History in Florida? It sounds almost unbelievable to non-Floridians. But nestled on the coast of the sunshine state rests the ancient city of St. Augustine—a bucketlist destination for foodies and history buffs alike. This week, we invite you to wander with us down its winding cobblestone streets.
A Walk Down History Lane
St. Augustine is the oldest continuously settled city in the United States (impressive claim to fame, right?). The original settlement was founded in September of 1565 by Spanish admiral Pedro Menéndez de Avilés. 100 years later, it became home to the oldest masonry fort in the United States—Castillo de San Marcos, which still proudly watches over the city today.
Where to Stay
We’ve visited St. Augustine twice. The first time, we stayed in the historic Sevilla house. The second time, we were running from Hurricane Florence and enjoyed a longer stay courtesy of two amazing locals who opened their home to us and were proud to show us around their beautiful city.
Since you’re probably not a hurricane evacuee, we can’t send you to the latter of the two (as much as we’d like to), so we’ll send you to the Sevilla house. Built in 1888, this historic home is now a beautiful B&B. It’s located within walking distance of all the city’s main attractions, and its scenic balconies are perfect for sipping wine and looking out over the narrow streets below. Our room even came with a CLAWFOOT TUB.
The owners of the Sevilla house take a lot of pride in their hospitality, which made it an amazing experience all around. They fed us a gourmet breakfast and loaded us with advice and local maps.

What to Do
We sure have a long list for you here. There’s so much to do in this brilliant little city that you probably won’t have time for everything, just do your best
- Wander: Before you tie yourself to an agenda, take some time to simply wander around the historic city center. You’ll come across sites like the old city gates, constructed in 1808, and the oldest wooden schoolhouse in the United States. Not to mention a whole caboodle of cute little boutique stores and coffeehouses.
- Castillo de San Marcos: You can’t miss a visit to Castillo de San Marcos, the impressive old fortress that stands proudly by the bay. Entry is a little steep at $15, but 80% of this goes right back into maintaining the fort.
- Flagler College: The college itself wasn’t founded until 1968, but it makes its home in the former Ponce de Leon hotel—built by railroad magnate Henry M. Flagler in 1888. Its Spanish Renaissance architecture and sprawling grounds make it well worth the visit.
- The Fountain of Youth: Want to stay forever young? Drink the sulfury waters at Ponce de Leon’s fountain of youth. The extensive park that houses the fountain is additionally home to a recreated Timucuan village and a strutting host of brightly colored peafowl.
- The Alligator Farm: This might sound a little cheesy and touristy, but it’s actually well worth the visit. There are food dispensers so you can feed the alligators yourself from the boardwalk, but the real attraction is the bird rookery, where a congregation of fascinating birds have chosen to (voluntarily) make their nests. Believe it or not, the alligators don’t eat them.
Where to Eat
Where not to eat? This bustling city is a foodie’s dream, with farm to table restaurants and wine caves around every corner. A couple of places you won’t want to miss:
- Casa de Vino 57: This hidden little getaway offers a free wine tasting in addition to some of the best charcuterie we’ve ever had.
- Juniper Market: Please try their magic cold brew coffee. You won’t regret it, we swear.
- Meehan’s Irish Pub: This friendly little drinking hole really comes alive at night. Stop by for the outdoor bar and an atmosphere that’s second-to-none.