Sleepy means “sluggish,” and “fishing village” represents a community dependent on the fishing trade. A Google search of that three-word term will bring up towns and cities around the world that clever promoters love to describe as former sleepy fishing villages that thankfully, they gush, have overcome that sad condition and are now drenched in glam and fabulousness.

The fact is, the town of Naples started out in the 1880s as a retreat for millionaires (billionaires by today’s standards) who had the wherewithal to build a fine hotel and one of America’s most prestigious sporting clubs. They built two-story vacation homes. They put in a lush beachfront golf course, where Charles Lindberg reportedly landed his plane to visit friends. They stayed all winter or visited often because they could afford to. In 1889, acting first lady of the United States Rose Cleveland was the first guest at the posh Naples Hotel, followed by a who’s who of politicians, industrialists, and movie stars the likes of Greta Garbo and Gary Cooper.

By the mid-1920s, Barron G. Collier was building a utopian new town called Everglade, with a wide boulevard and an imposing neoclassical courthouse. His exclusive Rod & Gun Club was soon dubbed the hideaway for presidents. Meanwhile, the Orange Blossom Special launched its route between New York and Miami, stopping at the Naples Depot to drop off wealthy vacationers. They all came to enjoy the weather and the beach and to fish and hunt with native guides. Were those hard-working Seminoles, gladesmen, and ranchers “sleepy?” I think not.

They were hardly sleepy a century before that, when the Seminoles and Miccosukee outsmarted the U.S. Army and defied defeat. Nor were the gladesmen who speared alligators to feed their children or the cowmen who worked from sun up to sundown tending cattle.

Collier County Mounties

Down in the Everglades, Collier was carving a road through the swamplands to connect his new town to Naples and Miami. But there was such lawlessness along the route that he built waystations to house rough, tough, armed motorcycle cops to ensure safe passage for travelers. While the lawmen kept order on the trail, Wild West style, their wives pumped gas, served meals, and sold necessities at the waystation. As for uniforms, Collier learned of a recently closed Broadway play that had featured Canadian Mounties, so off he went to New York and bought their costumes. The fierce lawmen were proud of their high leather boots, but the pink jackets not so much. The Collier County Mounties patrolled the Tamiami Trail until 1935.

So please, as we marvel at our town’s world-class dining, beyond-fabulous fundraising galas, and glam-to-the-max hotels and boutiques, it’s worth an honest look back to discover the rich tapestry of our anything-but-sleepy past. 

EXPLORE

Collier County Museums

Free exhibits and programs at five locations.

colliermuseums.com

Naples Historical Society

Field trips and programs for schoolchildren, Palm Cottage walking and house tours, and free family days.

napleshistoricalsociety.org

Everglades City

The town that Barron Collier built.

visitevergladescity.com

Cattle Drive and Jamboree

March 9, 2024

A ceremonial roundup of 100 head of cattle and procession from Main Street, Immokalee, to Roberts Ranch. The colorful, family-friendly event includes storytelling, roping, and whip-cracking demonstrations, traditional food, music, and crafts.

colliermuseums.com

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During Nights of Lights, businesses and organizations light up St. Augustine, with a particular focus on the waterfront buildings. Exploring this illuminated town in temperatures milder than our own will quickly put you in the holiday spirit. My top tip for experiencing the lights—ditch your car in favor of one of the many tours available. You’ll enjoy the experience much more if you are not dodging the heavy traffic and many pedestrians.

To experience the lights from the water, I booked a one-hour boat tour on Scenic Tours. Tickets were $20 each (plus $5 booking fee for a total of $45 for two adults), and included hot chocolate and cookies. The lights were beautiful and festive, but after about the third circle of the waterfront area, my 16-year-old and I would have gone ashore happily. Still, it was a pleasant night, and peaceful out on the water, and we had cookies. https://scenic-cruise.com

Next time, I would book a trolley tour rather than the boat. There also are tours by carriage, golf cart—you name it. Visit www.visitstaugustine.com to find them all.

What to do

Viewing the lights will not consume much of your time. Luckily, there is much to do in St. Augustine. We spent the first day exploring the area by Old Town Trolley (www.trolleytours.com ). This gave us a feel for the layout of the town, as well as a brief history of St. Augustine from the trolley drivers.  We also took a Ghosts & Gravestones tour with Old Town Trolley. Like St. Augustine, it’s fun and quirky. It’s not scary, so appropriate for all ages. Passengers disembark at a few stops along the way, including a graveyard and the Potter Wax Museum.

The area that centers on St. George’s Street is a bustling little city with lots of shops, restaurants, and bars. While there are lots of the usual tourist traps selling t-shirts and souvenirs, there also are plenty of unique stores. Our favorite shopping, as well as a Luli’s Cupcake & Bakery (well worth a stop) was on San Marco Avenue. Shops, including vintage and thrift, line the route between the historic district and the location of the Oldest Store Museum Experience and the Old Jail Museum (which offer interesting tours with older kids, but would skip with little ones). My teenager spent the bulk of her time at Declaration & Co. at 63 San Marco Ave., partly because of its stock of Gilmore Girls items and clothes that she drooled over, but also because she won a $50 gift card in their Black Friday giveaway (www.shopdeclaration.com). We devoted the rest of our shopping budget to Second Read Books, a tiny second-hand book store at 51D Cordova Street.

