1. Watch wild dolphins
The easiest, most reliable thrill on the coast. Wild bottlenose dolphins surf the wake at Gordon Pass and through the island cuts off Marco. A dolphin tour is the classic — and it’s a guaranteed kid-pleaser.
2. Hunt shells on a wild island
Southwest Florida is one of the world’s great shelling coasts, and the best beaches are reachable only by boat. A shelling tour drops you on a remote barrier island like Keewaydin to comb the tide line for whelks, conchs and the prized junonia.
3. Catch a Gulf sunset
The sunsets here are world-famous, and there’s no better seat than a boat. A sunset cruise is the perfect end to any day — and a romantic highlight for couples.
4. Cruise the Port Royal mansions
See the most exclusive waterfront homes and mega-yachts in Florida from the only place you really can — the water. A Naples & Port Royal cruise is jaw-dropping sightseeing.
5. Beach a roadless island
Trade the crowded mainland for your own stretch of sand. A beach & island tour beaches the boat on a roadless Gulf island for swimming, sandcastles and shells.
More ways to play
- Go fishing with a local guide on a relaxed inshore fishing charter.
- Book the tiki boat — a one-of-a-kind family-friendly tiki cruise.
- Throw a party afloat with a group charter or bachelorette cruise.
- Dine by boat on the Naples water shuttle between waterfront restaurants.
- Spot manatees & birds on a wildlife cruise through the Ten Thousand Islands.
New here and not sure where to start? Our first-time visitor guide picks the perfect trip for you.
From the Helm: Why an incoming tide moves our Keewaydin lagoon stop earlier in the day
First-time guests standing at the rail before we’ve even left the dock tend to ask the same thing in different words: what should we actually do out here. The honest answer is that we don’t plan the day off a fixed list — we plan it off the tide. A falling tide first thing in the morning is when the sandbars at the mouth of the Keewaydin lagoon start showing themselves, so that’s when we lean hard into a shelling stop there; wait until the water’s already flooded back in and that same spot is just open water with nothing to show for it.
If the tide’s already turned by the time we leave the dock, we’ll flip the order instead, working the open bay first while the light’s still soft and saving the island stop for whenever the water drops enough to expose sand again. Dolphins get worked into whichever window makes sense that morning — we watch for diving birds stacking up over bait more than we watch the clock, since a slick of nervous mullet usually means something’s pushing them from underneath, and that’s worth a slow pass before we move on anywhere else.
Somewhere in the middle of all that, we’ll cut the engine and just drift for a minute with no destination in mind, because half of what people remember from these trips is the quiet — water slapping the hull, an osprey working a fish overhead, nobody talking. It’s not on any list of things to do, and it doesn’t photograph as well as a dolphin fin, but guests bring it up on the ride back more than almost anything else we point out along the way.
Ask us which single stop we’d protect if the day ran short, and it depends entirely on who’s aboard — families with young kids usually get the beach time, anglers get pulled toward a passing school of fish, first-time visitors get steered toward whatever we think will surprise them most. That flexibility is the real difference between a fixed list and a dolphin tour or shelling tour run by someone adjusting to what’s actually happening in front of the boat instead of a script.
Weather changes the math too. On a blustery day we’ll tuck toward the back bay and the mangrove creeks instead of pushing out to open water, trading big horizon views for a calmer ride and better odds at herons and easier sightlines for shells along the bank. It’s a trade guests rarely mind once we explain it, especially with kids aboard who’d rather be dry than technically further out. We’d always rather adjust the plan early than grind through chop for an hour chasing the original one.