St. Augustine, Florida was always on my husband’s and my travel bucket list. We had wanted to visit the oldest continuously inhabited European-establishment in the United States and see that history for ourselves. So, we turned it into an easy road trip from our home base in Miami and drove north for about 4.5 hours along the Florida coast. Visiting around Christmastime made it even more special, with the historic district glowing during Nights of Lights, but this is the kind of destination that works year-round.
Founded in 1565 by Spanish admiral Pedro Menendez de Aviles, and long before Florida became what most people picture today, this stretch of coast was already fortified, mapped, and fought over. You feel that history immediately in historic St. Augustine as you see the stone walls of Castillo de San Marcos to the narrow brick streets that still follow a colonial grid.
St. Augustine is compact, walkable, and full of real history, not replicas. You can explore centuries-old landmarks in the morning, wander St. George Street in the afternoon, and catch the sunset by the water without ever needing your car. If you’re planning a weekend in St. Augustine, it delivers culture, architecture, coastal views, and just enough atmosphere to feel different from the rest of Florida.
If you’re wondering whether 2 days in St. Augustine is enough, it is the perfect amount of time to spend. With a smart itinerary, you can see the major highlights, experience the best of the historic district, and still have time to slow down and enjoy it. This guide breaks down exactly how to spend 2 days in St. Augustine visiting what’s actually worth it.
Best Time To Visit St. Augustine Florida
The best time to visit St. Augustine really depends on what kind of trip you want, but one thing to know right away is that the temperature is much cooler than in South Florida. When we visited a few days before Christmas in December, daytime temperatures were around 15 to 18°C and dipped to about 7 to 10°C at night. Meanwhile, Miami was sitting at roughly 28°C – so yes, it feels noticeably colder than Miami, especially once the sun goes down.
December is still a great time to go, especially because of the Night of Lights, when the historic district is covered in white holiday lights, and the cooler temperature makes it feel more like winter to really get the holiday vibes going. The weather is comfortable for walking, crowds are manageable compared to peak spring months, and you get a festive atmosphere without extreme heat.
If you prefer warmer weather, March to May is arguably the best overall window. Spring brings daytime temperatures to around 20 to 26°C, lower humidity, and comfortable conditions for exploring St. Augustine on foot. Summer, from June through September, is the hottest and most humid, with temperatures often above 30°C and frequent afternoon rain showers. Fall is quieter and slightly cooler, though it overlaps with hurricane season, which runs from June through November.
How To Get To St. Augustine, Florida And How To Get Around
The easiest way to get to St. Augustine is by car. We drove up from Miami, which is about 500 kilometers and takes roughly 4 hours and 30 minutes without stops or heavy traffic. It’s a straightforward drive mostly along I-95, making it an easy Florida road trip if you’re already based in South Florida like we were. Once you arrive, you’ll quickly realize why having a car is helpful for getting there, but not necessary once you’re in the historic district.
For this trip, Discover Cars provided a rental car for me, which I had picked up at the Miami International Airport. The booking process was simple, there were plenty of vehicle options, and all the key details were clearly outlined so I could make a confident decision. I selected a BMW 5 Series through Sixt, and the pickup was smooth – plus the car itself made the road trip feel elevated and much more fun. (One honest note, I accidentally left my Fitbit Inspire 3 and Prada sunglasses case in the car and even though I went back the next day after returning the vehicle, Sixt wasn’t able to find the car since it had already been processed and was unable to retrieve my items, unfortunately – but that being said, Discover Cars was solid and I would use them again and there are plenty of other providers under them as well.)
If you’re flying in, the closest major airport is Jacksonville International Airport, about 75 kilometers north of St. Augustine, roughly a 50-minute drive.
Once you’re in St. Augustine, the best part is how walkable everything is. Historic St. Augustine is compact and easy to explore on foot, and most major attractions are all within a short walking distance of each other. Parking in the historic core can be very limited, and traffic can be really bad, so if you’re staying nearby, you likely won’t need your car again until you leave. If you do drive into the historic center, there is a city parking garage near the Visitor Information Center and Castillo de San Marcos, as well as metered street parking, but both can be busy and limited during weekends and holidays.
If you prefer not to walk everywhere, the Old Town Trolley Tours run throughout the city with hop on hop off stops at major landmarks. It’s a practical option if you want historical commentary while covering more ground without moving your car.
