Clearwater & St. Petersburg, Florida
No ferry schedules. No strangers. No fixed route. Just your group, the open water, and Captain Keith — at the helm on every single charter.
The whole boat is reserved for you. No crowded public tour boats, no strangers aboard, ever.
Captain Keith runs every charter himself — USCG-licensed, former Navy diver, cardiac nurse.
Routes and stops adjust in real time around tides, conditions, wildlife, and what your group wants.
A 23-foot WorldCat catamaran — steadier in chop than a pontoon, with a restroom and shower onboard.
Eleven years as a Navy submariner leaves you with a habit you can't switch off. When guests are swimming, Captain Keith is on watch — and it shows up in small things most people never notice.
A manatee drifting under the anchor line. A current picking up. A boat coming in faster than it should. He's also a former Navy diver and a cardiac registered nurse, so he reads water the way most people read a room.
That happens to be about the number one person can genuinely keep track of. It's part of why we cap it there.
Finding live sand dollars, showing kids what's on the bottom, pointing out what you'd otherwise swim right past.
Cardiac care was his second career. It's the kind of thing you never think about until you'd want it.
Every Wayward Key charter is private, flexible, and built around your group. The experiences below aren't rigid packages — they're a starting point. Most days on the water weave a few of them together naturally.
Here's how it actually works: You tell us the kind of day you have in mind — chasing dolphins, relaxing on a sandbar, watching the sunset, hunting for shells — and how long you want to be out. Captain Keith handles the rest. Routes, stops, and timing adjust in real time around conditions, tides, and whatever your group is feeling that day.
Wildlife? Relaxation? Adventure? Sunset? Use the experiences below as inspiration — there's no wrong answer.
A 2.5-hour Gulf Escape ($395), a 4-hour Half-Day Island Escape ($575), or a 2.5-hour Sunset Escape ($425). All three fully private.
Captain Keith builds your day in real time around conditions, tides, wildlife, and what your group wants most.
These experiences naturally overlap and blend together. A dolphin tour often ends at a sandbar. An island hopping trip includes shelling on the beach. A sunset cruise might start with sightseeing along the waterfront. Think of these as the flavor of your day, not a fixed itinerary. Not sure where to start? Call or text 727-355-3717 and we'll help you figure it out.
Watch wild bottlenose dolphins, manatees, and shore birds from a private boat. Captain Keith knows where wildlife congregates in the waters around Clearwater and St. Petersburg. Often pairs naturally with a sandbar or island stop.
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Most sunset cruises run a route. Ours asks what you want behind the sun — an island silhouette, the skyline, open Gulf, or the Skyway lighting up from the St. Pete side. Dolphins are often out at dusk. Champagne flutes when the sun goes down.
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Anchor at a secluded sandbar in calm, shallow Gulf waters. Swim, wade, and float on the sunchill float in a setting you can't reach by car. A natural stop on almost any charter — dolphins are often spotted near sandbars too.
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Visit multiple Gulf Coast barrier islands by private boat — Caladesi, Honeymoon, Three Rooker, Shell Key, Anclote. Stops blend sightseeing, shelling, and wildlife viewing. Best on the 4-hour Half-Day Island Escape.
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See Clearwater and St. Petersburg from the water — the Don CeSar, Clearwater Beach, Caladesi Island, waterfront estates, and local landmarks. Great for first-time visitors, and the best option on a cool day when nobody wants to swim.
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Snorkel in clear Gulf waters guided by Captain Keith, a former Navy diver who knows the best spots for visibility and marine life. Gear provided for every guest. Pairs well with a sandbar stop or island visit.
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Collect sand dollars, whelks, conchs, and other Gulf Coast shells at beaches and sandbars Captain Keith has sourced from years on these waters. Often combined with island stops or a sandbar swim.
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A private, flexible charter built for families with children. The day is shaped around your family's comfort — dolphins, sandbars, shelling, island stops, or a relaxed mix. Restroom onboard. Minimum age 5.
Learn more →Not seeing exactly what you had in mind? That's fine — most of our best days don't fit neatly into a category. Tell us your group, your vibe, and how long you want to be out, and we'll build the day from there.
