Weekend in St. Augustine Itinerary

Take the Trolley to St. George Street

Whether you take the Trolley or walk, I suggest starting off at St. George Street, which many consider the heart of the city. Down the street, you will see the Old City Gates, the Oldest Wooden Schoolhouse, the Colonial Spanish Quarter, dozens of shops, and restaurants.

As you go through, you will also come across tons of sweet treats, including ice cream and fudge. It is one of the best-smelling alleys I’ve ever walked through.

Aside from the food, the Oldest Wooden Schoolhouse, Cathedral Basilica of St. Augustine, and Constitution Monument are the most popular attractions on the strip.

The Wooden Schoolhouse

Inside the Wooden Schoolhouse and Garden, you will learn about the Genopoly Homestead. The owner, Juan Genopoly, opened his home to teach reading, writing, and arithmetic to Minorcan Quarter residents.

This preserved space has been designed to reflect the school in the 1800s, bringing visitors back in time while learning about this historic gem.

Cathedral Basilica of St. Augustine

This historic cathedral was built in 1793 and opened its doors in 1797 after the Spanish took this area back over from Britain. While the inside is nothing you’d expect to see in Europe, it was the first Parish church in the States and a U.S. National Historic Landmark.

Aviles Street

One street over from St. George Street, you will find Aviles St. which is considered to be the oldest street in the USA. This charming street is known as St. Augustine’s art district, but it was originally known as “the hospital” street because this is where The Spanish Military Hospital was located. Now you can even visit the museum.

Plaza de la Constitución

Once you reach the end of St. George Street, you will be looking right at Plaza de la Constitución. Known as the oldest public space in the USA, you should certainly add a stop during your weekend in St. Augustine itinerary.

The square was laid out by the Spanish back in 1573, and the constitution monument at the center of the square is considered one of the only monuments remaining in the Western Hemisphere. The plaza has also been registered as a National Historic Landmark.

The plaza still acts as a meeting place and hosts events throughout the year. One of the largest events happens during the holidays, called Nights of Lights, where the plaza gets decked with Christmas lights.

Castillo de San Marcos National Monument

Hop back on the Trolley and get off at Castillo de San Maros, the oldest masonry fort in the Continental United States. This fort played an integral part in protecting the city from attack.

It is most popular to visit the fort over the weekend because this is when they do a live demonstration of firing the cannon. You don’t even have to enter the fort to enjoy it. They fire cannons or muskets at 10:30 AM, 11:30 AM, 1:30 PM, 2:30 PM, and 3:30 PM.

Castillo de San Marcos is a part of the National Park Service, so if you are a pass holder, you can enter with your pass. There are also Ranger-led programs.

The Fort has a ton of history inside the Coquina walls. When visiting, the views from the top overlook Matanzas Bay and the Bridge of Lions. You will also find old cannons and other recreations of sleeping quarters inside.

Across the street from the fort, you will also find a ton of restaurants and cafes.

Fun Fact: The British sieged the fort twice and retreated but were able to occupy the fort due to the Treaty of Paris in 1763. However, after the war, it was handed back to the Spanish until the Americans took it.

Flagler College (Timed Ticket Needed)

Next, take the Trolley to Flagler College. You need a timed ticket entry to visit, so plan your day accordingly. The Flagler College is one of the most popular attractions in St. Augustine, and it is done by group tour only.

The tour brings you through what was once the Ponce de Leon Hotel, built by no other than Henry M. Flagler. In fact, you will hear his name a lot during your visit, as this oil and railroad tycoon invested and spent a lot of money in this area. He is even considered to be the founder of Palm Beach and Miami.

The tour brings you through several rooms that include beautiful art, architecture, and original furniture. You can expect to spend a little over an hour here.

Optional St. Augustine Attractions For Day 1

Most of St. Augustine’s attractions are paid for, and they really start to add up, so you may want to consider some over others.

If you’re a group of adults, you may consider adding the St. Augustine Distillery and the San Sebastian Winery. Both have Trolley stops and are located in historic buildings while enjoying a local taste of Florida!

If you’re traveling as a family, you may consider Whetstone Chocolates of St. Augustine, Ripley’s Believe It or Not!, and St. Augustine Pirate & Treasure Museum, which are also trolley stops. The Old Town Jail Museum at the Old Town Trolley is also very cute for kids and even funny for adults.

Moreover, if you ride the trolley all the way through, you will also see a 600-year-old oak tree (The Old Senator), the Oldest House, and Villa Zorayda.

