Pick your must-dos
Start with what matters most to your group — shelling, dolphins, a beach day, the mansions, a sunset. You don’t have to choose just one; a custom charter can string several together. Just rank them so your captain knows the priorities.
Let the tide & light lead
The best days flow with nature. Shelling is best at low tide; dolphins follow the moving water; sunsets are, well, at sunset. Your captain sequences your must-dos around the tide and light so each one happens at its best moment — that’s the local-knowledge magic.
Choose your departure
Downtown Naples is closest to the bay, mansions, Gordon Pass and Keewaydin; Goodland (Marco) is the gateway to the wild Ten Thousand Islands and Cape Romano. Pick based on your must-dos and where you’re staying.
From the Helm: Sequencing a custom day around the Capri Pass tide swing
On a custom day we’ll often hold just inside Capri Pass for a minute before locking in the order, watching which way the current’s running and how much chop is stacking against it on the outgoing tide. That short pause, taken before anyone’s even settled into a seat, decides more of the day’s shape than the guest’s original wish list does — shelling first while the sand’s still exposed, or open water first and shelling worked in on the way back once the tide’s turned.
When the wind’s blowing hard out of the southwest, we’ll usually run north to Gordon Pass instead, where the pass mouth breaks up the fetch and the water inside stays flatter than the open stretch off Capri. On a calmer morning we’re happy to stay right where we are and work the Capri side, since it puts you closer to the shelling islands without the extra run. Which one we pick has less to do with the guest’s list and more to do with what the water’s doing that hour.
Heat is the other clock we’re quietly running against. Once the sun climbs past midday in the warmer months, the wind usually swings onshore and afternoon thunderheads start stacking over the mainland, so we’ll front-load anything that wants flat water — a slow pass along the mangrove edge for birds, a longer stretch of open running — and hold the beach time, when everyone’s happy to just sit still in the shallows, for whenever the group’s ready to slow down.
At the rail during that slower stretch, we’ll usually hand guests the binoculars first and the dip net second — the net’s for whatever drifts by close enough to scoop, a horseshoe crab or a stray shell, while the glasses go toward whatever’s working the shoreline. We keep both rigged and within reach rather than stowed below, because the best moments on a custom day tend to happen between the planned stops, and nobody wants to wait on gear once something’s spotted.
If a stiff wind ends up blowing straight onto the beach we’d planned to use, we’ll swap it for whichever lee shore is holding calm water that day, even if it means a longer run to get there, because a rolling anchorage isn’t where anyone wants lunch or a toddler handed off the ladder. That call usually gets made quietly before guests notice the original spot was ever in question — the same read, wind against tide stage, that decides whether we run the trip at all.
What guests want to know most while building a custom day is some version of “can we just decide as we go?” and the honest answer is yes, within reason — tide and daylight are the only two things we won’t bend for. Everything else stays flexible right up until the fuel and the clock start pushing back. If you already know the shape you want, a private charter built around your own list locks in that order, and our itineraries guide has a few templates worth stealing from first.