Have a Colonial Thanksgiving in Historic Florida

We all know the story of the first Thanksgiving, which took place nearly 400 years ago in the very beginnings of the Plymouth Colony.

The holiday (and its tradition of delicious food, gratitude and camaraderie) has long been tied to the colonial experience. But if a visit to Plymouth Rock this year seems just a bit too cold, there are other ways you can immerse yourself in an old-world, colonial environment for the holiday—like, for example, cruising down to Florida!

While a fall or wintertime trip to Florida never really needs a reason, here’s one anyway: The state’s gorgeous coastal vistas and centuries-old architecture offer a wonderful way for boaters to connect with the country’s past and, of course, express their gratitude for the thrill of travel by water.

One of the best examples of Florida’s colonial history is, of course, St. Augustine—renowned as the oldest city in America. Read on as we explore the charm and culture of this one-of-a-kind destination, a perfect warm-weather alternative to chilly Thanksgivings up north.

Getting there

Traveling from up north? One of the delights of visiting St. Augustine during Thanksgiving is the thaw you’ll feel as you make your way south, relishing in the sunshine and water-friendly weather that washes over you with every mile closer.

Even before you encounter any of the region’s rich history, you get to have some fun along the way. The St. Johns River, the longest in Florida, offers beautiful views throughout the entire northern span of the state—they begin by Jacksonville, where plenty of marinas and bright, sunny cityscape vistas lend an air of excitement to your journey. It’s the “big city” on the St. Johns—Florida’s largest, in fact—and there could not be a better place to welcome you on your southbound adventure.

Several parts of the river are wide enough for water sports, too, so don’t forget to bring your wakeboard or skis on your trip!

Of course, life on the St. Johns isn’t all hustle-and-bustle. In fact, quieter legs along the way offer a chance to reflect, recharge and rediscover a side of Old Florida we don’t often see in the brochures. Those who love springs and lush, untouched oases will enjoy cruising near the Ocala National Forest—dock your boat and hop into a canoe or kayak to experience the Central Florida springs, which sparkle against the lush backdrop and clear blue skies above.

As the St. Johns River keeps you inland, you’ll need to venture off course once you get toward St. Augustine. A quick trip eastward brings you to the coast and, naturally, to the one-of-a-kind environment—where “old” meets “new”—that awaits you there.

Step (and cruise) into the past

Bring your walking shoes, because there is a lot to explore on land, too. History buffs will love to see the sights such as historic, old-time facades of St. George Street and the famous Fountain of Youth (which they say drove Spanish explorer Juan Ponce de Leon to explore the region in the first place).

If you’re looking for the perfect place to have a Thanksgiving lunch, why not enjoy a delicious potluck picnic al fresco, perhaps by the beach? That’s probably what they did at the first Thanksgiving, after all—an event that, according to University of Florida professor Michael Gannon, actually took place in 1565 right here in St. Augustine. Though no one can deny the famous gathering of 1621, Gannon said the St. Augustine gathering of Spanish settlers and native residents was the first act of its kind on the land we now call the United States.

Water that “wows”

After getting your fill of history on land, take to the water! Of course, even here, the lessons never really let up. As you cruise through the gorgeous Atlantic water, take a peek up at the storied Castillo de San Marcos and its famous cannons—or indulge in the quaint charm of the beautiful Bridge of Lions, where you can really see the city in all its glory. The view has a special sort of glow around sunrise, so come early and stay late! Your Chaparral is your first-class ticket to exploring the dreamy, idyllic shores of St. Augustine, the Matanzas River and the scrub-lined Salt Run.

Looking to warm up? Get away? Immerse yourself in history or all of the above? Whatever you’re looking for this season, a Thanksgiving trip to St. Augustine’s got the solution. We hope you enjoy your Chaparral adventure to the fullest! Be sure to share your photos, stories and must-do tips along the way.