From Clearwater: Caladesi Island, Honeymoon Island and the new island that formed off its northern tip, Three Rooker Island, and Anclote Key. From Maximo Park in St. Petersburg: Shell Key Preserve, Egmont Key, Passage Key, and Fort De Soto. Your route depends on the departure point, the tides, and what your group wants to do.

On the 4-hour Half-Day Island Escape, most groups comfortably reach two or three islands with real time to swim, shell, and walk at each. The 2.5-hour Gulf Escape suits one or two nearby stops. Four hours is what buys the range — the shorter charter spends too much of itself travelling if you push it.

Most of them. Caladesi is reachable by boat or by the ferry from Honeymoon Island. Three Rooker, Anclote Key, Shell Key, Egmont Key, and Passage Key are boat access only. That is exactly what keeps them quiet — no road, no parking lot, no day-trippers who drove up.

All rates are flat, for the whole boat, up to 6 guests. The Half-Day Island Escape is $575 for 4 hours and is the one we recommend for island hopping. The Gulf Escape is $395 for 2.5 hours. The Sunset Escape is $425 for 2.5 hours with champagne flutes included.

Yes — those are two of the main draws. The barrier islands and surrounding sandbars have excellent shelling for sand dollars, whelks, and conchs, and the shallow water at most stops is calm enough for easy swimming and wading. Snorkel gear is aboard in kids' through adult sizes.

It is one of the best charters for families. The water at most island stops is shallow and calm, there is an enclosed restroom onboard, and the pace bends around your group. Minimum age is 5, per U.S. Coast Guard Type I life vest requirements.

Often. Dolphins are resident here year-round and the channels and passes between the barrier islands are active water — particularly on a moving tide. Captain Keith will slow down or stop when wildlife appears rather than pushing on to keep a schedule.

A new island formed off the northern tip of Honeymoon Island during the 2024 hurricane season and has since separated completely. There is no road, no ferry, and no foot traffic to speak of — it is reachable only by boat. It is also a good illustration of why we are called Wayward Key: the islands out here do not stay where you put them.

Clearwater departures reach the northern barrier islands and leave from Island Way Grill if you are staying on Clearwater Beach island, or the Belleair Causeway Boat Ramp otherwise. St. Petersburg departures reach Shell Key, Egmont Key, and Passage Key and leave from the Maximo Park boat ramp. Your exact meeting point is confirmed when you book.

No. Egmont Key and Passage Key are 40 minutes or more each way from Maximo Park, before you have anchored or spent any time there. Both need the 4-hour Half-Day Island Escape. We would rather say so up front than have you feel rushed.

Conditions decide the route. Some of these islands sit in open or exposed water, and Captain Keith checks the water before committing rather than pushing to keep a plan. If somewhere is not going to be enjoyable that day, he will take you somewhere that is — which is the entire argument for a private boat over a fixed itinerary.

Yes. While guests are swimming, Captain Keith stays on watch — the habit eleven years as a Navy submariner leaves you with. A manatee drifting under the anchor line, a current picking up, a boat coming in faster than it should. He is also a former Navy diver and a cardiac registered nurse. Six guests is about the number one person can genuinely keep track of.