Where To Stay In St. Augustine, Florida
When deciding where to stay in St. Augustine, the biggest factor is location. If this is your first time visiting and you’re only spending 2 days in the city, staying in or right beside the historic district makes the most sense. Being central allows you to step out for sunrise if you didn’t party too hard the night before, go back to rest mid-day if needed, and return for dinner or a ghost tour without needing your car.
Staying directly in historic St. Augustine typically means boutique inns, bed and breakfasts, and smaller historic properties, with some bigger chain hotels as well. They often come with charm and character, but rooms can be smaller and prices higher, especially during peak seasons like spring and December. If you stay just outside the historic core, you’ll find more budget-friendly motels and standard hotels with easier parking and larger rooms. The trade-off is that you may need to drive and pay for parking each time you head into town.
We stayed at a motel across the Bridge of Lions, as it was difficult to find good and convenient accommodations without overly jacked-up prices during the time we visited, and it truly helped us avoid traffic in the historic center and made it much easier for us to leave at the end of the trip. It was only about a 13-minute walk across the bridge (although I will warn you that the wind tunnel was strong if you decide to do the same), but well worth avoiding the inconvenience of traffic that lasted much longer than our walk.
Here are some places I’d recommend to stay in St. Augustine – focusing especially on walkability and quality experiences:
- Bayfront Westcott House Bed And Breakfast – Waterfront location right in the historic district with classic architecture, private decks, and views over Matanzas Bay.
- Casa Monica Resort And Spa, Autograph Collection – One of the most iconic hotels in St. Augustine, dating back to 1888. It’s right in the heart of the historic district with gorgeous period details, a rooftop pool, on-site dining, and luxury amenities.
- Old City House Inn And Restaurant – A themed historic inn with on-site dining if you want a mix of classic charm and convenience, and has a more relaxed, local vibe.
- Penny Farthing Inn – A Victorian-era bed and breakfast with personalized service – it’s an excellent choice if you want boutique character and a cozy, old-town feel.
- 44 Spanish Street Inn – A highly rated adults-only inn with modern comforts just off St. George Street.
- Agustin Inn – A locally-loved, high-rated adults-only inn with a welcoming feel and excellent location. Great for couples or anyone who wants cozy rooms and walkable access to everything.
- Best Western Historic Bayfront – Excellent value right on Avenida Menendez with bay views and walking access to attractions and restaurants.
- St. George Inn – This inn is romantic and intimate and puts you steps away from shops, restaurants, and historic sites.
Must-Try Foods In St. Augustine, Florida
St. Augustine’s culinary scene is delicious reflection of its centuries-old history, blending Spanish, British, Caribbean, and Southern influences. Even if your trip is only two days, there are a few iconic foods you won’t want to miss.
- Minorcan Clam Chowder – A spicy, tomato-based chowder unique to St. Augustine, brought over by settlers from the Minorca Island in one of Spain’s Balearic Islands. Unlike the creamy New England version, this soup has a bright, zesty kick.
- Datil Pepper Everything – From sauces to burgers, St. Augustine loves the local datil pepper, a small yellow pepper with a fruity heat that’s become a regional signature.
- Gator Or Local Seafood – If you’re feeling adventurous, sample gator bites or fresh local fish. Many seafood restaurants along the historic waterfront serve catch-of-the-day specials.
- Conch Fritters – A Caribbean-inspired treat that’s crispy on the outside and tender on the inside. These bite-sized fritters are usually served with a tangy remoulade or aioli and are a must-try at local seafood spots.
Some of the more notable restaurants include: Harry’s Seafood, Prohibition Kitchen, The Floridian, Cap’s On The Water, St. Augustine’s Fish Camp, Columbia Restaurant, Maple Street Biscuit Company, and Forgotten Tonic. These restaurants are popular and get filled up fast, so make sure you go before rush hour or be prepared to wait in line. Check out TripAdvisor if you want the full list of restaurants to choose from.
Tips For Visiting St. Augustine
It’s Smaller Than You Think
This is important – we booked our trip to St. Augustine for 2 nights, 3 days, but we really only needed 1 night and 2 days and that was more than enough to see the main highlights at a relaxed pace. You do not need to overpack your schedule and if you do want to hit up every single attraction that the city has to offer, then maybe consider staying the 2 nights, or even an extra one.
Go Early For Major Sites
If you want photos without crowds at major attractions or along the bayfront, go right at opening or just after sunrise. By late morning, tour groups start rolling in and it changes the vibe completely.
