Highlands To Islands

Highlands To Islands takes you fishing around the flats and skinny waters of the Florida Keys where you can sample some of the best fish this fisheries have - Tarpon, Bonefish, Permit, Jack Crevalle, and more. Capt. Jimi can accommodate anglers of all levels of expertise and will make sure you have a nice day on the water.

Capt. Jimi specializes in flats fishing and his signature technique is fly fishing for Tarpon. With over 20 years of local fishing experience during which he’s been the captain of thousands of fishing trips, Capt. Jimi has the edge that can make the difference. Fishing with him is a perfect way to experience the rich flats and backcountry waters that the Keys are famous for.

You will be fishing from a 17’ Maverick Mirage flats boat. She is powered by a 115 HP Yamaha engine. The boat is equipped with GPS, a fishfinder, and a live bait well. She carries fly fishing and conventional fishing equipment, mostly made by Shimano and Penn. You will find safety gear onboard too. Up to two anglers can come along and they will have enough space to enjoy fly fishing and sight fishing to the fullest.

All the fishing gear is waiting for you onboard. The captain will prepare live bait before the trip, as well as lures. If you want to bring small kids onboard, you should bring life vests for them. The fishing license is included in the trip.

Pack a hat, sunglasses, a camera, some food and drinks, and come along!



Select date to see available trips and rates:

  • Private trip
    Full Day Trip - Flats Fishing
    FREE Cancellation 7 days notice
    8 Hour Trip, starts at 8:00 AM
    Seasonal trip Mar 1 - Jun 15
    $650
    price breakdown
    $650
    This full day trip will give you plenty of time to explore Florida Keys riches and target a variety of species, including Tarpon, Permit, Jack Crevalle, Bonefish, and many more. All the gear is waiting for you onboard. You will be sight fishing around shallow waters. Bring polarized sunglasses, sunscreen, a camera, rain jacket, and food and drinks. This package is suitable for anglers with some experience.
  • Private trip
    Full Day Trip - Tarpon Fishin
    FREE Cancellation 7 days notice
    8 Hour Trip, starts at 6:00 AM
    Seasonal trip Mar 1 - Jun 15
    $650
    price breakdown
    $650
    Spend the day grappling with Tarpon. These fish are strong and acrobatic and will turn your trip into a lasting memory. Their season peaks from March until June, and this trip is something you must try if you’re a serious angler. The captain will provide all the fishing gear, but you should bring food, drinks, a hat, polarized sunglasses, a camera, sunscreen, and rain jacket.
  • Private trip
    3/4 Day Trip - Flats Fishing
    FREE Cancellation 7 days notice
    6 Hour Trip, starts at 8:00 AM
    Seasonal trip Nov 1 - Jun 15
    $550
    price breakdown
    $550
    This six hour trip will give you more time to fish than a half day but still won't take a lot of your schedule. You will explore the shallow waters, sight fishing in the Florida Keys. You can target Tarpon, Bonefish, Jack Crevalle, Permit, and more. All the gear is provided onboard, but you should bring food and drinks, a hat, polarized sunglasses, a camera, a rain jacket, and sun protection.
  • Private trip
    Half Day Trip - Flats Fishing (AM)
    FREE Cancellation 7 days notice
    4 Hour Trip, starts at 8:00 AM
    Seasonal trip Nov 1 - Jun 15
    $450
    price breakdown
    $450
    This morning trip will let you scout around the flats and target a variety of species, such as Bonefish, Jack Crevalle, Tarpon, and many more. It's important to bring polarized sunglasses, sun block, a camera, rain jacket, as well as food and drinks. You will have enough time to get a glimpse of how superb flats fishing is. The gear is supplied onboard. Live bait is prepared before the trip and is included in the price.
  • Private trip
    Half Day Trip - Flats Fishing (PM)
    FREE Cancellation 7 days notice
    4 Hour Trip, starts at 12:30 PM
    Seasonal trip Nov 1 - Jun 15
    $450
    price breakdown
    $450
    Come spend the afternoon exploring rich fisheries around the flats and chasing Bonefish, Jack Crevalle, Tarpon, and many more. All the fishing gear is supplied onboard as well as bait and lures. You should pack polarized sunglasses, sun protection, rain jacket, a camera, as well as food and drinks. This trip is suitable for novice anglers.
  • Private trip
    Half Day Trip - Tarpon Fishing (AM)
    FREE Cancellation 7 days notice
    4 Hour Trip, starts at 6:00 AM
    Seasonal trip Mar 1 - Jun 15
    $450
    price breakdown
    $450
    Spend the morning chasing Tarpon! Silver Kings are available year-round but come in full force as of March. It’s a chase everyone loves, from complete novice anglers to pros. All the gear is provided onboard. And, Tarpon fly fishing is the captain’s thing number one, so you’ll be in good hands. Pack polarized sunglasses, sun block, a camera, rain jacket, as well as food and drinks.
  • Private trip
    Half Day Trip - Tarpon Fishing (PM)
    FREE Cancellation 7 days notice
    4 Hour Trip, starts at 6:00 PM
    Seasonal trip Mar 1 - Jun 15
    $450
    price breakdown
    $450
    Evening Tarpon fishing is something you should definitely try if you’re fishing the Keys. It’s exciting, fast-paced, and super rewarding. All the fishing gear is supplied onboard, but you should bring some snacks and drinks, a hat, and rain jacket just in case, as well as a camera.

About the Captain

Jimi Mckillip
Key West, Florida, United States
Response time 8 hours
Member since February 2018
Started fishing at a very young age. I have a natural resources degree, love for the outdoors. Guiding became a way to feed my fishing passion.

About this listing

Targeted Species

Barracuda (Great) Barracuda (Great)
Bonefish Bonefish
Cobia Cobia
Permit Permit

Tarpon Tarpon

Boat Specs

Maverick Mirage (Flats boat) originally built in 2008. Powered by a 115HP Yamaha engine, with a maximum cruising speed of 40 knots.

Length
17 ft
Capacity
2 persons

Types of Fishing

Inshore Fishing
Nearshore Fishing
Flats Fishing
Backcountry Fishing

Fishing Techniques

Light Tackle
Spinning
Jigging
Popping
Fly Fishing

Amenities

GPS
Life Jackets
Fishfinder
Live Bait Well
Ice Box
GPS
Life Jackets
Fishfinder
Live Bait Well
Ice Box

Trip Includes

Rods, reels & tackle
Live Bait
Lures
Catch cleaning & filleting
Fishing License
Fly Fishing Equipment

Cancellation Policy

Free cancellation up to 7 days prior to trip

Customers can cancel or modify their booking up to 7 days before the trip date free of charge. If the trip is canceled or modified later, or in the event of a no-show, 100% of the deposit will be charged.

Listing Policies

Pickup not included
Transfer to/from departure site is not included in trip rates.
Child Friendly
You Keep Catch
Catch and Release Allowed

Payment

Book with 20% deposit
When the captain confirms your trip, FishingBooker charges your credit card a 20% deposit to guarantee your reservation.
Pay remaining balance to captain
The remaining balance is to be paid directly to the charter operator on or prior to your trip date in one of the following payment methods:
Cash
Visa
Mastercard
American Express
Checks
Bank Transfer
PayPal

When paying the remaining balance with a credit card, there is a 3% fee.

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