St Augustine and Jacksonville
Flying into Florida in January, I expect beaches and mild air. This trip is different.
I am here with the Society of American Travel Writers on a familiarization tour of St. Augustine and Jacksonville.
The base is the Holiday Inn Express St. Augustine – Vilano Beach. It turns out to be an easy and comfortable home for exploring both cities.
The first stop is not the hotel. I go straight from the airport to the Pirate Museum in St. Augustine, carry‑on bag still with me.
I have always liked pirate movies, but do not expect much beyond fun displays.
Instead, I walk into serious history. The museum is full of artifacts and detailed replicas from this coast, and the pirate story here is deep and specific to St. Augustine.
Our guide is dressed as a pirate and also speaks in character. This could feel corny, but he knows the material so well that it works.
He talks about attacks, shipwrecks, and real figures behind the legends. At one point he jokes that local children in fourth grade know pirates almost as well as he does, since school groups come here so often.
The comment is funny, and it also shows how important pirate history is in this city. St. Augustine does not just decorate with a theme. It owns the story.
Right outside, the Colonial Quarter adds another layer. There is a band playing and food available. We are hosted, but regular visitors can buy dishes and drinks and enjoy the music. I follow the group into a blacksmith shop run by an actor in period clothing.
He explains how a real shop would have worked. There is an actual fire, hot and active, as he heats metal and shows how it is shaped. It looks dangerous in a very real way and gives a good sense of how hard daily life used to be.
It is one thing to read about trades in a textbook. It is another to stand a few feet away from a working forge.
Later, I finally check into the hotel. The Holiday Inn Express at Vilano Beach is a pleasant surprise. My room is large, with two oversized beds that take up generous space without feeling cramped.
There is a proper desk where I can sit with a laptop and notes. The bathroom is modern and spotless, with a long counter that easily holds toiletries, notebooks, and other travel clutter.
It is the kind of room that makes it easy to work and then actually rest, not just crash between stops.
The beach is a short walk away. I do not have time to settle into a full beach routine, but it is reassuring to know that the ocean is always right there. The hotel also keeps simple beach and water gear on hand for guests. For a winter visit, that flexibility is welcome.
Travelers from colder regions can slip from meetings or tours straight to the sand without a lot of planning.
One evening is devoted to St. Augustine’s Night of Lights. At first, I picture a standard seasonal display. Many cities hang holiday lights and run a festive trolley. St. Augustine’s version is on a different scale.
We ride an open trolley through town, which makes it easy to see everything. Buildings across the historic district are fully outlined in white lights. Hotels, restaurants, small shops, and even quieter corners all participate. The town seems to glow from every angle.
The atmosphere is relaxed. There are no heavy crowds on the streets, but plenty of people are out, enjoying the scene.
Faces are lit by the soft white bulbs, and you can feel the shared pleasure in the air. It is easy to understand why visitors fly in just for this experience.
For anyone coming from a snowbound city, sitting on an open trolley in mild air, surrounded by historic architecture wrapped in lights, is a very appealing way to spend winter.
The trip also includes a visit to San Sebastian Winery. “Florida wine” may surprise some travelers, and it certainly surprises me.
The facility is large and busy. On the tour, we hear production numbers in the millions of bottles each year. It is a serious operation, not a novelty stop.
Tasting the wines shows a commitment to quality and a clear sense of style. Any preconception that wine cannot be part of a Florida itinerary starts to fade.
Upstairs, the hospitality space makes a strong impression. I stay for lunch, which is carefully planned and beautifully served. The chef is creative and confident, and the food would be at home in any established culinary destination.
Dessert is the highlight. A plate arrives with a variety of sweets.
As a committed dessert lover, this is both a temptation and a test. One item stands out. A lemon custard that turns out to be the best I have ever tasted. It is bright and smooth and perfectly balanced. Even after the trip, that single bite stays in mind.
The St. Augustine Distillery continues the theme of local production. Here, the focus is on spirits. Our guide is energetic and engaging. He walks us through the process from grain to glass and points out the equipment and stages along the way. The smell of the mash and the cool air in the production area give the tour a strong sensory base.
Tastings at the end confirm that this is another serious player in the region, not just a quick stop added to fill time. Together, the winery and the distillery show that St. Augustine is not only about old buildings and pirate stories. It is also about craft drinks and the people behind them.
Jacksonville offers a very different feel. If St. Augustine is compact and historic, Jacksonville opens out along the St. Johns River. Our group visits the new riverfront plaza, where open space meets the water and offers wide views. The city skyline rises in front of us, and the bridges cross the river in strong lines of steel.
A river taxi ride gives another angle on the city. The day is cooler than expected, and the air on the water feels crisp. As we move along the river, I notice a “Manatee Crossing” sign. It looks like the kind of warning usually seen on a highway, but here it protects slow-moving manatees instead of cars. It adds a touch of quiet humor and underscores how urban life and wildlife meet along this stretch of water.
From the boat, Jacksonville’s mix of buildings, bridges, and natural elements becomes easier to appreciate.
For many travelers, a city comes into focus through its neighborhoods. In Jacksonville, that moment arrives at the Shoppes of Avondale along St. Johns Avenue. This is a walkable, tree‑lined area with low buildings and a friendly scale.
I take part in a tasting tour that stays within this compact district. Five stops, all very close to each other.
We visit Casbah, with its Moroccan theme and atmospheric interior. Brick sits in a historic 100‑year‑old building with wide windows that open to the street. Cork & Thyme offers wine in a relaxed bar setting. Peterbrooke tempts chocolate lovers with rich displays. Biscotti adds its own baked goods and treats.
The samples are moderate, but the variety is wide. As we move from one place to another, the neighborhood begins to feel familiar.
Local hosts mention a monthly block party here. On that day, merchants step outside, music plays, and the street fills with neighbors and visitors. My visit does not coincide with that event, yet it is easy to imagine. The area seems ready for it. Even on an ordinary day, the Shoppes of Avondale give a clear sense of how Jacksonville lives and eats away from the more formal attractions.
A familiarization tour has a specific purpose. It offers a series of snapshots rather than deep immersion in a single place.
This trip follows that pattern. I move from pirate history to colonial crafts. From hotel comfort to a town wrapped in holiday lights. From wine and spirits in St. Augustine to river views and neighborhood tastings in Jacksonville.
There is not enough time to explore every corner of either city, and that becomes part of the story. St. Augustine stands out as the oldest city in the United States, with a strong sense of its layered past and a surprising food and drink scene. Jacksonville shows its strength through the river, new public spaces, and a charming neighborhood that reveals local flavor one tasting at a time.
For readers considering this region, the message is simple. It is possible to combine history, coastal atmosphere, and genuine culinary experiences in a single trip. St. Augustine and Jacksonville are close enough to share a hotel base, yet different enough to offer two distinct impressions.
A great all-season visit.
