bugsy running on lone rock beach with the airstream and f-150 in the background

Four days in St Augustine, FL (visit #1)–Southeast Lollipop trip

We were in St Augustine as part of our Southeast Lollipop trip in January 2020. Read about our second visit in 2022 here.

bugsy chasing a heron

Pretty little St Augustine is VERY touristy, especially around the holidays. Here’s the first impression I jotted down on our initial trip into downtown: “Holy hell people everywhere.” The holiday crowds were NUTS. But after we figured out how to avoid the most touristy areas, we had a lovely time in St Augustine admiring architecture, visiting historic sites, and of course eating and drinking. We did a pretty good job hitting the establishments and activities we targeted before the trip, and found a few gems not on that list.

[Pro tip: don’t count on being able to get a campsite anywhere near Savannah without a reservation on a Saturday during the holidays. We figured we’d just stop somewhere on the way from VA to FL when we were sick of driving, but when we started calling campgrounds there was nothing nothing nothing available. Somehow we lucked into a just-cancelled spot at Lake Harmony RV Park, a pretty park an hour south of Savannah, with sites surrounding a small lake and a dog-friendly off-leash area beyond the lake. There’s nothing nearby; we didn’t even unhook to go exploring, but it was a pleasant place to spend the night.]


the airstream in our campsite at North Beach Camp Resort

North Beach Camp Resort, in Vilano Beach, just across the Intracoastal Waterway from St Augustine, is an absolute delight. The roads are shady and nice for strolling, the spots are private with walls of greenery, and the location is prime with beach and river access and three waterfront restaurants in walking distance. There’s a decent Publix grocery a few miles away, and the campground is about a 15-minute drive/Lyft/Uber to downtown St Augustine. And this could be a pro or a con: it’s super family-friendly and there were kids galore.


We ate a lot of local seafood in various formats: ceviche, tacos, bowls, fillets. It was all fantastic, especially when paired with a water view… and Key lime pie.

local fish at The Floridian in St Augustine

The best food we ate was at The Floridian, a local/seasonal/sustainable healthyish Southern food restaurant with a beachy vibe. The bowls topped with local flounder were out of this world, and the Key lime pie was insane.

sunset cocktail at Cap's on the Water in Vilano Beach

Cap’s on the Water wasn’t on our radar before we arrived, but as it’s a waterfront seafood restaurant walking distance (!) from the campground we had to check it out. We had a pre-dinner cocktail on the pier over the Intracoastal Waterway, and then watched the sunset from our table while eating killer local grouper and slightly less killer local mahi mahi.

We mostly went to Odd Birds Bar for the craft cocktails (which I’ll write more about below), but they’re also known for their creative Latin small plates, and we thought the ceviche and–get this–avocado stuffed with Brussels sprouts (!!) were fantastic. Note that there’s a sibling, Odd Birds Cafe, serving breakfast and lunch in a strip mall near the bridge to Vilano Beach; they surely have delicious food, but maybe not as cool an atmosphere.

bowl from crave food truck in st augustine

The bowls at Crave were so good we got them twice. Crave is a waterside food truck with a breezy patio and yummy healthy bowls and smoothies. Well we didn’t actually try a smoothie but they looked good. You can top your bowl with local shrimp, which we did, and which we recommend.

tacos from Osprey Tacos in St Augustine

And last but certainly not least, tacos! Osprey Tacos is a small, busy spot across the Bridge of Lions on Anastasia Island, with a dog-friendly patio and a brewery next door. They have the standards, but also mix it up with some fun flavors, like Brussels sprouts, which I daresay was better than the fish taco!


smoked old fashioned at odd birds

I’ve already mentioned Odd Birds. We went for the cocktails, stayed for the food, and returned a different night for another cocktail. The downstairs bar is a cool spot, small and crowded (but with a covered patio), while the Loft room upstairs is a bigger, open space with sofas and tall windows. Highlights for us (more for the uniqueness than for the taste, honestly) were the smoked old fashioned, and the Capri Sun-like margarita in a bag.

sunset cocktails at Beaches at Vilano

My waterfront bar-radar alerted me to people drinking under the bridge on the Vilano Beach side as I ran over the Intracoastal Waterway. We returned for sunset and had a drink at Beaches. What a pleasant surprise to find a fun waterfront restaurant on our side of the bridge! The cocktails were adequate; the front row seat for sunset was the real draw.

inside Sarbez! bar

Sarbez!, a neato dive bar on Anastasia Island has a big beer selection, a dog-friendly patio, and gourmet grilled cheese! We didn’t eat there, but I was tempted to order a pickle dog as a snack while we sipped a post-park beer with Bugsy.

Last and least is Prohibition Kitchen, a giant, noisy, very touristy restaurant with interesting-seeming cocktails… which in reality were quite poor. It was crazy packed when we crammed ourselves into the bar, so maybe the food is good? We didn’t even finish our drinks.

Ice Plant was on our to-do list; we popped in during the day to scout for that night and it looked like a cool spot, but the bar is tiny and the restaurant didn’t take reservations, so we skipped it. Wish we’d gone there instead of Prohibition Kitchen!

