Pine Island Authentic
Always an adventure at the Ragged Ass Saloon
“Get your motor running, head out on the highway, looking for adventure and whatever comes our way.”
It has been a long time since I was at the Ragged Ass Saloon on Pine Island. In fact, the last time I was there, smoking was allowed and Milwaukee’s Best was on tap. I heard new owners had taken over this establishment that has been on Pine Island since the mid-’50s, so I decided to boat over there and check it out.
Friends Nick and Lori, who are always up for an adventure, came along. The weather could not have been better for a boat ride from Captiva to this unique waterfront restaurant. We left from McCarthy’s Marina on Captiva, traveled out of Roosevelt Channel, and then pointed the boat southeast toward Chino Island. We boated past Chino Island under the powerlines, past York Island, then after clearing Crescent Island, followed the channel into the Monroe Canal.
The Ragged Ass Saloon is in St. James City on the southern end of Pine Island. You can reach it by boat, car, bike, or walking. My favorite way to travel is by boat, which makes getting there half the fun. Canals were dug years ago on Pine Island to create more waterfront property. Ragged Ass is on the northernmost point of Monroe Canal, one of the longest canals in St. James City.
The Monroe Canal always holds a sense of wonder for me.
It is a kaleidoscope of water vessels, then and now. The canal is lined with forgotten dreams, old boats, new boats, and boats that haven’t moved in years, crab, shrimp, and tiki-bar boats, as well as fish-cleaning tables, boat lifts, and hot tubs. Midway up the canal you come to a bend; this is the point where, in Hunter S. Thompson’s words, you “buy the ticket, take the ride.” We are all in now, as we pass the Low Key Tiki Bar another favorite haunt of Pine Island locals.
We come to a boat ramp where much activity is going on. Just past that are Australian pine trees on the right where the canal can shoal, so stick to the west side of the canal when nearing the pines. Beyond the pines is our destination. A sign on the righthand side lets you know where to dock. If you are a new boater or do not do well docking with a current, head for the first set of docks you come to. The current is not as strong at that point as it is closer to the restaurant.
After getting the boat tied up and taking two steps off, I come face to face with an island cruiser Budweiser bike. Only at the Ragged Ass Saloon. A Kenny Chesney duet plays on the speakers as we sit down in the outside seating area. I am curious to see what the inside looks like since the last time I was here, so I step inside the bar. It looks to be the same guys sitting at the bar who were there 20 years ago—only this time there is no smokefilled air and no Milwaukee on tap. I do notice, however, without a sea of smoke clouding the walls, a “This Bud's for You” sign.
Back outside, our food arrives and we run into an old friend I have not seen in a long time. Good food is eaten, stories are shared, and memories are made. Next time I won't wait so long to return the Ragged Ass Saloon.
[Editor's note: Hurricane Ian exacted a toll on the Ragged Ass Saloon, but it is expected to reopen early next year. The Low Key Tiki Bar is open and as local as ever.]
Capt. Brian Holaway is a Florida Master Naturalist and has been a Southwest Florida shelling and ecotour 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.
It looks to be the same guys sitting at the bar who were there 20 years ago—only this time there is no smoke-filled air and no Milwaukee on tap.