Private Island Hopping Charters
Explore the coastal waters of Clearwater and St. Petersburg on a private island hopping charter designed just for your group. Cruise to secluded beaches, quiet shoreline areas, and beautiful barrier islands reachable only by boat — a relaxed, flexible day built around the kind of island experience you want.
Book This Charter →Some of Florida's most beautiful islands sit just off the coast of Clearwater and St. Petersburg — and the best of them can only be reached by boat. A private island hopping charter with Captain Keith lets you visit several in a single day, at your own pace, with no ferry schedules and no crowds.
What is a private island hopping charter?
Island hopping means visiting multiple Gulf Coast barrier islands on a single private charter. Captain Keith navigates between islands, beaches, and sandbars — stopping wherever your group wants to swim, shell, explore, or simply relax. Because the charter is private and flexible, there's no fixed route: the day is shaped around what you want to see and how long you want to linger at each stop.
Many of these islands are undeveloped and accessible only by boat, which means you experience them the way they were meant to be seen — quiet, natural, and uncrowded. It's one of the best ways to see a side of Florida's Gulf Coast that most visitors never reach.
Islands you can visit on a charter
The islands on your route depend on your departure point, the tides, and what your group wants to do. Here are the highlights Captain Keith knows well from years on these waters.
Caladesi Island
One of Florida's most celebrated barrier islands, Caladesi is accessible only by boat or ferry — a private charter lets you visit at your own pace with no ferry schedule. Pristine white sand, clear Gulf water, and excellent shelling. More on visiting Caladesi Island by boat.
Honeymoon Island & the New Island
Honeymoon Island's north end is beautiful from the water — and after the 2024 hurricane season, a brand-new island formed off its northern tip, accessible only by boat. Live sponges wash up here, and it's untouched by foot traffic. A genuine hidden gem. More on Honeymoon Island by boat.
Three Rooker Island
A quiet barrier island north of Clearwater with pristine Gulf waters, great shelling, and no day-trippers. Reachable only by boat, Three Rooker is a favorite anchoring spot for those who want beach and water to themselves. More on Three Rooker Island.
Anclote Key
At the northern end of the Clearwater charter range, Anclote Key offers a historic lighthouse, wide undeveloped beaches, and some of the clearest water on this stretch of coast. A rewarding stop for groups wanting to explore further afield.
Shell Key & Egmont Key (St. Pete departures)
From the Maximo Park departure in St. Petersburg, island hopping reaches Shell Key Preserve — an uninhabited barrier island with superb shelling — and historic Egmont Key, with its Civil War-era fort ruins and clear snorkeling waters.
What you can do while island hopping
Island hopping naturally blends several experiences into one day. Depending on your route and the conditions, your charter can include swimming and wading in calm shallow water, shelling for sand dollars and Gulf Coast shells, snorkeling in clear spots, wildlife watching (dolphins are often spotted between islands), and simply relaxing on a secluded beach with no one else around.
Because Captain Keith adjusts the day in real time, you're never locked into a schedule — if your group loves a particular island, you stay longer. If you want to see more, he keeps moving. That flexibility is the whole point of a private charter.
Charter options for island hopping
The 4-hour Full-Day Charter is recommended for island hopping — it gives your group time to visit multiple islands without rushing. The 2.5-hour Gulf Escape works well for a focused trip to one or two nearby islands.
Gulf Escape — 2.5 Hours · $350
Up to 6 guests. Great for one or two nearby islands or a focused beach-and-shell stop.
Full-Day Charter — 4 Hours · $400+
Up to 6 guests ($50/additional over 4). Recommended for island hopping — time to visit several islands at a relaxed pace.
Island Hopping — Frequently Asked Questions
What islands can you visit near Clearwater and St. Petersburg?
From Clearwater, island hopping charters reach Caladesi Island, Honeymoon Island (and the new hurricane-formed island), Three Rooker Island, and Anclote Key. From St. Petersburg's Maximo Park, charters reach Shell Key Preserve and Egmont Key. Your route depends on your departure point, tides, and what your group wants to do.
Are these islands only accessible by boat?
Many are. Caladesi Island is reachable only by boat or ferry, and Three Rooker Island, Anclote Key, Shell Key, and Egmont Key are all boat-access only. That's what keeps them quiet and uncrowded — a private charter lets you reach them without a ferry schedule.
How many islands can we visit in one charter?
On a 4-hour Full-Day Charter, most groups comfortably visit two or three islands with time to swim, shell, and relax at each. A 2.5-hour charter is better suited to one or two nearby stops. Captain Keith builds the route around your pace.
Can we shell and swim at the islands?
Yes — shelling and swimming are two of the main draws. The barrier islands and surrounding sandbars offer excellent shelling for sand dollars, whelks, and Gulf Coast shells, and the calm shallow water is perfect for swimming and wading. Snorkel gear is provided onboard.
Is island hopping good for families?
Yes — it's one of the most family-friendly charters. The calm, shallow water at the islands is great for kids, there's a restroom onboard, and the flexible pace means you can adjust the day around your family's comfort. Children must be at least 5 years old per U.S. Coast Guard life vest requirements.
Will we see dolphins while island hopping?
Very often. Dolphins are commonly spotted in the waters between the barrier islands, especially around Caladesi and the channels. Captain Keith will pause when wildlife appears. More about dolphins in Clearwater.
Where do island hopping charters depart from?
Clearwater departures (reaching the northern barrier islands) leave from Island Way Grill or the Belleair Causeway Boat Ramp. St. Petersburg departures (reaching Shell Key and Egmont Key) leave from Maximo Park boat ramp. Your exact meeting point is confirmed when you book.
Ready to Explore the Islands?
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