Two other places we missed but will try next time, if there’s a next time: Aunt Kate’s and The Reef, both seafood restaurants adjacent to the campground. Aunt Kate’s is on the Intracoastal Waterway side, and it was dead when we peeked in so we didn’t stay. We planned to visit The Reef, on the ocean side and apparently known for Sunday brunch, for a nightcap on our last night but didn’t realize they close at 9pm.


bugsy running over the vilano causeway

Running: It’s always fun to run over a bridge, and running over the Intracoastal Waterway was especially exciting! Park near the boardwalk entrance to the side of the Publix lot in Vilano Beach, take the boardwalk under the bridge, and then up and over the river for big views.

spanish moss streetscape near the Fountain of Youth

The bridge is about a mile long and dumps you into the start of the touristy area of town. I recommend extending your run with a jaunt down pretty moss-canopied Magnolia Street by the Fountain of Youth, over to the serene Mission of Nombre de Dios and the enormous cross, past the Castillo de San Marcos, and onto the Bridge of Lions for the view of the Old Town. The out-and-back is about seven miles.

Lifting: Our needs were simple: a gym offering day passes not too long a drive from home. Altro is not fancy at all, but did the trick for only $10.

Hiking: See my note about Anastasia State Park at the bottom of this post; I decided it doesn’t deserve to sit in the Hiking section which will remain sadly empty.


The City

st augustine waterfront

The best way to explore St Augustine is on foot! To start our exploration, we parked downtown near the Visitor Information Center where we picked up a map and asked for advice on walking tours (just make your own using their maps and brochures; the historical area is small) (also don’t bother downloading the Visit Florida app for their advertised walking tour–if the tour exists in the app, it’s impossible to locate).

bugsy outside castillo san marcos

St Augustine is the oldest continuously-occupied European settlement in the US, founded by the Spanish Conquistadors in 1565. The historic district is made up of narrow streets lined with houses, shops, and restaurants rebuilt after the British burned most of the city in 1702 to replicate the original Spanish Colonial and Spanish Renaissance Revival architecture, with colorful Victorians and occasional Moorish, Greek, Italian, and French architecture thrown in the mix.

plaza de la constitucion in st augustine
st augustine marina and the bridge of lions

The old town centers around the pretty green space of the Plaza de la Constitución and the bayfront seawall and promenade, and is the center of tourist activity. It’s lovely and important to see, but if you’re like us, you’ll admire it and then get the heck away from all those people.

bugsy on a palm-lined alley in st augustine

We very much enjoyed walking through the Lincolnville Historic District, a neighborhood founded by freedmen and freedwomen after the Civil War, and an important base during the Civil Rights Movement. Explore the area using the brochure for the ACCORD Freedom Trail self-guided tour you picked up at the Visitor Center. Lincolnville is also home to the highest concentration of Victorian-era buildings in St Augustine.

bugsy in front of flagler college

No tour of St Augustine architecture is complete without posing your dog in front of Flagler College, built in 1885 as the Ponce de Leon Hotel by Standard Oil tycoon Henry Flagler. The architects would later design the New York Public Library, and the building houses the largest collection of Tiffany stained glass windows. Flagler wanted to make St Augustine a winter resort for the East Coast elite and dreamed of an American Riviera running down the East Coast of Florida. He built hotels and railroads from St Augustine down through Palm Beach (which he founded) to Miami (of which he is considered to be the father) which spurred development along the corridor.

The Beach

bugsy playing in the ocean

Florida beaches are generally not dog-friendly. Luckily for Bugsy, Vilano Beach is very dog-friendly, not crowded (at least not when we were there at the end of December), and across the street from the campground. B LOVES the beach, can you tell?

bugsy running on Vilano Beach

We took her over there a few times. The campground has an outdoor shower near the pool that was handy for rinsing a beachy dog.

bugsy playing in the ocean

Anastasia State Park

Anastasia State Park has a beautiful beach, but your dog isn’t allowed there. She can hike on the Ancient Dunes Nature Trail, a pleasant but short (less than a mile) stroll through the woods next to the campground. It’s not a very exciting outing for your canine friend.

St Augustine lighthouse

On the way back from Anastasia State Park, wanting to give a Bugsy a little more walking since the nature trail was so short, we stopped at the St Augustine Lighthouse. Dogs are allowed on the grounds but there were so many people there that we just looked up at the lighthouse from a distance and left.

St Augustine in general seems to be a very dog-friendly city. You can easily find a water bowl in the downtown area, and many shops and restaurant patios welcome dogs. I saw too late that dogs are allowed at the Fountain of Youth, wish we’d taken her there for a drink!


5 responses to “Four days in St Augustine, FL (visit #1)–Southeast Lollipop trip”

  1. […] about our subsequent Florida destinations: Destin, St Augustine, and […]

  2. […] beaches in Florida to get you started. And Bugsy found a couple great spots on a later trip to St Augustine and […]

  3. […] St Augustine, it was an uneventful 4.5-hour drive across the top of Florida to Eastpoint, on the so-called […]

  4. […] We were in St Augustine from 1/28 to 2/1/2022 as part of our Florida in January trip. Read about our first visit to St Augustine in 2020 here. […]

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