Your Own Boat, Your Own Day
Start with the private charter
Start with the private charter. That’s the honest recommendation for anyone staying at Naples Beach Club, a Four Seasons Resort — beachfront on Gulf Shore Boulevard in Old Naples, on the site of the former Naples Beach Hotel & Golf Club, and the newest luxury flagship in a town that doesn’t open many of them. Book a private trip with us and you get the whole boat: your own captain, your own group, your own route and your own start time. No shared benches, no posted departure you have to build an afternoon around, no script anyone has to get through. You tell us what you want out of the water — estates, dolphins, the sunset, or all three in one run — and we point the bow that way.
The cruise that lands hardest with guests at this address is the Port Royal run. Port Royal is the waterfront neighborhood at the south end of Naples, where the canals feed out to Gordon Pass and the Gulf — effectively the water-side equivalent of the streets you’re already staying on. From the boat you read it the way it was built to be read: deep private docks, coral-stone seawalls, boat lifts, clipped mangrove edges, and long low houses turned to face the evening light. We idle those canals slowly and respectfully. We won’t point at doors or trade in who-owns-what, because most of that talk is myth repeated by people who weren’t there — but ask us about the water, the tide, or the osprey on the piling and you’ll get a straight answer.
Push that same charter to the back half of the afternoon and it becomes a sunset cruise, which is where owning your own timing really pays off. We slip out Gordon Pass as the light turns gold, with the color stacking up behind Keewaydin Island, the wild boat-only barrier island just south of the pass. Bottlenose dolphins live in this water year-round and often roll up alongside or surf the wake — a genuine chance most evenings, though they’re wild animals on their own schedule and we’ll never promise them. If you’re marking an anniversary, a proposal or a milestone birthday, say so when you book and your captain will shape the run around it. Bring a light layer; the bay turns cool and glassy once the sun is down.
- The whole boat, your own captain — and your own start time
- Port Royal’s canals and estates, read from the water
- Golden hour out Gordon Pass toward Keewaydin Island
- About a 10–15 minute drive east to our Naples Bay dock
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