Islamorada Sailfish Charters
The Acrobats of the Sea | Winter Prime Time
What Is a Sailfish Charter in Islamorada?
An Islamorada sailfish charter is a full-day offshore trip focused on live bait and kite fishing during the winter migration. DirtyBoat sailfish trips are a strong fit for serious anglers, but beginners can absolutely jump in because the crew handles the technical side and coaches you through the fight.
World-Class Sailfishing in Islamorada
Never hooked a sailfish? Come to Islamorada and you'll find out why people get hooked themselves. Sailfish are the acrobats of the sea. They never give up. They leap, twist, and dive, then leap 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, with live goggle-eyes dancing on the surface and fins cutting through the chop.
Claim Your Winter Dates
Sailfish season fills up fast. Select your date for an offshore pursuit.
That day's either booked solid or off our regular schedule. Call us: we keep a waitlist for last-minute openings, and we work with a fleet of sister boats that can run if we can't.
📞 Call (305) 209-5594 See Sister-Boat Fleet →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) is 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 hard to put you on fish. We hunt where the fish hide.
Voyage Details
-
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.
Islamorada Sailfish FAQs
Real answers to questions I actually get on the dock.
When is the best month for sailfish?
Season runs November through March, peak in January and February. The bite fires when cold fronts push north winds down the Florida Straits. 12 to 18 knots out of the north with water in the low 70s is the cheat code.
Why is Islamorada the Sailfish Capital?
The Gulf Stream sits closer to Islamorada than anywhere else on the East Coast: migrating sailfish run within 4 miles of the dock. The reef edge off the Islamorada Light is one of the most productive sailfish stretches on the planet. The Cheeca Presidential and Islamorada Sailfish Tournament both fish these grounds.
How do you actually catch them?
Kite fishing with live bait: the classic Islamorada technique. Two kites fly off the boat with three or four pilchards, threadfins, or blue runners suspended just below the surface. When a sailfish lights up on a bait, you see it before the eat. Slow-trolling live baits is the backup when kite conditions aren't right.
Where do you fish?
Along the reef edge in 100 to 300 feet, especially off the Islamorada Light. When a cold front hits, we work the color change where green inshore water meets blue Gulf Stream water. Lines hit water 15 minutes from Robbie's Marina.
How much does it cost?
Full-day private sailfish charter is $2,200 plus $200 fuel for up to 6 anglers: about $400 per person split six ways. The 8 hours include captain, mate, all the kite-fishing tackle, live bait, licenses, ice, water, and cleaning anything we keep.
Can beginners catch sailfish?
Yes. I teach first-timers the same technique I use at the Cheeca Presidential. Mate handles the kites and bait. You watch the kite, hold the rod, reel down and set the circle hook when it eats. Robin Hall on Team DirtyBoat won Top Female Angler at the 2025 Cheeca Presidential: the system works for anyone willing to fish hard.
Do you keep or release?
Sailfish are catch-and-release only by Florida law. We use non-offset circle hooks (also Florida law) which hook the corner of the jaw for a clean release. Fights run 15 to 45 minutes depending on fish size. Photo at the boat, revive, release. About 99% of Islamorada sailfish swim away.
How many fish in a day?
Peak season (January-February): 5 to 15 releases on a good day. Shoulder days: 1 to 3. Tournament-grade days have hit 25+. The Florida Keys single-boat record is over 30 in a day. DirtyBoat had a documented Perfect 10 Sailfish Day in 2023.
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