The Big Day Out
One trip south, and the boat goes first
DoubleTree Suites by Hilton Hotel Naples sits at 12200 Tamiami Trail N, on the Cocohatchee River side of US 41 — the Wiggins Pass and Vanderbilt Beach end of town, a good nine miles north of downtown. Our Naples boats tie up a long way south of that, at Naples Bay Resort & Marina, 1500 5th Avenue South. Straight down the Trail it runs about a 20–25 minute drive in ordinary traffic, and honestly longer on a January afternoon. We’re not going to pretend that’s nothing. What it means is simple enough: this isn’t an errand you squeeze between a beach morning and a nap. It’s the day you drive south and do the south end of Naples properly.
So put the boat at the front of it. Naples Bay usually lies flattest early, before the sea breeze fills in and puts a chop on the pass, and a morning slot means your crowd boards rested instead of sun-cooked. From the marina the bay runs south past Crayton Cove and the mangrove edges of Dollar Bay, then out through Gordon Pass into the Gulf, with the seawalls of Port Royal along one side and Keewaydin Island’s empty, boat-only shoreline along the other. Bottlenose dolphins live in that water year-round and often turn up in the pass or off the stern — a real chance on most trips, never a promise, because they keep their own schedule and not ours.
An hour and a half to two hours later you’re back at the slip with the car already parked downtown and the whole afternoon unspent. Tin City and the Bayfront sit right there at the water end of 5th Avenue South, and that street runs about a mile west from the marina into the middle of Old Naples — lunch, shade, shops, an ice cream that buys you another hour. If your group is slow in the morning, flip the order: come down mid-afternoon, wander first, finish on a sunset cruise, then drive the Trail home in the quiet. Either shape works. What doesn’t is deciding in the car at eleven — book the slot the night before and hang the day off it.
- About a 20–25 minute run south on the Tamiami Trail
- Take the earlier slot — the water is usually kinder before noon
- Grandparents, teenagers and toddlers all on the same boat
- Back at the dock with the afternoon downtown still ahead
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