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Introduction: The oldest city in Florida – St Augustine
Back a long time ago, St. Augustine was the winter retreat for the rich and famous wanting to get away from the cold of the north. Henry Flager, a rich guy who co-founded Standard Oil purchased a series of railroads and formed the East Coast Rail to get those rich folks to St. Augustine.
Mr. Flager opened a series of hotels; Hotel Ponce De Leon, Hotel Alcazar, and Hotel Cordova to accommodate the rich folks’ winter migration thereby changing the economic landscape for St. Augustine by making tourism its main source of revenue.
Even when Henry Flager expanded the East Coast Rail south to Miami, with the rich and famous going with the further south for their winter retreat, St. Augustine still remained a popular destination as the United States became a nation of car welding families taking road trips to the south.
The popularity of St. Augustine as a tourist getaway hasn’t changed one bit! In this article, I discuss things to do as a solo traveler, a few places to eat that you don’t wanna miss and the perfect place to stay during your visit.
Things to do in St Augustine
St. Augustine is sooooo charming and if you’re a history buff you will fall in love with this city and its people. However, you got to get past the surface touristy stuff to get to the authenticity of St Augustine and that takes a little digging; a little exploring.
Watch the cannon firing
Every Friday, Saturday and Sunday, Castillo de San Marcos – the oldest masonry fort in the U.S., shoots off the cannon guarding the city of St. Augustine – in full colonial Spanish military style. Park rangers are on hand to give a historical accounting of Castillo de San Marcos and its importance to the city.
Canon firing times are: 10:30 AM, 11:30 AM, 1:30 PM, 2:30 PM and 3:30 PM every Friday – Sunday. I suggest going at 10:30 AM to miss out on the crowds and get a great view of St. Augustine from the gun deck.
After watching the firing of the canon, check out the inside of the fort to get a glimpse of what life might have been like for the Spanish soldiers who manned Castillo de San Marcos.
Castillo de San Marcos (1 South Castillo Dr) is run by the National Park Service; admissions is $15 and is good for entrance into the fort for 7 days from the date of purchase. For more information on the firing of the canon, go to Visit St Augustine by clicking here.
Take a tour
1. Great historic commentary by the tour guide of the Colonial Experience Living History Tour – click here for more information on the tour. Learn about how St. Augustine was founded and what life was like for the early settlers of St. Augustine. This tour is located at 43 St. George Street.
You will also learn about other aspects of colonial life such as blacksmithing and demonstrations involving firing a cannon and musket. Be prepared to hear about the restaurants and gift shops that are part of the Colonial Quarter (I do recommend checking out St. Augustine Seafood Company – more about that later).
Don’t leave without climbing the watchtower and taking a selfie with the view of Castillo de San Marcos in the background.
2. Take a tour of Flager College (17 King Street) – Flager College used to be known as the Ponce De Leon Hotel. This luxury hotel was one of 3 hotels owned by Henry Flager, the captain of industry who placed St Augustine on the map as a vacation spot.
It became Flager College in 1968. In 1976 the college restored the building to its former glory. Visitors are only allowed to explore the courtyard and first floor.
This is a 90-minute fully narrated tour of St Augustine’s points of interest and attractions. The local guide will wow you with key historical facts about the city of St. Augustine. What’s so great is that the trolley makes 23 stops at various points in St. Augustine, allowing you to explore the city.
Read my review of Old Town Trolley Tours St Augustine by clicking here.
One of the stops that the Old Town Trolley makes is at San Sebastian Winery – stop #13. If you’re a wine lover you’ll want to get off at this stop and take their free tour and wine-tasting. This winery is family-owned and operated.
During the tour, you will get to see a short but entertaining film presentation that goes over the history of San Sebastian Winery (157 King Street). After the tour, you get to sample about 14 different wines.
My favorite wine is their Rosa and the Chardonnay. But after sampling their Port, you might want to purchase a bottle or two for home – AMAZING.
4. Take an eco-tour of St. Augustine’s wetlands
Become one with nature while learning about St Augustine wildlife via boat by taking the Dolphin and Wildlife Adventure.
This tour takes you on a cruise through the Intracoastal Waterway; giving you a chance to spot dolphins, manatees and various species of bird native to the area. Wet your whistle with a $4 mimosa while experiencing nature, the vocal stylings of the late Bob Marley and the cool ocean breeze.
You will love the 90-minute ride along with the knowledgeable guide that discusses St. Augustine’s wetlands, the history of St Augustine and other amazing facts.
The company that runs the tour donates a portion of the ticket price towards educating kids about St. Augustine’s estuaries and the effect of climate change to the region.
