Miss Penny sportfishing boat - Islamorada fishing charters in the Florida Keys
Miss Penny Islamorada Fishing Charters - Veteran Owned Sportfishing in the Florida Keys

Islamorada Fishing Charters

The Origin

Built on a
Mother's Legacy.

The Miss Penny isn't just fiberglass and diesel. It’s the physical manifestation of a trust left by Penny, a mother who believed in the dream of life on the water. Every trip we run is a tribute to her spirit.

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The Menu

Featured Trips

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Swordfish Charter
10 Hours

Swordfish Charter

$2,500

Full Day Charter
8 Hours

Full Day Charter

$2,000

3/4 Day Charter
6 Hours

3/4 Day Charter

$1,600

Fresh From The Dock

Latest Fishing Report

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Angler aboard Miss Penny holding a large mutton snapper at the dock in Islamorada

March 11, 2026

March 11 Fishing Report — Mutton Snapper & Cero Release

Tougher fishing, but the crew made it happen with a big mutton snapper on a live pilchard in 115 feet and a quick cero mackerel release on the troll.

Competitive Fishing

Tournament Mode

Do you have what it takes to compete against the best? We fish the Gold Cup, the Sailfish Tournament, and the Summer Mahi Circuit.

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