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Paddling the Gulf Islands: A 5-Day Kayak Route Worth the Drive.

By the Boat Journal Staff · May 2026 · 11 min read

There's a stretch of the Florida Gulf coast where the islands sit close enough to hop between by kayak, far enough apart that the day still feels like a passage, and undeveloped enough that you'll share your campsite with shorebirds instead of RVs.

The Route

Five days, four island camps, roughly 8 to 14 miles of paddling per day depending on how you cut the crossings. The route works in either direction, but running it south-to-north keeps the prevailing afternoon wind at your back when you're tired, which is the kind of detail that separates a good trip from a long one.

When to Go

Late April through early June. Earlier and the water's still cold; later and the afternoon thunderstorms become a daily planning exercise. Mornings are glass — be on the water by 7 and you'll have three hours of the kind of paddling people frame photos of.

What You Need

A sea kayak (not a recreational sit-on-top — the crossings are real), a chart and compass you know how to use together, and double the water you think. Cell coverage is decent on the north half of the route and absent on the south. Treat it accordingly.

Permits, put-in coordinates, and the camp-by-camp breakdown are coming in the full guide. The short version: it's the best five days you can spend at sea level.