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NeverStopTraveling

Road Trip: Orlando – St. Augustine – Amelia Island

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Last Updated on February 28, 2025

man standing on air boat seen on a trip from Orlando to Amelia Island
Captain Mike on his Cypress Lake airboat / photos by the authors

Estimated reading time: 11 minutes

By John and Sandra Nowlan

With some water spray and wind in our hair, it felt like an exhilarating theme park ride, but it was in the open air with natural surroundings and real wildlife. Wild Florida, just outside Orlando, features exciting, hour-long airboat rides through Cypress Lake’s shallow, boggy edges.

A large sign at the entrance also gives credit to Nova Scotia, where Alexander Graham Bell invented the shallow-bottomed airboat driven by a large aircraft-type propeller mounted over its stern.

Then, as we slowed down after speeding past alligators and a wide variety of bird life, Captain Mike verbally credited Canada for presenting the United States with more than 30 breeding pairs of bald eagles in the 1930s. This generosity, he noted, basically kept the U.S. bald eagle population from extinction. It was a gesture we particularly appreciated after a few weeks of tense Canada-U.S. relations.

people walking along the walls of an old Spanish fort
St. Augustine’s 1672 Castillo de San Marcos

Our main goal for a week-long road trip from Orlando to St. Augustine and Amelia Island on the northeast coast of Florida was to explore the fascinating history and culture of the area and sample the cuisine, especially seafood, for which the state is justly famous.

Renting a car at Orlando Airport was relatively easy, with no shuttle required to reach the rental lot. Unfortunately, printed road maps are no longer available at check-in, so an effective GPS, perhaps on your mobile phone, is a necessity, especially with Orlando’s heavy traffic and complex highway system.

Our tour included hotels and a B&B while visiting Orlando, St. Augustine, and Amelia Island. All three communities love to share their rich history and vibrant culture with guests like us. Here are some of the attractions we particularly enjoyed:

a rhythm and blues band playing in a small auditorium seen on a trip from Orlando to Amelia Island
Rhythm and Blues in the intimate Judson’s Live auditorium

Orlando: Much More Than Theme Parks

Winter Garden, a small city (pop 48,000) that’s part of greater Orlando, has a charming downtown. It’s filled with small, unique boutiques (with no chain stores in sight) and also has a welcoming vibe we found very attractive.

Two no-charge museums stand out. The Winter Garden Heritage Museum has a well-maintained caboose out front and an interior focused on the community’s native and African American heritage as well as the rise and fall of the citrus industry. Dozens of labels from former orange producers fill the walls.

a man standing by a collection in a railroad museum
Bill Puckett in the Railway Museum

Winter Garden was also a significant railway center served by both the Atlantic Coast Line and the Seaboard Coast Line. The Central Florida Railway Museum honors those past years with photos, models, and railway memorabilia. Knowledgeable volunteers like Bill Puckett are delighted to discuss their passion for railroading.

The SOBO Art Gallery and Studio (named for its location on South Boyd Street) features excellent local art for sale and monthly art exhibits. In a back room, aspiring artists also have classes and workshops.

two women viewing an art exhibit seen on a trip from Orlando to Amelia Island
Local artist selling her works at SOBO

Since 2014, downtown Orlando has included the magnificent Dr. Phillips Center for the Performing Arts. The venue includes both 2700-seat and 1700-seat theaters. We were fortunate to be able to attend a more intimate concert by a local neo-soul, rhythm and blues band in the Judson’s Live auditorium with table settings for just 150 guests and a menu of cocktails and small, creative plates.

A black actor standing by a table covered with old china seen on a trip from Orlando to Amelia Island
An actor talks about his life as a slave at the Ximenez-Fatio House

Historic St. Augustine

St. Augustine, founded by the Spanish in 1565, is the oldest continuously inhabited European-established settlement in the United States. The city core is very walkable, but the best way to absorb and appreciate its remarkable history is with the 90-minute, 22-stop, Hop-on, Hop-off Trolley Tour.

people walking by an old wooden schoolhouse
Oldest wooden schoolhouse in the U.S.

Several attractions on the Trolley Tour stood out for us. Castillo de San Marcos is the oldest masonry fort in the United States. The Spanish started construction in 1672 to defend Florida and protect the Atlantic trade route. It is also remarkably well preserved. Also well preserved is the oldest wooden schoolhouse in the United States. There an animatronic teacher and “Dunce” student provide humorous commentary.

Two former luxury hotels in St. Augustine were built in the Spanish Renaissance Revival style by oil and railway magnate Henry Flagler. They were also among the first buildings in the world to use poured concrete.

people in an ornately decorated foyer seen on a trip from Orlando to Amelia Island
The remarkable interior of Flagler College

Hotel Alcazar, built in 1887, is now the Lightner Museum, housing a grand collection of Gilded Age antiques. The 1888 Ponce de Leon Hotel is now the 2500-student Flagler College. The design of its glorious interior was headed by Louis Tiffany. The woodwork, gold gilding, and stained glass windows are stunning. In fact, the college has the largest private collection of Tiffany stained glass in North America. It’s insured for more than 100 million dollars.

