St. Augustine Perfect Day

Enjoy a Fun Day in St. Augustine, FL

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St. Augustine is the oldest city in Florida. There are dozens of interesting historical sites to visit as well as a lovely beach and other unique attractions. I love history and am always searching out ways to incorporate it on our vacations, but sometimes you just want a relaxing and fun day. Luckily, St. Augustine is the perfect place to do just that!

Start your day with coffee

Historic downtown St. Augustine is chock full of delicious coffee shops. The hardest part will be deciding which one to enjoy! We tried several, but if you park in the Visitors Center Garage ($15 for the day), one of the first ones you’ll walk by is City Perks Coffee Co.

We stopped in this adorable shop and tried a few of their monthly specialty drinks. Yum! If you haven’t had breakfast yet you can also pick up some tasty baked goods to munch on while savoring your drinks. Plus, if it’s later in the day, they also have a wine bar! Coffee and wine? I’m in.

Explore Old City

Since you’re already in the Historic Downtown area (often called Old Town or Old City), enjoy the next few hours checking out all the cute shops. We discovered plenty of jewelry shops, island clothing, fun decorations for your house, and more. One of my favorite shops is Whetstone Chocolates (there is a tour about a mile from Old City at the factory too). We enjoyed frozen hot chocolates and I picked up one of their chocolate liqueurs to enjoy later.

Frozen Hot Chocolate from Whetstone Chocolates

There are two main streets through Old City, George Street, and King Street with dozens of offshoots. It’s easy to get lost, but don’t worry, head back to one of those two streets and you can get your bearings again.

Old Town St. Augustine

Even with all the shopping, you can still pick up a bunch of history in the midst of the retail stores. Many of the buildings are original – some even from the 1700s! There are interesting historical markers and buildings all throughout Old City, so be sure to stop and soak up a little history too!

Lunch is a tough choice in the Historic Downtown Area

There are SO many delicious choices for lunch in Old City, so whatever you are in the mood for, you are sure to find it. We discovered a hidden gem in The Floridian. With several outdoor seating areas with a garden feel it was a lovely break from the hustle and bustle of the shops and busy streets.

The Floridian specializes in upscale Southern food. We indulged in salads, soups and a cheese plate. All with fresh bread. I saw a few burgers go by to other tables and they looked amazing so if you want something a little heartier, I say go for it!

Check out the fort and waterfront

After lunch, stroll down to the waterfront to check out the boats and get some fresh air. Also on the waterfront is the Castillo de San Marcos. Whether you decide to take one of the tours and go inside or just walk around outside, it’s well worth exploring.

Castillo de San Marcos was built by the Spanish in the early 1670’s to protect the area against pirates and other threats. If you enjoy history, it doesn’t get more interesting than this location!

Enjoy an afternoon drink

Old City is full of fun places for an afternoon break. Many of the restaurants and bars have a terrific happy hour. We stopped at Boat Drinks for a tasty cocktail. fresh oysters and yummy chips and dips.

Boat Drinks offers quite a few happy hour specials – fun versions of typical beach drinks like margaritas, mules and more as well as regular-priced specialty drinks. It’s a great way to take a quick break and refuel for the rest of the day.

👉 One of the 2022 TOP 20 Viator Experience Awards is this amazing Feast of Saint Augustine Walking Tour. Sounds like a winner to me too!

Check out a distillery

St. Augustine is well known for distillery, winery, and brewery tours. We chose to stay in Old City and visit City Gate Spirits. This distillery offered free tastings of quite a few of their drinks. The pours were generous (we actually had to ask them to give us half pours)!

If you like any of the liquors or drink mixes, you can pick something up to take home and enjoy later.

By now you’ve had a full day in historic downtown St. Augustine – all on foot, so head on back to your lodgings and relax. Perhaps you can enjoy some of the chocolates or drinks you purchased and play a few family games to unwind!

Be sure to get your FREE copy of 5 Fun Family Experiences to keep those family fun experiences going even AFTER you return from vacation!


Get ready to enjoy a perfect day exploring the historic downtown area of St. Augustine. With great food, drinks, shopping and a little history, there is something for everyone! #floridatravel #travel #daytrips
Get ready to enjoy a perfect day exploring the historic downtown area of St. Augustine. With great food, drinks, shopping and a little history, there is something for everyone! #floridatravel #travel #daytrips