Island Hopping in May: Marco Island & Naples

Why May Is the Ten Thousand Islands’ Insider Month

By the time May rolls around, Marco Island has quietly emptied out. The snowbirds who filled the marina lots all winter have flown north, spring break traffic has cleared the passes, and the summer camp crowds haven’t landed yet. What’s left is a stretch of warm, dry, wide-open water that our captains genuinely look forward to every year — the ramps are calm, the sandbars are wide open, and you can anchor off Keewaydin or Kice Island without another boat in sight. If you’re trying to decide whether island hopping around Marco Island and Naples is worth it in May, the honest answer is yes — this is one of the best-kept secrets on the calendar.

May sits in a genuine sweet spot: summer-warm water without summer-crowded docks, and dry skies without the daily thunderstorm pattern that builds through June, July and August. It’s the transition month between winter’s cooler, clearer water and the humid, stormier stretch of true Gulf summer — which is exactly why it’s the month our repeat guests quietly ask for, year after year, without ever quite telling their friends why.

Gulf Water Temps, Weather & Tides in May

Gulf water off Marco Island and Naples climbs steadily through spring, and by May it’s usually sitting in the high 70s to near 80°F — warm enough to jump straight off the boat onto a sandbar without a second thought. Air temperatures follow the same climb, typically running into the mid-to-upper 80s by afternoon, with humidity still noticeably more comfortable than the thick, heavy air of July and August. It’s the kind of water that makes island hopping feel less like a boat ride between stops and more like one long swim with scenery changes in between.

Weather-wise, May is one of the driest months of the year in Southwest Florida — the tail end of the region’s dry season before the classic summer rain pattern kicks in with June. That means mostly clear mornings and a noticeably lower chance of the pop-up afternoon storms that become a near-daily fixture later in the summer. Hurricane season doesn’t officially open until June 1, so May tends to run calm on the tropical weather front too, though our captains always check the day’s forecast before any trip regardless of the month. Tides still call the shots on how much sandbar you actually get to stand on — a mid-to-low tide exposes far more sand than a high one — so if you’re booking a May island-hopping trip, it’s worth asking what the tide is doing that day and timing your departure around it.

Best Places to Island-Hop in May

The real draw of island hopping out of Marco Island and Goodland is that so much of the Ten Thousand Islands is boat-access only — no bridges, no parking lots, no crowds unless a boat brought them there. In May, with the winter traffic gone, our captains tend to run to the same handful of go-to stops: Keewaydin Island’s quiet Gulf-side beaches, Kice Island’s shell-strewn sandbars, the half-submerged dome ruins off Cape Romano, and Sand Dollar Island at the north tip of Tigertail Beach, where the sand shifts and rebuilds with every tide.

Cape Romano deserves a special mention: the famous dome-shaped structures were toppled by Hurricane Ian back in 2022, so what you’ll see today is a scattered, half-submerged ruin rather than the standing domes from old photos — still a striking stop, just an honest one about what’s actually left out there. From any of these anchorages, Goodland’s backwaters and the mangrove edge of Rookery Bay are usually just a short run away, which is part of why a May charter can string together three or four completely different stops in a single afternoon without ever feeling rushed.

What You Might Spot in May

May puts you on the water right as the wildlife calendar shifts too. Loggerhead sea turtles begin nesting on Southwest Florida’s beaches in May, a season that runs into October, so it’s not unusual to see fresh crawl tracks on the quieter stretches of Keewaydin or Kice early in the morning. Bottlenose dolphins live in these passes and around these sandbars year-round, and our captains usually spot a pod working the tide lines or riding the bow wake on a typical run — though, like any wild sighting, it’s never something we can promise. Manatees are more of a cold-weather story here; they gather in warmer, protected water below about 68°F from roughly November through March, and by May most have already dispersed back out into Rookery Bay and the open backwaters, so a manatee sighting in May is a bonus, not the plan. Ospreys, herons and the occasional roseate spoonbill working the tidal flats round out a pretty typical May afternoon on the water, and you can read more about who else shares these waters with you on the wildlife guide.

What to Pack & How to Book a May Island-Hopping Trip

Pack like it’s already summer: reef-safe sunscreen, a hat, polarized sunglasses, water shoes for the oyster-shell edges around the sandbars, and plenty of water — May sun is stronger than it looks even with a breeze off the Gulf keeping you comfortable. A dry bag is worth having for phones and cameras if you plan on wading or snorkeling off the sandbar. Because May quietly books up with locals and repeat guests who’ve figured out the secret, it’s worth locking in your date early, whether that’s a scheduled island-hopping tour or a private charter built around exactly the stops you want. If you’re weighing island hopping against a dedicated sandbar tour, our captains are happy to help you match the stop list to what you actually want to see this month.