CLEARWATER & ST. PETERSBURG FLORIDA

Private Boat Charters in Clearwater & St. Petersburg

No ferry schedules. No strangers. No fixed route. Just your group, the open water, and Captain Keith.
Wayward Key Tours offers private boat charters in Clearwater and St. Petersburg for dolphin watching, sandbars, island hopping, snorkeling, shelling, and sunset cruising — built around your group, your pace, and your perfect day.

Private boat, Just Your Group

Enjoy a private boat charter reserved only for your group — no crowded public tour boats or strangers onboard.

Local Captain, Better Routes

Captain Keith knows the Clearwater and St. Petersburg waters, from scenic routes and sandbars to islands and wildlife areas.

Flexible Charter Experience

Choose the kind of private charter day you want — dolphins, sandbars, sightseeing, snorkeling, shelling, sunset cruising, or a little of everything.

Comfortable Boat

Relax on a comfortable private boat with space for your group, easy water access, and a restroom onboard.

Clearwater & St. Petersburg, Florida

What Kind of Day Do You Want?

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.

01 Pick your vibe Wildlife? Relaxation? Adventure? Sunset? Use the experiences below as inspiration — there's no wrong answer.

02 Choose your length A 2.5-hour Gulf Escape or a 4-hour Half-Day Charter. Both are fully private, reserved only for your group.

03 We handle the rest 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 — Captain Keith and the water take care of the rest. Not sure where to start? Call or text 727-355-3717 and we'll help you figure it out.

Explore the experiences

Bottlenose dolphin leaping from the Gulf waters near Clearwater, Florida

Dolphin & Wildlife Tours

Watch wild bottlenose dolphins, manatees, and shore birds from a private boat. Captain Keith — a former Navy diver — knows exactly where wildlife congregates in the waters around Clearwater and St. Petersburg. Often pairs naturally with a sandbar or island stop.

WildlifeFamiliesNature lovers

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Sailboat silhouetted against a vivid orange Gulf sunset near Clearwater, Florida

Private Sunset Cruises

A private sunset cruise timed around golden hour on the Gulf of Mexico. Often starts with sightseeing along the Clearwater and St. Petersburg waterfront before drifting into the sunset. Ideal for couples, honeymooners, and celebrations.

CouplesRomanceCelebrations

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Guests wading and relaxing at a secluded sandbar in calm shallow Gulf waters near Clearwater

Private Sandbar Charters

Anchor at a secluded sandbar in calm, shallow Gulf waters off Clearwater and St. Petersburg. 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.

SwimmingRelaxationGroups

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Aerial view of pristine Gulf Coast barrier islands with turquoise water near Clearwater, Florida

Private Island Hopping

Visit multiple Gulf Coast barrier islands — including Caladesi Island — by private boat. Stops naturally blend sightseeing, shelling, and wildlife viewing in a single trip. Ideal for groups who want to explore places inaccessible by car.

AdventureNaturePhotography

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View of the iconic pink Don CeSar hotel from the water in St. Petersburg, Florida

Private Sightseeing Tours

See Clearwater and St. Petersburg from the water — the Don CeSar (the Pink Palace), Clearwater Beach, Caladesi Island, waterfront estates, and local landmarks. A natural anchor for any charter, especially for first-time visitors to the area.

First-time visitorsHistoryFamilies

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Snorkeler exploring clear Gulf waters near Clearwater and St. Petersburg, Florida

Private Snorkeling Charters

Snorkel in clear Gulf waters guided by Captain Keith, a former Navy diver who knows the best spots for visibility and marine life near Clearwater and St. Petersburg. Pairs well with a sandbar stop or island visit on the same charter.

SnorkelingMarine lifeAdventure

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Sand dollars, whelks, and Gulf Coast shells collected on a private shelling tour near Clearwater

Private Shelling Tours

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 on the same charter.

ShellingFamiliesNature lovers

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Family enjoying a private boat charter in the crystal-clear Gulf waters near Clearwater, Florida

Private Family Boat Tours

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 of all of them. Restroom onboard makes longer trips comfortable for all ages.

Kids welcomeAll agesFlexible pace

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Build Your Own Day

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.

Any groupFully customYou decide

Reach out to us

Not sure which to pick? That's the point.

