Recommendations for a Microtrip to St. Augustine, Florida

Recommendations for a Microtrip to St. Augustine, Florida

Weekend getaways and microtrips are a great way to do more exploring. We recently enjoyed a quick weekend getaway to the compact and historic city of St. Augustine, Florida. Below are our recommendations from that trip.

Spending six weeks living and working remotely in Savannah, Georgia, as a digital nomad is nice for a lot of reasons. One reason is the possibility of fun weekend getaways and microtrips. So one Friday after work, we packed up and hit the road heading south. Our destination: St. Augustine, Florida.

Recommendations for a microtrip to St. Augustine includes the beautiful Flaglar College.

The plan was to spend two days exploring this historic U.S. city. In reality, we only needed one day. This town is compact and easy to see. We stayed at a cheap hotel that I would not recommend. Luckily, there are plenty of accommodation options, so pick something that suits your style.

Something to note: We did not visit the beaches, which is a main attraction for some folks. We visited in January and although we had fantastic weather, it was not swim-in-the-ocean weather. We were, however, within the window for holiday lights, which we very much enjoyed. Honestly, no matter what time of year you visit, you will have a good time.

The holiday lights from a boat tour, a great recommendation for a microtrip to St. Augustine, Florida.

Our Recommendations for a Microtrip to St. Augustine, Florida

  • Head to Drake’s Bistro for breakfast. This place is located a bit north of the main tourist area, but it is a tasty and worthy breakfast spot.
  • Visit the Castillo de San Marcos National Monument. You will learn a lot about the history of St. Augustine and things like tabby and coquina–that is what the fort is made of. Catch the cannon firing if you can, which only happens on the weekends. Pro tip from a friendly volunteer: sit on a bench directly across from the cannon. You can relax while watching stuff explode and you do not have to fight the other tourists for a good view. 
  • Wander the cobblestone streets on foot or take the hop on/off trolley. Or do both.
  • Visit St. George Street. It will be full of people. But there is a lot of history and shopping and eating so it is worth a stroll. I can recommend shopping at the Red Pineapple.
  • Speaking of shopping, if you like maps and leather, stop by Dan Holiday Leather.
  • Cool off by eating a Hyppo’s fresh fruit popsicle. There are SO many flavors and it is a perfect treat on a hot day.
  • Enjoy a Peace Pie (a.k.a. ice cream sandwich). They are a little different than what you might be expecting. But they too are a nice treat on a hot day.
  • Burrito Works Taco Shop has good tacos if you are feeling Mexican food. You can also get a good Cuban sandwich in St. Augustine because, well, Florida.
  • Stroll around Flagler College. If you want to tour the college, get your tickets early. They will most likely sell out. If you do not get tickets in time, there is still plenty to see in the courtyard and main entrance. In fact, the WC is even worth a look.
  • If you are there around the holidays, book a holiday lights boat tour. We got a Groupon for Red Boat Tours and it was the perfect way to end our time in St. Augustine.
Cannon fire demonstration at the Castillo de San Marcos National Monument.


St. Augustine, Florida, is a compact, historic city with a Spanish vibe. This city makes a perfect weekend getaway or microtrip. If you visit, check out some of our recommendations and let us know what you think.

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