Three ways. By private boat charter, which takes 20 to 30 minutes from Clearwater and anchors wherever conditions are best that day. By the state park ferry from Honeymoon Island, which runs on a fixed schedule with limited capacity and lands at the bayside marina. Or on foot from the north end of Clearwater Beach — Hurricane Elena filled in Dunedin Pass in 1985 and the two have been joined by a land bridge ever since, though it narrows and partly submerges at high tide.

Yes, and most visitors have no idea. Hurricane Elena filled Dunedin Pass with sand in 1985, connecting Caladesi to the north end of Clearwater Beach. The two are separated by little more than a welcome sign. The land bridge has widened and narrowed with every storm since, and at the moment it is fairly thin and partly underwater at high tide, so check conditions before setting off. It is a long walk in soft sand either way.

Flat rates for the whole boat, up to 6 guests. The Gulf Escape is $395 for 2.5 hours and includes time at or near Caladesi with a sandbar stop. The Half-Day Island Escape is $575 for 4 hours and allows a longer, more relaxed visit plus other islands. The Sunset Escape is $425 for 2.5 hours.

As of the state park's June 2026 update, Caladesi is open for day use and the Honeymoon Island ferry has resumed, but limitations from Hurricane Helene damage remain. C-Dock is open for day use with 26 slips and the T-Dock takes a larger vessel. Power and water are not available on the dock, overnight marina accommodation is closed, and food service may be limited. Worth planning around — bring your own food and water rather than counting on the concession.

It depends on the wind and the tide, and that decision matters more than most guests expect. On a calm day the Gulf side gives you open water, white sand, and the turquoise colour. With a strong sea-to-land wind against an outgoing tide, the Gulf side gets choppy with real current — not comfortable or safe for swimming. On those days Captain Keith anchors on the protected bayside instead, where the water stays calm regardless of what the Gulf is doing.

Dr. Beach ranked it the best beach in the United States in 2008, after placing it fourth in 2005 and second in both 2006 and 2007 — then retired it from the list, which is what happens to a winner. It has no roads, no hotels, and no development, which is why it still looks the way it does. Yes.

About three to four miles north of Clearwater Beach by water. By private charter the run takes roughly 20 to 30 minutes from our Clearwater departure points.

Swimming and floating on a gradual sandy bottom, shelling — lightning whelks, horse conchs, and sand dollars are common — sandbar stops in knee-deep water, and wildlife watching. There is also a three-mile nature trail through the island's interior leading to the ruins of the Scharrer homestead, and a kayak trail through the bayside mangroves.

Not from our boat. The 23-foot World Cat cannot access the shallow mangrove trail. Guests who want to paddle it can rent kayaks at the island marina after arriving by ferry, or go through a separate kayak outfitter. It is a genuinely beautiful trail and worth knowing about, but it is not something a charter can deliver.

Good, and better after a storm or a strong wind event that stirs the bottom and pushes material ashore. Lightning whelks, horse conchs, and sand dollars are the common finds. The less-walked stretches of beach produce the best of it, which is an argument for arriving by boat rather than joining everyone at the ferry landing.

The Tocobaga people lived and fished here for thousands of years, and burial shell mounds remain. In the 1780s a Spanish Cuban fisherman known as Desi or Caldees established a rancho on a bayou at the southern end — 'cala' being Spanish for cove — which is where the name comes from. For much of the 1800s it was called Hog Island, after the free-ranging pigs on it. Homesteader Henry Scharrer settled permanently in 1890, and his daughter Myrtle was born on the island in 1895 — the only child ever born there. She wrote a memoir about it at the age of 87, called Yesteryear I Lived in Paradise.

Yes. They were a single six-mile barrier island called Hog Island until a hurricane in 1921 cut straight through it, creating what is now Hurricane Pass. One half was left largely alone and became Caladesi; the other was developed and became Honeymoon Island. Caladesi became a state park in 1968.

Frequently. The passes and channels around the island are active water, and dolphins are resident here year-round rather than migratory. Ospreys, herons, and pelicans are common along the shoreline too.

Very. The Gulf-side bottom is sandy and gradual, the water at most stops is shallow and calm, and there is real beach to walk. Minimum age aboard our boat is 5, per U.S. Coast Guard Type I life vest requirements. Captain Keith stays on watch the entire time guests are in the water.

Depends what you want. The ferry is good value for a solo traveller or anyone happy to spend a full day on the island independently — but it runs to a timetable, sells out on busy weekends, and lands you at the bayside marina with everyone else. A charter goes when you want, anchors where conditions are best rather than where the dock is, stays as long as it is good, and can add a sandbar or another island on the way.