Tell us the vibeActive and adventurous? Relaxed and slow? Romantic? Family-friendly? There's no wrong answer — just tell us what sounds good.

Pick your lengthA 2.5-hour Gulf Escape or a 4-hour Half-Day Charter. Both are fully private, reserved only for your group of up to 6.

Captain Keith does the restRoutes and stops adjust in real time around tides, conditions, wildlife, and whatever your group feels like doing.

Questions? Just call or textReach us at 727-355-3717 and we'll help figure out the right kind of day for your group.

All charters are private, fully customizable, and built around your group.

Book your private charter Questions? Call or text 727-355-3717 · contact@waywardkeytours.com

Simple, transparent pricing

Choose your perfect charter

Fully private — your group only. No strangers, no rigid schedule.

2.5 hours

Gulf Escape

☀ Also perfect for sunset cruises

$350 flat rate

Up to 6 guests

What's included

✓ Fully private — your group only
✓ USCG-licensed captain
✓ Dolphin watching & sandbar stops
✓ On-water photos sent to you after
✓ Depart Clearwater or St. Pete
✓ Cooler, ice & water provided

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Most popular

4 hours

Half-Day Charter

$400 up to 4 guests

+ $50 per additional guest (up to 6)

Everything in the Gulf Escape, plus

✓ More time to explore & swim
✓ Ideal for celebrations & special occasions
✓ More sandbar & snorkeling time
✓ Perfect for groups wanting to fully unwind
✓ Longer dolphin watching windows

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Perfect for more than a boat ride

Made for every kind of getaway

Whether you're celebrating, relaxing, or planning something special, we'll help you create a private experience your guests will never forget.

Families

Couples

VIP guests

Corporate groups

Wedding parties

Vacationers

Popular guest occasions

Weddings & celebrations

Welcome weekend boat day

Bridal party cruise

Honeymoon add-on

Post-wedding recovery cruise

Corporate & group outings

Team sandbar day

Client appreciation outing

Post-conference experience

Small group networking cruise

Vacation & romance

Sunset cruise for couples or VIP guests

Executive sunset charter

Elopement weekend experience

Meet Tessa, Your Wayward Key Tour Guide

Tessa is our playful sea turtle guide who helps guests find the private charter that fits their perfect day on the water. Whether you want dolphins, sandbars, shelling, snorkeling, island stops, sightseeing, or a peaceful sunset cruise, Tessa makes planning your day feel easy, fun, and unforgettable.

Why Guests Trust Wayward Key Tours

Meet Captain Keith & Your Private Charter

Captain Keith is a licensed U.S. Coast Guard captain who knows the waters around Clearwater and St. Petersburg, from scenic cruising routes and island stops to 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 private charter. Your trip takes place on a private boat reserved just for your group, creating a more personal, flexible, and comfortable day on the water.

Coast Guard licensed captain
Cardiac Registered Nurse
Former Navy diver and 11-year submariner
Local knowledge of Clearwater & St. Petersburg waters
23-foot World Cat for a stable, comfortable ride
Restroom, Fresh water shower, Bluetooth music & easy water access

Questions Travelers Ask Before Booking

Can't find what you're looking for? Call or text us at 727-355-3717 — we're happy to help you figure out the right kind of day.

Planning your day

Do we have to choose just one activity, or can we combine experiences on the same trip?

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.

How long are the charters, and which length is right for us?

Wayward Key Tours offers two charter lengths. The Gulf Escape is 2.5 hours and starts at $350 flat for up to 6 guests — great for a focused experience like dolphin watching, a sandbar stop, or a sunset cruise. The Half-Day Charter is 4 hours ($400 for up to 4 guests, plus $50 per additional guest up to 6) and gives your group more time to explore, swim, combine multiple stops, and fully unwind. If you're unsure, call or text us at 727-355-3717 and we'll help you decide.

What can we do on a private boat charter in Clearwater or St. Petersburg?

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.

Can we customize our private boat tour?

Yes — every charter is private and flexible by design. Your day can be shaped around whatever your group wants most: dolphins, a sandbar swim, island stops, sightseeing, snorkeling, shelling, a sunset cruise, or a relaxed combination of everything. Captain Keith adjusts the route in real time based on conditions, tides, wildlife, and your group's energy on the day.

When is the best time to go on a private boat charter in Clearwater?

