that celebrates its history without being stuck in it.

Whether you are a sucker for historic landmarks, enjoy the culture of a historic theatre, would like to get out and explore historic parks, or just want something good to eat, you can do it all in St. Augustine.