Sun & Sea in St. Augustine

“I followed my heart, and it led me to the beach.”

Our big vacation of the year was supposed to be an Alaskan cruise – complete with whale-watching, stunning glaciers, majestic mountains, and eating exorbitant amounts of freshly caught salmon. After unforeseen circumstances forced us to cancel this trip, we opted for a shorter, less expensive jaunt to the opposite corner of the country: Florida. Having endured a long, cold winter in New York, Ohio, and Kansas, this turned out to be exactly what our vacation-deprived souls needed. Did you know 18th and 19th century doctors used to prescribe spending weeks by the sea? Where can I find a doctor like that?? 😉
We’ve been to several places in Florida, each with its own flair and personality. For this getaway we settled on the historic beachside town of St. Augustine.

A Little History

Ponce de Leon first landed in what is now St. Augustine in 1513 on his quest for the fountain of youth. The city was formally established in 1565, giving it its claim to fame as “America’s Oldest City”. You will hear tales of legendary pirate exploits, notable sieges and battles, and the original Underground Railroad. Minorcans who were seeking refuge from indentured servitude found a safe haven there. It played a pivotal role in African American history as both the home of the first free Black settlement in the 1700’s, and as a focal point for the civil rights movement in the 1960’s.
It first became a tourist destination in the late 1800’s when Henry Flagler built an opulent hotel in the middle of the city. The luxurious accommodations drew the rich and famous to experience Florida’s climate and scenery. Some decades later Flagler College boosted the local economy and brought a vibrant student population to the city’s cultural landscape.

Today St. Augustine honors its’ roots with museums and landmarks to explore and enjoy. Family-run inns, restaurants, and shops handed down for generations create a unique blend of past and present. At the same time the city looks to the future, embracing entrepreneurs and visitors. All of this, directly on intercoastal sailboat-laden waterways, and just a few minutes from grassy dunes, sandy beaches, and the Atlantic!
So now that you’re thinking about taking a trip there, here’s a few notes and ideas to help you plan…

When To Go

Florida is hot and humid even by southern standards, so “if yer not from ’round here” you might want to avoid June, July, and August. Hurricane season officially goes from June 1 to November 30, but the likelihood of storms is highest from mid-August to the end of October. If weather is a concern for you, plan on springtime or the winter holiday season. They have a Night of Lights festival that looks magical!

Itinerary

If you are highly motivated and/or energetic, you can fit all the main attractions into two days; we opted for a more leisurely pace, since we also wanted plenty of beach and pool time.

Day 1
We caught the early flight from Rochester to Jacksonville, so after picking up our rental and driving an hour south, we arrived in St. Augustine around lunchtime. We grabbed a bite to eat and then hopped on the Old Towne Trolley Tour St. Augustine Tours and Sightseeing with Old Town Trolley This is a hop-on/hop-off open air bus with stops at 22 local attractions. You can buy one or two-day tickets, and visit most of downtown without having to navigate narrow, tourist-filled streets. We chose to use the tour to get a feel for the layout of the city, learn some of the history, and see if there were any other sights we wanted to explore that hadn’t made it on my list. Note: the trolley seats are not very comfy, so if you have a bad back at all you might want to hop off a few times!
After we completed the 90-minute circuit, we had time for some wandering along St. George Street. This is a pedestrian-only route through downtown with colonial-era buildings, museums, shops, restaurants, and landmarks. By late afternoon, we were more than ready to head to the hotel. Our evening concluded with dinner at their in-house restaurant, and a stroll on the beach.

Day 2
This morning began with breakfast at the hotel, then we drove downtown to start exploring. First up was touring Castillo de San Marcos Castillo de San Marcos National Monument (U.S. National Park Service) – the oldest masonry fort in the continental U.S. It was built in the late 1600’s by the Spanish, and though it changed ownership a few times, it was never taken in battle and is now a national monument.
Across the street from the fort is the Pirate and Treasure Museum St. Augustine Pirate & Treasure Museum – Home. The area around St. Augustine was home to marauders and rogues, shipwrecks and plunder, and this museum merges the legends with history. I loved learning about Anne Bonny, a famous pirate queen originally from Cork, Ireland. A distant relative, maybe? 😉 And if you’re willing to pay the price, you can even bring home real treasure salvaged from the ocean floor.
Now is a good time to check out the Colonial Quarter. Experience | Colonial Quarter You can explore on your own or take the Living History tour. They have blacksmithing and musket demos, and a watchtower to climb. This section of town also has shops, restaurants, and live music.
The rest of our afternoon was filled with pool and beach time, then dinner. If your accommodations are in town, try out Anastasia State Park for sand and surf! They have trails, beaches, kayaks, even a local turtle population.