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, often uncrowded, and still perfectly enjoyable on the Gulf. Dolphins are active in all seasons.

Pricing & booking

How much does a private boat charter cost?

Wayward Key Tours offers two pricing options. The Gulf Escape (2.5 hours) is a flat $350 for up to 6 guests. The Half-Day Charter (4 hours) starts at $400 for up to 4 guests, with an additional $50 per guest up to 6. Both are fully private — your group only, no strangers. There are no hidden fees; cooler, ice, and water are included with every charter.

How far in advance should I book a private charter?

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.

What happens if the weather is bad or the water is rough?

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.

The experience

What is the best private boat tour in Clearwater, Florida?

The best private boat tour depends on what your group wants most. Wayward Key Tours offers fully private charters out of Clearwater and St. Petersburg for dolphin watching, sandbar retreats, island hopping, snorkeling, shelling, sunset cruising, sightseeing, and family-friendly days on the water. Because every charter is private — reserved exclusively for your group — the experience can be shaped around your pace, interests, and the conditions on the day. Most guests say the private setting and Captain Keith's local knowledge are what set it apart.

What's the difference between a private boat charter and a public boat tour?

A private charter with Wayward Key Tours is reserved exclusively for your group — no strangers, no fixed route, and no rigid schedule. The day is built around your interests, your pace, tides, weather, and whatever your group feels like doing. Public boat tours typically carry a larger mixed group on a set itinerary with little flexibility. With a private charter, if you want to stay at the sandbar longer, head to a different island, or skip the sightseeing and just watch dolphins — you can.

Is Wayward Key Tours good for special occasions like bachelorette parties, birthdays, or anniversaries?

Absolutely. Private charters are a great fit for celebrations because the boat is reserved just for your group, the experience is fully customizable, and you're not sharing the day with strangers. Popular occasions include bachelorette parties, birthday cruises, anniversaries, honeymoon add-ons, welcome weekend boat days, post-wedding recovery cruises, and corporate outings. Let us know the occasion when you reach out and we'll help make the day feel special.

Captain & boat

Who is Captain Keith?

Captain Keith is the owner and captain of Wayward Key Tours. He holds a U.S. Coast Guard captain's license and brings an unusual depth of experience to every charter — he's a former Navy diver, an 11-year Navy submariner, and a cardiac registered nurse. That background means every trip has a calm, safety-minded captain who also has deep local knowledge of the waters, wildlife areas, sandbars, and islands around Clearwater and St. Petersburg. He's the reason most guests say the experience feels different from anything else they've tried on the water.

What kind of boat does Wayward Key Tours use?

Wayward Key Tours uses a 23-foot World Cat, a catamaran-style hull known for its stability and smooth ride — especially important in Gulf chop. The boat 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. It comfortably fits up to 6 guests for a private charter.

Where does Wayward Key Tours depart from?

Wayward Key Tours departs from both Clearwater and St. Petersburg, Florida. The exact departure location is confirmed when you book. If you have a preference or are staying near a specific area, let us know and we'll do our best to accommodate you. You can reach us at 727-355-3717 or contact@waywardkeytours.com with any questions about meeting location.

What to know before you go

Are private boat charters good for families with kids?

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. Captain Keith is great with kids and will tailor the experience to keep everyone engaged and comfortable.

How many people can come on a private boat charter?

Wayward Key Tours accommodates up to 6 guests per charter. The smaller group size is intentional — it keeps the experience personal, comfortable, and genuinely flexible. 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.

What should we bring on a private boat charter?

We recommend bringing sunscreen, sunglasses, a hat, towels, and a phone or camera for photos. You're welcome to bring drinks and snacks — a cooler and ice are provided. 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. We provide a fresh water shower onboard so you can rinse off before heading back.

Is there a restroom onboard?

Yes. Wayward Key Tours has a restroom onboard, which makes a meaningful difference on longer trips — especially for families with young children, older guests, and anyone who wants to feel comfortable being out on the water for a full half-day charter without worrying about it.

Here's What some of our guests Have to Say

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.

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.

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.

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See What Your Private Day on the Water Could Look Like

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Ready For Your Private Day On The Water?

Experience Clearwater and St. Petersburg the way locals do — relaxed, uncrowded, and completely customized to your group. Every tour is private. Every experience is designed around you.