2 days in St. Augustine, the U.S.’s oldest town

Read post

Sharing is caring!

St. Augustine is a charming town just south of Jacksonville in northern Florida. You will find pristine beaches, beautiful Spanish architecture, and lots of history on every corner. The U.S.’s oldest town is quite a gem. The United States, being such a young country, might not seem to have much to offer a history enthusiast. You just need to look closer. In my weekend trip to St. Augustine, I learned a lot about the turbulent beginnings of colonial America and what the French, Spanish, and English had to do with it. I only spent two days here, but I found the city to be full of history and unique attractions. Let me give you a brief preview in this 2 days in St. Augustine itinerary.

Day 1 in St. Augustine

Start sightseeing St. Augustine by focusing on the historic old town. All the old town attractions are close together, making it easy to navigate on foot.

Take a self-guided tour of the Castillo de San Marcos National Monument

Castillo de San Marcos is the oldest Spanish fortifications in the continental U.S. For 235 years, St. Augustine was the political, religious, and military capital of Florida. The fort’s role was to protect the city from pirate raids and from Spain’s biggest enemy, the United Kingdom.

Today, you can take a self-guided tour of various rooms in the fort. You can learn about the fort’s construction, the various nations that owned it over the centuries, and notable individuals who shaped its history.

Save yourself time and avoid lines by arriving early. There is a fee to enter the monument. Several passes are accepted here, including the America the Beautiful annual pass along with military and senior passes.

Learn about pirates at the St. Augustine Pirate and Treasure Museum

If you’d like to learn about the golden age of piracy, the St. Augustine Pirate and Treasure Museum is the perfect place to do that. You will find artifacts belonging to pirates, including the authentic pirate treasure chest of Captain Thomas Thew.

Here you will learn about the pirates’ early days to their golden age, along with most notable figures of the time. In addition, you will learn a lot of interesting facts including the code of conduct, pirates’ favorite drinks, and torture devices and punishments.

St. Augustine Pirate and Treasure Museum

Walk on the Bridge of Lions

Enjoy a mile-long walk on the Bridge of Lions that connects downtown St. Augustine and Anastasia Island. The bridge is listed on the National Register of Historic Places. Get a different perspective on the Castillo de San Marcos, and see a marina full of boats. Snap a selfie with one of the lion statues guarding the bridge on each side. The bridge raises at the hour or half hour throughout the day to allow boats to pass beneath.

Bridge of Lions in St. Augustine

Glimpse into the city’s past at the Colonial Quarter

Stroll through the Colonial Quarter and catch a glimpse into St. Augustine’s past. You can explore separate eras of the town: the first 16th Century Spanish City, the Spanish Fortified Town of the 17th century, the Spanish Garrison Town of the 18th century, and the 18th Century British and the 14th Colony. The Colonial Quarter is on St. George’s Street.

Check out the old city gates and Aviles Street, the oldest street in town and the oldest street in the U.S. Explore each corner of the Colonial Quarter, get a bite to eat at one of many restaurants, window shop the boutiques, get a souvenir, or visit art galleries.

Colonial Quarter in St. Augustine

Visit the oldest wooden schoolhouse in the U.S.

In the Colonial Quarter, you will find the oldest wooden schoolhouse in the U.S. Dating back to the 18th century, the schoolhouse is open to visitors for a small fee.

Tour the small classroom displaying furniture and artifacts belonging to students, including copies of textbooks. Upstairs is a bedroom where the schoolmaster and his wife lived. You can also enjoy a walk through the garden and stop to see the kitchen, which was located in a separate building to avoid fire hazard.

The oldest wooden schoolhouse in the U.S.

Take a tour of Ponce De León Hotel, aka Flagler College

Book a historic tour of Flagler College to learn about the former Hotel Ponce de León. Hotel Ponce de León was built in 1888 over a span of 18 months by the millionaire of the day, Henry Flagler. During the tour, you will gaze at the impressive 68-foot doomed ceiling, dining room, and the Flagler Room.

Hotel Ponce de León is one of the finest examples of Spanish Renaissance architecture. You will get to see chandeliers made by Tiffany himself, a Thomas Edison clock, original furniture, handcrafted murals, and personal photos, among other items.

Tours are available daily at 10 am and 2 pm and last about an hour. Book your tickets online, as spots are limited.

The tour of the hotel was one of my favorite paid attractions of the city. You learn so many interesting facts. The building itself is stunning inside and out. Make sure to stop by, even if you don’t take a tour.

Flagler College in St. Augustine

Go wine tasting at the Cellar Upstairs, San Sebastian Winery

Wine enthusiasts will enjoy a visit to San Sebastian Winery, one of Florida’s premium wineries. You can enjoy a complimentary self-guided tour and wine tasting that are offered daily. No reservations are required.