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Flat rates for the whole boat — not per person. Fully private, your group only, no strangers and no rigid schedule.
2.5 Hours
$395 flat
Up to 6 guests · fully private
A full day on the water, closer in. You sightsee on the way out — waterfront estates, the coastline, the Don CeSar from the St. Pete side — watch for dolphins along the Intracoastal, then anchor at a nearby sandbar to swim, wade, and float.
It all happens on the same run. Nothing gets cut; you just stay closer to home than the four-hour trip does.
On a cool day, skip the water entirely and make it a sightseeing and wildlife run. You stay dry the whole time.
What's included
4 Hours
$575 flat
Up to 6 guests · fully private
Everybody's boat goes to the islands. Caladesi, Honeymoon, Three Rooker, Shell Key, Anclote — we go there too. What's different is how many people get off the boat with you, and who's watching while you're in the water.
Four hours is what buys the range. The Gulf Escape covers sightseeing, wildlife, and a nearby sandbar; this one has the time to actually get out to the islands and stay a while once you're there.
Six guests, maximum. When we anchor at a quiet stretch of beach, it stays quiet — and with no fixed itinerary, if somebody beat us there, we go somewhere else.
Everything in the Gulf Escape, plus
2.5 Hours
$425 flat
Up to 6 guests · fully private
Most sunset cruises run a route. Ours asks you a question first: what do you want behind the sun?
From Clearwater — an island silhouette, the skyline, or open Gulf with nothing in the frame at all. From St. Pete — the Skyway lighting up as the sky goes dark, the downtown skyline, or staying inside Boca Ciega Bay where the light falls across the trees and waterfront homes. Captain Keith knows which works that night; it depends on the tides as much as the sky.
Dolphins are often out at dusk. Stop at a sandbar or step off onto an island if you want to — or stay aboard and watch the light change.
Champagne flutes when the sun goes down. That part isn't optional.
Everything in the Gulf Escape, plus
Every charter is private, flexible, and built around your group. Captain Keith is at the helm on every trip — not a rotating crew — and while guests are in the water, he's watching it.
Bring your own drinks and snacks; non-glass containers only, please. Minimum age 5. No pets.
Questions? Call or text 727-355-3717 · contact@waywardkeytours.com
Whether you're celebrating, relaxing, or planning something special, we'll help you create a private experience your guests will never forget.
Captain Keith is a licensed U.S. Coast Guard captain who knows the waters around Clearwater and St. Petersburg — scenic cruising routes, island stops, wildlife areas, and sandbars.
His background as a cardiac nurse, former Navy diver, and 11-year submariner brings a calm, safety-minded presence to every charter. He's at the helm on every trip, not a rotating crew, and your boat is reserved for your group alone.
Tessa is our sea turtle guide, and she came from a real moment on the water — we were struggling to fish a stray balloon out of the Gulf when a turtle surfaced and nudged it toward us.
Balloons and plastic bags look like jellyfish to a sea turtle. They eat them, and it kills them. Tessa is how we talk to guests — especially kids — about keeping this water healthy without turning a good day into a lecture.
Can't find what you're looking for? Call or text 727-355-3717 — we're happy to help you figure out the right kind of day.
Planning your day
You don't have to choose just one. Most Wayward Key charters naturally weave several experiences together — a dolphin watching trip often ends at a sandbar, an island hopping day typically includes shelling on the beach, and a sunset cruise might start with sightseeing along the waterfront. Think of the experience types as the flavor of your day, not a fixed itinerary. Tell us what sounds good, how long you want to be out, and Captain Keith builds the route from there.
Wayward Key Tours offers three private charters, all capped at 6 guests.
The Gulf Escape is 2.5 hours at a flat $395. You still get the full mix — sightseeing on the way out, dolphins along the Intracoastal, and a sandbar stop — just closer in. It's 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 at a flat $575, and it's 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 at a flat $425, timed to 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. Champagne flutes at sundown.
If you're unsure, call or text 727-355-3717 and we'll help you decide.
