Why We Fell in Love with St. Augustine

People often ask us why we chose St. Augustine.

The easy answer is that it’s beautiful.

The real answer is a little more complicated.

Like many visitors, we first came for a getaway. We expected history, great restaurants, and a charming downtown. What we didn’t expect was how quickly St. Augustine would start to feel like home.

There is something different about this city.

Maybe it’s the brick streets and centuries-old buildings. Maybe it’s the way locals greet you with a smile. Maybe it’s the feeling you get walking through town at sunset when the crowds have thinned and the city seems to slow down just enough for you to appreciate it.

For us, St. Augustine became more than a vacation destination. It became a place where we could reconnect, recharge, and spend time with the people we love.

Over the years, one trip turned into many. We discovered favorite restaurants, hidden courtyards, quiet beaches, and local events that most visitors never find. We built friendships. We became part of the community. Before long, we found ourselves spending more and more time here.

That love for the city eventually led us to create St. Augustine Guest Houses.

Our goal was simple: create places where families, couples, friends, and remote workers could experience St. Augustine the way we do.

Whether you’re staying at the Art House, the Downtown Guest House, or the Uptown Cottage, we want you to feel like you’re staying in the home of a friend who genuinely wants you to fall in love with St. Augustine too.

One of our favorite things about hosting is hearing from guests after their stay. Many tell us they arrived planning a quick vacation and left already thinking about their next visit.

We completely understand.

That’s exactly what happened to us.

In this blog, we’ll share our favorite places, hidden gems, local recommendations, seasonal events, and insider tips we’ve collected over years of exploring America’s oldest city.

If you’re planning a visit, welcome. We can’t wait to share our St. Augustine with you.

— David & Wendy
St. Augustine Guest Houses

2021 at the St. Augustine Guest House

Wendy and I made a decision after the new year.  We were going to do what we always talked about, spend the winter in St. Augustine as snowbirds.  On January 4th we packed everything in our work van and like the birds, we flew south for the winter, although we didn’t fly, we drove.  The drive itself wasn’t bad, it was 17 hours or so, door to door.  We stayed the first night in Baltimore and brought our own pillows to the hotel which was pretty empty so it was easy enough to be COVID-19 safe.  The next day it was a little longer and we drove to Savannah, GA and we really enjoyed it.  By Tuesday afternoon we were set up in the guest house for the foreseeable future.

We had guests in December and our kids, Sam, Baylee, and Ty stayed over the holidays through New Year’s Day and we currently are guests in our own guest house as the winter in Boston goes on without us and we work remotely as does our team at TeamBonding.  St. Augustine is the same as we left it when the pandemic started in March, much more the same than life in Boston as the city is open, restaurants are open, Nights of Lights happened and people came and are still coming.  We are wearing our masks, eating outside at the restaurants we love, listening to live music from afar, walking, biking, and boating.   We’re planning to go back home in April and open the guest house to guests again in April as more people get vaccinated here and at home.

We are happy to be here and are updating and upgrading the house that guests already love and we want to continue to improve the house for you and your family.  There may be no place like home but we want our guests to feel at home here in St. Augustine.