The winery’s tours are offered from 10 am to 5 pm Monday to Saturday and 11 am to 5 pm on Sundays. If you’re visiting on a weekend, check out the rooftop bar and restaurant. Relax with a glass of wine while overlooking the city skyline and enjoying music by local artists. There is no cover charge.

Try local favorites at St. Augustine Distillery

St. Augustine Distillery is a locally owned distillery that produces bourbon using local Florida ingredients. The company maintains close ties with local farmers and gives back to the industry. Even though the distillery mainly focuses on bourbon, it also produces gin, vodka, and rum.

Sample four of their signature cocktails, learn about the distillation process, and snap a selfie with the oak barrels as a part of a self-guided tour. Tours are available daily during the operating hours of 10:30 am to 5:30 pm. No reservations are required.

Day 2 in St. Augustine

Venture outside the historic district on your second day. Visit attractions away from historic old town and enjoy the great outdoors.

Stop by the Johns County Ocean Pier

St. Johns County Ocean Pier is a pier on St. Augustine Beach on the A1A Beach Boulevard. The pier area offers access to the beach, bathrooms, and splash park, and has free parking. There is a small fee to enter the pier. The end of the pier is a popular spot for fishing enthusiasts.

The area offers many dining options. I recommend lunch or early dinner at Salt Life Food Shack, right across the street from the pier on a way back downtown. The restaurant offers a great selection of seafood, an outdoor patio, two bars, and live music on weekends.

the Johns County Ocean Pier

Visit Fort Matanzas

Fort Matanzas is a national monument and is free to visit. It is located south of St. Augustine. The Spanish built Fort Matanzas in 1565 to keep the British away and establish their colony in Florida. The fort served an important role in defending the Florida coast and preventing enemies from invading St. Augustine.

You can only reach the fort by ferry. Tours are available from Wednesday to Sunday and can only be booked at the Visitor Center in person on the day of your visit. I recommend arriving early, as a limited number of visitors are allowed per ferry. Tours leave at 9:30 am, 10:30 am, 11:30 am, 1:30 pm, 2:30 pm and 3:30 pm. Tickets are first come, first served. I arrived around 9 and managed to get in the tour at 9:30. However, people at the end of the line had to wait for the next ferry.

If you happen to have to wait for the ferry, use your time to hike trails through the coastal forest and dunes. You can see a unique mix of plants adopting to the various conditions. You might even spot wildlife, such as bald eagles, pelicans, gopher tortoises, or ghost crabs, to name a few.

Take a walk on Crescent Beach

Crescent Beach, situated on Anastasia Island just south of St. Augustine, was my favorite beach. Extending as far as the eye can see, Crescent Beach was perfect for a peaceful stroll. I loved the wide shoreline perfectly reflecting the sky. The beach is free, dog friendly, and easily accessible by car, with parking available on the beach.

Crescent Beach in St. Augustine

Hike at Anastasia State Park

Enjoy the afternoon at Anastasia State Park, which is accessible with a small fee. It is a great place to enjoy the outdoors and walk off any extra calories after lunch. Anastasia State Park is especially popular with beachgoers. You can rent kayaks, stand up paddle boards, and bicycles here. There are hiking trails and camping as well.

Walk the Ancient Dunes Succession trail for 0.7 miles. The trail leads through shaded areas and provides informational signs about the variety of flora in the park. If you want to extend your walk, consider the 0.9-mile Marsh Trail, leading by the coastline with a view of the dunes in the distance. The trail is exposed, so wear sunscreen. This trail connects with restrooms and water sports rentals.

Shoreline at Anastasia State Park

Climb to the top of the St. Augustine Lighthouse

Climb 219 steps to the top of the lighthouse to enjoy the 360-degree views of the shoreline, port, and historic downtown. The St. Augustine Lighthouse, built in 1874, is the city’s oldest surviving brick structure.

While visiting the lighthouse, learn about its keepers and their families in the restored Keepers’ House. The site also features the Maritime Museum, where you can explore shipwreck artifacts and WWII exhibits from the time that the U.S. Coast Guard was stationed here. There is a small fee, but the views are worth the visit.

Drink from the Fountain of Youth

The Fountain of Youth Archeological Park is where the first European colony in North America was established by Spanish Admiral Pedro Menéndez de Avilés in 1565. In 1587, the first Franciscan mission, Nombre de Dios, was built here. Today, you can drink from the same spring that Juan Ponce de León and his men drank from in 1513 when they first discovered the place.

The Fountain of Youth Archeological Park is the oldest U.S. settlement. It is open to the public for a fee. It is a fun place to visit, full of history and daily demonstrations, including cannon shooting. There are  even peacocks wandering the grounds. It is a great place for family fun that’s also pet friendly.