For more information and to book your ticket to the Dolphin and Wildlife Boat Tour, click here.
5. Partake in the St. Augustine’s food scene by taking a walking food tour. The Savory Faire Food Tour is a 3-hour award-winning walking tour that explores some of the best restaurants in St. Augustine.
It starts off with mimosas at the meeting point (4 Granada Street – across from Flager College) then you’re on your way – with a tour guide in tow – to the first of 5-6 restaurants and gourmet shops.
Definitely, not to be missed! Click here for more information. One of the few food tours that accept solo travelers.
Visit a shrine
The St. Photios Greek Orthodox National Shrine (41 St. George St) is dedicated to the first colony of Greek settlers that came to St. Augustine in 1777 after the uprising of a New Smyrna (Turnbull) plantation located south of present-day Daytona Beach.
Read more about the uprising here
The St. Photios Shrine features an exhibit of artifacts, photographs and historical documents of the first Greek colony of the United States. The chapel features beautiful Byzantine frescoes of apostles and saints. Say a prayer, burn a candle and leave an offering.
Don’t leave without checking out the video presentation that discusses Greeks and their migration to America.
Take a stroll through Old Town St Augustine
St. George Street is sort-of the Main Street of historic St Augustine. This quant pedestrian-only street is lined with different shops, restaurants, and historical buildings.
At night, St George Street takes on a more festive atmosphere with its live music, outside cafes and beer taverns. I recommend exploring St. George Steet early before it gets hot and crowded. Once noon hits move to the side streets such as Hypolita, Charlotte or Spanish Street to explore.
Be sure to stop off at the Oldest Wooden School House (14 St. George St)– The outside of this building fascinates me. However, the mannequin staring out from the second-floor attic is sort of creepy so I haven’t worked up the nerve to go inside this old schoolhouse. But I’m a little curious about what it looks like on the inside. Hey, maybe…one day?
Places to eat in St Augustine
Stop at St. Augustine Seafood Co. (33 St. George St) – The seafood here is amazing! You have the choice of the catch of the day; either shrimp or fish or oysters. And you have a choice of how you want it cooked; either fried, blackened or grilled. But what is really cute is that they have a board that tells you the name of the boat that your catch of the day came from…cool, right?
I am addicted to Cousteau’s Waffle and Milkshake Bar (15 Hypolita Street) and I never leave St Augustine without getting something amazingly delicious from this spot. As the name implies you have the choice of waffles or shakes. You can’t go wrong with either one!
You can not leave St. Augustine without having a few scoops of Mayday Ice Cream (100 St George Street). This ice cream shop is named in honor of American military pilots, flying missions over Europe during WWII.
These pilots would make ice cream by strapping buckets of cream and sugar to the gunner pods while flying at high altitudes. Pretty cool story, right?
Well, Mayday Ice cream is hand-crafted and made not far from their shop on St. George Street. My favorite flavor is Gillespie Bourbon Pecan which I can’t get enough of – with some days a little bit more bourbon-y than others.
This ice cream is freaking delicious and the staff is always friendly.
Another restaurant on St George Street that has great food is the Florida Cracker Cafe (81 St George Street). Like most restaurants on St. George Street it’s a bit small but cozy and the staff is very nice. Lunchtime is a madhouse but if you go around 2:00 PM for a late lunch you should be good. Be sure to have a glass of Sangria!
Do yourself a favor and stroll over to Aviles Street to check out the art galleries on that street. But don’t leave without tasting the best Cuban cuisine at La Herencia Cafe (4 Aviles Street). My favorite is the Roasted Pork Dinner which comes with plantains, beans, and rice. Be sure to try the White Sangria!
Where you should stay in St Augustine
There are a lot of Bed and Breakfasts in historic St. Augustine and staying in one of them is a great way to experience St Augustine up close and personal. I recommend staying at Centennial House. The Centennial House is an 8-room inn located at 26 Cordova Street.
Why is the Centennial House Bed and Breakfast the perfect choice?
- close proximity to historical downtown St Augustine (3-minute walk to St George St)
- close proximity to a number of St Augustine attractions (6-minute walk to the Castillo De San Marcos)
- close proximity to a number of great eating places
- free parking is included
- free breakfast included
- awesome rates – less expensive than a lot of bed and breakfast in the area
To research rates for the Centennial House in St. Augustine, click here
If you still prefer hotel accommodations instead of a stay at a B&B, click here to research prices through booking.com
More articles on St Augustine:
For information on Jacksonville, Florida read my article – “Why you should consider Jacksonville an ideal city for road trips from Florida“