Aerial view of pristine Gulf Coast barrier islands with turquoise water near Clearwater and St. Petersburg Florida

Clearwater & St. Petersburg, Florida

Private Island Hopping Charters

Explore the Gulf Coast barrier islands of Clearwater and St. Petersburg on a fully private charter designed just for your group. Caladesi Island, Honeymoon Island, Egmont Key, and more — your pace, your stops, no strangers.

Book This Charter → Call 727-355-3717

Tessa the Wayward Key Tours sea turtle mascot holding a Gulf Coast map showing Clearwater and St. Petersburg islands

"I made that map myself. Every island, every sandbar, every shortcut. Follow me."

— Tessa, your Gulf Coast guide 🐢

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Multiple Island StopsCaladesi, Honeymoon Island, Egmont Key, Shell Key & more

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100% Private CharterYour group only — no strangers, no shared boat, no fixed route

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Captain KeithUSCG-licensed with deep local knowledge of island routes and conditions

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Tessa's RoutesOur Gulf Coast guide knows every island, sandbar, and shortcut out there

🗺️ Made the Official Gulf Coast Map 🏝️ Knows Every Island Stop 🐢 Expert Sandbar Lounger 🌊 Tides & Current Expert

What to expect

A Day of Island Exploration

Private island hopping charters explore the Gulf Coast barrier islands around Clearwater and St. Petersburg. Every trip is shaped by your group's interests, the tides, and conditions — here's what a typical day looks like.

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

🏝️ Scenic Island Destinations

Caladesi Island, Honeymoon Island, Three Rooker Island, Egmont Key, Shell Key — pristine barrier islands accessible only by boat

Shoreline stop on a private island hopping charter near Clearwater and St. Petersburg Florida

Shoreline Stops

Wade ashore, explore island beaches, and spend time at quiet coastal spots along the way

Scenic coastal cruising on a private charter in the Gulf waters near Clearwater Florida

Scenic Cruising

The ride between islands is part of the experience — open water, coastal scenery, and a relaxed private-charter feel

Family enjoying a private island hopping charter near Clearwater and St. Petersburg Florida

Family & Groups

A great fit for families, couples, and small groups who want quality time together exploring the Gulf Coast

Relaxed Adventure

Sightseeing, exploring, swimming, and relaxing — combined into one flexible day on the Gulf

Routes vary by day: Island stops and routes are shaped by tides, weather, and water conditions. Captain Keith — with Tessa's input — will always guide your group toward the best available route for a scenic, memorable day on the water.

Islands We Explore

📍 Clearwater Departure

The Clearwater departure gives access to some of the most beautiful Gulf barrier islands in Pinellas County — including Caladesi Island, one of the top-rated beaches in the US.

Caladesi Island Honeymoon Island Three Rooker Island Anclote Key

📍 Maximo Park, St. Petersburg

The St. Petersburg departure opens up the southern Gulf islands — including historic Egmont Key with its 19th-century lighthouse and sea turtle nesting beaches.

Egmont Key Shell Key Preserve Fort De Soto area Pass-a-Grille area

Guests enjoying a private island hopping charter with Wayward Key Tours near Clearwater Florida

Why Guests Love Island Hopping

More Than Just a Boat Ride

A private island hopping charter gives your group more flexibility and comfort than any public boat tour. Instead of sharing the boat with strangers on a fixed schedule, you explore at your own pace — stopping where you want, staying as long as you like, and combining island visits with scenic cruising, wildlife watching, or a sandbar swim.

Caladesi Island is consistently rated one of the most beautiful beaches in the country, and it's only accessible by boat. Egmont Key has a 19th-century lighthouse and sea turtle nesting beaches. These are places that reward going slowly — and a private charter is the best way to do it.

Private charter — your group only, no strangers
Flexible stops shaped around your interests
Access to islands only reachable by boat
Family-friendly for all ages
Restroom onboard for longer trips
Locally owned and veteran operated

Tour Details

Everything you need to know before you book

Every island hopping charter is fully private and built around your group's interests. The Half-Day Charter is recommended for island hopping — it gives enough time to explore multiple stops and really enjoy the islands at a relaxed pace. Captain Keith handles the route in real time based on tides, conditions, and what your group wants most. Tessa has already mapped out the options.

