3 Days in St. Augustine: The Perfect Itinerary for Florida’s Oldest City

Planning on spending 3 days in St. Augustine and need an itinerary? I’ve been numerous times since I live fairly close and I love this charming historic town. Regardless of when you visit, there is history, small town charm, beaches and nature that can fill your 3 day itinerary!

This 3 day St. Augustine itinerary is easy to tailor to your preferences, includes tour suggestions, and offers restaurants to consider. Let’s help you plan a great trip the oldest city!

Quick Itinerary Overview

Here’s a quick look at the 3 day itinerary for St. Augustine. It focuses on the historic downtown, giving time to stroll along the cobblestone streets, visit the top sites, and enjoy the food scene! There is also a day focused on nature and wildlife, giving a well rounded St. Augustine experience.

Day	Theme	Highlights	Where to Eat
Day 1 – Historic Charm & Iconic Landmarks	Explore the heart of the old city	Castillo de San Marcos • Fountain of Youth • Magnolia Avenue • St. George Street • Oldest Wooden Schoolhouse	☕ Breakfast: The Kookaburra or Maple Street Biscuit Co. 🍽️ Lunch:Juniper Market or The Columbia 🌅 Dinner: Raintree, Catch 27, or Harry’s Seafood
Day 2 – Culture, Hidden Gems & Relaxation	Dive deeper into St. Augustine’s art, history & food	Lightner Museum • Flagler College • St. Augustine Distillery • San Sebastian Winery	☕ Breakfast: Ragga Surf Café or Southern Grounds 🍽️ Lunch: La Cocina or St. Augustine Fish Camp 🌇 Dinner: Ice Plant Bar or Forgotten Tonic
Day 3 – Nature, Ocean & Local Flavor	Enjoy the outdoors and coastal side of the city	Anastasia State Park • Alligator Farm • Kayak or Boat Tour	☕ Breakfast: Beachside Diner or Zaba’s 🍽️ Lunch: Osprey Tacos or Kusina Colorado 🌅 Dinner: Llama Restaurant, Asado Life, or Beaches at Vilano

Day 1 – Historic Charm & Iconic Landmarks

Your first day in St. Augustine will focus on the main sites! If you only had 1 day in St. Augustine, these stops would be the focus. It will give you a good overview of the history of St. Augustine, while also enjoying the charm of the downtown.

The beauty of having 3 days in St. Augustine is you won’t have to rush while enjoying your time in the oldest city in the United States.

Breakfast

If you’re not staying at a B&B or your hotel doesn’t offer free breakfast, let’s review some options! I recommend having breakfast in the historic area today so you can find parking easily in the morning, if you are not staying in this area.

For coffee and a lighter breakfast, I love The Kookaburra! It’s an Aussie themed coffee shop that’s been around for years and now has multiple locations across St. Augustine, including downtown! They have great coffee and egg or meat pies.

Maple Street Biscuit Company is another good option to consider. I love a biscuit sandwich and that is what Maple Street offers! They are just on the edge of the main historic downtown area (not far from Columbia Restaurant) so you can walk to it if you’re staying in the historic area.

For a nicer option, consider Harbor View Café. They open at 7AM which allows you to get to the fort when it opens at 9AM.

Today the focus is on the historic and main sites of St. Augustine. While a tour is not necessary, it can offer interesting information and easy access to some stops further away. The St. Augustine Hop-On Hop-Off Trolley Tour can be purchased for one or two days, making it a great tour to consider.

Castillo de San Marcos

The Castillo de San Marcos opens at 9AM and I recommend getting there in the morning since it’s not shaded. Most people spend about an hour here, so it won’t take a huge chunk of your day.

If you’re visiting on a weekend day, definitely try and plan around the historical weapons demonstrations. Their website will have the latest information on times, but 10:30AM is the typical first demonstration of the day.

I recommend arriving before to enjoy the fort before it gets super crowded and then enjoy the demonstrations after.

Magnolia Avenue

This beautiful street is right next to the Fountain of Youth Park, making it an obvious stop before or after your visit. There’s limited parking on this oak lined street, so it’s worth just walking from the Fountain of Youth parking lot.

