Frequently Asked Questions

Wayward Key Tours offers three private charters, all flat rates for the whole boat rather than per person:

Gulf Escape — 2.5 hours, $395 flat, up to 6 guests
Half-Day Island Escape — 4 hours, $575 flat, up to 6 guests
Sunset Escape — 2.5 hours, $425 flat, up to 6 guests, champagne flutes included

All three are fully private — your group only, no strangers. The rate is the same whether it is two of you or six. There are no per-guest add-ons and no hidden fees, and a cooler, ice, and water are included. There is a full breakdown on the charter pricing page.

The Gulf Escape is 2.5 hours. You still get the full mix — sightseeing along the coastline, dolphins along the Intracoastal, and a nearby sandbar stop — just closer in. It is also the right pick on a cooler day when your group would rather sightsee and stay dry.

The Half-Day Island Escape is 4 hours and it is the one most groups pick. Four hours is what it takes to actually reach the barrier islands — Caladesi, Honeymoon, Three Rooker, Shell Key, Anclote — and have real time there to swim, shell, and snorkel rather than just turning around.

The Sunset Escape is 2.5 hours, timed around the evening’s actual sunset. You choose the backdrop — an island silhouette, the skyline, open Gulf, or the Skyway lighting up from the St. Pete side.

Not sure? Call or text 727-355-3717 and we will talk it through.

We recommend booking at least 1–2 weeks ahead, especially for weekends and peak season (spring break, summer, and holiday weekends). Popular dates fill quickly because every charter is fully private — only one group goes out at a time. For last-minute trips, it is always worth reaching out at 727-355-3717 to check availability.

Yes — departure times are flexible and we work around your schedule. Sunset charter start times shift with the season to make sure you catch the best light. Reach out and we will find a time that works for your group.

Booking details including any deposit are handled through our secure booking system when you reserve your charter. If you have questions about payment before booking, call or text Captain Keith at 727-355-3717 and he will walk you through it.

Tipping is always appreciated but never expected. If Captain Keith made your day special, a gratuity is a kind way to show it — most guests who tip do so in the 15–20% range, in cash or added through the booking. That said, the best compliment you can give is a 5-star review and sending friends our way.

You can cancel up to 24 hours in advance for a full refund. Within 24 hours, there is no refund. If Captain Keith needs to cancel for weather, a Small Craft Advisory, tropical storm, or hurricane threat, you will receive a full refund or the option to reschedule. For complete details, read our full weather and cancellation policy.

If you are staying on Clearwater Beach island, we pick you up right there at Island Way Grill. If you are staying elsewhere, we pick up at the Belleair Causeway Boat Ramp. Your exact meeting point is confirmed when you book — and if you are not sure which works best for where you are staying, just ask and we will help you figure it out.

St. Petersburg charters depart from the Maximo Park boat ramp on the south end of St. Pete. Maximo Park puts you right on Tampa Bay with quick access to Fort De Soto, Egmont Key, Shell Key, and Passage Key. Your exact meeting point is confirmed when you book.

No — your group will be the only one on board. The Coast Guard allows up to 6 people within your party on the boat. The price is the same whether it is just a couple or a full group of 6.

Up to 6 guests per charter. The smaller group size is intentional — it keeps the experience personal, comfortable, genuinely flexible, and easy for one captain to keep track of on the water. Whether you are a couple, a family, or a group of friends, the boat will not feel crowded.

Yes. While guests are swimming, Captain Keith stays on watch — that is the habit eleven years as a Navy submariner leaves you with, and he cannot switch it off. It shows up in small things: a manatee drifting under the anchor line, a current picking up, a boat coming in faster than it should. He is also a cardiac registered nurse and a former Navy diver. Six guests happens to be about the number one person can genuinely keep track of, which is part of why we cap it there.

We cannot guarantee dolphin sightings because they can appear at any time. They tend to like the wakes of boats and forage for fish around mangroves, and we have seen them along the barrier islands too. Most charters do see dolphins — just keep your eyes peeled. For more on where and when to spot them, see our guide to dolphins in Clearwater, Florida.

Dolphin and wildlife watching, sandbar stops, island hopping, sightseeing along the waterfront, snorkeling, shelling, sunset cruising, or a relaxed mix of several. Each charter is shaped around your group’s interests, the weather, tides, and conditions on the day. There is no fixed route — the day is built around what you want most.

