The oldest, continuously-occupied European settlement in North America is St. Augustine, Florida. It’s a little treasure, densely-packed with rich history. A favorite destination of mine, I’m happy to present this Editor’s Pick for 4 Perfect Days in St. Augustine.

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In 1513, Spanish explorer Juan Ponce de Leon came ashore while looking for the isle of Bimini where he’d heard he could find the Fountain of Youth. His wrong turn was the right move for America, naming the land he set foot upon “La Florida.”

Originally occupied by the Timucua Indians, there was much strife, with lots of fighting, pillaging, burning down of the city multiple times and rising from the ashes. Tour guides will tell you about this group battling that group and gruesome deaths. But tra, la, la, there are also plenty of tales of hopes and dreams of creating a vacation destination for visitors looking for easy access to warm weather and beautiful beaches. The end result of all that strife, turmoil and also optimism, resulted in a city full of charm, amazing architecture with intricate details -plus, plenty to discover around every corner. After spending 4 perfect days in St. Augustine myself, I am sharing what turned out to be an ideal itinerary that explored the best of this northern Florida city.

A courtyard view of the Lightner Museum. The building itself is stunning. Just wait until you see what’s inside!

Been There Done That TIP: To make sure you get to take in everything suggested here, go online and make tour and dining reservations in advance to avoid disappointment and wasted time!

Day 1: Arrive, get settled in and grab a bite

Start at the Visitor Information Center, itself in an historic building, built in the Mediterranean revival style in 1938. In addition to interesting and very informative exhibits, friendly staff can answer all of your questions.

Check in at Casa De Suenos Bed & Breakfast. Feeling more like a home than lodging, the charming and historic building is perfectly-situated for your full itinerary. Walking distance to just about everything, you’ll enjoy comfort, a full, hot breakfast every day and lovely extras like a decanter of sherry in your room and a dessert delivered to your room every night.

Your home away from home when in St. Augustine is Casa de Suenos.

They’ve thought of everything at Casa de Suenos, including a decanter of sherry in your room and dessert delivered nightly.

Have dinner at Catch 27 on your first night. Enjoy a craft cocktail, delicate Lion Fish ceviche if it’s available (it’s an invasive exotic fish which the Florida Fish & Wildlife Commission lets area fishermen round up periodically so they don’t overrun the indigenous fish population), and be sure to have a bowl of the Minorcan Clam Chowder. The Minorcan influence is ingrained in St. Augustine and the chowder features fresh seafood, potatoes (grown in the area) and the famous and beloved Datil pepper. With its sweet heat, it’s indigenous to the area and is essential to having an authentic culinary experience in St. Augustine! You’ll encounter it many times – used with savory, sweet and even in beverages.

An absolute “must” when experiencing authentic cuisine in St. Augustine, is a bowl of Minorcan Chowder at Catch 27 restaurant.

Hungry for more? Here’s a recipe for Minorcan Clam Chowder.

Day 2: Ride around, tour and taste

Get multi-day tickets for trolley tours around town from either the Old Town Trolley or the Red Train which will take you around town and often offer discounts or combo deals to venues or things like ghost tours. Get on and off at any stop if you see something that catches your eye. Or, I suggest staying on for the whole tour to give you the lay of the land so you know how far you are from everything else on your itinerary. Expect corny jokes the drivers have clearly told hundreds of time. It’s all part of the fun.

St. George Street in St. Augustine is pedestrian-only but the whole city is very pedestrian-friendly. Enjoy the walk under moss-covered trees, past fortress-like walls, cemeteries, cottages, shops and restaurants.

Make time to visit the Lightner Museum. The grand and elegant Museum (including its much-photographed, lush garden courtyard), is a trip through time, a gathering of things that captivated Otto Lightner, who purchased the collections of Chicago millionaires when their estates were sold for taxes during the Depression.  Have a Mediterranean-inspired lunch in Café Alcazar in what was the massive, former swimming pool of the Alcazar Hotel (now the Lightner Museum).

Allow yourself plenty of time to explore at The Lightner Museum. There’s so much to see.

