- contact@waywardkeytours.com
CLEARWATER & ST. PETERSBURG FLORIDA
- 727-355-3717
A fully private dolphin and wildlife charter in the Gulf waters of Clearwater and St. Petersburg. Your group, your pace — dolphins, manatees, rays, sea turtles, and more. No strangers, no fixed route.
"I know every dolphin hangout between Clearwater and St. Pete. Follow me."
— Tessa, your Gulf Coast guide 🐢
Before Wayward Key Tours existed, Captain Keith and Dede were out on the Gulf on their jet skis — frustrated they hadn't spotted any marine life. Even the laughing gulls sounded like they were mocking them. Then a head popped up out of the water.
She was floating on her shell, catching rays in the current. She laughed at their shyness and said — "This is Florida." When they asked why they couldn't find any marine life, she told them they were looking in all the wrong spots — and offered to show them where her friends hang out.
They kept running into her on the water after that. When the business started, they asked if she'd like to come along. She loved the idea. Now she greets guests, keeps tabs on currents and tides, and helps Captain Keith find the best spots every single day.
The coastal waters around Clearwater and St. Petersburg are rich with Gulf Coast marine life year-round. Every charter is different — here's what guests sometimes spot.
Bottlenose dolphins are common in local waters — Tessa knows their favorite hangouts near Caladesi Island, Three Rooker Island, and Honeymoon Island
A special sighting in calmer inlets and seagrass areas
Tessa's relatives — spotted gliding through the clear Gulf waters near sandbars
Pelicans, terns, gulls, and osprey fill the skies and shorelines
Often spotted gliding through shallow, clear water near sandbars and coastal flats
A note on wildlife: Sightings are never guaranteed — these are wild animals in their natural habitat. Captain Keith will always take your group to the best areas, and Tessa keeps tabs on where her friends are hanging out that day.
Wayward Key Tours always observes wildlife respectfully and follows federal guidelines for marine wildlife interaction. We never chase dolphins, approach manatees unsafely, or disturb nesting birds. Swimming with wild dolphins is not permitted. Our goal is to observe Gulf Coast wildlife in their natural environment without affecting their behavior — the way Tessa taught us.
Comfortable temps, calm water, very active marine life.
Warm water and long days — book morning departures.
Crowds thin, temps drop, wildlife stays active.
Quiet and uncrowded — dolphins are year-round residents.
Access to pristine Gulf barrier islands and waterways rich with dolphin activity and wildlife habitat.
Access to the southern Pinellas waterways — historic Egmont Key, Fort De Soto, and Shell Key Preserve.
Instead of sharing the boat with strangers, your group enjoys a relaxed, customizable trip built around your pace and interests. Whether you want to look for dolphins near Caladesi Island, cruise around Honeymoon Island, or watch for manatees in the seagrass flats — this experience is designed to feel personal and memorable.
Captain Keith's background as a former Navy diver means he knows these waters deeply. And Tessa keeps him posted on what's happening out there every day.
Every dolphin and wildlife charter is fully private and flexible — built around your group's interests and the day's conditions. Captain Keith adjusts the route in real time. Tessa keeps him posted on the currents and where her friends are gathering.
Questions? Call or text 727-355-3717
Book your private dolphin and wildlife charter in Clearwater or St. Petersburg. Your group, your pace, Captain Keith — with Tessa keeping tabs on where the dolphins are hanging out today.
Book Your Private Charter → Questions? Call or text 727-355-3717 · contact@waywardkeytours.com