With a mild climate, fascinating history, and a mix of natural and cultural attractions, St. Augustine, Florida, makes for a wonderfully romantic getaway! In today’s post, I’ll share the best 3-day itinerary for St. Augustine, encompassing the highlights of the historic district, as well as a few overlooked jewels in the oldest city in the United States.
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Get the Lay of the Land
The Historic District
I recommend spending your first full day in St. Augustine getting the lay of the land. One easy way to do this is by taking a walking tour. Two of the most popular options are the St. Augustine Historic Walking Tour and the St. Augustine Free Walking Tour.
We opted for the Historic Walking Tour, which runs daily at 8:30, 10:30, 12:30, and 3:00 PM. The tour runs for 90 minutes and covers about a mile and a half of ground. During the tour, we learned about periods of historical significance in St. Augustine: the two Spanish periods, the English/Minorcan period, and the Civil Rights period.
The tour takes you to some of the most important sights in the historic district, like the Plaza de la Constitución, the Castillo de San Marcos, the Basilica, historic Aviles, St. George and Treasury Streets, and Flagler College. In between learning bits of history, our guide also pointed out recommended dining spots and small details often missed by travelers.
The Ponce de Leon Hotel/Flagler College
After the tour, we had about 2 hours before our next big event of the day, the Flagler College/Ponce de Leon Hotel tour. Use this time to grab a bite or wander the streets of the historic center. We opted for lunch at the picturesque Columbia Restaurant, where we tried the Cuban sandwich and the famous 1905 salad. Both were excellent! NOTE: Reservations accepted, but if you forget, the line seems to move pretty quickly.
We walked the short distance to the Flagler College rotunda, where we met our guide for a one-hour tour of the Ponce de Leon Hotel and all of its Gilded Age splendor. Current students lead the tours, which run at 10, 2, and occasionally 3 PM most days from early October to early May. Advance tickets are recommended.
Highlights include the ornate Spanish Renaissance-style architecture seen from the Courtyard, the 68-foot domed ceiling rotunda, and the dining hall, which is home to one of the largest collections of Tiffany glass windows in the world. The Ponce/Flagler College tour is a must-do in St. Augustine and truly one of the most stunning pieces of architecture we’ve observed in the US.
Following your tour, consider walking through the Moroccan-inspired lobby of the Casa Monica hotel across the street, perusing a few more of the historic district side streets, or returning to your lodging for a quick rest/refresh.
If you’re sensitive to heat or have difficulty walking, Old Town Trolley Tours provides transport and narration to the city’s major sights.
A Foodies Florida
St. Augustine is a foodies paradise! While the best meals don’t come cheap, the three suggestions I share today are all worth the splurge. First up is the top-rated Peruvian restaurant, Llama. Reservations are a must at this popular and small (12-table) venue.
While I love ceviche and this would be an excellent place to try it, it’s off limits while I undergo chemo. Therefore, we started with the chicharones. They’re one of the most popular options and were outstanding. For our entrees, we ordered the Cordero Cusqueno and the Arroz con Mariscos. Lamb is a recommended specialty of the restaurant and didn’t disappoint. My dish was described as a paella but with risotto. It was beautifully presented, rich, and delicious.
We ran out of room by the time dessert was offered, but I did try one of their specialty drinks, chicha morada. It’s a combo of purple corn, pineapple, key lime, and spices. A fun N/A option if you’re looking for one!
As you work your way back into town, be sure to stop by the basilica on the Plaza de la Constitución! It’s the oldest Catholic parish in the United States, and its stained glass windows are backlit at night. The resulting display is magical, and I wish more churches would adopt this practice!
Enjoy the Healing Waters
No visit to St. Augustine would be complete without a trip to the Fountain of Youth and one of the area’s wide and easy-to-walk beaches. Today you’ll visit both.
The Fountain of Youth & Lady of La Leche
After breakfast, take a cab or a ride share to the Fountain of Youth Park just north of the historic district. While this attraction has a distinct touristy vibe, exhibits here are set at the original site of the first St. Augustine colony and offer insight into the lives of the Timucua (the original inhabitants circa 2400 BC) as well as the Spanish settlers of the early 1500s.
Even more importantly, your admission gives you access to that legendary Fountain of Youth Water and great photo ops of the peacocks that graze the park. Don’t worry too much about the water; a guide told us it’s safety-tested weekly. It’s not the best-tasting water we’ve ever drank, but hopefully it can still work some magic on our mid/late-50s bods!
TIP: Should you find yourself here at lunchtime, the on-site BBQ restaurant is great!
A short walk away is the Lady of La Leche Shrine at Mission Nombre de Dios. This sight represents the first Catholic parish in the United States. The grounds are shaded and peaceful, and the mission (dating to the 1620s) is worth a short visit regardless of whether you are a practicing Catholic.