Walk across the street for a tour of Flagler College. Very enthusiastic and poised students serve as your guides to tell you about the history, art, and architecture of the building daily at 10am and 2pm when classes are in session. During summer and winter break, the tours are hoursly between 10am and 3pm. The tour ends in the cafeteria where the students eat – it’s like something out of Harry Potter! The whole building is beautiful and it’s amazing to think that it really is a functioning school. But young people walking around in the school and all over town let you know you’re in a college town, providing a youthful energy (without any craziness).

Flagler College is a functioning (and beautiful) school in the heart of St. Augustine, with a long and interesting history.

It’s time for some chocolate – but isn’t it always? Walk a few blocks down to Whetstone Chocolates and take a tour. The guide moves the group along, stopping for brief lessons in the history and composition of chocolate, through the actual factory for a behind-the-scenes glimpse, ending in the shop, of course, where you can sample syrups, ice cream and purchase chocolates individually, or in bags. There are samples to enjoy throughout the tour. Worried chocolates would melt before I could return home (and then I’d have to eat them, preemptively), I purchased a can of Whetstone Minorcan Hot Chocolate which contains the Datil pepper. We’ve enjoyed it several times back at home and the flavors and heat always take me right back to my trip to St. Augustine.

Have dinner at Michael’s Tasting Room, a calm, intimate space in a former home, where you can unwind from a busy day, attended by friendly, totally on-top-of-it servers who’ll whisk your cares away along with your empty plate. It’s just a short stroll back to Casa de Suenos where you’ll undoubtedly have a great night’s sleep.

Day 3: A little violence and a foodie tour

After breakfast at the B&B, walk up to Castillo de San Marcos, one of the most iconic sites in St. Augustine. Completed in 1695 by authorization of Queen Mariana of Spain, it’s the oldest masonry fort in the U.S. You can take tours of the inside but when time won’t allow, strolling around the outside is still very impressive. Walking beside the stony seawall, in the grassy moat intended for livestock seeking refuge when the city was under siege, seeing where cannon balls got embedded in the walls, and trekking the boundaries of the fort is impressive in and of itself. Canon firing demonstrations take place throughout the day, Friday-Sunday.

At water’s edge, Castillo de San Marcos is a stunning site, whether on land, or from a boat.

Walk across the street to the St. Augustine Pirate & Treasure Museum. If you’re a fan of pirate lore and movies, you’ll go nuts in this place. Past the entry room that’s all gift shop and ticket desk, the museum is dark, brooding, mysterious and meandering. Even if you’re an adult, ask for a scavenger hunt paper and pencil at the start because it helps you pay attention to certain aspects of the stories and objects you might otherwise gloss over. It’s fascinating, kinda disturbing, and a lot of fun.

Just up the street, grab a bite at the St. Augustine Seafood Co. It is the antithesis of the Pirate Museum, all bright, white and blue. They display the type of seafood, including the name of the fishing boat, on a board so you know the “back-story” of what you’re going to be eating that day. Get shrimp, a fish sandwich, oysters or any other option you can’t go wrong with, but be sure to get a half and half bowl of Minorcan Clam Chowder and New England Clam Chowder. It’s a treat to experience the two, contrasting flavors.

Eat up! It’s super-fresh seafood served in a variety of ways at St. Augustine Seafood Co.

Stroll around the streets of this village-fortress-like part of the city, stopping into shops, some touristy, some not. Be sure to go into The Spice & Tea Exchange, which originated in St. Augustine. Take the flavors of St. Augustine back home with you, with a spice blend containing Datil pepper. I’ve been enjoying the “Signature Spice Blend” in my home cooking since I returned from St. Augustine.

Stop in at The Hyppo Gourmet Ice Pops for one of the most unique popsicle experiences of your life. Inside the cheery space, you’ll be faced with the very difficult decision of what flavor to get. Will it be Pistachio Orange, Rosewater, Beet Pineapple, Cucumber Lemon, or Avocado Serrano? Yes, yes, yes, yes, and also, yes. Keeping with the Datil pepper theme, I had the gorgeous and delicious Strawberry Datil flavor.

The indigenous Datil pepper pops up again! This time, in a frosty treat with strawberry at Hyppo Gourmet Popsicles.

