Captain Jimi McKillip | Cell: (305) 304-4229 | Email: capjimi@aol.com
  • Highlands to Islands

    From the Highlands of Montana to the Islands of Key West, Florida

  • Fish Key West

    Guided fly fishing and light tackle, flats fishing trips in Key West and the lower Florida Keys


  • Fish Montana

    We've chosen two world class venues to challenge your angling skills.

Welcome to the Highlands to Islands homepage!

Welcome to the Highlands to Islands homepage! We offer guided fly fishing and light tackle, flats fishing trips in Key West and the lower Florida Keys. We sight fish for Tarpon, Permit and Bonefish, as well as many other species in the clear shallow water flats surrounding the lower Keys. We also offer guided fly fishing trips in Southwestern Montana during the summer months. Float fishing is popular in Montana and we will work many of the western rivers in pursuit of Rainbow, Brown and Cutthroat Trout.

We've chosen two world class venues to challenge your angling skills. We look forward to having you on our boat real soon.

- Captain Jimi

Charter Rates

About Captain Jimi

Captain Jimi attended college in Missoula, Montana where his passion for fly fishing grew into a way of life. Jimi started guiding for Headwaters Angling in 1983 and soon became one of the top guides on the Madison River. He has earned the reputation as a friendly, hardworking guide and is respected by both his fellow guides and anglers.

In the early 90s Jimi came to Key West to Tarpon fish and caught a bad case of Tarpon fever. He soon moved to the Keys and began to guide flats anglers in 1995. Having a U.S. Coast Guard Captains License as well as an outfitters license in Montana, has given Jimi a well rounded approach to fishing. Jimi now spends the majority of his time in Key West, Florida pursuing Tarpon, Permit and Bonefish.

Summers are still spent in Montana, fly fishing for trout. Jimi is a full time guide and an avid fly tyer who has not lost his enthusiasm for his sport.

Learn More

Highlands to Islands
From the Highlands of Montana to the Islands of Key West, Florida
Captain Jimi McKillip | Cell: (305) 304-4229 | Email: capjimi@aol.com