About Wayward Key Tours
Private boat charters in Clearwater and St. Petersburg, Florida
Private Charters
Your boat, your group, your day. No crowds- just a personalized experience on the water.
Local Knowledge, Better Experience
Local, experienced, and passionate about sharing the best of Florida's Gulf Coast.
Dede, First Mate
Organized, creative, and here to make sure every detail of your day is perfect.
Tessa the Turtle
Our friendly mascot who brings smiles, high-fives, and a love for the ocean to every adventure!
How Wayward Key Tours Began
Wayward Key Tours began with one unforgettable private boat tour in Grand Cayman. It reminded us how different a day on the water feels when it is personal, peaceful, and never shared with strangers.
That feeling became the inspiration for what we wanted to create in Florida — private boat charters where families, couples, and small groups could slow down, explore, and enjoy the Gulf Coast at their own pace.
Now, Captain Keith, Dede, and Tessa the Turtle help bring that vision to life through private charters in Clearwater and St. Petersburg designed around your group, your comfort, and your perfect day on the water.
Meet the Wayward Key Crew
Captain Keith
Captain Keith is the calm, capable heart of Wayward Key Tours. With experience as a U.S. Navy submariner, Navy diver, and cardiac nurse, he brings safety, confidence, and local Gulf Coast knowledge to every private charter.
Dede, First Mate
Dede brings creativity, care, and a storyteller’s eye to every charter. As a past travel writer, she loves noticing the special moments and capturing candid photos guests can look back on long after their day on the water.
Tessa the Turtle
The official mascot of Wayward Key Tours!
Tessa loves adventures, meeting new
friends, and reminding everyone to
respect and protect our oceans.
A private Boat Tour that Feels Personal
Wayward Key Tours was created for guests who want something more relaxed and meaningful than a crowded public boat tour. We focus on
quality over quantity, with flexible routes, local insight, and genuine hospitality. Every day on the water is shaped around your group, the
conditions, and what will make it an unforgettable experience.
why Guests Love Our Tours
Our 230SD WorldCat Catamaran
- Stable and smooth 23-foot WorldCat catamaran
- Private charters for up to 6 guests
- Comfortable seating with shade and plenty of space
- Swim platform with ladders for easy water access
- Onboard restroom and freshwater sink
- Bluetooth stereo to set the perfect vibe
- Sunchill float and Bean Bag Chairs
Private, Flexible, and Built Around Your Group
Unlike crowded public tours, a private charter with Wayward Key Tours is all about you. We customize the day based on your interests, the tides, and the weather to create the best possible experience on the water.
- Private boat reserved just for your group
- Up to 6 guests per charter
- No crowded public tour boat
- Flexible route based on your interests
- Family-friendly and comfortable
- Locally owned and Veteran operated
