On the water

The two boats we'd send our own family on.

There are a lot of captains running tours out of Marco. We're only going to tell you about the two operators we actually book ourselves when family flies down. Different boats, different vibes — both worth every dollar.

Daytime adventure boat cruising clear turquoise water near Marco Island

Best for · families, all ages, daytime

Marco Island Excursions — the daytime classic.

This is the trip you remember in winter. A private charter that slips out through the back bays and into the Ten Thousand Islands — the wild, mangrove‑edged labyrinth that nobody in the brochures ever quite captures. Expect bottlenose dolphins riding the wake (they always do), pristine bird‑filled shellbanks, a quiet beach landing where you'll find sand dollars the size of a fist, and a captain who's been doing this his whole life and treats your kids like his own niece and nephew.

• Private shelling & dolphin excursions
• Inshore fishing charters (snook, snapper, trout, sheepshead)
• Family‑friendly — bring a cooler, bring grandma

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Private luxury sunset cruise on the Gulf of Mexico near Naples

Best for · couples, adults, the sunset

Naples Luxury Boat Tours — the grown‑up sunset.

Same captain, dressier boat. This is Captain Nick's adults‑only luxury fleet running out of nearby Naples — and it is the move when you want a slow rosé sunset on glassy water, a cruise past the unreal Port Royal waterfront mansions, or a private dropoff on Keewaydin Island for shelling and a swim. Six guests max. Bring your significant other. Don't bring shoes.