History, Great Food, and Coastal Charm in Northeast Florida
🎉 A Birthday Getaway to Florida’s Oldest City
I wanted to plan something special to celebrate my husband Bob’s birthday. Knowing he isn’t a fan of big parties but loves to travel, a fun weekend getaway with our great friends Gary and Mary seemed like the perfect idea.
We wanted somewhere we could drive to easily, but that still felt like a real escape. St. Augustine immediately came to mind. Located about three hours from our home, it’s a destination we had visited briefly years ago for an overnight stop. Ever since that short visit, we had talked about going back to explore it properly.
A St. Augustine weekend trip sounded like the perfect birthday celebration.
🏛️ What Is St. Augustine Known For?
St. Augustine proudly holds the title of the oldest continuously inhabited European-established city in the United States.
Spanish admiral Pedro Menéndez de Avilés founded the settlement in 1565, more than 50 years before the Pilgrims arrived in Plymouth.
Because of its Spanish origins, the city still reflects a strong Mediterranean influence in its architecture, courtyards, narrow streets, and historic landmarks.
Today, St. Augustine is known for:
- The historic Castillo de San Marcos, the oldest masonry fort in the United States
- A charming Old Town historic district filled with shops, museums, and restaurants
- Beautiful waterfront views along Matanzas Bay
- Easy access to beaches and outdoor recreation
- Several excellent golf courses along Florida’s northeast coast
The combination of history, coastal scenery, and vibrant tourism makes it one of Florida’s most interesting cities to visit.
🏡 Where We Stayed
St. Augustine offers a wide range of places to stay:
- Waterfront hotels
- Historic bed-and-breakfast inns
- Condos and resorts
- VRBO and Airbnb homes
I tend to gravitate toward VRBO or Airbnb rentals because I enjoy having a full kitchen and living space when traveling with friends.
In St. Augustine, the vacation rental market is booming. Many historic homes are being purchased and beautifully restored with modern interiors while maintaining their original charm.
We stayed in a charming two-bedroom cottage called the Pink Hen House, located within walking distance of the Old Town district.
The house had been recently remodeled and was perfect for the four of us. Best of all, it allowed us to avoid driving into the crowded downtown area and hunting for parking.
🚗 Driving Around St. Augustine
We quickly learned that downtown St. Augustine traffic can be intense, especially on weekends.
When we arrived Saturday afternoon around 4:30, it took us 45 minutes to travel just three miles through the center of town. Cars and pedestrians filled the streets, and the city was buzzing with activity.
We had planned to meet my daughter Danielle and some friends who were spending the weekend aboard their 38-foot boat docked at a marina near the historic district.
Parking near the marina proved impossible, so we improvised. We picked Danielle up at a nearby intersection, drove to our VRBO to park the car, and then walked back to the marina.
Fortunately, traffic improved considerably by Sunday and became very manageable on Monday and Tuesday.
🌅 Sunset Cruise on the Matanzas River
After introductions, we headed out for a relaxing sunset cruise along the Matanzas River.
We passed beneath the famous Bridge of Lions, a beautiful drawbridge guarded by two marble lion statues modeled after those in Florence, Italy.
Our destination was Beaches at Vilano, a lively waterfront restaurant located across the river.
After docking the boat, we enjoyed cocktails while waiting for our table. A musician was playing classic rock favorites that perfectly matched the relaxed atmosphere.
The food was good, but the real highlight was watching the sunset over the water while the evening sky slowly turned shades of orange and pink.
Heading back after dinner, the Bridge of Lions was illuminated, creating a spectacular scene reflected on the water.
If you enjoy boating, St. Augustine offers many great opportunities for sunset cruises, sightseeing tours, and water adventures.
🚋 Touring Historic St. Augustine
Gary and Mary love exploring new places as much as we do, so the next morning we set out to see as much of the city as possible.
After researching online, we purchased tickets through Viator for the Hop-On Hop-Off Old Town Trolley Tour, which circles the historic district and stops at many major attractions.
The trolley offers a great overview of the city and helps visitors understand the layout of Old Town.
However, we quickly discovered something important:
Many attractions along the trolley route charge separate admission fees, typically ranging from $10 to $25 per person.
While the trolley office sells discounted attraction packages, we decided to purchase tickets individually so we could explore spontaneously. On the bright side, we discovered that many attractions offer senior discounts — one of the few perks of getting older.
Families visiting St. Augustine may want to consider the Discover St. Augustine pass, which bundles several attractions with trolley access.
🏛️ The Lightner Museum
We boarded the trolley and listened as the driver shared stories about St. Augustine’s long history while passing the waterfront and the massive walls of Castillo de San Marcos.
Rather than completing the full loop, we hopped off at Stop #10 — the Lightner Museum, which had been on our must-see list.
The museum is located inside the former Alcazar Hotel, part of a luxury resort complex built in the late 1800s by railroad and oil magnate Henry Flagler.
