South Florida Loop through Everglades

by | Feb 20, 2022 | Eastern U.S. | 0 comments

Map showing trip directions for South Florida Loop through Everglades road trip.

Quick Stats

Distance: 1000 miles

Recommended time: 5-6 days

Highlights: Everglades, Key Largo, seafood, random backroads

Main Highways: FL-75, 41, 29, 997, 1, 95, 11, Orman Beach Drive

Note before we get rolling on this awesome road trip: Though the map above shows a full loop of the southern half of Florida, the trip really didn’t start until the western entrance to the Everglades. Since I was on limited time and seeing friends, the rest of the trip (from Everglades to Key Largo to Flagler Beach and back to Tampa) was a blitz with many key sites left out. Doh!

Florida Initial Observations

Aside from the spectacular cloud formation in front of me as I headed south on I-75 to my hotel in Naples, there were three things I noticed since landing in Tampa: (1) How green Florida is (I read it has over 2800 native plant species), (2) How flat it is (no hills in site anywhere). (3) How muggy it is (it sticks to ya).

Driving on freeway with green grass and trees on both sides, cars in front and a sundown sky with layers of white and dark clouds

I-75 near Sarasota

Everglades

Everglades City

The first goal of Florida was hitting the Everglades, and in particular, an airboat tour (a bucket list item for years). While waiting for the airboat tour, I decided to check out Everglades City (pop. 400), a sleepy lost-in-time community with historic buildings dating to the 1920’s. It’s worth a drive through, and is the only town in this part of the Everglades.

Two-story square green building with white trim at right, narrow road leading into green trees in horizon, street lined with palm trees. Blue sky with scattered white clouds in background.

Everglades City

Wooden post with seven signs attached pointing different directions, labeled from food to boat slips. Green grass at bottom and some yellow flowers behind the post. Grey sky behind.

Everglades City

Airboat Tour

There are dozens of airboat tour companies, and I chose Everglades City Tours. It was a great rush gliding through the thin channels and byways and into open areas for alligator spottings.  As much as I enjoyed the ride, I would recommend two things if you’re interested in an airboat tour: (1) Use one of the tour companies in the eastern section of the Everglades (alligators like fresh water, and since our location was close to the ocean, our tour only spotted one gator.) (2) Go for a two hour ride on a private tour as opposed to a six-person group tour.

Round blue tower pointing to sky, with balcony and sign hanging from it saying "Everglades City Airboat Tours."

Everglades City Airboat Tours

Swamp view from edge of boat, with water at bottom leading thru a tunnel of green leaves and sticks point every direction.

Everglades Airboat Tour

Video of Florida Everglades airboat ride

Backwoods Everglades and Skunk Ape

Aside from swamp and gators, the Everglades has its share off head-turning road curios. As I was driving along Highway 41, I noticed what looked like an ape-like creature coming out of the woods. Turns out it was a lure for nearby Skunk Ape Research Center. The Everglades has its own version of Bigfoot, and the owner says there are seven or eight of these cryptids wandering the Everglades.

Thick two-foot high grass at bottom, with a statue figure resembling an ape walking through the grass. Green trees behind the figure, and blue sky with scattered clouds above.

Skunk Ape spotting

Statue of ape looking figure with "skunk ape" printed at bottom. Small single story shack behind the figure, saying Skunk Ape Research Center. Blue sky behind the shack and figure.

Skunk Ape Research Center

Looking sideways at river with three alligators at bottom somewhat hidden among some rocks and bushes. Some bushes on then a road are on other side of river.

Alligator spotting (three at bottom of photo)

The Everglades is also home to the smallest post office in the US – a tiny shack (60 sq. feet) with just enough room for one postal worker. It has a plaque next to it detailing its history.

alt="Small white shack at right with lady in front, post office sign at left, with green trees behind. Blue sky above."

Smallest post office in the US

Key Largo

As much as I wanted to drive the distance of the Florida Keys after leaving the Everglades, I only had time for one night at Key Largo.  I stayed at the Marriott Key Largo Bay Beach Resort, which has a huge pool overlooking the bay, jet skis you can rent, and Cactus Jack’s and Senor Frijoles next door for music, drinks and food. Both have a great laid back Jimmy Buffett “it’s five o’clock somewhere” vibe.

alt="Two umbrella covered tables at left, overlooking calm water reflecting the bright white and orange clouds above at sundown. A few people in beach chairs below the huts."