This road is “one of the most photographed streets in the United States” and offers a beautiful canopy of oak trees. It’s not a long stop, but worth admiring while you’re there.

Ponce de Leon’s Fountain of Youth Archaeological Park

Your next stop can be the Fountain of Youth if it’s a nice day. Most of the exploration here is outdoors, but there is some shade unlike at the fort. However, if it’s rainy or super hot, consider making this a 9AM stop on another day.

Ponce de Leon’s Fountain of Youth Archaeological Park is said to be the site where Ponce de León searched for the legendary spring of eternal youth. Beyond the myth, the park is peaceful and surprisingly scenic, with live peacocks wandering around, shaded walking paths, and views over the Matanzas River.

I visited this park again as an adult and found it very interesting. It’s definitely a worthwhile stop on your 3 days in St. Augustine. Most people spend a couple hours here, so give yourself enough time to enjoy the park.

The Old Senator Tree

Only a five minute walk or two minute drive, you will find the Old Senator. It’s an oak tree estimated to be over 600 years, so it’s seen St. Augustine through a lot! This isn’t a long stop, but worth it while you’re in the area!

Lunch

For a lighter lunch, head to Sunday or Juniper Market. If you’re walking, both sit between the Fountain of Youth and the historic downtown.

Sunday is a bright, modern spot in St. Augustine with fresh, seasonal ingredients. They offer creative brunch dishes, locally sourced produce, and a relaxed, welcoming vibe.

Juniper Market is a cozy, farm-to-table café and market offering hearty breakfast and lunch options, artisanal baked goods, and locally roasted coffee. It’s perfect for a casual, flavorful stop while exploring the city.

For an option in the historic downtown, consider The Columbia. It serves authentic Spanish cuisine in a beautiful, old-world setting. Known for its signature 1905 Salad, rich paellas, and classic Cuban sandwiches, it’s a must-visit for anyone wanting a taste of Florida’s culinary history.

I’ve been to The Columbia in St. Augustine and to their Celebration location (one of the best areas to stay near Disney) and enjoyed it. It’s worth trying while in St. Augustine! If you’re walking, it’s about 19 minutes from the Old Senator tree, but it sits at the end of St. George street which is perfect for your afternoon stroll.

Stroll St. George Street

Spend some time after lunch strolling down St. George street, which is one of the best things to do in St. Augustine in 3 days. Enjoy the cafes, shops, and colonial architecture. Of course, don’t stick to just St. George as this entire historical downtown has charm around every corner.

I’ll list some highlights in this area and you’ll soon realize this small zone packs a punch!

Museums

Make a stop at the Oldest Wooden Schoolhouse. There is a small fee, but it’s definitely worth doing at least once during your 3 days in St. Augustine.

Not far from the Old Wooden Schoolhouse on A1A is the St. Augustine Pirate & Treasure Museum. My friend said she took her sons when they were younger and they enjoyed it!

Another museum in this area worth considering is Colonial Quarter, living-history museum tracing early St. Augustine life.

Sweet Treats

For sweet treats stop at Le Macaron for a French dessert. The Hyppo Gourmet Ice Pops are a delicious fruit ice pops. I love the coconut one, but they have so many great flavors!

For gelato, head to Café Del Hidalgo- Ice Cream, Food, And Drink and for chocolate, Kilwins Ice Cream – Chocolate – Fudge is worth checking out!

Off of St. George Street you can try to Cousteau’s Waffle and Milkshake Bar or Peace, Love and Little Donuts of St. Augustine for delicious donuts.

Ice cream will always be my favorite dessert and Castillo Ice Cream and Coffee is highly rated.

Beverages

For more on St. George Street, stop at Savannah Bee Company and try honey mead or enjoy a cocktail or mocktail at Prohibition Kitchen. Head to The Tini Martini Bar for a martini with bay views.

If you need a pick me up, head to Myth & Legend. It’s a coffee shop I tried on a recent visit and loved. Of course, The Kookaburra Downtown is always a favorite stop for me! Crucial Coffee Café offers coffee in a historical, wooden building which really fits the vibes.

