Sailfish Charters
When the air is cold, the bite is hot. Winter is best time to catch sailfish and will stick around through spring.
Islamorada Offshore Fishing
Targeting Sailfish in Islamorada
Experience peak sailfish action in the Sportfishing Capital of the World. Islamorada’s winter sailfish season delivers world-class kite fishing, tailing sails, and double-digit days when the conditions line up. Our captains specialize in reading the water, working live baits, and putting anglers on fast-paced, high-energy bites. Whether you're chasing your first sail or trying to raise a dozen flags, our Islamorada sailfish charters offer premium boats, top-tier gear, and the expertise needed to capitalize on every opportunity. Book your winter trip early—prime dates fill fast.
Pricing
Sailfish Charter Pricing
Our offshore trips are priced per boat, not per person, and include the preparation, planning, and equipment required for a productive day in blue water. The captain adjusts each trip to the conditions, targeting pelagic and reef species depending on what’s active.
Half-Day (4 hours)
Designed for quick offshore action when the bite is close. A strong choice for targeting reef species or working productive water within a short run of Islamorada.
All bait, tackle, and fishing licenses included. Bottled water and ice provided. Gratuity for the captain is appreciated but not included.
Book Now3/4 Day (6 hours)
Designed for a longer offshore run than a half day. A strong choice for targeting reef species or working productive water within a short run of Islamorada.
All bait, tackle, and fishing licenses included. Bottled water and ice provided. Gratuity for the captain is appreciated but not included.
Book Now
Full Day (8 Hours)
A full day offshore with the range and time needed to chase mahi, tuna, sailfish, wahoo, snapper, and other blue-water species. Allows the captain to work edges, color changes, and offshore structure throughout the day.
All bait, tackle, and fishing licenses included. Bottled water and ice provided. Gratuity for the captain is appreciated but not included.
Book NowCharter Highlights
Trip Essentials
Everything needed for the fishing itself is provided. A few personal items will make the day more comfortable.
What’s Included
- All offshore tackle and gear
- Live bait and rigged lures
- Insulated fish boxes
- Multiple livewells
- Fishing licenses for every guest
- Bottled water and ice
- All safety equipment
- Fish cleaning and bagging
What to Bring
- Reef-safe sunscreen
- Polarized sunglasses
- Light jacket for early mornings
- Hat or sun protection clothing
- Snacks or additional drinks
- Motion sickness medication (if needed)
- Camera or GoPro
- Small cooler for fillets to go(optional)
"Big Guru"
39’ Contender
Big Guru is a 2023 Contender 39 ST built for long offshore runs and consistent performance in open water. Powered by triple outboards, the boat delivers the range, speed, and stability needed to reach productive blue-water grounds quickly and comfortably. The open deck layout keeps the cockpit clear during a bite, while advanced Garmin electronics help the captain track structure, bait, and pelagic movement throughout the day. Forward seating, padded leaning posts, a console head, and shade from the T-top add comfort without compromising fishing space. It’s a clean, well-rigged offshore platform designed for mahi, tuna, sailfish, wahoo, snapper, grouper, and other species that migrate along the edge of the Gulf Stream.
Ready to Fish Islamorada Offshore?
Big Guru is rigged, fueled, and ready for the blue water. Choose a half day or full day, and the captain will run the most productive water based on current conditions, species movement, and what’s been biting.
Have Questions?
FAQs About Sailfish Charters in Islamorada
Here’s what most guests want to know before they book, from licenses and weather, to what to bring and what we're catching.
How many people can we bring on a charter?
Offshore charters accommodate up to 6 guests aboard Big Guru, our 39’ Contender ST with triple outboards.
Where do inshore trips depart from?
Offshore trips leave from:
Three Waters Marina
84001 Overseas Hwy
Islamorada, FL 33036
What time do offshore trips start?
Departure times vary by season, weather, and targeted species. Your captain will confirm the best start time for current conditions.
What’s included in the trip?
All tackle, bait, rigged lures, licenses, ice, bottled water, and safety equipment are included. Fuel is also included in the charter rate.
What should I bring?
Polarized sunglasses, reef-safe sunscreen, snacks or drinks, and a light jacket for early mornings. Motion-sickness medication is recommended for anyone sensitive to offshore conditions. A small cooler for your fillets is optional.
What happens if the weather is bad?
If conditions are unsafe, the trip will be rescheduled or canceled. Weather-related cancellations receive a full refund or credit.
What is your cancellation policy?
Full refund with 7+ days notice (minus 4% booking fee)
50% refund with 48 hours–7 days notice
No refund within 48 hours
Weather cancellations are fully refunded or rescheduled
Can children join the offshore trip?
Yes. However, offshore conditions can be more demanding than inshore fishing. Please consider each child’s comfort level with boat motion and longer runs.
Can we keep what we catch?
Yes, for all legal species in season. Your captain will clean and bag your fillets at the end of the trip.
Is the boat accessible for guests with mobility needs?
The boat is suitable for most guests, but please let us know ahead of time if anyone in your group has mobility considerations. This allows the captain to prepare and ensure safe, comfortable boarding and movement around the deck.