The plan was to have no plans. This is how my husband and I wanted to spend our first wedding anniversary. So we chose a city within driving distance of our South Florida condo, took the days off from work and booked a motel-turned-AirBnb. And that was it. Those three things were the extent of our “planned” anniversary trip to St. Augustine, Fla.

Any regrets? Nope. It was the least stressful vacay we’ve had in our 11-year relationship. And shouldn’t that be the goal: To vacay, staycay and daycay with as little stress and anxiety as possible?

Now, we feel like pros and are already not planning our next long weekend getaway. This time to Seattle. And you can, too. Here’s how to spend a long weekend in America’s oldest city with so few plans that each day there will feel like a self-contained day trip.

The AirBnb

We had no idea that this decision would set the stage for our entire trip, but it did. Apparently, “Old Florida” motels are being flipped into the sweetest AirBnb’s — complete with retro A/C window units, pastel decor and poppin’ beach cruisers. (Of course, there are some contemporary amenities too, like a flat screen and K-cups.)

While the draw is to a simpler time, it was hard for us not to think about a movement being planned in our very room. It was so retro that we even ran through an “Eyes on the Prize” playlist on Spotify on our first night, which to our pleasant surprise, included the unabridged recording of Martin Luther King’s “I have a dream” speech. We laughed but listened. It really was quite fitting. After all, this is the city where the Civil rights leader, on the night before he was arrested June 11, 1964, for demanding service at a St. Augustine hotel's restaurant, expressed: “If we have to go to jail, we are going. We are determined to make this city the kind of place that the oldest city in our nation ought to be.″

We stayed at the Florida Motel, which was about a mile from downtown St. Augustine. And yes, we rode our bikes every single day.

View On AirbnbFlorida Motel #3 KING "new" 50's Classic Cool!

The Vibe

If you’re really aiming for a memorable unplanned getaway, the vibe you set will become as much a part of your trip as you and your boo. It’s basically the third wheel, and right from jump, it’s up to you if this third wheel will be the life of the party or a total buzz kill.

If you’re not careful, your relaxing trip to this historic city can be swept up in the shuffling feet of tourists and the echoing of tour guide voices through bullhorns. But just make like Ali, and float like a butterfly through it all. For us, the motel was the beginning, and that chill, slow-moving, beautiful but unplanned vibe wrapped its arms around us, the city and our trip.

The Wheels

The two free beach cruisers that came with each room made the Florida Motel an even more perfect AirBnb. These bright teal rides were our wheels for the weekend, and they got us a lot of attention and saved us a ton of money on parking or bike rentals.

On our bikes, we could keep moving, never at risk of killing our vibe with traffic jams and impatient, horn-blasting drivers. We could also explore more. Staying about a mile from downtown meant we’d be biking 10-15 minutes each way, and as a result of some road work and a detour, we wound up in a pretty magical historic neighborhood.

But bikes aren’t your only option. You can also rent these little two-seater “ScootCoupes.” We saw them everywhere, and while they looked pretty cool, they’d get stuck in traffic like everyone else. And, of course, there are tours. Tons of tours. Tours on Segways. Tours on street karts. Tours on trolleys. Tours on bikes. So. Many. Tours. We didn’t jump aboard any of them. Instead of following the other out-of-towners, we skipped the organized experiences for some “found adventures” of our own.

The adventures

It’s impossible to avoid history lessons in St. Augustine. Everything in this city has a story. Every person, every building — everything. A few of our favorite adventures were biking to the lighthouse, eating at the Ice Plant, listening at the Fountain of Juice (you read that right, Juice not Youth) and walking around downtown. Here’s a quick rundown:

The Lighthouse

With no planned destination, we jumped on our bikes and headed toward downtown. We ended up at the Lighthouse after a tasty Aussie meat pie at The Kookaburra for breakfast. The ride was kind of crazy. But the sidewalks were great, and while traffic was stopped at the bridge, we just put those babies in gear and pushed ourselves toward, up and over the bridge.

Honestly, we were looking for the beach, which we never actually found. When we saw the lighthouse over the trees, we thought, that’s gotta be the beach so we headed that way. But nope — not a huge miss for us since we live near several in West Palm anyway. Instead, we explored Lighthouse Park and added another 240 stairs to our belt.

Talk about a great photo opp: Whether you’re capturing the walk up or the moment you arrive at the top, the lighthouse is beautiful. And with plenty of platforms for resting, you can pace yourself.

View this post on Instagram

366th day of marriage and still honeymooning... #oldflorida #lighthouses #bicycles

A post shared by Samantha Leigh (@sammyragland) onFeb 15, 2019 at 8:11pm PST

We biked 7.5 miles this day and our butts felt every one of them the following morning, but the pain wasn’t bad enough to keep us from unlocking our cruisers again and again.

The Ice Plant

A quick Yelp search landed us at the Ice Plant, a former (you guessed it) ice plant turned farm-to-table restaurant. The building dates back to 1927; it was the first of its kind to make commercial block ice in Florida more than 100 years ago. And it’s beautiful. As the website states: “[The building] is complete with the original bridge crane on rails overhead the bar. The crane was used to pick up huge blocks of ice to then be broken down and sold to local customers and the shrimp boats.”