Sunset

I love chasing a sunset when on vacation, and this 3-day St. Augustine travel guide wouldn’t be complete without mentioning it. Some of my favorite memories are watching the sun disappear over the horizon when on vacation (looking at you, Tinos).

St. Augustine is on the east coast, so the sunset isn’t the flex as much as the sunrise, but with the bay and river views, it’s still worth enjoying!

For your first day in St. Augustine, head to the Bridge of Lions, enjoy an evening stroll and watch the sunset. You can enjoy the views of downtown St. Augustine and the fort while the sun is setting.

Dinner

You won’t be lacking for dinner options in the historic downtown area, but here are a few to consider.

Raintree Restaurant is set in a beautifully restored 19th-century Victorian home, offering a relaxed, yet upscale dinner. Just be advised it’s just beyond the historic downtown (15 minute walk from the fort), which is important to know if you didn’t rent a car.

Both of the below seafood options are in the historic downtown and especially easy to get to if you’re staying in this area.

Catch 27 specializes in fresh, locally caught seafood prepared with a modern Florida twist, served in a cozy, coastal-style setting that feels both refined and laid-back.

Harry’s Seafood Bar & Grille brings New Orleans flair to the heart of St. Augustine, with Creole favorites, live music, and a lively patio that’s especially charming in the evening.

After Dinner Options

If you’re not ready to end the night, here are some options to consider.

For drinks, head to Prohibition Kitchen or Forgotten Tonic. On the bay you have The Tini Martini Bar or Meehan’s Irish Pub & Seafood House. For music and drinks, Trade Winds Lounge is worth considering.

If it’s Christmas in St. Augustine, definitely stroll and enjoy the lights. If you’re done with walking, book a golf cart or boat tour!

If you’re into haunted tours, St. Augustine offers those as well. St. Augustine Ghost Tour: A Ghostly Encounter has great reviews.

Day 2 – Culture, Hidden Gems & Relaxation

I’m making day two more of the historic downtown area, in case you purchased the two day hop-on, hop-off trolley. If you want a break from the historic downtown, do day three today and save this for your last day.

Breakfast

Breakfast options to consider today, if your accommodations don’t offer free breakfast include Ragga Surf Cafe. It’s a food truck on the San Sebastian River, with outdoor seating. It has 5 stars and over 500 reviews, so it’s worth checking out during your 3 days in St. Augustine.

Southern Grounds & Co. is another good, casual spot to consider for breakfast and The French Pantry – St. Augustine is a great option to consider for breakfast or lunch!

Lightner Museum

Let’s start the day by heading to Lightner Museum. It is housed in the old Hotel Alcazar and includes Gilded Age artifacts, Victorian glassware, and decorative arts.

There is a fee to visit this museum, so if you’re not into museums, I’ll offer a tour option to consider!

Flagler College

Explore Flagler College after spending some time at the Lightner Museum. It’s right across the street, so it’s an easy add-on. You can book their walking tour for a fee, or simply walk around the lobby and courtyard on your own.

Lunch

For lunch consider La Cocina at the Cellar Upstairs, which is on the second floor of San Sebastian Winery. It’s perfect if you’re wanting to add some wine tasting to your day!

Another option in this area is St. Augustine Fish Camp. It’s highly rated and on the river, offering beautiful views.

Of course, by this point you are aware of the many options you have in the historic downtown, so pick whatever you’re in the mood for and you’ll probably find an option!

More History & Tastings

St. Augustine has plenty of museums, but if you want a change of pace, consider a wine tasting at San Sebastian or bourbon tasting at the St. Augustine Distillery!

You can also do a chocolate tasting at Whetstone Chocolates Store and Tasting Tour.

Consider booking an afternoon tea at The Chatsworth Pub and Tea Room. I have enjoyed an afternoon tea in London and Montreal and LOVED both times! If you do want to enjoy tea time, be sure to book days in advance and eat a lighter lunch!

For more history, head to the Oldest House Museum Complex. You can tour Florida’s oldest Spanish Colonial house. There is a fee and the complex is open until 5PM, making it a good afternoon stop.