Private charter boat near a Gulf Coast island with guests relaxing on the water near Clearwater Florida

Charter Details

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Charter Length2.5-hr Gulf Escape or 4-hr Half-Day

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RecommendationHalf-Day strongly recommended for island hopping

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PricingGulf Escape $350 · Half-Day $400Up to 4 guests · $50 per additional guest · Max 6 guests

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DepartureClearwater or Maximo Park, St. Pete

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Group SizePrivate — up to 6 guests

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IncludedSunchill float, Bluetooth, fresh water shower, restroom, cooler & ice

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What to BringSunscreen, water shoes, camera, drinks & snacks

Book This Charter →

Questions? Call or text 727-355-3717

Frequently Asked Questions

What islands do you visit on a private island hopping charter near Clearwater?

Depending on your departure location, weather, tides, and charter length, private island hopping routes from Clearwater may include Caladesi Island, Honeymoon Island, Three Rooker Island, and Anclote Key. From the Maximo Park departure in St. Petersburg, routes may include Egmont Key, Shell Key Preserve, and the Fort De Soto area. Captain Keith — with Tessa's input on conditions — will help shape the route around what your group most wants to see.

What is the difference between island hopping and a sightseeing boat tour?

A private island hopping charter is focused on visiting multiple island destinations — stopping to explore beaches, shorelines, and natural areas along the way. A sightseeing charter is more focused on relaxed cruising and taking in views from the boat. With a private charter both experiences can often be combined depending on your group's preferences and charter length.

Can we stop and get off the boat at islands?

Yes. Depending on the route, tides, and conditions, your group can stop to explore island beaches, wade in shallow water near shorelines, or spend time at quiet coastal areas. Some islands have accessible beaches while others are best enjoyed from the water. Captain Keith will guide your group to the best available stops for your charter day.

Will we see wildlife too?

Yes — wildlife is often a natural part of island hopping near Clearwater and St. Petersburg. Guests may spot bottlenose dolphins, seabirds, rays, and sometimes sea turtles along the way. The coastal waters around Caladesi Island, Honeymoon Island, and Egmont Key are particularly rich with Gulf Coast marine life.

Is island hopping near Clearwater good for families?

Yes. A private island hopping charter is a great fit for families because the pace is relaxed, the boat is reserved exclusively for your group, and the day can be shaped around your family's comfort. There is a restroom onboard and Captain Keith tailors the experience for all ages including young children and older guests.

How long is a private island hopping charter?

Wayward Key Tours offers a 2.5-hour Gulf Escape and a 4-hour Half-Day Charter. The Half-Day is strongly recommended for island hopping as it gives your group more time to explore multiple stops and enjoy the islands at a relaxed pace. The Gulf Escape works well for a scenic cruise with one or two island highlights.

How much does a private island hopping charter cost near Clearwater?

The Gulf Escape (2.5 hours) starts at $350 for up to 4 guests, with additional guests at $50 per person up to a maximum of 6. The Half-Day Charter (4 hours) starts at $400 for up to 4 guests, with additional guests at $50 per person up to 6. Both are fully private — your group only, no strangers.

Can we customize the island hopping route?

Yes. One of the biggest advantages of a private charter is flexibility. Captain Keith can shape the day around what your group most wants — more time at one island, a mix of stops, scenic cruising, shoreline visits, or combining island hopping with dolphin watching or shelling. The route is built around your interests and the day's conditions.

Where does Wayward Key Tours depart from for island hopping?

Wayward Key Tours departs from two locations. The Clearwater departure gives access to Caladesi Island, Honeymoon Island, Three Rooker Island, and Anclote Key. The Maximo Park departure in St. Petersburg gives access to Egmont Key, Shell Key Preserve, and the Fort De Soto area. Captain Keith confirms the departure location when your booking is confirmed — both have parking available.

What should we bring on an island hopping charter?

We recommend sunscreen, sunglasses, a hat, towels, water shoes for beach stops, comfortable clothes you don't mind getting wet, drinks and snacks, and a phone or camera. A cooler and ice are provided. There is a fresh water shower onboard to rinse off after any beach or water stops.

Tessa the Wayward Key Tours sea turtle mascot relaxing at a Gulf Coast island near Clearwater Florida

Ready to Explore the Islands?

"The map's ready. The islands are waiting. Let's go." — Tessa 🐢

Book your private island hopping charter in Clearwater or St. Petersburg. Your group, your route, Captain Keith — with Tessa already plotting the best stops for your day on the Gulf.

Book Your Private Charter → Questions? Call or text 727-355-3717 · contact@waywardkeytours.com

Private Island Hopping Charters in Clearwater & St. Petersburg new