Boat trip to Cabbage Key and visit to a historic restaurant

Your day begins with a peaceful cruise from a charming little marina on Captiva Island, setting course for the picturesque island of Cabbage Key. 

The journey itself is an experience to remember. You’ll sail through the beautiful Pine Island Sound, while the captain shares fascinating stories about the area’s history and rich wildlife. Keep an eye out for dolphins often playing in the boat’s wake, and take in the stunning views of mangroves and tiny islands. Drinks and snacks are available to purchase on board, so you can sit back, relax, and fully enjoy the voyage. 

After around an hour’s sailing, you’ll arrive at Cabbage Key – a small, lush island of roughly 100 hectares, where time seems to stand still. The island can only be reached by boat and has no cars, which adds to its authentic “Old Florida” charm.

Once you arrive, it’s worth stopping by the island’s landmark – the historic Cabbage Key Inn & Restaurant (also known as the Dollar Bill Bar), which dates back to the 1930s. It’s a good idea to book a table if you’d like to enjoy lunch here (not included). The restaurant has a reputation that reaches far beyond Florida’s borders – its walls and ceilings are covered in dollar bills signed by famous guests such as Jimmy Buffett, John F. Kennedy Jr., Ernest Hemingway, Katharine Hepburn, and Julia Roberts. You might even catch sight of some of the island’s resident sea turtles that live close to the restaurant.

After lunch, you’ll have time to explore the island at your own pace. Take a short walk along the small nature trail, discover the rich wildlife, or climb the old water tower to enjoy the stunning views over the surrounding archipelago. The island’s lush nature makes it the perfect place to unwind and truly relax.

In the late afternoon, the tour returns towards Captiva. Sit back on the boat, feel the sun and the sea breeze, and enjoy the final part of the journey – perhaps once again accompanied by dolphins – before arriving back after a day filled with nature, history, and authentic island atmosphere.

Remember to bring: appropriate clothing, sunscreen

Duration: 4–5 hours depending on wind conditions

The tour includes: boat trip to and from Captiva Island and Cabbage Key

The tour does not include: lunch at Cabbage Key, drinks and snacks on the boat, and tipping for the guide on board

Weekly departures: Tuesday, Thursday, and Saturday

Worth noting: Feel free to bring your own dollar bills if you’d like to hang them up in the restaurant. There is a toilet on board. The boat has both a covered area and an open deck – seat reservations are not available. You can park your car right next to the marina where the tour departs from (approx. USD 5), payable locally. Children under the age of 1 travel free of charge, but a reservation is still required. The tour may be cancelled at short notice.