I haven’t tried San Sebastian, but I have enjoyed the bourbon tasting at St. Augustine Distillery. The building itself is so cool and it houses my favorite restaurant, Ice Plant Bar, which I recommend for dinner. The distillery closes at 6PM, so come around 5PM and then stay for dinner at the Ice Plant Bar.

Dinner

I recommend Ice Plant Bar! I’ve been twice and loved it both times! My foodie brother-in-law mentioned he loved it, so I was excited to try it! I took some friends there recently and they also loved it!

Go around 5PM to enjoy the bourbon tasting at the distillery which closes at 6PM. If it’s a weekend, I recommend making a reservation at the Ice Plant Bar.

Another option to consider is Forgotten Tonic or any of the many great options in St. Augustine! Truly, you will not be lacking for options.

Evening Options

Consider a Blood On The Cobblestones True Crime Tour of St Augustine. It’s a pub crawl meets true crime! Tour starts at 8PM, which is perfect for an after dinner event.

If you’re visiting for Nights of Lights, be sure to enjoy it! Stroll on your own or book a golf cart or boat tour if you didn’t last night!

It’s also beautiful to stroll by the bay and the fort at night. The lights reflecting off the water offers such a peaceful escape.

Day 3 – Nature, Ocean, and Local Flavor

Today will be a nature focused day! While the historic downtown is sandwiched between two rivers, the beach is not far. This geography really makes St. Augustine a year round destination, even though the summers can be brutal!

No matter the time of year you are visiting St. Augustine you can enjoy the nature it offers. While I wouldn’t swim in the ocean in the winter, there are still opportunities to walk or paddle and enjoy the beauty around you.

If you want to simply enjoy a beach day, that is a great option for today! The below is an itinerary that could be utilized any time of year.

Breakfast

For breakfast, head to Beachside Diner for an American style breakfast in a classic diner feel. It has great reviews and offers a quality standard breakfast.

For a quality, hole in the wall, head to Zaba’s. What it doesn’t offer in ambience, it makes up for in service and a local feel.

The previous options are in St. Augustine Beach area, but if you want something near the historic area consider Cornerstone Cafe. It’s on the lighter end with breakfast sandwiches and coffee.

Anastasia State Park

When it comes to nature, you don’t have to go far! A five minute drive from the historic downtown of St. Augustine will bring you to the entrance of Anastasia State Park. You can visit this state park on your own, or a book a tour of the waterway.

If you’d prefer to explore on your own, you can rent bikes or kayaks inside the park, or simply walk the trails or beach! I’ve camped here before and had a great experience. The campsites aren’t on the beach, but they are close.

If you rent kayaks, be sure to check the tide schedule. While I recommend getting to the park early, especially on the weekends, you may want to ensure the conditions will match your expectations. Low tide can limit where you go, but will give you more sandbars.

Discuss the current tide and conditions before renting at the concession stand. One reviewer mentioned this frustration so it’s good to consider.

Tip: There is a small entrance fee and it can get busy on the weekends, so go early!

Book a Kayak Tour of Anastasia

If you want to paddle, but a self guided kayak doesn’t appeal to you, there are tours you can book that will take you through this waterway! Dolphin, Manatee and SeaTurtle SUP Adventure Tour of St Augustine is highly rated, offers three different tour times, and you can choose between a kayak or SUP.

Most wildlife sightings have higher likelihood in the morning, so I do recommend choosing one of the morning time slots.

Book the Dolphin, Manatee and SeaTurtle SUP Adventure

Boat Tour

If you’d prefer a more leisurely tour, this Dolphin and Wildlife History Tour on a boat is for you! You will possibly get to see wildlife (never a guarantee with wild animals) while passing sites like the St Augustine Lighthouse, Bridge of Lions, the Fort, and The Great Cross.

Book the Dolphin and Wildlife History Tour

Lunch

For a delicious taco lunch nearby, head to Osprey Tacos. It’s highly rated and I can confirm it’s delicious! I visited for lunch on a Sunday afternoon when I was in town and enjoyed it!

