What fishing tournaments are held in Islamorada?
The Keys tourism council lists more than 30 for 2026. Sailfish tournaments run from December to February, tarpon fly events from May to July with the invitation-only Gold Cup Tarpon on 15–19 June, dolphin tournaments from May to August, and backcountry events for snook, redfish and bonefish in the fall.
Still to come in 2026
| Dates | Tournament | Fish |
|---|---|---|
| 10–11 Oct | Hurricane Cup, benefiting the Guides Trust Foundation | Permit, tarpon, bonefish, redfish, snook |
| 16–18 Oct | Ladies, Let’s Go Fishing! seminar and Fishing Fever tournament | — |
| 16–17 Oct | Casting for Cats Backcountry Tournament | Backcountry |
| 12–14 Nov | Cheeca Lodge & Spa All-American Backcountry Tournament | Snook, redfish, bonefish, tarpon, permit |
| 4–6 Dec | Islamorada Sailfish Tournament (first leg of the Gold Cup trifecta) | Sailfish |
| 11–13 Dec | Islamorada Junior Sailfish Tournament (61st year) | Sailfish |
The year’s shape
- Winter, sailfish: January 2026 alone had the SailFly, Fish for Holly, the Captain’s Cup and the Cheeca Lodge Presidential, the last two legs of the Florida Keys Gold Cup Sailfish Championship, with more sailfish events into February. The Free Keys Kids Sailfish Tournament is held every winter during peak sailfish season.
- Late spring, tarpon on fly: the Golden Fly (18–20 May 2026), the Don Hawley Tarpon Fly (1–5 June), the Ladies Tarpon Fly, held each June since 1977 during the height of the tarpon migration (9–11 June), and the 63rd Gold Cup Tarpon (15–19 June), which the council calls the Wimbledon of tarpon fishing.
- Summer, dolphin: the Nick Sheahan Dolphin Rodeo (1–3 May), the Captain’s Cup Dolphin (24–25 June) and the Coast Guard Station Islamorada Dolphin Rodeo (10–11 July).
- Opening day for grouper: the Jeff Leonia Reel and Steel Classic is held each year on the opening of hogfish and grouper season (30 April–1 May 2026).
- Backcountry: the Swamp Guides Ball (January), the Herman Lucerne Memorial, fished only inside Everglades National Park (18–20 September), and the fall events above.
Read for this page on 6 October 2026: Keys tourism council: fishing and tournaments .
Check it at the source
- Florida Keys & Key West tourism council: fishing The Monroe County Tourist Development Council’s fishing pages, tournament calendar and Fishing Opportunity Calendar. Link checked 6 October 2026
Tournaments: questions
When is the Gold Cup Tarpon Tournament?
The 63rd Gold Cup Tarpon Tournament ran 15–19 June 2026 in Islamorada. The Keys tourism council describes it as invitation-only for 25 anglers and all-release.
When are the Islamorada sailfish tournaments?
December to February. The 2026–27 season opens with the Islamorada Sailfish Tournament on 4–6 December and the Junior Sailfish Tournament on 11–13 December, and January brings the legs of the Gold Cup Sailfish Championship.
Next step
Looking for fishing trips in Islamorada?
Islamorada Charters Fishing is an independent guide — no boats, no bookings, nothing to sell. It exists so you can ask better questions before you hand an operator a deposit.
Islamorada Charters Fishing takes no bookings and earns nothing from a click. You book with the operator directly.