Life’s a Beach
Late morning or early afternoon, head out to one of the beach areas of St. Augustine. We had our car drop us off at the St. Augustine pier, where we enjoyed watching some surfers before taking a nice, long walk along the beach. Spend the afternoon swimming or fishing from the pier or head back towards town, stopping at the St. Augustine lighthouse for views of the city, the Matanzas River, and outlying islands.
A Japanese-Style Jewel
Tonight’s dinner recommendation is ramen. Yes, ramen. In Florida. Now hear me out…we came across Lotus Noodle Bar on a Reddit thread where people touted it as a near-Michelin experience. They were not wrong. This is the best Japanese-style cuisine we’ve had since visiting Japan.
We started with the sweet & spicy sunomono (aka cucumbers). They were fresh, crispy, complex, and addictive. For our entrees, we chose the spicy duck tan tan and the lobster & noodles. The broths were rich, umami perfection. We wasted not a drop. Our dessert choice was the NYC Dreams, a perplexing combo of cheesecake mousse, brown butter sable crumbs, and caviar. Yes, you read that correctly. But it worked!
Like Llama, this is a small and popular restaurant. Reserve ahead. Seats inside have a great view of the kitchen, where you can observe the care they take in creating each dish, and there is also a patio for those who prefer to dine al fresco. The restaurant isn’t too far from the city gates and Castillo, beautifully lit at night, and is worth walking by!
Revisit History
Wrap up your last full day with a post-breakfast stroll of the historic district. Do some shopping or snacking on St. George Street, buy souvenirs, and enjoy a slow-paced morning. Later on, pass back over King Street going towards Lincolnville to see the oldest house, the O’Reilly House museum, the Spanish Military Hospital, and stroll through some more residential neighborhoods.
At 81 Bridge Street, near Rose Dog Brewing, you’ll find a placard marking the house of Ms. Cora Tyson. Ms. Tyson often welcomed Dr. Martin Luther King in her home. Today, she is 103 years old and still living in this house. Our walking tour guide noted that if she’s sitting on her porch, be sure to say hello, as she loves sharing stories about her pivotal role in history.
The Lightner Museum
After a leisurely lunch, consider checking out the Lightner Museum. Formerly the Alcazar Hotel, another Flagler property, the building now houses the private collection of Otto Lightner. A man of eclectic tastes, the museum has often been called a collection of collections.
Complementary guided tours of the pool area of the Alcazar Hotel take place at 11 AM and 2 PM. The tour lasts 15-30 minutes, and our guide was excellent, providing context on what life was like during the Gilded Age. In total, 1.5-2 hours are needed to view the ground and collection.
Alternatively, you could enjoy a boat ride on the Matanzas River or head south of town to see the Classic Car Museum of St. Augustine.
Live Fire Grilling & Waterfront Views
For your last meal in St. Augustine, I recommend heading slightly south of the historic center to Asado Life. The waterfront views and live fire/asado grilling make for a wonderful way to recap your time here. Asado Life is much larger than the other restaurants mentioned today, but reservations are still recommended.
When reserving on OpenTable, you’ll note that some reservations mention pre-ordered entrees. These must be paid for in advance and booked before 10 AM on the day of your visit. We opted for one pre-ordered entree (the branzino) and a hanger steak, which appears on the regular menu. For starters, we enjoyed the provoleta and focaccia. The portions were large, and we once again had no room for dessert.
Additional Resources
I’ve listed a few additional resources that may help plan your trip below.
- The GPSMyCity and FloridaStories apps both have a nice collection of self-guided walking tours for St. Augustine.
- Many venues offer live entertainment. Check this schedule for specifics.
- Ghost tours are a popular post-dinner entertainment option! The historic district of St. Augustine is spooky as all get out. So much so that I often got freaked out while walking home or when we’d run into costumed tour guides wearing cloaks and carrying lanterns.
Seasonal Events:
- St. Augustine Beach Farmer’s Market: Wednesdays at the Pier, May-Oct from 8-12, Nov-Apr from 8-1
- St. Augustine Amphitheatre Farmer’s Market: Saturdays at the Amphitheatre 8:30-12:30
- St. Augustine Amphitheatre Night Market: Set Tuesdays at the Amphitheatre 5-9 PM, 2026 Dates: 3/31, 6/16, 9/15, and 12/8
- Night of Lights Holiday Display: Nightly from Saturday, Nov. 21, 2026 – Sunday, Jan. 18, 2027. NOTE: Expect major crowds!
Stay tuned for a future post on the best hotels in St. Augustine’s historic district!
Until next time…
Hi Betsy. I loved this post. It made me want to return to St. Augustine, after more than 40 years. Tim and I went there when we were dating. Now, you’ve made it sound so interesting, that we may go back, for our anniversary, in May. I hope you are doing well. ❤️
Hi Christina! I’m so glad you enjoyed the post. It would make for a fantastic anniversary trip, and I’d love to hear if/how it’s changed since your last visit.
I remember renting a bicycle built for two, and riding around the old town. 😊
That is really sweet! Now that you mention it, I’m not sure that we saw many bikes on our recent trip.