If you want a light lunch that’s not tacos, consider Une Autre Histoire La French Bakery. It offers delicious croissant sandwiches and French pastries!

While the two options above are casual and it’s Florida (always casual), there is a delicious food truck near to Anastasia State Park. Kusina Colorado is a food truck offering flavorful Filipino comfort food made from scratch.

Of course, if this doesn’t appeal to everyone, all is not lost since it’s part of The Village Garden Food Truck Park, Florida and everyone can find something they want to eat!

Wildlife Park

The St. Augustine Alligator Farm Zoological Park is a must-visit for wildlife enthusiasts, featuring alligators and crocodiles from around the world, plus exotic birds, reptiles, and fun interactive exhibits. Guests can watch thrilling feeding demonstrations, stroll along boardwalks through natural habitats, and even try the zipline over the alligator enclosures if you’re feeling adventurous.

There is extra fees for the zipline experiences or special animal encounters. The reviews are overwhelmingly positive for this alligator farm, so it makes a great afternoon experience!

Dinner

Llama Restaurant offers Peruvian-inspired cuisine with bold flavors and creative dishes, from ceviche to roasted meats. It’s not far from the Alligator farm or Anastasia State Park, but is one of the most popular restaurants in St. Augustine.

Asado Life is a cozy, South American grill specializing in authentic Argentine-style meats in a relaxed setting. It’s on the San Sebastian River and about a 7 minute drive from the historic downtown and 9 minutes from the Alligator Farm.

Beaches at Vilano is a river front eatery serving casual American fare. It’s ideal for a laid-back dinner and perfect if you are able to catch the sunset! It’s in Vilano Beach so it’s about 13 minutes by car from the Alligator Farm.

Forgotten Tonic is a lively, modern restaurant and bar known for craft cocktails, small plates, and elevated comfort food. With a stylish interior and fun, social vibe, it’s a great spot for dinner and drinks in the historic downtown.

Where to Stay in St. Augustine

If you’re looking for more detailed breakdowns of where to stay in St. Augustine, I have a post dedicated to that topic. While it’s centered around Christmas in St. Augustine, the hotel recommendations include inside the historic downtown as well as the surrounding area.

LUXURY Casa Monica Resort & Spa

B&B The Kenwood Inn Oldest Bed and Breakfast

MID-RANGE Hotel Amalga, St. Augustine, A Tribute Portfolio Hotel

BUDGET The Local – St. Augustine

OCEAN VIEWS Embassy Suites St Augustine Beach Oceanfront Resort

For detailed explanations of where to stay checkout my post:
Where to Stay in St. Augustine for Christmas: Best Areas & Festive Hotels

How to Get Around St. Augustine

One of the best things about St. Augustine is how easy it is to explore. The historic district is completely walkable, and wandering its cobblestone streets is part of the charm. You’ll find most major attractions — like Castillo de San Marcos, Flagler College, and the Lightner Museum — within a few blocks of each other.

If you’d rather save your steps (or the heat’s getting to you), the Old Town Trolley offers hop-on, hop-off passes that stop at all the main sights. Parking can be tricky downtown, so many visitors leave their car in the main parking garage by the Visitor Information Center and explore from there.

For beach days or spots across the bridge — like the St. Augustine Lighthouse or Anastasia State Park — it’s easiest to drive or grab an Uber. You can also consider renting a bike or e-scooter which could be a fun way to get around while soaking up those Old Florida vibes.

Tips for Visiting St. Augustine

Here are some quick tips for your 3 days in St. Augustine.

• Wear comfy shoes. St. Augustine is super walkable, especially around the historic district — but those cobblestone streets can be tough in sandals.
• Start early (on weekends). Popular spots like Castillo de San Marcos and St. George Street get busy fast, so mornings are your friend.
• Plan for parking. The main parking garage near the Visitor Information Center is your best bet if you’re exploring downtown on a weekend. Otherwise, keep an eye out for metered spots and smaller lots.
• Take the trolley if you’re short on time. It’s a fun way to see the highlights without worrying about parking, and you can hop on and off all day.
• Stay hydrated and bring sunscreen. Even in winter, the Florida sun can surprise you — especially if you’re walking from the fort to the Fountain of Youth or on the beach.
• Book popular restaurants in advance. Spots like The Columbia and Catch 27 fill up quickly, especially on weekends.
• Don’t skip sunset. Whether you watch from the bayfront near the Bridge of Lions or over the river at Vilano, St. Augustine sunsets are magic and those vacation sunsets always hit.

