If you only get out on the water once during your stay, make it this. Several operators run evening cruises out of the marinas along Main Street and Fisherman’s Wharf, heading down Matanzas Pass and out into the Gulf as the light goes golden. The dolphins here are used to boats and will often ride the wake right behind the stern, which never stops being fun no matter how many times you have seen it.
Most cruises run around ninety minutes to two hours, on catamarans or pontoon-style boats with shade and a restroom, and many have a bar on board. You’ll pass the shrimp fleet, the pier and the beachfront resorts from the water, then turn to watch the sun drop into the Gulf. Sightings of dolphins are nearly guaranteed; manatees and sea turtles are a bonus.
Book a day or two ahead in season, and arrive early for the best seats along the rail. Bring a light layer for the ride home; it cools off quickly once the sun is down. This is a relaxed, no-effort way to end a day and it works for every age.
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