Oldest City in America?

When I think of the United States of America’s oldest city, my mind reverts back to grade school, Christopher Columbus and Plymouth Rock. So when I learned that the Florida city of St. Augustine claims to be the oldest city in America, I was surprised–I would have thought it was a city somewhere in the northeast. However, what makes St. Augustine the oldest city, is that they are the nation’s oldest continually occupied European settlement in America’s history. The city was conquered by the Spanish…then the British…then the Spanish again…and eventually the United States during the civil war. The large fort, Castillo de San Marcos, dates back to the 1500’s and to this day you can still see the heavy Spanish influence in the city.

Flagler College in St. Augustine, FL

Flagler College

Throughout the city, there are attractions showcasing the city’s claim to fame, such as “The Oldest Schoolhouse”, “The Oldest House” and “The Oldest Street”. Areas such as the lighthouse, Ponce de Leon’s Fountain of Youth, Castillo de San Marcos National Monument, the Lightner Museum and the historic district with cobblestone streets, show some of the history and age of the area.

St. Augustine Lighthouse in St. Augustine, FL

St. Augustine Lighthouse

We opted to check out a combination of the historic sites as well as some of what St. Augustine has developed into today. Our first stop was the Old City Farmers Market located near the St. Augustine amphitheater . The market runs from 8:30 AM – 12:30 PM, and the hand crafted foods and organic produce looked amazing–I would have loved to purchase a few items if we would have had a place to store them out of the heat.

Old Town Farmers Market in St. Augustine, FL

Old Town Farmers Market

Since we ended up at the Castillo de San Marcos in the afternoon, we rushed through it a little faster than I would have liked, but it was just too hot to stand out in the sun much longer. If it is a hot day, make sure to visit in the morning as there isn’t much shade and the rooms inside get crowded and muggy. My favorite part of the fort was the upstairs, where you could look out over the intercostal and the city.

Castillo de San Marcos in St. Augustine, FL

Castillo de San Marcos

Castillo de San Marcos in St. Augustine, FL

Sign showing how the fort had to be rebuilt since it was 3 ft too low

Castillo de San Marcos in St. Augustine, FL

Interior of the Castillo de San Marcos

Seeking refuge from the sun, we decided to wait out the daylight at the San Sebastian winery–it was a long walk, but we were rewarded with air conditioning and a free tour and tasting. The website states that tours are around 1 hour-long, but ours lasted around 20 minutes total. I can’t complain because the tour was free, but it did feel very rushed and you didn’t get to see how they make the wine. Hopefully you can go on a day when they are offering full tours, but we did still enjoy the shortened version. They allowed you to taste 4-8 of the wines–you had a choice between two different wines each of the 4 times they came around, but if you were with someone who wanted to share, you could push your glasses together and try both. My favorite was the Rosa, least favorite was the Cream Sherry. Since we thought the tour would take up more of our time, we then decided to sit in the shade and listen to some relaxing music at “The Cellar Upstairs”, the winery’s rooftop patio, where they served drinks and appetizers.

San Sabestian Winery in St. Augustine, FL

San Sabestian Winery Tasting Bar

Wine Barrels at San Sabestian Winery in St. Augustine, FL

Wine Barrels

Heading back to the historic district to explore after sunset, we decided it was time for dinner. Many of the restaurants in the area served pizza and bar type food, but only a couple blocks away from the main streets of the historic district, we found a little cobblestone street with a variety of sidewalk restaurants. It turns out that this was Aviles Street, the oldest street in America. We chose an Italian restaurant, Nonna’s Trattoria–it was a nice and relaxing way to spend the rest of the evening. St. Augustine is a great place to visit for the weekend, and we would definitely go back again.

Aviles Street in St. Augustine, FL

Aviles Street

8 Comments
  • Richard Daybell
    Posted at 14:23h, 10 August Reply

    It certainly is. And you described it very well.

  • 5sOnTheFly
    Posted at 20:19h, 13 August Reply

    We also enjoyed our stop in St. Augustine during our travels down Route 1 last month. The historic district and lunch at the Present Moment Cage were our highlights. Thanks for the great post and pics!

    • Jenna Kvidt
      Posted at 23:08h, 13 August Reply

      Thanks, 5sOnTheFly! We really enjoyed the historic district too–I’ll have to check out that restaurant next time we are in the area. Thanks for the recommendation!

  • Heather
    Twitter:
    Posted at 04:05h, 23 February Reply

    I am a Florida native (now living in San Diego) and I, too, was surprised to learn of St. Augustine’s place as America’s oldest city years ago when it came to my attention! Thoroughly enjoyed my visit there. Thanks for a great recap!
    Heather recently posted…Barcelona Bound…Notes from the SkyMy Profile

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