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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Crew working a sailfish boat-side aboard Miss Penny during the April 18 trip

April 18, 2026

Best of the Upper Keys Trip Delivers (April 18, 2026)

A donated Best of the Upper Keys charity trip benefiting the Florida Keys Children's Shelter produced a perfect 2 for 2 on sailfish, plus mahi mahi, cero mackerel, and mutton snapper.

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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