Guests can enjoy dolphin and wildlife watching, sandbar stops, island hopping, sightseeing along the waterfront, snorkeling, shelling, and sunset cruising — or a relaxed mix of several. Each charter is shaped around your group's interests, the weather, tides, and local water conditions on the day. There's no fixed route, so the day is genuinely built around what you want most.
Clearwater and St. Petersburg offer great boating year-round, but spring and fall tend to have the most comfortable weather, calmer waters, and excellent wildlife activity. Summer brings warm water and longer days — ideal for sandbars and snorkeling — though afternoon thunderstorms are common, and we'll keep an eye on conditions for you. Winter months are 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.
Pricing & booking
Wayward Key Tours has three flat rates, all for the whole boat rather than per person:
Gulf Escape — $395, 2.5 hours, up to 6 guests
Half-Day Island Escape — $575, 4 hours, up to 6 guests
Sunset Escape — $425, 2.5 hours, up to 6 guests, champagne included
Every charter is fully private — your group only, no strangers aboard. There are no per-guest add-ons and no hidden fees. Cooler, ice, bottled water, snorkeling gear, and photos of your day are all included.
We recommend booking at least 1–2 weeks ahead, especially for weekend dates and during peak season (spring break, summer, and holiday weekends). Popular dates fill up quickly because every charter is fully private — only one group goes out at a time. That said, if you're looking for a last-minute trip, it's always worth reaching out at 727-355-3717 or contact@waywardkeytours.com to check availability.
Safety is always the priority. If weather or sea conditions make it unsafe or uncomfortable to go out, we'll work with you to reschedule your charter. Captain Keith monitors conditions closely in the days leading up to your trip and will communicate with you directly if anything needs to change. Florida weather moves fast — what looks uncertain in the morning often clears by midday, and we'll do our best to find the right window for your group.
Safety & what to know
Yes. While guests are swimming, Captain Keith stays on watch — that's the habit eleven years as a Navy submariner leaves you with, and he can't 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's 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.
Yes — private charters are especially well-suited for families because the boat is reserved just for your group, the pace is relaxed, and the day is shaped around your family's comfort and interests. There's a restroom onboard, which makes longer trips much easier with kids. Families can enjoy dolphin watching, sandbar swimming, shelling, island stops, sightseeing, or a calm mix of everything. Minimum age is 5, due to USCG life vest requirements.
Wayward Key Tours accommodates 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're a couple, a family, or a group of friends, the boat won't feel crowded and the day can be shaped entirely around your group.
We recommend sunscreen, sunglasses, a hat, towels, and a phone or camera. You're welcome to bring drinks and snacks — a cooler and ice are provided, and non-glass containers only, please. Comfortable clothes you don't mind getting wet are ideal if you plan to swim or wade at a sandbar. Water shoes are handy for shelling stops. There's a fresh water shower onboard so you can rinse off before heading back.
We run a 23-foot WorldCat — a catamaran-style hull known for its stability and smooth ride, which matters in Gulf chop. It has comfortable seating, easy water access with a dive ladder, a sunchill float and chair floaties, Bluetooth music, a fresh water shower, and a restroom onboard. We depart from both Clearwater and St. Petersburg; the exact location is confirmed when you book, and if you're staying near a specific area, let us know.
★★★★★
"It was so fun to take my wife to a secluded beach so that we could snorkel. Taking a private tour with our own captain was so much better than going by ferry or with a bunch of other people that you don't know."
Gerry M.
★★★★★
"I loved the private tour compared to being among people I didn't know. I don't know the area, but I just told the captain the types of activities I wanted to do, and he found the perfect spots to show me around."
Dawna
★★★★★
"The water was gorgeous, and the wildlife was spectacular. We saw a couple dolphins while we were out. Wayward Key Tours knows just where to go and how to give you a relaxing day."
Megan M.
Real moments from our Clearwater and St. Petersburg charters — dolphins, sandbars, snorkeling, and unforgettable afternoons.
Experience Clearwater and St. Petersburg the way locals do — relaxed, uncrowded, and completely built around your group. Every charter is private. Captain Keith is at the helm on every one.
Book your private charter Or call and text 727-355-3717 · contact@waywardkeytours.com
