If you asked me where the oldest city in America was two months ago, I would’ve guessed somewhere in New England. To my surprise, the oldest city in the U.S. is actually a historic beach town in Northeast Florida called St. Augustine. Once you arrive in St. Augustine, its rich history shines through as you start to feel a mixture of different cultures coursing through the town. It is part Spanish, part Caribbean, and part lazy beach town. The combination of different influences in St. Augustine makes it impossible to describe the city in one word – and also makes it one of the most unique and interesting cities in the U.S. Here are 15 reasons to visit St. Augustine, Florida and see the oldest city in the United States for yourself.
1. As the oldest city in the U.S., St. Augustine is steeped in history
If you’re a history buff like me, you will find yourself easily spending the bulk of your time in St. Augustine visiting the more than 40 historical sites there. Among these are the Castillo de San Marcos, built in 1695 by the Spanish to defend against the British and now the oldest masonry fort in the U.S.; the St. Augustine Lighthouse, the oldest maritime port in the U.S.; the Fountain of Youth, the oldest settlement of St. Augustine; Avilés Street, the oldest public street in the U.S.; and Fort Mose, the first free African settlement in the U.S.
Even if you choose not to visit any of St. Augustine’s many historical sites, you will still notice its 450+ year history through its architecture, historic homes, and brick-paved streets.
2. You can ride trolleys through St. Augustine to see and learn about its history
The best way to get an overview of St. Augustine is by taking a trolley tour through the city with Old Town Trolley Tours of St. Augustine. These trolley tours run for a total of 90 minutes and stop at 23 places with over 100 points of interest. My favorite part about these tours is that you can hop on and off all day, so rather than sitting through the entire 90 minute tour, you can hop off at stops that seem interesting to you, check out the attractions there, and hop back on as many times as you want and at any time throughout the day. You also get free admission to the St. Augustine History Museum and a free beach shuttle ticket with your trolley pass. If you’re planning for a more slow paced vacation, you can add a second day onto your pass for only $5 more, giving you even more time to see the many sites that St. Augustine has to offer. Make sure you get your ticket online before you go, as you’ll receive a discount online.
3. You can see historic artifacts from the 19th century in a beautiful mansion
The Lightner Museum, also known as Florida’s Smithsonian, is located in the former Alcazar Hotel. This building was built in 1888 by Henry Flagler and houses an extensive collection of Tiffany glass, natural history and science exhibits, a Victorian village, and antique mechanical musical instruments.
4. You can also find some of the oldest buildings and streets in the oldest city in the U.S.
It’s no surprise that the oldest city in America would also have some of the oldest buildings and oldest streets. Notably, St. Augustine is home to the oldest house, oldest school house, and oldest maritime port in the U.S. All three buildings have been preserved and converted into museums for visitors to have a glimpse into what life used to be like hundreds of years ago. You can also walk Avilés Street, the oldest public street dating back to 1570, and visit Mission Nombre de Dios, where the first Holy Mass was led by Father Francisco Lopez in 1565.
5. You’ll run into more ghosts and pirates in St. Augustine than you ever have before
If ghosts and pirates are your thing, well you’re in luck because St. Augustine has plenty of ghost tours and pirate museums to satisfy your craving of the dark and supernatural. Want to combine your love of ghosts AND pirates? Then you’ll want to sign up for the Haunted Pirate Ghost Trip on the Pirate Ship Black Raven for a fully immersive experience interacting with the many ghosts and pirates of St. Augustine.
6. But if you get too spooked, there are plenty of bars you can go to in St. Augustine to shake it off
The relaxed beach town vibe of St. Augustine shines through when its rich nightlife comes to life during the day. There are plenty of bars, breweries, wineries, and distilleries to get your night started during the day, shake off those eerie ghost vibes, and soak up some sun. Most bars in the historic district have outdoor patio space or a rooftop area so you can enjoy the nice weather and enjoy some people watching as well.
7. There are also plenty of delicious restaurants to enjoy in St. Augustine
One way in which I try to be socially conscious when I travel is by supporting local businesses in the community. I found this to be incredibly easy to do in St. Augustine, as almost all the dining options I found in St. Augustine’s historic district were locally owned and independent restaurants. Not only is the cuisine in St. Augustine inspired by a variety of international influences, thus providing dining options for every palette, but the food is also sourced from local farms, resulting in dishes that taste delicious, fresh, and healthy. A few must try restaurants are The Columbia, Catch 27, and Cap’s on the Water.