Day 3
Today we slept in a bit and then went out for brunch. A bit of rain was in the forecast, so the plan was to visit more of the indoor attractions today. We started with the Lightner Museum, formally a beautiful hotel and wellness retreat from 1888, now filled with stained glass, vintage bicycles, Victorian-era musical instruments, and European and American art from the Gilded Age. There’s even a restaurant in what used to be the giant swimming pool!
Walking distance from the museum is the Whetstone Chocolate Factory, a family-owned business that started as an ice cream shop back in 1966. They create artisan chocolates, candies and caramel corn, and they offer tasting tours of the production factory. It was so much fun to see behind the scenes, and everything we tried was delicious!
Not far from the chocolate factory is the St. Augustine Distillery – a great option for pre-dinner drinks. There is a tour you can buy tickets for, but you can also do the self-guided tour, which is free, and still includes bourbon tastings. They have a restaurant on their third floor if you want grab a bite, but we had dinner reservations at Columbia Restaurant. (See my review below. 😊)

Day 4
A trip to St. Augustine is not complete without drinking from the famed Foutain of Youth! Fountain of Youth – St. Augustine Historical Attraction This archeological park is located at the Timacua village where it is believed Ponce de Leon first landed. Legend says he was searching for the Fountain of Youth, and you can get a sip of the mineral-rich water from the spring he might have discovered. Honestly, it tastes like tap water, but hey – it was worth a shot! 😂 There are many other exhibits and activities at the park including blacksmithing and crossbow demos, cannon firings, a reconstruction of the Timacuan village, the 1587 mission, and the Spanish lookout tower. Peacocks wander the grounds, and it’s a fascinating place to spend an hour or two!
Back on Anastasia Island, we found the St. Augustine Lighthouse. Home – St Augustine Light House Built in 1874, it is still operational, and if you have the fortitude, you can climb the 219 steps to the observation deck for some spectacular views. I have mad respect for lighthouse keepers who used to make that trek carrying 30 lbs of oil several times a day to keep the light burning! Tours of the keeper’s house and a maritime museum are included with your admission.
If you are looking for more adventures, you can check out the Alligator Farm, or try one of the ship tours in the bay. As for us we indulged in a little more pool and beach time for our last afternoon before dinner.

Where to Stay?

When you are looking at accommodations for St. Augustine, first you have to make one big decision: do you want to stay in town, or by the beach? The main advantage to staying in town is that you won’t have to deal with parking, which can be a serious hassle. You will have to drive about 15 minutes to a public beach. Since we wanted both chill time and exploring, we chose a cute little resort on the water, which meant we did have to hunt for parking when we went to town, but the ocean was right out our back door past the pool.

The Guy Harvey Resort Guy Harvey Outpost Resort St. Augustine Beach Hotel Vacation
We thoroughly enjoyed our time here and would stay again if we return to St. Augustine! It is a smaller resort, the staff is welcoming and helpful, and it’s also dog-friendly. They have a good restaurant (see below), an outfitter’s shop with everything from clothing to sunscreen, and the ability to book local excursions. Behind the buildings is the pool, a tiki bar, beach chair & umbrella rentals, and direct access to the beach. You can enjoy live music out by the pool most evenings. A trolley is available to get you downtown – something we didn’t learn about til our last day but will definitely take advantage of next time!

Favorite Places to Eat

St. Augustine is a seafood-lovers paradise, and it also offers an eclectic array of global cuisines. Southern biscuits and gravy? Spanish empanadas? Australian coffee? You can find it here. There are dozens of options, so here were our favorites:

• Santiago’s SANTIAGO’S FLORIDA KITCHEN
  This is the restaurant connected to the resort, and we got dinner there our first night, ate breakfast there twice, and stopped by for drinks and appetizers one night we had late dinner reservations elsewhere. I know sometimes hotel restaurants are “meh”, but if you are staying at the resort, don’t pass this up! All of our servers were fantastic, the food was very good, and they have indoor and outdoor seating. The Jerk Pork Belly Nachos are big enough for two, and we also recommend the Macadamia Crusted Fresh Catch and the “& Grits”.
• Casa Reina Home – Casa Reina

• Ancient City Brunch Bar BRUNCH BAR
  A search for Saturday morning brunch landed us here, and we were not disappointed! This is a cozy little family-owned restaurant with a fun concept for brunch – boards! They have several different “bruncharcuterie” boards, but even their regular entrees are served on a board, perfect for sharing. Barry is not usually a “quiche guy”, but he ordered it here and said it was possibly the best he’s ever had.
• Columbia Restaurant Historic District, St. Augustine | Columbia Restaurant
  Another beautiful building – filled with hand-painted tiles and Spanish-style fountains – is home to probably some of the best food in the city. Columbia Restaurant started in 1905, has seven locations in Florida, and award-winning Spanish/Cuban food. You’ll want to make reservations for this one and come hungry! We stuffed ourselves on empanadas, paella, ropa vieja, and a guava turnover for dessert. They even make a hot sauce in house, which was so tasty we bought a bottle to bring home.
• Kookaburra Coffee The Kookaburra
  This is a fun little Australian coffee shop (yes, Australian coffee is a thing – who knew??) that sells coffees, teas, kombucha, pastries, and breakfast and lunch pies. They have locations downtown and beachside (on Anastasia Island), so we stopped here a few times. Their signature drink is called the “Hot Aussie” (which you can also get iced) and is a latte with house vanilla and cream. My favorite was the “Honey Badger” – a latte with honey, vanilla and cinnamon.
• Prohibition Kitchen Prohibition Kitchen – Gastropub in St. Augustine, FL
  A 1920’s and Prohibition Era themed pub on St. George Street. It gets pretty busy – we were there for lunch on a Monday, and there was a 20-30 minute wait. Fortunately we were able to get two seats at the bar, which is full service. I recommend the Bootlegger Burger, which comes with bacon, fried green tomato and house pimento cheese and is delish, and the drink menu has a build-your-own old-fashioned section, which Barry really appreciated. 😉

If you have enjoyed this review, or if you’ve been to St. Augustine, or if you have questions, please comment below and let’s chat!
Whatever your vacation plans are this season, I hope they bring you refreshment and joy, laughter-filled moments and memories for years to come.

Til next time, shine bright friends!
~Dawn 🌻