Tours for Your 3 Days in St. Augustine

Historic & Sightseeing Tours

• Old Town Trolley – Hop-On Hop-Off Tour (1 or 2 day option)
• Guided Historical Tour of St. Augustine (Golf Cart)
• Walking History Tour of St. Augustine’s Historic District
• Flagler College Walking Tour (official tour from the college)

Themed & Specialty Tours

• St. Augustine’s Sweets & History Walking Tour
• Blood on the Cobblestones: True Crime Pub Crawl Tour
• St. Augustine Ghost Tour: A Ghostly Encounter

Nature, Wildlife & Water Tours

• Dolphin, Manatee & Sea Turtle SUP/Kayak Adventure Tour of St. Augustine
• Dolphin and Wildlife History Boat Tour

Christmas / Nights of Lights Tours

• Golf Cart Nights of Lights Tour
• Boat Nights of Lights Tour

Day Trip Ideas from St. Augustine

If you’ve been before or only want to spend one day in St. Augustine exploring the historic downtown, I have some day trips for you to consider adding to your 3 days in St. Augustine itinerary.

Jacksonville (45 minutes)

Great for museums, the Cummer Museum gardens, Riverside dining, the Jacksonville Zoo, and beaches like Jacksonville Beach & Neptune Beach.

I don’t visit zoos often, but I’ve seen the Land of the Tiger at Jacksonville Zoo make the top 10 for the country!

Jacksonville also has good shopping. Their Ikea that is way less busy than Orlando’s, and St. Johns Town Center is my friend’s favorite shopping area in Florida.

Amelia Island & Fernandina Beach (1 hour)

A charming coastal town with Victorian architecture, Fort Clinch State Park, quiet beaches, and great seafood.

Daytona Beach (1 hour)

Famous hard-packed beaches, the Boardwalk, Ponce Inlet Lighthouse, and historic spots like The Casements (Rockefeller’s winter home).

I just visited the Casements and loved it! The free tour was excellent (donations welcome), and Ormond is charming! The Ponce Inlet Lighthouse is the biggest one in Florida, and the fee to visit is minimal.

Of course, if you’re looking for a Daytona Beach itinerary, I’ve got you covered! From the lighthouse, to historic homes, or visiting the Daytona Speedway, Daytona has variety to offer.

Blue Spring State Park (1 hour 15 minutes)

One of the best places to see manatees in the winter; also great for kayaking, swimming (in summer), and nature walks.

Orlando (2 hours)

If someone wants a theme-park day, Disney + Universal are doable. Downtown Winter Park or Lake Eola are great non-park options.

Ocala National Forest (1 hour 30 minutes)

Beautiful springs (Juniper, Alexander, Silver Glen), shaded hiking, and lots of freshwater swimming. If it’s winter, consider Silver Springs and their famous glass bottom boat tours.

Small Town Hopping

Green Cove Springs (45 minutes) is peaceful riverfront town with historic buildings, and scenic St. Johns River views.

Flagler Beach is a cute beach town near Palm Coast. I love visiting Flagler, though it has grown a lot in recent years. They have some good restaurants, so it would be a good lunch spot!

For things to do in DeLand (80 minutes), you can walk the cute downtown, stroll around the beautiful campus of Stetson, or even skydive!

FAQ

3 Days in St. Augustine

I hope this article was helpful for planning your 3 days in St. Augustine! The oldest city has charm, history, and amazing restaurants! Of course, beaches and nature are just minutes away, making it a great destination year round!

If you need more help in planning your Florida trip, I have more to share from my home state! I hope you have the best time in St. Augustine and enjoy your Florida trip!