View from Key Largo Bay Marriot

The Cloisters of the Ancient Monastery

Out of Key Largo, I headed north up the coast and bypassed most of Miami, but did have to stop at what is supposedly the oldest standing structure in the Western Hemisphere: The Cloisters of the Ancient Monastary. Dating to 1130’s AD in medieval Spain, It has a fascinating history. Originally brought over from Spain in bricks by William Randolph Hearst, it almost never got assembled due to his bankruptcy. AtlasObscura, a favorite site of mine, has a detailed article on it

Arched doorway lined with black iron design at top and black iron gates. Through door is stone monastery building in the distance.

The Cloisters of Ancients Spanish Monastary

White and grey stone monastery corner section, with bell tower and arched doorway. Blue sky behind building.

The Cloisters of Ancients Spanish Monastary, Built (1133-1141 AD)

Jensen Beach and Flagler Beach

North of Miami, I headed up Highway 1 for the beautiful beach drive and nonstop palm tree beach towns (Delray and Palm Beach are couple favorites) and isthmuses (Highway A1A). In Jensen Beach, I had excellent seafood at the Dolphin Bar and Shrimp House. In Flagler Beach (named after the “father of Miami”, Henry Flagler), I had a hearty omelette at the Funky Pelican. Flagler Beach has a laid back beach vibe and is worth checking out!

Front of Funky Pelican restaurant doors, with Funky Pelican in blue letters in sign above and two blue doors with circles for windows below.  Grey sky above.

Funky Pelican, great for brunch

Road lined with palm trees and the edge of a stucco roof home on left and ocean on right. Cloudy blue skies behind the road.

Highway 1 north of Miami

Calm ocean water reflecting the bright yellow and white clouds at sunset, with American flag at bottom right.

View from deck of Dolphin Bar and Shrimp House, Jensen Beach

Wooden walkway with two people standing at end overlooking beach and ocean, and boat at bottom right. Grey clouds in the sky above.

Flagler Beach

Silver Springs

After Flagler Beach I headed west to one of the most iconic (and retro!) tourist destinations in the state: Silver Springs.  A National Historic Landmark, Silver Springs started its famous glass bottom boat tours just after the Civil War in the 1870’s. Six Tarzan movies from the 1930s were filmed there, along with Moonraker and Creature From the Black Lagoon.  Sadly, Disney ended up taking all of Silver Springs’ glory.

Arched sign entryway reading Silver Springs flanked by two white canopies for shade. Thick green trees behind the sign, and pavement below.

Silver Springs

Wooden bridge structure disappearing straight ahead into think green trees, grey sky in background.

Trail at Silver Springs

Webster

One of the main reasons I came to Florida was to see some true swampy backwoods towns. I found that in Webster, a city of 800 off Highway 471 in the middle of nowhere. Founded in 1855, it is considered the “cucumber capital” of Florida. Once central to the citrus industry, the great freeze of 1894-95 forced the town to change over to vegetables. That’s literally all the info I could find on it. Hanging moss trees cover the town.  Many of the Main Street buildings are boarded up, the main gas station is abandoned, and the local barber shop is in a wooden shack.

Thick hanging moss trees overhang neighborhood street. Road disappears into horizon ahead.

Webster neighborhood

Orange Gulf gas station sign at upper left, with road at right and grey sky above. Dark green trees line the street.

Abandoned gas station in Webster

Red shack in middle of photo sitting on green grass and below a thick green tree.  The shack is a barber shop.

Webster neighborhood

Street corner with stop sign and sign reading "NE First St," orange painted single story building at corner.

Webster, Florida

Spook Hill

Noted on all these of “cool and unusual things to check out in Florida” lists is Spook Hill in Lake Wales. A National Historical Landmark, this “gravity illusion” hill is the type of “mystery spot” the Griswolds from National Lampoon’s Vacation may have stopped at. You park your car on this white line, put car in neutral, and while the optics fool you into thinking you will roll forward, you end up rolling backwards!

Sign displaying the history of Spook Hill, with a painted ghost pointing to the sign. Green grass below the sign, and some thick green trees behind it.
Road leading over a small hill, lined with grass and trees on both sides, and an archway above the road saying "Spook Hill."

