Chastain Beach / Indian River

This paddle is one of our absolute favorites—but timing is everything. From February through March, the winds can shift in an instant, and today was no exception. Strong southern winds turned the journey into a battle, making every stroke toward the island (and back) feel like a test of endurance.

Despite the challenge, the destination is always worth it. Given the conditions, we made the call to skip the northern route to Boy Scout Island—facing a brutal crosswind for a mile just wasn’t in the cards. And here’s a pro tip: plan your trip while the tide is still rising. Get caught on the flats, and you’re in for a long, exhausting walk.

But when everything aligns—the tide, the winds, and your timing—you’re in for a show. Almost always the waters are clear, Manatees glide beneath your SUP/YAK, eagle rays leap from the water, shovel-head sharks prowl the shallows, and fish dart like silver flashes beneath the surface. It’s a paddle you won’t forget—if you’re up for the challenge.