Buy Attraction Tickets Online
For the more popular attractions or if you want to guarantee entry for yourself, buying tickets will help you save time as lines usually move slower than you’d expect in a small city.
Expect Tourist Pricing
Historic St. Augustine is beautiful, but it is a very touristy town. Food, parking, and attraction tickets are priced accordingly.
Plan Your Meals Strategically
There are several highly-rated restaurants in the historic district, but most of them do not take reservations. During peak season, especially around holidays and spring break, wait times can easily hit minimum 1 to 2 hours. Your best move is to go early – aim for late morning before the lunch rush, or around 4 to 5 PM for dinner. Anything in the prime 6 to 8 PM window usually means a long wait.
Sunset Is Better Than Midday
The city really shines at golden hour and the light hits the stone buildings and the waterfront in a way that makes everything look warmer and softer. If you’re building your St. Augustine itinerary, leave your most scenic stops for late afternoon.
Don’t Underestimate The Temperature
It can get surprisingly cold in the evenings, especially near the water or if you’re staying across the Bridge of Lions as we did. I brought a Burberry trench coat, which was a little warm during the day, but also not warm enough at night. Layering is your best bet, and having a jacket is very much needed. I would’ve been much more comfortable with a proper insulated layer like my Arc’teryx Atom Hoody (light, really warm, and easily packable) that I left in Miami in hopes that it wouldn’t have been too cold to need it.
Wear Good Shoes For Walking
The streets in historic St. Augustine are a mix of brick, uneven pavement, and cobblestone. It looks beautiful in photos, but it is not heel-friendly and you will be walking a lot. Comfortable sneakers or supportive flats will make a major difference in comfort.
Things I’d Skip In St. Augustine, Florida
Not everything in St. Augustine is worth your limited time so here are some things I’d skip to make the most of your time:
Visiting Every Museum
You do not need to visit every single historic attraction – there are plenty, and some are worth it, some are not. Castillo de San Marcos is a must – after that, choose an attraction that appeals to you and, based on your interests, but picking 2 or 3 strong ones and enjoying them properly is your best bet. Whether that’s the Old Jail Museum, Flagler College tour, the Fountain of Youth, or something else. Doing all of them back-to-back can start to feel repetitive, so make sure you do your research and read other visitor reviews if you need some help deciding.
Driving In And Out Constantly
If you’re staying near the historic core, park once and leave the car. Parking fills up quickly and traffic gets especially busy in the evenings and during special events. Moving your car repeatedly just adds stress and wastes a lot of valuable time and money.
Expecting Night Life Energy
Although it is a touristy area, it is unlike some other cities in Florida like Miami – the nightlife here is more laidback and relaxed, and you can feel that vibe right away. Restaurants close earlier than major cities too. The appeal is history, architecture, and atmosphere – not party culture. If you adjust your expectations, you’ll enjoy it more.
Overhyping It
St. Augustine is beautiful and historically significant, but it is much smaller than I even thought. It’s perfect for a weekend in St. Augustine or as part of a Florida road trip stop. It’s not a week-long destination unless you’re deeply into colonial history and want to visit every single attraction they have.
Other Stops To Make Before Or After Visiting St. Augustine
If you’re driving up from Miami as I did, or spending a bit of extra time exploring the surrounding area, there are a couple of stops worth considering before diving into the historic district. These stops are easy to do on your way into St. Augustine or as a small detour, and they help balance your road trip with both historic and natural experiences.
Crescent Beach
Just a short drive from the city center, Crescent Beach is a quitter alternative to some of Florida’s more crowded beaches. The sand is soft and wide, and the water can be calm, making it perfect for a morning stroll or sunrise shots, and it can also get wavy enough for you to go surfing. It’s especially nice if you want a quick beach stop to break up your drive or get some photos in a more natural setting. However, when we visited in December and since this area is much more north than Miami, it was too cold and windy to even get in the water. The beach was mostly empty except for some brave locals who are used to the cold. It’s a beautiful beach and I’d highly suggest visiting when it’s a good, sunny day.
St. Augustine Lighthouse And Maritime Museum
Located on Anastasia Island, the lighthouse offers some of the best views of the city and the Atlantic Ocean. The climb is manageable and the surrounding grounds are photogenic with historic buildings, gardens, and occasionally resident seabirds. Even if you don’t go all the way up, the area is worth a walk around for photography and to soak in the coastal vibe.
Vilano Beach
About 10 to 15 minutes north of St. Augustine, this is another quieter beach with dunes and open space. It’s perfect for sunrise or sunset photos, sweeping ocean views, and capturing that “coastal Florida” look without a crowd.
