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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Anglers posing with a keeper cobia and a row of yellowtail snapper aboard Miss Penny at the dock

April 6–7, 2026

The Wind Paid Off (April 6–7, 2026)

After nearly a week at the dock due to severe winds, the rebound has been excellent with sailfish shots on most 3/4 and full day trips, yellowtail snapper fishing as good as it gets, and a keeper cobia in the box.

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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