Fountain of Youth Archaeological Park

If you still have time left in the day, end it with the Fountain of Youth! If not, you can add this to your 2nd or 3rd day. I am not going to lie, the Fountain of Youth feels touristy, but it is still a unique place to visit.

If you’re traveling with kids, I think it’s great. They have live demonstrations throughout the complex where you can learn more about how blacksmiths would have made tools, cannons, and about the Chalupa boats. There are also nice views from the Spanish Lookout and Founders Riverwalk.

The actual fountain of youth is much smaller than I expected, but you can actually take a cup and have a drink from this natural fountain. Get ready to live forever, lol.

St. Augustine is most famously known as the oldest city in the United States, being founded by the Spanish, but long before the Spanish arrived, the Timucua Indians occupied these lands. At the Fountain of Youth, they pay tribute to the natives and include artifacts found here from these ancient tribes.

The Fountain of Youth is also located on Magnolia Avenue, known as one of the most beautiful streets in the USA.

Fun Fact: Ponce de Leon believed he landed on an island and named the “new land” La Florida because it was during the Festival of Flowers at Easter time.

They also have BBQ and drinks on the site, along with a free restroom.

---

Day 2: Anastasia Island

After a fun-filled day exploring St. Augustine’s historic district, dedicate this day to beach time and nature.

Anastasia State Park

Known for 1,600 acres of beaches, ancient dunes, and woodlands, Anastasia State Park should certainly be a part of any weekend in St. Augustine itinerary.

Relax on the beach, hike through the Ancient Dunes, or enjoy several water sports, including paddleboarding and kayaking, while there. Rentals are available inside the park at Anastasia Watersports.

If you didn’t pack enough in your cooler, you can always visit Island Beach Shop and Grill, for a quick bite.

The park also includes campgrounds for the adventurous type.

Related: Ultimate Beach Packing List

St Augustine Lighthouse & Maritime Museum

After getting enough “vitamin-SEA,” make your way over to the St. Augustine Lighthouse nearby. Here, you can climb 219 steps to the top of the lighthouse. Standing at 165 feet high, the lighthouse offers some incredible coastal views.

After climbing to the top of the lighthouse, explore the Nation’s oldest port with gardens and several exhibits, including underwater archeology, the shrimping business, boat building, learning about shipwrecks, and St. Augustine’s role in WWII.

Furthermore, they also offer additional experiences and tours such as Lighthouse Ghost Tales and Lighthouse Keeper’s Tour. You can purchase these on their official website in advance.

Travel Tip: While in the area, consider grabbing some food or a drink at The Conch House Restaurant, a very popular and unique joint on the water. Seating is on a first-come, first-serve basis.

St. Augustine Alligator Farm Zoological Park (Optional)

I am being honest with you; zoos are not my thing. However, I know the alligator farm is a hot attraction in the city, so it felt wrong not letting you know about the option. Plus, this St. Augustine itinerary is not about me, but about helping you plan a fun trip.

The Zoo is also located near the Lighthouse, so it makes sense to do them both on the same day. During a visit, you can expect to see tons of gators, wildlife shows, and other zoo animals, including African birds, sloths, and other exotic birds and mammals.

Afternoon Options

For an afternoon activity, consider a sunset cruise or boat tour down the coast. There are a handful of really lovely cruises and tours to choose from. We really enjoyed seeing the city from the water.

If being on a boat is not your jam, consider enjoying the sunset at the St. Augustine Beach, walking the pier, or even participating in a Ghost tour.

---

Day 3: Beaches or Day Trip

If you have 3 days, you have some options. If the weather is nice, I would suggest visiting another beach in St. Augustine. You can also head back downtown and visit any attractions you missed on your first day.

Or, you can take a day trip to a nearby city. I will go into more depth below! Decisions, decisions, lol.

St. Augustine Beaches

You really can’t go wrong with a beach day in St. Augustine. Some of my favorite beaches to visit include:

• Vilano Beach (dog-friendly)
• Saint Augustine Beach (has a pier and food)
• Mickler’s Landing Beach (dog-friendly near Ponte Vedra on the A1A Scenic & Historic Coastal Byway)

While on the beach, you may see sea turtle nests roped off, so be careful.

Downtown St. Augustine – Lightner Museum

One place we didn’t explore during our first day in St. Augustine is the Lightner Museum – but I think it is worth adding to your itinerary if you’re interested in art. To be honest, I think I enjoyed it more than Flagler College.

This museum is located in the former Hotel Alcazar, which was also built by Henery Flagler. Then, in 1948, a collector named Otto Lightner turned it into a museum.

