Sailfish fishing out of Islamorada is a winter fishery on the reef edge, 3 to 5 miles offshore, worked with live bait. Ramps, channels and the forecast are on the Islamorada port page, so this page skips them. For the general species picture and tackle detail, see the sailfish guide. What follows is meant to help you decide where to start, and it makes no promise of fish.
When sailfish are around Islamorada

Winter is the prime time, with consistent catches November through March. That window sits inside the wider Southeast winter run (see also the Atlantic Southeast region guide).
| Window | What to expect |
|---|---|
| November through March | Consistent catches |
| April or May | Occasional spring tailing, a couple of days |
November through March
A trip in this window falls in the main season.
Spring tailing in April or May
Spring tailing is occasional and lasts a couple of days, so it isn’t a pattern to plan a trip around.
Where boats run and the grounds that hold fish

Boats run 3 to 5 miles offshore to the edge of the reef. A sensible order is the edge first, then the water inside it, then wherever the bait has moved after a front, then the named structure you can mark.
- Reef edge: the default starting zone, 3 to 5 miles offshore.
- Inside the reef: sight fishing on many days, in about 20 ft.
- After a cold front: bait shifts to the reef edge.
- Named grounds: the table below.
The reef edge, 3 to 5 miles out
Most sailfish boats fish near the edge of the reef. Start here unless the day suggests otherwise.
Inside the reef and sight fishing (about 20 ft)
On many days, sailfish are sight fished inside the reef in about 20 ft of water. You spot the fish, then cast live bait to it.
After a cold front
After a cold front, bait moves from the bay-side shallows to the reef edge, so look there first.
Named grounds and structure
The table lists the named grounds and structure near Islamorada.
| Name | Type | Depth | Note |
|---|---|---|---|
| Islamorada Hump | Seamount | 200 ft | About 15 miles offshore |
| Alligator Reef | Reef | ||
| Molasses Reef | Reef | ||
| Eagle Wreck | Wreck | ||
| Bibb Wreck | Wreck | ||
| Duane Wreck | Wreck | ||
| San Pedro Underwater Archaeological Preserve | Spanish galleon | 18 ft | |
| Alligator Lighthouse and Cheeca Rocks | Shallow reefs | 6 ft | Shallow reefs |
Mark these spots on Chart Contours before you run. Chart layers are not for navigation.
How sailfish are fished locally

Four methods cover most of the fishing: kite fishing, slow trolling live bait, sight casting from the tower, and working fish that are showering ballyhoo.
- Kite fishing with release clips
- Slow trolling live bait
- Sight casting live bait from the tower
- Bait showering on feeding fish
Kite fishing with release clips
Lines are clipped to release clips on the kite line. The bait is held away from the boat, and a strike pulls the line from the clip.
Slow trolling live bait
Slow trolling live bait is a core local method. Work it along the reef edge described above.
Sight casting from the tower
From the tower, you spot fish inside the reef and cast live bait to them. This is the zone of about 20 ft.
Fish showering ballyhoo
Ballyhoo showering is the visible sign of sailfish feeding. When you see it, work the fish with live bait.
Who fishes for sailfish out of Islamorada

Charter fleets and a run of winter tournaments shape sailfish fishing out of Islamorada. If you are weighing options, compare billfish options before you commit a trip.
Charters
- Bud n’ Mary’s Islamorada Fishing Marina lists sailfish. Its fleet includes Thats Right (50, John Oughton).
- Go Time Sportfishing Charters is run by Capt. Galon on a 26 ft World Cat 266 SF, offering private charters out of Robbie’s Marina.
Tournaments
Sailfish tournaments out of Islamorada, by usual month:
- Cheeca Lodge Presidential Sailfish Tournament: usually January
- Fish for Holly Sailfish Tournament: usually January
- Islamorada Fishing Club Captain’s Cup Sailfish Tournament: usually January
- Al Flutie Over the Hill Rip-Off Sailfish Tournament: usually February
FAQ: sailfish fishing out of Islamorada
What are the best months for sailfish off Islamorada?
November through March gives consistent catches. Spring tailing is occasional, in April or May, for a couple of days.
How far offshore do boats run for sailfish?
Boats run 3 to 5 miles, near the edge of the reef.
What depth do you sight fish in?
About 20 ft, inside the reef, on many days.
What happens after a cold front?
Bait moves from the bay-side shallows to the reef edge, so look there.
Which sailfish tournaments run out of Islamorada, and when?
Cheeca Lodge Presidential, Fish for Holly and the Islamorada Fishing Club Captain’s Cup usually run in January. The Al Flutie Over the Hill Rip-Off usually runs in February.









