Sunshine, History & Coastal Charm: A Mini Getaway to America’s Oldest City!

Why Visit St. Augustine?

If you’re a history lover or someone who craves European charm, beautiful street strolls, unique shops, cozy cafés, and great food—all without leaving the U.S., then St. Augustine is the perfect pick. As America’s oldest continuously inhabited city, it blends Spanish colonial architecture, 300‑year‑old landmarks, cobblestone streets, and European‑style courtyards with Florida’s laid‑back coastal vibe. It’s the kind of place where you can tour a centuries‑old fort in the historic district in the morning and unwind on a wide, white sandy beach just a few minutes later.

Arrival in Orlando & Getting Settled

We began our trip with a red‑eye from Seattle, landing in Orlando early in the morning. To avoid starting the trip exhausted, we booked a day(hours) - use hotel near the airport to catch a nap, freshen up, and enjoy a late lunch before driving north.

By early evening, we reached St. Augustine and checked into our Airbnb near the beach. We chose not to stay downtown, being close to the ocean was peaceful, convenient, and the perfect base. Still adjusting from the overnight flight, we kept our first evening easy and quiet.

Exploring the Historic District

The next morning, we headed into St. Augustine’s Historic District, known for its pastel buildings, cobblestone streets, charming shops, cafés, and strong Spanish influence.

Helpful Tip

Take an Uber or shuttle instead of driving. Parking was quite busy during Valentine’s week, weekends, and especially during Nights of Lights, which runs from Thanksgiving through mid‑January. (We were originally planning to visit during that season last year but couldn’t make the dates work.).  But if you’re hoping to experience Nights of Lights, make sure to book everything as far in advance as possible, flights, hotels, and especially the popular night trolley tours or ferry/light‑cruise tours, as these sell out quickly during the peak season.

A few iconic stops worth visiting, We covered a good mix of historic and quirky attractions, naming a few below:

Famous Colonial Buildings

• Villa Zorayda Museum – inspired by the Alhambra in Spain (offers seasonal candle light tours)

• Flagler College – once a luxury hotel built by Henry Flagler

• Lightner Museum – another grand former Flagler hotel, filled with art, antiques, and beautiful courtyards

• Casa Monica Hotel – A stunning Moorish‑Revival landmark built in 1888, it’s one of the city’s most iconic historic buildings.

Museums & Attractions

• Castillo de San Marcos – the iconic waterfront fort and the oldest masonry fort in the continental U.S., remarkably well‑preserved after centuries of battles and sieges

• Medieval Torture Museum – intense, dramatic, and very informative (not recommended for young kids!)

• Ripley’s Believe It or Not! – the very first Ripley’s museum in the U.S.; quirky and fun, built in 3 floors

• Old Jail Museum – fascinating look at jail life and justice from the late 1800s, the stories are gripping, and the night haunted tour adds an extra layer of fun.

The next day, we added a few more historic stops:

• Shrine of Our Lady of La Leche – serene grounds, known as a place, where women have prayed for healthy pregnancies; also, near the site of the first Catholic parish in the U.S.

• Fountain of Youth Archaeological Park – famous for its spring water and early colonial history, and of course the legendary belief that drinking from the spring could keep you young 😊. Beyond the folklore, the grounds are beautiful and full of wandering peacocks (such a highlight!).

• Cathedral Basilica of St. Augustine – The oldest Catholic parish in the U.S., stunning inside and out.

  
  

• Memorial Presbyterian Church – Known for its Venetian‑Renaissance design and gorgeous stained glass.

• St. Augustine Lighthouse & Maritime Museum - Its on the Anastasia Island is absolutely worth including in your itinerary. They host seasonal Illuminations events and ghost tours as well.

  • The lighthouse climb is one of the most iconic experiences in the city, truly reminded me of our Europe trip:

  • 219 steps to the top (a great workout!)• Panoramic views of the coastline, Matanzas Bay, Anastasia Island, and the historic district• A beautifully preserved black‑and‑white spiral tower, one of the most photographed spots in St. Augustine!

Budget Tip

Attraction fees can add up. Bundling experiences with Old Town Trolley passes can help reduce overall cost a bit.

Trolley Tours, Ghost Tours & More

Over the next couple of days, we used the Hop‑On Hop‑Off Trolley Tour, which made getting around incredibly easy. It stops at all the must‑see places — historic buildings, museums, forts, scenic viewpoints, and shopping areas.

We also took the night ghost tour, a fun storytelling experience that dives into St. Augustine’s spookier history and takes you to a couple of well‑known haunted stops.

You can also opt for horse‑drawn carriage rides or smaller guided tours — there are plenty of options depending on your pace and interests.

Weather Note

The water was cold, but the weather overall was sunny and pleasant. We didn’t need jackets except in shaded areas, during windy moments, or near the beach in the evenings.

Beach Time, Pool Days & Relaxation

Our Airbnb was one of the highlights, a heated pool in February, pickleball courts, and amenities just steps from the beach. Let me know if you want the link — it was truly a great find.

Beaches worth visiting: Each beach had a different feel:

• Anastasia Beach – wide, soft, peaceful

• Vilano Beach – breezy with beautiful rolling waves

• St. Augustine Beach – perfect for sunsets and evening strolls

• Crescent Beach - calm and spacious, great for long walks

The beaches here are wide, white, walkable, and even drivable in some areas, great for families, couples, and long shoreline walks. It was a bit chilly in February, but with the sun shining it felt wonderful, especially for us, coming from a place that isn't exactly known for its sunshine for the most of the year :)

Food Highlights: Must‑Try Spots

We treated ourselves to a few local favorites:

• Whips Waffle Company – fresh waffles with creative toppings

• Cousteau’s Waffle & Milkshake Bar – fantastic desserts

• Cookie Bird Ice Cream – delicious cookie + ice cream combos

• Pizza Time – frequently ranked among the top 2 pizza spots in the U.S.

All of these were easy stops within or near the historic district.

Heading Back: Fort Matanzas + Disney Springs

On our final day, we began the drive back toward Orlando. You can stop at Fort Matanzas, a small but scenic historic site, and even Daytona Beach if timing allows.

We took A1A for the first stretch lined with colorful new beach houses and gorgeous water views, making for an enjoyable drive.

As we approached Orlando, the traffic picked up significantly. Orlando traffic is very busy, so plan accordingly, it took us more than two hours each way.

We grabbed lunch at one of the many great restaurants in the area, then spent our final afternoon at Disney Springs. Parking is free, and while the shops can be pricey, it’s a fun place to wander, browse, enjoy entertainment, and soak in the lively atmosphere before heading to the airport.

Final Thoughts

Florida continues to be one of our favorite states whether you want activities, beaches, city life, palm‑lined streets, or simply a place to relax, it truly has it all. And St. Augustine, with its blend of history, architecture, and coastal beauty, made for the perfect mid‑winter escape.