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.

Read The Full Story
The Menu

Featured Trips

View All Charters →
Swordfish Charter
10 Hours

Swordfish Charter

$2,700

Full Day Charter
8 Hours

Full Day Charter

$2,200

3/4 Day Charter
6 Hours

3/4 Day Charter

$1,800

Fresh From The Dock

Latest Fishing Report

View All Reports →
Angler holding a big bull mahi aboard Miss Penny during May offshore fishing

May 2026

May 2026 Fishing Report

May was a great month in Islamorada with a 30-pound bull mahi, Captain Chad going 7 for 10 on big permit, steady black grouper fishing, and sailfish still biting when the edge pushed in close.

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.

View Tournament Schedule
Call Now Book Now
Miss Penny Sportfishing ยท Islamorada
Welcome aboard. I'm Miss Penny โ€” leave your name and number and I'll help you plan a trip.

We'll only text you if you leave the page mid-conversation. By starting, you grant Miss Penny Sportfishing permission to send text messages about your inquiry.