DirtyBoat Charters - Islamorada Fishing Charters

04/21/2026

Big congrats to the team at Miss Penny - Islamorada Fishing Charters and the Florida Keys Children's Shelter on a great day of fishing for a great cause. Sailfish, snapper, mackerel, and a sushi finish at The Islander at Ocean Reef— hard to beat that. Grateful to be part of a charter community that shows up for Keys kids. 🙏

04/11/2026

🚨New crew member alert. 🚨

Meet Captain Jack — our AI booking mate and the first autonomous booking agent in the Florida Keys.

He checks real-time availability, pulls live NOAA marine forecasts, knows every FWC fishing season, and can get you booked 24/7 — no waiting, no phone tag.

Try him right now:
- Chat: dirtyboat.com (blue bubble, bottom right)
- Text: (305) 209-5594

Ask him about dates, weather, what's in season, pricing — whatever you need. He's got a little pirate flair but he knows his stuff.

And if you need me? Just ask him. He'll hand you off to the real captain.

Fair winds and tight lines.
Captain Kit Carson
DirtyBoat Charters | Islamorada



https://www.dirtyboat.com/reports/2026-04-11-captain-jack-ai-booking-agent/

Book your Islamorada fishing charter aboard DirtyBoat 2.0, a 42' Liberty Express out of Robbie's Marina (MM 77.5). Half-day reef trips, offshore adventures and split charters. Call Captain Kit today.

03/16/2026

🚨 Only 2 seats left on Monday s split charter (March 23). 3/4 day aboard the 42 Liberty Express out of Robbie s Marina, Islamorada. /person — gear, bait, license included. Book now: https://www.dirtyboat.com/islamorada-fishing-charters/split-charters/

03/16/2026

Gulf Stream parked on the reef this week. 79° blue water inside 8 miles off Alligator Light. Sails crashing kite baits, kings smoking the edges, deep drops producing limits.

Spring sailfish season is ON. Full Keys Weekly report 👇
keysweekly.com/42/florida-keys-fishing-report-gulf-stream-parks-on-the-reef-and-the-sails-are-loving-it/

03/13/2026

Weekend is here. Sailfish still firing on the kite, snappers stacking on every reef drop. March in the Keys waits for nobody. Last spots open this weekend - lock yours in before they are gone. DM or book at dirtyboat.com ?? What are you chasing this weekend?

03/12/2026

This weekend's hit list: mutton snapper, yellow-eye, and yellowtail stacking up on the reef. The bite's been filthy all week and it's only getting better. Blood on the deck, fillets in the fridge. Limited spots left - DM or book now before you're watching from the couch u{1F3A3}

03/09/2026

March in the Keys: Know Your Target. Most anglers fish blind - here's what the pros know. Yellowtail on the chum line, amberjacks trying to pull you overboard, yellow-eye snappers stacking deep. Each one demands different gear, different approach. Blood on the deck, knowledge in the head. What species is giving you the hardest fight?

03/07/2026

Saturday's haul hit different. Yellowtail snapper stacked up, mutton snapper crushed it, and the vermillion kept the rods bent all day. Big smiles, full coolers, fillets for days. Limited spots this weekend - DM to lock in.

03/06/2026

March in the Keys hits different. Yellowtail, mutton, vermillion, yellow-eye snappers all stacking up. Sailfish still firing off on the kite. If the boat''s clean, we didn''t fish hard enough. Book your trip before spring break fills up. What species are you chasing this month?

03/06/2026

What most people get wrong about reef fishing in the Keys. Yellowtail, mutton, yellow-eye snapper, amberjack, sailfish - each one demands a different approach. Skip the basics and you skip the bites. Blood on the deck, knowledge in the head. What species gave YOU the hardest fight?