St. Augustine, Florida

St. Augustine, Florida, is rich in history and is considered the oldest continuously inhabited European-established settlement in the United States. Founded on September 8, 1565, by Spanish explorers, St. Augustine was established to protect Spain’s claims in the New World and to defend the Spanish treasure fleets. But the British fought for control of this land, so the Spanish built large forts, such as Castillo de San Marcos. Although the British did take control of St. Augustine for a short period of time, it was primarily a Spanish settlement before Florida became part of the United States in 1821.

St. Augustine transformed significantly in the late 19th and early 20th century with influence from Henry Flagler, a wealthy industrialist and co-founder of Standard Oil. Flagler built the Ponce de León Hotel (now part of Flagler College) and the Hotel Alcazar, bringing luxury and high society to the city. He also extended the railroad to St. Augustine, making it easier for visitors from the North to travel there. Flagler’s investment helped to establish St. Augustine as one of the premier tourist destinations in the United States with centuries of preserved history and architectural wonders.

Today, St. Augustine is known for its rich cultural heritage and historic charm. The city hosts numerous historical sites, museums, and reenactments, offering visitors a glimpse into its past. It is also a vibrant community that attracts tourists from all over the world, who come to experience its mix of Spanish colonial history, beautiful beaches, and modern attractions.

We spent just over a week in St. Augustine, staying at Ocean Grove RV Resort, which was a little tight for the motorhome but met our general needs. Even with over a week long stay, we were still hard pressed to see many of the sites so it does take some careful planning and prioritization of activities to get the most out of your visit. The following are some of our favorite attractions, places to eat and drink and tips for getting the most out of your visit.

There are three primary ways of getting around in St. Augustine: walking, the trolly or horse-drawn carriage. The trolly is a hop-on, hop-off system that is the best way to explore the broader area and determine what you might want to go back and explore further. You can also package a trolly trip with other attraction entrance fees. Yes, just about everything costs money to visit. As a bonus though, the trolly start location, co-located with the Old Jail Museum and St. Augustine History Museum, has free parking. Keep in mind though, you can start the trolly trip from any stop.

TIP: Parking in the central downtown area is limited with the best bet being the main parking garage. If you are planning on visiting for more than a day or two you can get an extended stay parking pass which is a big cost savings. Just stop by the walk up window near the exit on your way out of the garage on the first day.

Even with the trolly, to fully experience St. Augustine you will need to do some walking. Fortunately, many of the attractions are located in the central downtown area and it is easy to get around. In fact, walking the streets is one of the best things to do, as this is how you will truly experience this historical town with all of its charm. A great place to start your journey is at the St. Augustine Visitor Center, conveniently located next to the parking garage. There are lots of helpful folks there to provide guidance and supply maps.

One of the most popular attractions in St. Augustine is Castillo de San Marcos, the original massive Spanish fort that still stands today. The Fort has survived centuries of everything from cannon fire to hurricanes in big part to the Coquina stone it is built with. Coquina, unique to this area, is formed under the sea through a process of releasing calcium carbonate from shells, quartz sand and clay formations. Your national park pass will get you into the fort where you can explore and learn extensive history about the fort and the early settlers to this area.

Flagler College is an amazing site to see, from its meticulous gardens to amazing architecture. Henry Flagler built this originally as the Hotel Ponce de Leon, complete with its 80-foot domed ceiling and Spanish renaissance architecture. The active college campus can be toured for free, but a more extensive paid tour is also available which includes the dining room with its 79 Tiffany-stained glass windows.

There are plenty of historical churches in St. Augustine to simply adore from the exterior or walk in to get a closer look. We did a tour of the Cathedral Basilica, an 18th-century cathedral that claims to be “America’s First Parish”. It is quite beautiful.

The Old Jail, now museum, was the place where St. Augustine’s most notorious criminals lived in the late 19th and early 20th century. The structure, designed by Henry Flagler, was moved to the outskirts of town away from his hotels and made to look like an unassuming hotel itself from the outside. However, a very different story is told from the inside of the walls. Prisoned actors provide an in-depth tour and although this starts out as a “fun” adventure, it becomes very real when you hear many of the stories about the condition that the prisoners lived in. We were told that no prisoner ever left this jail alive. Be sure to stop in the St. Augustine History Museum next door while you’re there.