Anastasia State Park
Just a few minutes south of Vilano Beach and roughly a 10-minute drive from downtown St. Augustine, Anastasia State Park is one of the area’s best outdoor escapes. The park blends sandy beaches, salt marshes, tidal creeks, river views, and nature trails.
Itinerary For 2 Days In St. Augustine, Florida
Day 1 – Historic St. Augustine And Waterfront Highlights
On the first day in St. Augustine, it’s all about immersing yourself into the heart of the city – exploring the cobblestone streets and visiting iconic landmarks that make historic St. Augustine so photogenic. I will say, that the energy and architecture gave me a bit of a New Orleans, Louisiana vibe, with its mix of history, color, and character around every corner – and you may notice that too when you visit.
Start At Aviles Street
Time Spent – 30 minutes
Why You Should Visit – This is the oldest street in Florida and it dates back to the 1930s in its current layout. It sits on one of the oldest documented European-era thoroughfares in the United States. It was once part of the original Spanish colonial settlement grid from the 1500s and you can see plenty of historic buildings with lots of history along the way. There are signs in front of each with the history as well, which makes this a great self-learning experience. You can just take your time walking through the streets as you start to make your way towards the more major attractions.
Explore Lightner Museum
Time Spent – 1 to 1.5 hours
Why You Should Visit – Housed in the former Alcazar Hotel, it was built in 1888 by railroad manage Henry Flagler during Florida’s Gilded Age boom. The building once featured one of the largest indoor swimming pools in the world. The structure itself represents how Flagler transformed St. Augustine from a colonial outpost into a water playground for America’s elite. Even if you skip the exhibits, the architecture alone tells the story. As soon as you walk into the courtyard, you can see how beautiful it is (they also do wedding photoshoots here).
Tour Flagler College
Time Spent – 1 hour
Why You Should Visit – Originally the Hotel Ponce de Leon, also built by Henry Flagler in 1888, this building was one of the first major structures in the United States constructed entirely of poured concrete. The interior features Tiffany-stained glass windows and ornate Spanish Renaissance Revival design. It represents the shift from colonial survival to Gilded Age extravagance in St. Augustine’s history. In 1968, it became a liberal arts college and is consistently ranked among the top regional colleges in the South.
Walk St. George Street
Time Spent – 1 to 2 hours
Why You Should Visit – This pedestrian-only street follows the original Spanish colonial town plan from the 16th century. It runs north to south through the historic district and connects multiple preserved structures, including reconstructed colonial homes and early American-era buildings. You’re literally walking along a street pattern laid out over 400 years ago. There are plenty of unique boutiques, restaurants, bars, and other shops along the way. One shop we really liked was the Savannah Bee Company – they had many different bee and honey products, but at the back is a Mead Bar with lots of specialty beers you can’t find anywhere else and you can get a beer tasting too.
St. Photios Greek Orthodox National Shrine
Time Spent – 30 minutes
Why You Should Visit – We stumbled upon this place without really knowing what it was, as the entrance was a little obscure, but as we entered, we discovered a serene and beautifully maintained space honoring Saint Photios and the early Greek settlers who arrived in Florida in the late 1700s. Built in 1749 and restored in 1979, this shrine is dedicated to the 400 Greeks who arrived in St. Augustine in 1768 and helped settle the colony of New Smyrna. The interior is filled with Byzantine icons, mosaics, and artifacts that offer a striking contrast to the Spanish colonial architecture that dominates St. Augustine. The adjacent Heritage Garden and interpretive displays provide insight into the contributions of Greek immigrants to the city’s early history.
Cathedral Basilica Of St. Augustine
Time Spent – 15 minutes
Why You Should Visit – As the oldest Catholic Parish in the United States, the Cathedral Basilica dates back to the late 18th century. Its stunning Spanish Colonial Revival architecture, intricate stained-glass windows, and ornate interior make it both a spiritual and photographic highlight. Even a short visit lets you appreciate centuries of religious and cultural history in the heart of historic St. Augustine.
Plaza De La Consititucion
Time Spent – 10 to 15 minutes
Why You Should Visit – This historic public square has been the center of St. Augustine life since the city’s founding in 1565. Once the site of military parades, public executions, and colonial celebrations, today it’s a relaxed gathering space. It’s also home to the city’s famous obelisk, originally a Confederate monument, which locals famously refused to remove – making it likely the only one left in the world.
