Islamorada Sailfish Charters
The Acrobats of the Sea | Winter Prime Time
World-Class Sailfishing in Islamorada
You say you have never hooked a sailfish? Well, come to Islamorada and experience the thrill of a lifetime! Sailfish are the acrobats of the sea. They never give up—leaping, twisting, diving, and leaping again in a desperate dance. Our Islamorada fishing charters are built around putting you on the fish that matters most.
Winter is Prime Time. When the north winds blow, the bite turns on. Live bait and kite fishing are the keys to victory here, and there is no telling how many you can hook when the school moves through.
🏆 Record Day: DirtyBoat has hauled in as many as 15 sailfish in a single outing!
Tournament Rigged & Ready
From the DirtyBoat Catch Log
From the DirtyBoat Catch Log
Lance, Todd & First Mate John
Blue skies, flat horizon, and a sail lit up in the spread. Lance and Todd got the perfect Islamorada day — a big Atlantic sailfish fully-finned at the boat before the release. First Mate John doing what he does.
Sailfish are the number one target from December through April. The kite program off Islamorada is as good as it gets — live goggle-eyes dancing on the surface, fins cutting through the chop.
Claim Your Winter Dates
Sailfish season fills up fast. Select your date for an offshore pursuit.
Check Affiliate Private Availability
If DirtyBoat is booked, we can still get your group on the water. Our partner fleet—Miss Penny, Just Cuz, Blue Heaven, and Islamorada Luxe—are vetted to the DirtyBoat standard. From deep sea fishing to private sandbar trips and sunset cruises.
Luxury Meets Combat
Hunting Sailfish requires a high-quality vessel and precise positioning. We offer a high-class experience on the 42-foot Liberty Express.
- ❄️ Climate Controlled: Fully air-conditioned salon to recover between bites.
- 🌊 Sea Handling: A heavy, stable ride that eats the winter chop for breakfast.
- 🎣 Elite Tackle: Custom-rigged kite fishing setups for multi-hook spreads.
"When you book our charters, you get the bounty without the misery."
Master of the Hunt
Success on the water relies heavily on the captain. Captain Kit Carson has spent a lifetime learning the subtle tell-tales of sailfish movement in the Florida Keys.
Whether you are a seasoned tournament pro or a first-timer looking for your first "Sail," Captain Kit and the crew will work relentlessly to ensure your day is a perfect success. We hunt where the fish hide.
Voyage Details
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Duration
Full 8 Hours
-
Crew
Up to 6 People
Bring to the Boat
- 🔱 Quick-dry Layers (Winter)
- 🔱 Polarized sunglasses
- 🔱 Sunscreen & Lip Balm
- 🔱 Provisions (Food & Drink)
- 🔱 Booty for the Mate (15-20%)
Provisions Included
- ✔️ Tournament Kite Gear
- ✔️ Live Goggle-Eyes/Bait
- ✔️ Federal Fishing Licenses
- ✔️ Ice & Cold Water
- ✔️ Catch Cleaning
Articles of Agreement
Payment of Bounty
Online bookings require full payment via modern currency (Credit Card/Digital). Cash is always king at the Robbie's Marina dock.
The Mate's Tip
"A hardworking crew deserves a share." Customary gratuity is 15%-20%.
Voyage Cancellation
- • 14+ Days: Full refund (less 6% fee).
- • 7-13 Days: 50% refund.
- • Weather/Captain Call: Full refund or credit.
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