8. Many of the bars and restaurants in St. Augustine have free live music
Not only are the restaurants and bars in St. Augustine great for eating, drinking, and people watching, they also double up as free music venues in the afternoons and evenings. You might also find outdoor concerts taking place in open plazas around town, and these events take place year round. Whether you’re at an organized event or just walking down the street in the historic district, you’ll hear music flow through the streets of St. Augustine.
9. St. Augustine gets completely decked out in lights during the holidays
Don’t let the palm trees and sunny weather fool you – St. Augustine takes the winter holidays very seriously. From the beginning of November until the end of January, you’ll find over 3 million white lights from floor to ceiling at St. Augustine’s Nights of Lights event. You may find it strange to see holiday lights and Santa Clauses in front of palm trees and coconuts, but St. Augustine’s residents are not shy at all about getting into the holiday spirit. St. Augustine is the perfect place to visit around Christmastime if you’re looking for a warm and sunny place to celebrate the holidays.
10. The weather in St. Augustine is always nice
St. Augustine was actually experiencing a cold front when I visited last month and hit a low of 30 degrees, which is extremely abnormal for the city. Having come from Chicago where it was at least 30 degrees colder than that, I thought the weather was great. However, locals begged to differ. Barring extreme circumstances, the weather in St. Augustine is warm and sunny year round, making it the perfect winter destination.
11. The sunsets in St. Augustine are even nicer
I have always said that sunsets become twice as beautiful when they fall over the water. Since St. Augustine borders the water, there are miles of waterfront where you can watch the sunset intensify in beauty as it sets over the Matanzas River. Head over to the waterfront around dusk for a romantic sunset walk on the beach or a quiet moment of reflection as you take in the beauty of St. Augustine.
12. There are 42 miles of unobstructed beaches to choose from
With 42 miles of unobstructed beaches to choose from, it may seem more overwhelming than relaxing to choose a beach to spend the day at in St. Augustine. Here are six of the best beaches in St. Augustine and its neighboring cities: St. Augustine Beach, Ponte Vedra Beach, Vilano Beach, Anastasia State Park, Butler Beach, and Crescent Beach. Head over to the one closest to your accommodation, and you can’t go wrong!
13. And so many unique and interesting shops to visit
While you’ll certainly find your fair share of tourist shops in St. Augustine’s historic district, you’ll also find a wide array of unique trinkets and gadgets ranging from handmade jewelry to artwork to taffy making machines. If you’re looking for a unique souvenir, this is the place to find one. And even if you’re not a big shopper, it is still interesting to walk into some of these shops and see one-of-a-kind trinkets you’ve never seen before.
14. All while having the coziest accommodation to go home to every night
St. Augustine specializes in cozy inns and bed & breakfast type accommodations like the Jaybird Inn, where I stayed during my time there. The accommodations in St. Augustine are characterized by a mix of history and modernity, with the history component providing a vintage, cozy feel, and the modern elements providing comfort and luxury. There are numerous accommodations located within walking distance of the historic district, and many offer free parking as well, saving you the trouble of finding parking downtown.
15. The best part is you can have the time of your life in St. Augustine while on a budget
You can easily find comfortable accommodations in St. Augustine for under $100, and there are plenty of free things to see and do as well. Some of my favorite free things to see are the beaches, Fort Matanzas (including the ferry boat ride), First Friday Art Walks, tours and tastings at San Sebastian Winery, and historic church tours including Mission Nombre de Dios, where the first Holy Mass was led by Father Francisco Lopez in 1565.
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A big thank you to the St. Augustine, Ponte Vedra & The Beaches Visitors & Conventions Bureau for making our stay possible. As always, all opinions are 100% our own.
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Hi, I’m Diana, the big sister in the sister duo. I left my job as an attorney in March 2017 to pursue the work-from-anywhere/travel-everywhere life aka The Dream. I blog about off the beaten trail travel destinations, adventure travel, immersing in local cultures, and publish plenty of travel guides for all you who are too lazy to plan your own trips. I’ve traveled to 53 countries to date, and some of my recent adventures include hiking Mt. Kilimanjaro, visiting a child I’ve sponsored for over 10 years in Rwanda, and exploring the Middle East.