Peace, Love, And little Donuts Of St. Augustine
Time Spent – 15 to 20 minutes
Why You Should Visit – We passed by this donut shop randomly and it caught my eye because I have such a big sweet tooth, love donuts, and they had really unique flavors. What made it even better was that their mini donuts so I could get a bunch of different ones and be able to try more flavors. I also got a maple coffee and let me tell you, it was delicious! This donut shop is family-owned and the owner, Jen, is super nice and enthusiastic about what she does. This makes for a quick but sweet break to take during your explorations.
Medici Lion Marble Statue And Bridge Of Lions
Time Spent – 5 minutes
Why You Should Visit – The Bridge of Lions opened in 1927 and reflects Mediterranean Revival architecture, which defines much of modern St. Augustine’s aesthetic. The marble lion statues are replicas of Medici lions from Florence, reinforcing the city’s European influence centuries after its founding.
Castillo De San Marcos National Monument
Time Spent – 1 to 2 hours
Why You Should Visit – Castillo De San Marcos is the oldest masonry fort in the continental United States, completed in 1695 by the Spanish. Built from coquina stone, a compressed shell limestone that absorbs cannon fire instead of shattering, it never fell in battle despite multiple sieges and attempts by the British. The fort changed flags four times: Spanish, British, Spanish again, and finally American – making it a physical record of colonial power struggles in North America.
Old City Gates
Time Spent – 5 minutes
Why You Should Visit – The Old City Gates mark the original entrance to St. Augustine during the 18thcentury. Walking through them gives a tangible sense of stepping into history, connecting you to the city’s colonial past and the centuries-old defensive walls that protected it.
Take A Ghost Tour With US Ghost Tours
Time Spent – 1 to 1.5 hours
Why You Should Visit – As St. Augustine is one of the oldest cities in North America, it’s no surprise that its history is full of real drama – from colonial history, pirate activity, military sieges, epidemics, and shifting rule between nations have created generations of folklore. Whether you believe the stories or not, ghost tours often highlight documented historical events tied to specific buildings, giving you context daytime visits sometimes miss. A ghost tour with US Ghost Tours brings that layered history to life in a way a daytime walk never can. They don’t just tell ghost stories, but they tie paranormal tales to actual historical events and real places, giving context to old buildings, hidden courtyards, and winding alleyways that you might otherwise overlook. Tours are led by local guides who love their city and who know the history intimately. In a place this old, a ghost tour is less about fear and more about connecting more deeply with the past in an engaging, memorable way.
Day 2 – Deep History And Unique Experiences
On the second day in St. Augustine, you can dive deeper into the city’s rich past and explore landmarks that really capture its colonial roots. It will be a perfect mix of history, storytelling and photogenic stops that show a different side of the city. And of course, feel free to add in other attractions that have caught your attention or re-visit places you might have missed or didn’t have enough time for the day before.
Explore The St. Augustine Pirate And Treasure Museum
Time Spent – 45 minutes to 1 hour
Why You Should Visit – Housing over 800 authentic pirate artifacts from the Golden Age of piracy, including Blackbeard’s blunderbuss, one of only a few original Jolly Roger flags, and even historically documented treasure chests. The museum blends immersive exhibits with interactive elements like exploring a ship’s gun deck and learning real pirate history tied to St. Augustine’s coastal past. It’s very entertaining and educational, even for adults.
Visit The Fountain Of Youth Archaeological Park
Time Spent – 1 to 1.5 hours
Why You Should Visit – This park marks the spot where Spanish explorer Juan Ponce de Leon first landed in Florida in 1513. Beyond the legend of the Fountain of Youth, the park offers a fascinating look at Timucua Native American history, reconstructed Spanish colonial structures, and exhibits that trace Florida’s early European settlement.
Tour The Old Jail Museum
Time Spent – 40 minutes to 1 hour
Why You Should Visit – Built in 1891, the Old Jail Museum showcases a fascinating slice of late 19th-century life in St. Augustine. Commissioned by Henry Flagler to improve the city’s image for tourists, the jail housed some of St. Augustine’s most notorious criminals. Walking through the cells and hearing stories of life behind bars offers both a historical and slightly eerie perspective.
If you’re planning a weekend in St. Augustine, use this 2-day itinerary as your guide to make sure you explore the iconic highlights and the unique stops that make this historical city so interesting.
For more travel inspiration, be sure to check out more blog posts under Destinations.