A little bit north of town is the Fort Mose Historic Park. We didn’t quite know what to expect about this visit, but it ended up being one of the highlights of our trip. We got there just as they were starting a tour, so our timing was perfect. What we got was one of the best “real” educational experiences with a historical reenactment tour of this 1738 fort which was a sanctuary for escaped slaves. The actors along the trail did a magnificent job of recreating the experience, however, one individual was not an actor. A chief of the Yamasee Tribe gave us a chilling story of his people, how they were treated and their role during these times.

We love visiting historic lighthouses, but the St. Augustine Lighthouse is not your ordinary lighthouse. The St. Augustine Lighthouse & Maritime Museum is another step back in time with its various maritime museums and unique artifacts. And oh yeah, a lighthouse that (if you dare) you can climb the 219 steps to the top to get a close up of the lenses and the best views in the area. Be sure to dedicate an hour or two to this attraction.

Magnolia Avenue is one of the most photographed streets in America and for good reason. A canopy of oak trees dripping with Spanish moss line this residential street in a magnificent way. Enjoy it from the trolly, your personal vehicle or just take a leisurely stroll down the street.

There is no shortage of beautiful beaches in the area, especially Butler and Crescent Beaches which stretch for miles. One of the unique things about these beaches is that you can drive your 4WD vehicle on them within the designated pathway. It’s so fun driving on the silky white sand and then stopping for a long walk. We also enjoyed the beach at Anastasia State Park, where there’s also several nature trails. We found these beaches reminiscent of some of the Florida beaches in the panhandle.

When history mixes with liquor, wine and chocolate, you get some unique experiences on a very different level. If this is your cup of tea, you will enjoy our next three attractions.

In a town where there’s an entrance fee to just about everything, it was refreshing (pun intended) to find the St Augustine Distillery that offers free tastings. The distillery is located in an early 1900’s ice factory that you get to tour as you do tastings of different gins, vodka and whiskies. Each tasting station provides a unique experience, but if you want more, head upstairs to the Ice Plant Bar. The restaurant and bar are a 10 on the cool factor with its industrial decor and old-style bar. We didn’t eat there but really enjoyed a cocktail at the bar.

Henry and Esther Whetstone have been producing chocolate products since the 1970’s and later established Whetstone Chocolates, a bean-to-bar company. Their factory still operates today in St. Augustine and does tasting tours for a nominal fee. The tour was great and the chocolates where even better. And of course, the tour ends in the store so no worries, there’s plenty to take home. So, after some chocolate, our next stop should make perfect sense.

San Sebastian Winery is conveniently located a block from Whetstone Chocolates so this seemed like the logical next stop, especially since we had previously been to their sister company, Lakeridge Winery, and enjoyed it. And who can pass up a free wine tasting anyway! This was a fun wine tasting and we even got some great additional recommendations from our bartender.

There are way too many places to eat and drink in St. Augustine to mention all of them, but we did our fair share of indulgence. In particular, we loved Carrera Wine Cellar which was recommended by our friend at San Sebastian Winery. This local wine cellar is a favorite among locals and was such a great experience. They specialize is Spanish wines and are the wine provider for the annual St. Augustine Spanish Food and Wine Festival. We felt like a welcomed local, enjoying some wine and a charcuterie board with our bartender and new friend, Bob.

We take recommendations from locals seriously and Bob provided us an outstanding one with the Raintree Restaurant. This upscale restaurant is located in a 19th century Victorian house and did not disappoint. Although our plans did not allow for dinner, we had an amazing Sunday brunch. We look forward to visiting here again.

Three honorable mentions that we did not have the opportunity to visit, include the; Pirate & Treasure Museum, Lightner Museum and Ponce de Leon’s Fountain of Youth. We heard great things about all of these attractions and they should be considered as part of any St. Augustine visit.

St. Augustine’s history is a fascinating blend of Indigenous cultures, Spanish exploration, British and American rule, and modern-day tourism. Its rich historical legacy, combined with its beautiful architecture and coastal charm, makes it a unique place to explore the past and present of Florida and the United States. We will share more early American history in the weeks to come as our travels take us up the eastern US coast.

See you down the road a piece and be sure to check out all of our pictures from St. Augustine.