The museum has 3 floors where you you will view a vast collection of furniture, music instruments, antiques, and new and changing art exhibitions. They also highlight the former hotel with rooms like the Turkish and Russian Bath.

This stunning building even used to have an indoor pool that is now used as a dining room.

If nothing else, the outside of the building and the fountain are very pretty to sit by if you don’t go inside.

Day Trip From St. Augustine

Day trips from St. Augustine are not uncommon, especially if you’re not visiting the city during the summer. Some of the top day trips to consider that are under 2 hours from the city include:

• Fort Matanzas National Monument – A 1742 coquina watchtower run by the National Park Service. You can only reach it by ferry, and it’s free. It is closed on Monday & Tuesday. Tickets are first come, first serve (get here early)!
• Orlando – Just under 2 hours from St. Augustine and a perfect day trip for those wanting to visit Universal Studios and/or Disney.
• Jacksonville – Just North of St. Augustine (approx 1 hour), Jacksonville is a lively city with art museums, botanical gardens, and Little Talbot Island State Park
• Daytona Beach – A hot spot for those interested in NASCAR, or families looking to enjoy amusement rides on the beach boardwalk – it’s the best of both worlds.
• Silver Glen Springs – A really cool and popular hot spring not too far from St. Augustine in Ocala. We saw manatees and alligators kayaking.

---

Best Time To Visit

The best time to visit St. Augustine is during the late Spring and early Fall. This will still allow you to enjoy the beaches without overwhelming hot days.

We have been during the summer many times, and I don’t mind the heat, but I know many do.

If you’re searching for a warm winter getaway, St. Augustine has the Nights of Lights that starts in Mid- November through the last week in January. During this time, the city will be lit with over 3 million lights.

If the beach is not a main component, March through May have pleasant weather and few crowds.

---

Major Saint Augustine Events

When planning a weekend in St. Augustine, knowing when some of the major events in the city can be important for planning a trip. Visiting during these events will result in larger crowds and require you to book accommodations in advance.

• The Players Championship Golf Tournament – March
• Drake’s Raid (a re-creation of the 1586 attack on the city) – April
• Florida’s Birding and Photo Fest (over 110 photography workshops) – last week in April
• Gamble Rogers Folk Festival (live music) – first week in May
• Fourth of July (live music and fireworks at the plaza)
• City of St. Augustine Birthday Celebration (August & September)
• Sing Out Loud Festival (one of the largest free music festivals in Florida) September
• Greek Festival – October
• Colonial Night Watch Weekend (recreation of the 1740 siege and torchlight parade – early December
• Nights of Lights (3 million+ Christmas lights) – mid-November – January (city is very crowded)

---

---

Where to Stay

Don’t know where to stay in St. Augustine? I have vetted out the below hotels that are centralized and have great reviews. If you want a more in-depth guide with pictures and links, here is my guide on the top 10 best hotels in St. Augustine!

• Casa Monica Resort & Spa, Autograph Collection
• Renaissance St. Augustine Historic Downtown Hotel
• St George Inn – Saint Augustine
• Casa De Solana & Victorian House Bed and Breakfast

---

How to get To St. Augustine

If you plan to fly to St. Augustine, Florida, you will likely fly into Jacksonville International Airport (JAX). St. Augustine does have some regional airports, but the chances of you scoring a good flight to one of them are rare.

From the Jacksonville Airport, it is just a little over an hour to Downtown St. Augustine.

If you decide to rent a car, you should look to pick up and return from this airport as well.

St. Augustine is also close to a lot of major cities, so a road trip is another great option for visiting the Historic Coast.

---

How Many Days Do You Need?

Ideally, you need at least 2 to 3 days to explore the top attractions in St. Augustine, making this destination perfect for a weekend getaway.

If you want more time to spend at the beach, you may consider adding an extra day of relaxation.

Is St. Augustine Worth Visiting

With pristine beaches, a great food scene, art, and history, St. Augustine is certainly worth visiting.

Founded in 1565 by Pedro Menéndez de Avilés and his Spanish explorers, it is known as the oldest continuously inhabited European-established settlement in the USA. St. Augustine is also home to the Fountain of Youth.

Moreover, Jacksonville, Daytona, Orlando, Ocala National Forest, and Gainesville are all nearby points of interest for an extended Florida vacation.

---

Weekend in St. Augustine (2-3 Days) Wrap-up

This concludes how to spend a weekend in St. Augustine. As you can see, the city has a lot to offer. I hope you have the best time exploring the Historic Coast!

Do you need additional help or have any questions about this itinerary? Reach out in the comments below, via email, or social media.

If you found this Guide helpful, I’d appreciate it if you could share it below!