For younger kids who dislike shopping, head over to the St. Augustine Alligator Farm (www.alligatorfarm.com). Other kid-friendly attractions include: Colonial Quarter (https://colonialquarter.com), The Fountain of Youth (www.fountainofyouthflorida.com), and the Castillo de San Marcos National Monument (www.nps.gov/casa).

No matter the ages of your kids, the campus of Flagler College worth a visit, especially when it is lit up at night.

Where to eat

There are many dining choices in St. Augustine. We visited The Columbia, the Florida-based Spanish restaurant chain at 98 St. George Street, for a delicious dinner with attentive service. (The Tampa location is Florida’s oldest restaurant, and the largest Spanish restaurant in the world).  It was harder to find open spots for breakfast, but we did stumble across Schmagel’s Bagels at 69 Hypolita Street. Schmagel’s serves bagels (obviously) and breakfast sandwiches, as well as coffee and hot chocolate. Schmagel’s limited indoor seating was closed, but its large patio was very comfortable, and the food and service both were excellent. Dessert options, however, are wide and plentiful. We were in town for just two days, so we were able to sample only Luli’s (as mentioned above) and fantastic ice cream sandwiches at Peace Pie World at 8 Aviles Street (https://peacepieworld.com).

Where to stay

I stumbled across the Pirate Haus while searching for a hotel. It was cheap, but I was little leary—maybe it’s too cheap and too quirky. In the end, I decided we could deal with quirky for two nights. It turned out to be a wonderful decision. We couldn’t have landed in a better location. It’s smack in the middle of the historic district. Parking is very limited (we managed to snag one of the hotel’s three spots for $10 a night), but there are lots very close by for $10-$20 a day. A pancake breakfast for everyone is included in the room rate. We enjoyed coffee, tea, and our names written in pancake batter. The pancakes are massive and will fuel your kids all day.

It’s a family-oriented hotel (bachelor and bachelorette parties are banned), and kids will love the brightly decorated rooms and roof deck. I knew going in that it might be noisy, and it was, but it was not excessive. I normally travel with a noise machine, but forgot it on this trip, and had no trouble sleeping.

The beds and pillows were comfortable. We only were in the the room to sleep, but the location was so perfect that we would stop back during the day to use the bathroom or drop off jackets and shopping. There is no individual temperature control in the rooms. The hotel guide provides advice on adjusting the vents, or how to contact staff if you want a different temperature. The entrance to the hotel is a steep flight of stairs, so it would be a bad choice for someone with mobility issues, and I also wouldn’t want to haul a stroller up and down the stairs. The hotel guide states that they buy the cheapest possible soap and shampoo, and this is accurate, so just bring your own.

Pirate Haus is old and unique. If you go in wanting luxury and perfection, you will be disappointed. But if you want a bargain and have some fun, it’s the perfect spot.

Pirate Haus Inn.  32 Treasury Street, St. Augustine.

Another option:  Casa Monica Resort & Spa.  95 Cordova Street, St. Augustine.

Originally built in 1888, Casa Monica is nestled in the heart of St. Augustine’s Historic District and within walking distance to popular sites such as Flagler College, Lightner Museum, Castillo de San Marcos and St. George Street. 

Getting there

The drive from Naples “should” take about 5 hours. Our trip north took more than 7. My advice: no matter what Waze tells you, just stay on I4 and deal with the traffic around Orlando. The side roads are congested, too, and even more frustrating.

A final note: If Verizon is your cell provider, plan for lots of frustration in St. Augustine. Our phones would occasionally have reception, but more often not.

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One Love Bob Marley

Every Little Thing Bob Marley

I Have a Dream Martin Luther King, Jr.

The Story of Rosa Parks Patricia Pingry

If a Bus Could Talk: The Story of Rosa Parks Faith Ringgold

The Bus Ride That Changed History Danny Shanahan

Chocolate Me Taye Diggs

Sweet Clara and the Freedom Quilt Deborah Hopkinson

I am Mixed Garcelle Beauvais

The ABC’s of Black History A Children’s Guide Craig Thompson

You Are Important Todd Snow

Sit-In: How Four Friends Stood Up by Sitting Down Andrea Davis Pinkney

Who Was Frederick Douglass? April Jones Prince

Who Was Nelson Mandela? Meg Belviso

Who Was Sojourner Truth? Mona Zeldis McDonough

Who Was Martin Luther King, Jr.? Bonnie Bader

The Story of Ruby Bridges Robert Coles

Escape North!  The Story of Harriet Tubman Monica Kulling

28 Days: Moments in Black History that Changed the Word Charles R. Smith

Freedom in Congo Square Carole Weatherford

Two Friends: Susan B. Anthony and Frederick Douglass Selina Alko

Courage has No Color: The True Story of the Triple Nickles, America’s First Black Paratroopers Tanya Lee Stone

The Life of Bessie Coleman: First African-American Pilot Connie Plantz

Tuskegee Airmen: American Heroes Lynn Homan and Thomas Reilly 

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