Snap a selfie at Magnolia Ave

Stop by Magnolia Ave, considered one of the ten most beautiful streets in the U.S. by the National Geographic Society. Wander underneath majestic old oak trees covered in Spanish moss.

Note that this street is a part of a residential area. You will see locals engaging in daily activities such as jogging and walking their dogs. Be mindful as you stop by to take pictures. There is no parking except for residential parking on nearby streets. This is the same street where you will find the Fountain of Youth Archeological Park.

Oak tress covered in Spanish moss at Magnolia Avenue in St. Augustine

Catch a sunset at Vilano Beach

Get away from the busyness of the city by making your way to Vilano Beach. Vilano Beach is a coastal community located north from the historic old town on Matanzas Inlet. Enjoy a peaceful stroll on a public beach while listening to the sound of the waves. Due to strong currents, Vilano Beach is a perfect place for surfing.

You will also find a few small parks by Florida State Road A1A if you want to catch a sunset in a peaceful location. Note that some of them close at sunset.

Sunset at Vilano Beach

Logistics to plan your St. Augustine trip

How to get to St. Augustine

If you’re flying to Florida, the closest airport is Jacksonville, from which you’d need to drive about an hour south to reach St. Augustine. The second closest is Orlando. I recommend Orlando Sanford International Airport, as this one is located northwest of the city, an hour and forty minutes. If you plan to spend time in Orlando, check out my Budget Orlando vacation in Kissimmee post.

Best time to visit St. Augustine

  • Winter: If you’re planning to do a lot of walking, sightseeing, and outdoor activities, winter is the best time to visit. Although temperatures drop to the 40s during early mornings and evenings, throughout the day they reach up to 70° F.
  • Spring: March is spring break time, bringing lots of visitors eager to enjoy warmer weather and sunshine. April to May bring warmer weather that is perfect to enjoy a trip to the beach.
  • Summer: From June to August, expect hot weather, rain, and crowds. That’s also the beginning of the hurricane season that lasts until October.

How many days are enough for sightseeing St. Augustine?

If you’re in the area and have a day to spare, I would add St. Augustine to your itinerary. It is a fun and affordable city to visit. With many attractions close together, you can cover a lot in one day.

However, if you want to go to the beach and enjoy the great outdoors, I recommend at least two days. Even if you just want to spend time in historic downtown St. Augustine or sightsee at a slower pace, two to three days might be ideal.

Sunset at Nease Beachfront Park

How to navigate St. Augustine

When it comes to historic old town, St. Augustine is small enough to be easily manageable by foot. If you don’t want to walk, try the hop-on-hop-off trolleys. Trolleys cover all historic downtown points of interest included in this article and more. If you plan to go to the beach, a vehicle will be handy. Beaches come with free parking, and some of even let you park on the beach.

Where to park in St. Augustine

Parking in St. Augustine can be tricky. It gets busy quickly, especially on the weekends. If you don’t want to deal with searching for parking downtown St. Augustine, I recommend the St. Augustine Visitors Center. The parking garage offers 1,200 parking spots for a flat fee, and you can leave your car there for the day. Otherwise, except for selected attractions that offer parking, you will need to look for a spot and pay at the meter. If you pay at the meter, you can only park at that location for three hours. On Sunday, you don’t have to pay for parking if you manage to find a spot.

Where to stay in St. Augustine

St. Augustine is a small city. Where you stay depends on which attractions you are interested in. There are plenty of accommodation options, including hotels and vacation rentals.

I planned to sightsee the city, so I chose to stay near historic downtown in an Airbnb. The price was about the same as staying at a hotel. My accommodation came with a beautiful outdoor patio and a pool. The hosts were thoughtful and offered great recommendations.

Note that there is a 5% transient tourist tax imposed by St. Johns County that will be added to your bill. I was asked to pay the tax in cash.

St. Augustine airbnb rental


Visiting St. Augustine was fun. I found the town to be small enough that it was manageable to navigate and visit multiple attractions in a day. I even ventured outside the city to see what the surrounding areas had to offer. It was a perfect winter break to enjoy warmer weather.

I found 2 days in St. Augustine to be ideal for getting to know the city. However, I covered a lot of attractions in a short amount of time. Three days would have been more relaxing. You can definitely spend more time here as there is plenty to do, including free and paid attractions. If you have any questions, leave them in the comments.

Share your thoughts

Leave a Comment

Your email address will not be published. Required fields are marked *


  1. A.M. Charlebois
    July 10, 2022 at 15:34

    There is a fee to drive on the beach fromMarch 1 until Labor Day. It is Ten dollars or you can buy a seasonal pass, residents purchase this, I’m a resident.


    • Sylwia
      July 10, 2022 at 21:04

      Thanks for the info! I'm sure readers will appreciate an insider's input. :)


Related posts