Cruising to Cabbage Key, Pine Island Sound, Florida


Cabbage Key, Gulf Coast, Florida 

Cabbage Key is a Gulf Coast island in Pine Island Sound accessible only by boat, helicopter, and seaplane. It’s a 100 acres of tranquility and history, with no paved roads and no cars.  The island consists of a dock, a restaurant/Inn, a few private houses, rental cottages, a former water tower/now lookout, and a nature trail.

Visitors come by cruise boat and water taxis to experience for a few hours what Old Florida felt like in the day – and to grab a “cheeseburger in paradise.” Cabbage Key is one of many islands Jimmy Buffet visited and enjoyed a cheeseburger.  The jury is still out on which island was indeed the inspiration for his famous song. During the daytime, especially “in season,” the island is busy with tourists and boaters.  After dusk its a quiet haven for those lucky enough to stay over.  

Captiva Cruise boat Lady Chadwick

The Lady Chadwick arriving at the South Seas dock at the South Seas Resort at the north end of Captiva Island.

Overnight visitors come for the peace and tranquility.  Fishing, shelling, writing, painting, reading, and boating are some of the island’s main activities.  Forget TV and Internet. Did I mention tranquility? 

Okay, so after awhile peace and tranquility are overrated.  Sitting at the quirky bar listening to tall tails of the fish caught, or the ones that got away is a possible (and likely) distraction. 

Bar at Cabbage Key Restaurant

The bar at the Cabbage Key Restaurant, can you spot the Jimmy Buffet autographed dollar bill over the bar?


Lots of history in these rooms. The Inn was the former residence of a famous mystery writer, Mary Robert Rinehart and is built on a Calusa Indian Mound

The Historic Cabbage Key Restaurant and Bar 

The Cabbage Key restaurant is the main focal point of the island. There are tables inside and out, and a small bar, however, the main attraction is the Dollar Bill dining room.  Our boat crewman told us that on any given day there are 75,000 signed dollar bills taped to every available surface, walls, ceiling, posts, ledges and each other.  Ask your server for tape and a marker and leave your autographed George Washington.  You’ll join celebrities like Julia Roberts, Kevin Costner and of course – wait for it – Jimmy Buffet.  They do make a great cheeseburger; it’s a two-fisted wonder, I know from experience! 

The History of the Dollar Bill Tradition

An amusing Captiva Cruises employee explained that the Dollar Bill tradition started many years ago. Fisherman, flush from a good catch (and after a few beers) taped dollar bills to the walls of the bar ensuring they would have money available for a future brew if money were tight. Nowadays 1000s of autographed bills are added every year, perhaps by visitors hoping to return.  Over time, when the tape lets go, and the cash drops to the floor, they’re donated to local children’s causes – about $14k a year.  

Captiva Cruises

My friends and I booked our cruise to Cabbage Key through Captiva Cruises. The departure point that day was South Seas Island Resort on the northernmost tip of Captiva Island. The cruise leaves at 10 am and returns about 3:15. The ride to the island is a little over an hour, leaving guests about 2 hours to have lunch and explore.
The boat is comfortable and safe.  Our boat crewman explained that the water in Pine Island Sound is 5 ft at its deepest so even if the ship sank we could continue drinking on the upper deck until the liquor ran out and we had to call for a tow.  

Dolphin Companions 

Dolphins kept us company for part of our cruise.  We were encouraged to make as much noise as possible while these freewheeling dolphins used our wake to propel themselves through the water.  Apparently, they love the attention and will step up their act if the silly humans make enough noise.   

More info: 

Mystery writer Mary Roberts Rinehart and her son Alan bought the island in 1938 for $2500 and spent $125,000 to add the house and necessary improvements to the island.  Rumor has it Mary wrote several novels while staying on the island.  The house was later turned into the Cabbage Key Restaurant and Inn created initially to attract Tarpon fisherman.      

The house was built on a 38 foot Calusa Indian shell mound.  There was a Calusa settlement on the island from 100BC to 1570.  

Presidents, famous writers, and Hollywood celebrities (George W. Bush, Jimmy Carter, John Kennedy Jr., Ernest Hemingway, Julia Roberts, Kevin Costner, Jimmy Buffet….) have come for the cheeseburgers, fish sandwiches and Key Lime pie, and to add  autographed bills to the walls. 

Info and tips:

Captiva Cruises

Captiva Cruise Cabbage Key boats depart from South Seas Plantation at the north end of Captiva Island (but check when you book your cruise as they have two departure points.  The cruise is $40, and $5 to park your car.  The cruise leaves at 10 am but get there early and line up if you want to choose a seat on the upper deck under the shade canopy. There is a bar with hard and soft drinks, coffee, and limited snacks, souvenirs.   

Website for Captiva Cruises 

Telephone: 239-472-5300

Cabbage Key Restaurant and Inn

The cruise to Cabbage Key takes a little over an hour leaving you a couple of hours to have lunch and tour the small island.  I suggest going straight to the restaurant to get a table.  Besides the people on your cruise (in season that could be as many as 140) there are small boats docked and the people that stay in the cottages. It gets quite crowded. The restaurant takes credit cards but won’t do separate checks so plan accordingly if you have a group. 

Cabbage Key Inn and Restaurant:
Address: Pineland, FL 33945
Phone: (239) 283-2278 

Pictures from our cruise to Cabbage Key…

Map of Pine Island Sound and Cabbage Key 


I'm in my sixties with the world at my feet and thoughts mostly of "where to next?". I retired in 2017, sold my house in Massachusetts and most of my furniture and "stuff." When not traveling you can find me in Florida in the winter and Rhode Island in the summer. Travel has been a passion from a young age, over the years I've discovered I'm a traveler, not a tourist. I prefer traveling solo, with a travel friend, or small groups. Whenever possible I would rather spend time in one place rather than moving around. I'll never turn down an opportunity to go to France, but my travels have taken me all over the world. I've met some incredible people and had some fantastic experiences.

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