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RSW Living Magazine

Paradise at the End of the Road: A Quiet Getaway in Chokoloskee

Sep 07, 2021 05:00PM ● By CAPT. BRIAN HOLAWAY

There is a place where the sidewalk ends / And before the street begins, / And there the grass grows soft and white, / And there the sun burns crimson bright, / And there the moon-bird rests from his flight / To cool in the peppermint wind.  —Shel Silverstein (Where the Sidewalk Ends


Chokoloskee Island is literally at the end of the road. Connected by a causeway to Everglades City on the mainland, the island is as far south as you can drive on the west coast of Florida. It has been home to fishermen and their families for centuries. The entire island is an ancient pre-Columbian Native American shell mound and one of the highest elevations in the Ten Thousand Islands and Everglades. 

My destination on this outpost of an island is the Parkway Motel and Marina; the goal is to relax and recharge at the end of the road. The marina has been on the island since the 1950s, and according to an eighth-generation local fishing guide, Kent Daniels, not much has changed except for the roof over the main dock. The original owner was Robert Smallwood, a descendant of Ted Smallwood, a postmaster who in 1906 built the nearby Smallwood’s Store, made famous in Peter Matthiessen’s Shadow Country trilogy, his retelling of legendary events that occurred in the area in the 19th century.  

Today the marina and motel are operated by two young ambitious individuals, David Ardlean and Aaron Tabor, who are the fourth owners of the property. They have been improving and updating this piece of paradise over the past year. 

Upon checking in at the Parkway, I was asked, “Coors Light, Miller Lite or Amstel Light?” After handing me my ice-cold Amstel Light and room key, the owners said, “Grab your beer and come down to the dock and meet everyone.” I did exactly that. People pulled up in golf carts and listened to the music emanating from the portable speaker resting on the ice machine. Stories ranged from the fish caught, golf-cart batteries, why Pandora has commercials, the unique fragrance in the air and the search for a blue lighter that was lost the night before. Conversations and anecdotes went on past sunset, new friends were made and old stories retold, but the blue lighter was never found. 

Enjoying the moment and getting away from everyday life was the plan at the Parkway Motel and Marina, and I felt I had succeeded in every way. 

As Tatum, who works in the office, says, “As long as I have shrimp in the tank, gas and ice, I am good to go.”  

Ardlean says, “We are at the end of the line on highway 29.” 

Tabor, who grew up in the area, says, “It is what it is.” 

I say, “I give it five stars on great hospitality and very clean rooms.” 

If you look past where the sidewalk ends, you will find the smiling faces at the Parkway Motel and Marina at the end of the road, where paradise begins and your troubles are left behind… on Chokoloskee Island. 


Capt. Brian Holaway is a Florida master naturalist and has been a Southwest Florida shelling and eco-tour guide since 1995. His boat charters visit the islands of Pine Island Sound, including Cayo Costa State Park, Cabbage Key, Pine Island and North Captiva. 


1180 Chokoloskee Drive, Chokoloskee 

The Parkway Motel and Marina has motel rooms, a historic cottage and modular fishing lodges for rent. The marina has a handful of boat slips available for boats up to 24 feet, and it sells the only gas available on the water in Chokoloskee.  

Nearby attractions are the historic Smallwood Museum and the Havana Café of the Everglades (the café is open seasonally). Three miles up the road in Everglades City is Hole in the Wall Pizza and other eateries, including Island Café and Triad Seafood Market and Café