Yes. The boat has a swim platform with a ladder for easy water access, and we anchor at sandbars and calm shallow areas where swimming, wading, and floating are perfect. We provide a Sunchill float and bean bag chairs so you can relax right on the water.

Yes — dock and dine is available on any charter. Captain Keith navigates to a waterfront restaurant with boat access, ties up, and your group goes in for lunch or drinks. He has personally docked at Island Way Grill, Wahoo’s Bayside Pub and Grill, Caddy’s Indian Shores, Doc Ford’s at the St. Pete Pier, and The Shore on Longboat Key. Just mention it when you book.

Our WorldCat 23-foot powered catamaran provides a very stable platform to walk around and view wildlife. Compared to a monohull it cuts through waves more comfortably — great for guests who get motion sickness. Onboard you will find marine bean bag chairs, an enclosed restroom, a freshwater rinse wand for washing the salt off, a freshwater sink on deck, and a Bluetooth stereo.

Yes — an enclosed restroom, and you are welcome to use it for whatever you need. Nobody is going to be told otherwise. It makes a meaningful difference on longer trips, especially for families with young children, older guests, and anyone who wants to be comfortable out on the water for a full half-day charter.

Yes — we carry masks, snorkels, and fins in sizes from kids up through adults, and we disinfect everything before every trip. If you are an avid snorkeler with gear you love, you are welcome to bring your own.

Worth setting expectations honestly: this is not reef snorkeling. The Gulf here is sand bottom, and visibility depends on the day. What it is good for is exploring the shallows — sand dollars, crabs making their way across the sand floor, and whatever else turns up. Kids in particular tend to love it.

Yes — the boat has a shaded area so you can get out of the sun when you want to. Between the shade, the restroom, and the freshwater rinse wand for washing the salt off, the boat stays comfortable even on hot Florida days. We still recommend bringing sunscreen and a hat.

Yes — you are welcome to bring your own snacks, drinks, and alcohol (please, no glass, and drink responsibly). We provide a cooler, ice, and water. We do not have space for multiple large coolers, so pack reasonably for your group size.

Check the weather and bring a jacket and coverup — conditions on the water can get chilly. Bring flip-flops for island stops, sunscreen (lotion not spray), a hat, and lip balm. You are welcome to bring snacks, drinks, or alcohol — just drink responsibly. We provide water and ice. There is a fuller list on our what to bring guide.

Children must be at least 5 years old to come aboard. This is a safety requirement — under U.S. Coast Guard regulations, children need to properly fit into a Type I life vest, and children under 5 do not safely fit the vests we carry. For families with kids 5 and up, a private charter is one of the most comfortable and flexible ways to enjoy the water together.

At this time we do not allow pets on board. Unfortunately toenails puncture our cushions, and we cannot be responsible for pets jumping into the water near wildlife.

Yes — children are required to wear properly fitting life vests on board, in accordance with U.S. Coast Guard regulations. We carry Type I life vests. Because children must fit these vests safely, we have a minimum age of 5 for guests.

Our 23-foot WorldCat catamaran is known for a stable, smooth ride that is much gentler than a monohull — it is one of the reasons guests prone to motion sickness do well on it. If you are concerned, we recommend taking motion sickness medication before your trip, staying hydrated, and letting Captain Keith know so he can plan calmer water.

Captain Keith is a licensed U.S. Coast Guard captain, a former Navy diver, an 11-year Navy submariner, and a cardiac registered nurse. He is at the helm on every single charter — not a rotating crew — which is something multi-boat operators physically cannot offer. That combination means every trip has a calm, safety-minded captain with deep local knowledge of the waters, wildlife, sandbars, and islands around Clearwater and St. Petersburg.

Safety is always the priority. If weather or sea conditions make it unsafe to go out, we will work with you to reschedule or issue a full refund. Captain Keith monitors conditions closely and communicates directly if anything needs to change. Florida weather moves fast — what looks uncertain in the morning often clears by midday. See our complete weather and cancellation policy for full details.

Clearwater and St. Petersburg offer great boating year-round, but spring and fall tend to have the most comfortable weather, calmer water, and excellent wildlife activity. Summer brings warm water and longer days — ideal for sandbars and snorkeling — though afternoon thunderstorms are common. Winter is quieter and often uncrowded, and a cool day is ideal for a sightseeing run along the coastline without getting in the water. Dolphins are active in all seasons.