Tired of walking, sit a spell on one of the many pretty restaurant patios for a drink. But don’t eat anything – you have a big night of eating ahead!

Taking a Tasting Tour is a great way to get to know more of the area’s restaurants and sites. One of the options is the Wine, Dine & Roadster Tour. Step into the friendly guide’s revamped, red roadster with a few of your soon-to-be-great-buddies. Driving, eating, drinking, and laughing together (over the course of three hours), will do that to you.  Book a pre-set tour or, with advance planning, they’ll create a tour for you, based on your interests. Our tour had us starting at a wine tasting room, visiting historic and newer restaurants, each with mini-courses that showed off their particular type of cuisine. We were full, happy, and exchanging email addresses by the end.

During a Tasting Tour, you’ll get to experience a variety of restaurants and food items that show off St. Augustine’s culinary scene.

Day 4: Head out on the water

After another hearty breakfast at Case de Suenos, stroll past the Costillo for a St. Augustine Ecotour. You can book a kayak excursion, or a boat tour which is what I did. Get your camera ready but don’t forget to just look around and take it all in. St. Augustine Ecotour takes you on inland waterways that surround the city. The staff are all marine naturalists who are doing research on land and in the water, even during the boat tours. You will learn a ton from the passionate guides who help you understand the history of the area for bird and sealife, and how to recognize unique behaviors like a “boil,” when something spooks a school of fish, causing frantic splashing on the surface, as they try to escape. If you’re lucky, you’ll see dolphins leaping by and even listen to them with underground microphones. After enjoying views of the water the past few days, these views back to the city offer a unique perspective.

See birdlife up close, fish and maybe dolphins on a St. Augustine Ecotour trip.

It’s time for lunch and this time, it’s at The Floridian. Sit out on the secluded patio or eat inside where Florida kitsch meets seaside cottage. Share the Company’s Coming plate that is a salute to the South with pickled veggies, fried green tomatoes, pimento cheese and more. Between that, the Cornbread Panzanella Bowl and Not Your Mama’s Meatloaf Sandwich had us thinking we would never be hungry again. Until we were.

The Panzenela salad bowl (brilliantly served with cornbread croutons) with the Company’s Coming appetizer in the background. It’s all at The Floridian restaurant.

Walk off lunch, taking in some galleries and shops or, when your feet give out, hop on the trolley again for a lift over to the Fountain of Youth Archaeological Park and the Oldest Drug Store. Both are touristy but fun.

It’s your last night in St. Augustine, so have a really memorable supper at Preserved Restaurant. Whether you sit inside or out on the wrap-around porch, take a break from recounting all of the wonderful things you’ve done the past few days long enough to really revel in each course of your meal. From a cheese and charcuterie plate to your entrees, and dessert, everything is clearly so well-conceived that you know, with each bite, you are topping off your trip the best way possible. The night I was there, sitting on the patio, a warm rain fell but we were protected and sheltered. The rain ended just as we stepped off the porch – a dreamy night.

“Preserve” your memories of your trip to St. Augustine with dinner at Preserved restaurant. This duck breast with French lentils dinner was a great, final meal.

A soak in the jetted tub in your room, accompanied by a nip of sherry and maybe just one bite of the evening’s dessert delivery (pack it for your wait at the airport the next day), and you’ll fall asleep, wonderfully exhausted from your busy day.

Heading out and saying goodbye

Make the most of your last morning in St. Augustine. As you head out of the city, drive over to North Beach, which is on the barrier island between St. Augustine and Ponte Vedra Beach. Stop along the Coastal Highway and walk along the beach, shoes in hand, letting the tide tease your feet. Look up at the clouds, across at the shoreline as far as you can see in either direction, the water without end, but also down for seashells and even shark’s teeth.

Lunch with one heck of a view at The Reef,, as you head out of town, sad to leave St. Augustine, but so happy you were there.

I found several just below The Reef restaurant for a great meal overlooking the beach and the water. It’s a fond and fitting farewell before heading back to the airport, back to what’s familiar. You’ve been in another world for a few days. It’s hard to leave.

— Story and photos by Courtney Drake-McDonough

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