But it was our final stop in St. Augustine that was among the most moving. The three-story Ximenez-Fatio House, built in 1798, was a boarding house for many years during the American slave era. An hour-long tour includes talented, costumed actors performing short scenes that relive those dark days. It was a vivid eye-opener.

two shrimp boats at their dock seen on a trip from Orlando to Amelia Island
Shrimp boats along the shore of Amelia Island

Beautiful Amelia Island

Our final stop on our Orlando-St. Agustine-Amelia Island-road trip was Fernandina Beach on Amelia Island. And our far-from-ordinary Bed and Breakfast accommodation in the historic district of Fernandina Beach on Amelia Island, close to the border with Georgia, was a happy surprise.

Fairbanks House is a glorious 8,000-square-foot Italianate villa built in 1885 at the height of Fernandina’s Golden Era. The upscale neighborhood has dozens of other stunning homes built in the late 1800s in Victorian or Classical Revival style. The city has published a complimentary pamphlet showcasing many of them.

a US flag flying above an old fort
Fort Clinch, Fernandina Beach

Like many visitors, we took the Cumberland Coastal Tour (Amelia River Cruises), sailing between Florida and Georgia along the shorelines of Amelia and Cumberland Islands. Wildlife sightings included playful dolphins and Cumberland wild horses. Several colorful shrimp boats are tied to docks on this pristine island, but sadly, the mood is broken by a huge, steaming shore-side pulp mill.

For a small city (population, 14,000), Fernandina Beach has an excellent Museum of History in a former jail and a well-preserved Civil War-era coastal garrison called Fort Clinch. The fort promotes living history, and we enjoyed interacting with a knowledgeable gentleman in period costume.

people dining outside restaurants in an old market
Plant Street Market in Winter Garden: local vendors, organic food

Wonderful Cuisine

Shrimp and grits on a white plate
Shrimp and grits at O.C. White

We love fresh seafood, so on this Orlando-St. Augustine-Amelia Island road trip we looked forward to stuffing ourselves with Florida’s famous shrimp and local fish, such as grouper, mahi-mahi, and pompano. Large (often too large) portions are common in Florida restaurants, but we were usually impressed with the quality of our meals.

Our excellent Orlando accommodation (The Terraces at The Grove) had a dinner restaurant, Valencia, which was more like an aging Denny’s. Still, its breakfast had outstanding coffee and a good choice of standard fare.

Plant Street Market in Winter Garden is an indoor artisan venue featuring the Crooked Can Brewery and 20 local vendors serving wonderful natural, organic food. We enjoyed a delicious lunch with Bento Sushi and BBQ pork and beef. At the Judson’s Live venue in downtown Orlando (mentioned earlier), creative small plates prevailed.

Stand-Out Dishes

a colorful salad on a white late
Winter salad at Lo Cocino

Two shrimp dishes stood out in St. Augustine. Our best large shrimps came from the Salt Life Food Shack. They were served on skewers with glazed pineapple and pineapple fried rice. O.C. White’s Seafood Restaurant combines history (located in the Worth House, circa 1790) with excellent cuisine. Its blackened shrimp and grits with cheese, bacon, and green onions were a hit with both of us.

The Columbia Restaurant is a substantial Spanish/Cuban eatery holding 700 guests. It’s usually full, but the service is very efficient, and the food, especially our fresh grouper topped with local blue crab, was succulent.

seafood in a take-out carton
Our golden basket at Timoti’s

Being on a Orlando-St. Agustine-Amelia Island-road trip we expected fresh salads and two restaurants delivered. La Cocino, part of the San Sebastian Winery, had an excellent winter salad with roasted squash, cucumber curls, and local red datil peppers. The Ice House, a spacious converted 1927 ice storage warehouse, now a popular farm-to-table restaurant, served our best arugula and kale salad with apple, fennel, hazelnuts, and pomegranate. A creative chef!

Florida’s lucrative shrimp industry had its beginnings in Fernandina Beach on Amelia Island in the early 1900s. As expected, even its fried fish take-out was extraordinary.

blue crab dip on a skillet
Blue crab dip at the Salty Pelican

Our golden basket at Timoti’s included deep-fried shrimp, fries, hush puppies, and a giant fish sandwich.

At The Salty Pelican, a busy waterfront restaurant and sports bar, we enjoyed its signature blue crab dip. We could also choose among Shrimp & Oysters, a pound or a half pound of local ‘peel ‘n eat’ shrimp, or fried gator bits.

A Historic B&B

We can’t talk about food on Amelia Island without mentioning the breakfast at our historic B&B, Fairbanks House.

a beautiful Victorian-style house
The Fairbanks, a beautiful 1885 B&B

The full breakfast, served with real silverware and lovely china, included juice, fresh blueberries with sweet cream, blackberry waffles with chicken sausage, and banana bread. A wonderful ending to a week of outstanding hospitality.

Sadly, there is now some tension in U.S.-Canada relations because of the tariff threats and talk of Canada becoming the “51st State.” Florida tourism officials we met were very concerned about a drop in Canadian tourists.

Hopefully, relations can soon return to their normal friendly state.

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