Flagler played a huge role in transforming Florida tourism by building grand hotels and extending the Florida East Coast Railway down the state.
Inside the museum we found an eclectic mix of fascinating exhibits, including:
- Decorative art and antique furniture
- Stunning cut-glass crystal collections
- Historic musical instruments
- Vintage bicycles dating back to the early 1800s
- Natural history artifacts and even a mummy
The museum grounds are also beautiful, with lush landscaping and tranquil courtyards.
🍽️ Great Restaurants in St. Augustine
🇮🇪 Meehan’s Irish Pub
After leaving the museum, hunger struck. We walked along St. George Street, the pedestrian heart of Old Town, and eventually made our way toward the waterfront.
Our trolley driver had recommended Meehan’s Irish Pub & Seafood House, and we were glad he did.
Gary ordered the turkey meatloaf, which our waitress enthusiastically recommended and which turned out to be excellent.
The rest of us ordered:
- Irish Cuban sandwich
- Fried oysters
- A burger (gluten-free option without the bun)
Everything was delicious and it was a perfect place to escape the heat and crowds.
🇮🇹 Nonna’s Trattoria
After a busy day of sightseeing, we were tired and decided to grab takeout for dinner instead of sitting in a restaurant.
We discovered Nonna’s Trattoria, which offered a great combination of Italian dishes and seafood.
Bob and I ordered chicken parmigiana, which may have been the best we’ve had — even compared to some restaurants in Italy.
Gary and Mary chose perfectly prepared grouper, light and flavorful.
🇵🇪 Llama Restaurant — A Culinary Highlight
For Bob’s birthday dinner we reserved a table at Llama Restaurant, a small Peruvian restaurant just across the Bridge of Lions on Anastasia Island.
We had discovered it while researching the top restaurants in St. Augustine, and reservations were required weeks in advance.
The restaurant only has about ten tables, giving it a cozy and intimate atmosphere.
The food, however, was extraordinary.
We shared appetizers including:
- Pulpo Octopus Carpaccio
- Crab Causa mini crab cakes
For entrées we ordered:
- Seafood risotto
- Andean-style rack of lamb
- Surf and turf
- Arroz con mariscos
The flavors were incredible — fresh ingredients combined with unique Peruvian spices and sauces.
By the end of the evening we all agreed Llama ranked among the top three restaurants we’ve experienced anywhere in the world.
Chef Mircel Vizcarra has truly created something special.
🏛️ Exploring St. Augustine’s Historic District
St. Augustine’s Old Town district covers a surprisingly large area filled with historic landmarks and attractions.
Highlights include:
- Flagler College, originally built as the luxurious Ponce de Leon Hotel in 1888
- The Oldest Wooden School House
- The Old Jail Museum
- Numerous historic churches, including Grace Methodist Church and Flagler Memorial Presbyterian Church
However, the centerpiece of the city is the massive Castillo de San Marcos.
Constructed by the Spanish in the late 1600s using a unique coquina stone made from compressed shells, the fortress successfully defended the city from numerous attacks over the centuries.
Today the fort is a National Park Service historic site.
Visitors can explore the interior rooms and watch cannon-firing demonstrations performed by reenactors in period uniforms.
🌊 The St. Augustine Seashore
Getting out on the water is one of the best ways to enjoy St. Augustine and escape the downtown crowds.
Popular options include:
- Scenic boat tours
- Dolphin-watching cruises
- Sunset cruises (highly recommended)
- Airboat rides through nearby marshlands
If you prefer a beach day, the region offers more than 40 miles of Atlantic coastline including:
- St. Augustine Beach
- Crescent Beach
- Mickler’s Landing
Before heading to the beach, we recommend visiting the St. Augustine Lighthouse & Maritime Museum.
Climbing the lighthouse is manageable and rewards visitors with 360-degree views of the coastline and historic city.
The museum also highlights St. Augustine’s maritime history, including the early shrimping and shipbuilding industries.
🌴 Final Thoughts on Our St. Augustine Experiences
Our St. Augustine getaway turned out to be a perfect birthday celebration filled with great friends, fantastic food, and fascinating history.
Although we spent three enjoyable days exploring the city, we barely scratched the surface of everything there is to do.
A week-long vacation would allow visitors to experience more of the city’s museums, beaches, restaurants, and outdoor adventures.
And we didn’t even get to mention the excellent golf courses nearby — something Bob and I definitely plan to return for in the future.
A Few Takeaways
Things to Know Before Visiting
- Saturday crowds in Old Town can be intense
- Many attractions charge individual entrance fees
- Research ahead if traveling with a family to manage costs
With its blend of Spanish colonial history, coastal scenery, and vibrant dining scene, St. Augustine remains one of Florida’s most unique and enjoyable destinations.
We’ll definitely be back.
It was a great mini vacation
Interesting read, I love St Augustine and you gave us more great attractions to explore next time we get there.
Thanks – we will definitely need to plan a trip up there together. Lots to do and see and we only scratched the surface.