Spook Hill, Lake Wales

Lakeland

After arriving in Lakeland (the base for checking out Bok Gardens early the next day) the Lakeland Marriott front desk recommended checking out the Italian Renaissance Polk Theatre (1928) where Elvis played three shows in his prime in 1956 (view photos here). He also came back for some more shows well past his prime in 1976 (view video here).

Vertical blue sign at upper right saying "Polk,' with shop lined street disappearing into horizon straight ahead at sunrise. Light blue sky above with a few clouds.

Polk Theatre (1928), where Elvis played three shows in 1956

Large multi-story orange arch in front of a shopping mall, blue sky with scattered clouds above the sign.

60’s style retro architecture in Lakeland

Bok Tower Gardens

Bok Tower Gardens is a massive “contemplative garden” and bird sanctuary with numerous trails to explore. Located about 45 minutes east of Lakeland, it was built in the 1920’s in Spanish Revival style by Frederick Olmstead, who is noted for planning Washington DC’s layout and projects in Yosemite.  It’s a nice peaceful escape.

Pond with lily pads floating in it and palm trees at the edges. Grey cloudy sky above.

Bok Tower Gardens

Circular light grey stone tower covers the length of the photo, with trees on both sides and cloudy grey sky above.

Bok Tower

Plant City

On the way from Bok Gardens to Tampa, I explored some of Plant City, and found some cool Art Deco architecture from Florida’s initial growth years in the 1920’s-30’s.

Green Art Deco style building at right saying Waller Center with a clock on it.  Street at left disappears into the horizon. Blue sky with clouds above.

Art Deco architecture in Plant City

Oranges and orange slices painted on side of building at right, with palm tree at left and blue sky with scattered clouds above.

Mural in Plant City

Dragon head protruding from a front lawn with big white teeth in center of picture. Some green trees behind dragon, and street lamp at left. Blue sky with scattered clouds above.

Dragon spotting in Plant City

Tarpon Springs

I had some time to burn before hitting the Rays game in Tampa for my final night, so I headed about 45 minutes north of Tampa to Tarpon Springs. While it is known for its Greek heritage, I stumbled upon the Replay Pinball Museum, which has over 100 pinball and video games (including some awesome classics and rare oldies). Rather than having to lug around a pound of quarters, you pay one price at the door and have unlimited play on all the games. It was great fun and I found some old favorites here like Donkey Kong, Defender and Galaga.

After the game bonanza, I drove through Tarpon Springs with it’s Greek-style white and blue buildings. It was packed with tourists, and luckily I found parking for a lamb shawarma. Founded by Greek sponge fisherman in the early 1900’s, it has the highest percentage of Greeks of any American city. You can still watch the sponge fisherman from the docks.

Street leading into a town with street lamps on both sides and American flags hanging from them. Some shops and trees on both sides of street. Blue sky above.

Tarpon Springs, entering Greek area

A row of pinball machines on left side and brick wall behind them. Walkway at right with a few pinball players in the distance.

Replay Museum, Tarpon Springs

Tropicana Field

While Tampa Bay Rays’ Tropicana Field routinely gets voted the worst major league ballpark, I beg to differ on that; in my book, the worst either goes to Miami Marlins Stadium or Oakland Coliseum, both of which have virtually no redeeming qualities. While Tropicana Field has worn turf and a dreary grey ceiling (which outfielders lose fly balls in), a couple things saved it from ranking at rock bottom.

First off, the food court and bar area plaza behind centerfield is a fun open space to wander around, and there are various spots to stand and watch the game while hanging out and having a beer. Though I paid for a ticket behind home plate, I ended up watching the game from here for the fun atmosphere. Second, behind the center field wall is a pool of real sting rays swimming around. No joke! You can even wait your turn in line and pet them.

View of inside of indoor baseball field from behind center field, with baseball field below and some spectators watching from edge of the fence. Grey dome tower above with bright white lights hanging from it.

The outfield plaza at Tropicana Field

From inside the indoor baseball park, a pool below the outfield stands with sing rays swimming in it. Blue color seats and scoreboard is above the pool.

Sting Rays in the outfield

Cement walkway path disappears in center of photo into the horizon, lined by palm trees on both sides and grey clouds above at sundown.

Walkway out of Tropicana Field

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