View this post on Instagram

A post shared by Ice Plant Bar (@iceplantbar) onJul 19, 2016 at 11:23am PDT

We sipped cocktails while we waited for our table. And we drank some more once we sat down. With the most personable foodie waiter we’ve ever had, we were given a grand tour of the menu and then ordered two appetizers, two entrees and a dessert.

The pork belly sliders were the most memorable, delivering such an out-of-body experience that we went back a second night just for them. They were the right blend of salty, sweet and spicy. The truffle fries were also worth every bite.

The St. Augustine Distillery, which is credited with making Florida’s first bourbon, is downstairs from the Ice Plant and worth some time. There are free tours and free tastings! The rum was so buttery and sweet, we should have bought a bottle of it instead of opting for the rum cake, which was surprisingly dry and bland compared to the rum in its recipe.

The Fountain of Juice

Mr. Jim’s Fountain of Juice is right across the street from the Fountain of Youth, a landmark stop we didn’t make — though the pit BBQ wafting through the air nearly had us.

View this post on Instagram

A post shared by Samantha Leigh (@sammyragland) onFeb 17, 2019 at 9:17am PST

Instead, we hung with Mr. Jim, the 70-plus-year-old veteran who lost his arm in a war he didn’t detail. Had we not been exploring the neighborhood between our motel and downtown, we may have missed him altogether.

He told us about using the GI Bill to go to Mexico City College. He told us about the federalis and about his surfer son living in Argentina. We shared our mutual love for Cuban coffee, and he asked us to stop by Havana Cuban Restaurant when we get back to West Palm — of which we assured him, it’s one of our favorite 24/7 spots for curbside cafe con leche and empanadas.

Instead of seeing the Google-rated history at the Fountain of Youth, we were put to work, being Mr. Jim’s right hand to spoon out the rest of our fruit smoothies from his $20 Goodwill-bought blenders in his garage-turned-juice stand. There, we enjoyed another kind of history lesson and were in no rush to get wherever we were going because we knew the Spanish moss canopied over the street would wait.

The downtown

While you can enjoy St. Augustine without going on an organized tour, I think you’ll find it pretty difficult to bypass the city’s historic downtown. And why would you want to? It’s like walking into a time warp. The architecture is nothing short of inspiring. The shops are a blend of touristy and local gems. The bars are, well, bars.

We hit up the Maple Street Biscuit Company — a complete chaos zone at brunch time but sooo worth it. And kicked up our feet at a bar before biking by Castillo de San Marcos National Monument and setting our taste buds on Brisky’s BBQ for dinner. Don’t be curious for other things if you stop here: Just get the brisket, people. Trust me.

The honorable mentions

Our trip to St. Augustine wasn’t exactly typical. We skipped so much of the city’s history because we really wanted to vacation — not just travel. Is that strange? Maybe. Is there even a difference between the two?

Anywho, I can’t wrap this day trip article without sharing some “can’t-miss things to do in St. Augustine” for all my travelers out there. These are coming from the awesome locals we met on our vacation, and I can’t wait to visit the city again and knock these spots off the list.


Ghost Tours of St. Augustine: The walking tours are a fan favorite. And the tour guides are incredibly knowledgeable about juicy town gossip and messy relationships. Even if you don’t believe in ghosts and aren’t planning to try to capture any spirit activity on camera, the history interesting enough to keep you engaged. Learn more here.
The Prohibition Kitchen: This vintage gastropub is a go-to spot for locals and tourists alike. Step inside and “escape into the clandestine, mysterious, and yes, illegal world of flapper dresses, speakeasies, moonshine, and swing,” the website says. Learn more here.
The Hyppo, gourmet ice pops: With more than 450 flavors, all made with fresh fruit and love, the Hyppo started as a pitch to a random woman on an airplane. Millions of ice pops later and it has become a St. Augustine mainstay. From classic flavors to adventurous ones, Hyppo even offers a spiked ice pop: Think Riesling Pear, Sangria Pineapple and Piña Colada with Rum. Learn more here.
Lincolnville Museum and Cultural Center: This is one of Mr. Jim’s favorite spots in St. Augustine, so of course, it had to make this list. Opened in 2007 in the historic Excelsior School building, which was the first high school for African Americans in St. Augustine, the museum sits in the heart of St. Augustine’s Lincolnville Historic District and shows more than 450 years of African American history in the nation’s oldest city. Learn more here.
The Floridian: Call it “innovative Southern fare,” because they do, and you really shouldn’t miss it. This farm-to-table hipster spot may feel too cool for school, and it probably is, but the food is just too good — not to mention, the “Old Florida” vibes are on point. Try the (shrimp/tofu/fish) ‘N grits or ‘N waffles and don’t forget the fried green tomatoes. Learn more here.

For more Florida trips and adventures, sign up for the Palm Beach Post’s free weekly newsletter, Day Trippin’.