The Don CeSar — the Pink Palace

A 1928 hotel that has hosted F. Scott Fitzgerald, served as a military hospital during the Second World War, and anchored the St. Pete Beach skyline ever since. From the water you get the full facade at once — that improbable pink rising straight out of the Gulf, with no parking lot or palm tree in the way.

It photographs best in late afternoon when the light warms and the pink goes almost coral. Guests who have driven past it a dozen times still reach for their phones when they see it from this angle.

The Sunshine Skyway

We go right up to the Skyway and pass beneath it. From the water you look up at cars and trucks shrunk to toy size, and the bridge reads completely differently depending on the angle you approach from.

The best version is when a cruise ship, a commercial freighter, or a loaded barge passes under. The bridge makes the ship look small until the ship gets close, and then neither of them looks real. Those vessels throw enormous wakes, and dolphins come in to surf them, jumping in front of the bow as the ship moves through.

After dark the Skyway lights up and the colours change. On a sunset charter you often get both versions in one evening.

Under the Pinellas Bayway

The Skyway gets the attention, but the Bayway is the one that surprises people. Passing beneath it, the columns and arches line up into a long repeating corridor — closer to a cathedral nave than a road bridge, and running much further than you expect.

The Bayway opened in 1962 as a two-lane crossing with a drawbridge. That original western span was replaced with a high-level fixed bridge, dedicated in October 2014 and built 65 feet above the water so boats can pass underneath without traffic stopping. A second Bayway bridge, between Isla Del Sol and Tierra Verde, was replaced the same way and finished in January 2023. It lights up at night too.

The St. Petersburg Pier and downtown skyline

The Pier’s angular cantilevered design over Tampa Bay is one of the most photographed modern landmarks on this coast, and approaching it by boat gives a completely different read than walking up to it. The downtown skyline behind it is one of the backdrops you can choose on a sunset charter.

Clearwater Beach from the Gulf side

Consistently ranked among the best beaches in the country, and most visitors only ever see it from the sand. The approach from the water shows the full sweep of it — the beach, the hotels along the shore, and Clearwater Pass.

Inside Boca Ciega Bay the water stays comfortable when the open Gulf does not, which makes it the right call on a windy afternoon or when someone in the group is uneasy about chop. It is also, frankly, beautiful — the waterway runs past waterfront estates with private docks and landscaping you cannot see from the road at all.

Mangroves line long stretches of this shoreline, and they are doing more work than they look like they are. The root systems shelter enormous numbers of small fish, which is exactly why dolphins patrol this edge — they know where the food is. Easing along a mangrove line is one of the more reliable ways to see them close in.

Dolphins are common along the Intracoastal and in Tampa Bay. Brown pelicans, ospreys, great blue herons, snowy egrets, and roseate spoonbills turn up regularly — occasionally right on the bow rail, entirely of their own accord. Manatees appear in calmer stretches, though they spend most of their time submerged and are far easier to see than to photograph.

More on dolphin and wildlife charters →