Key West's Premier Night Fishing Charters

Published Date: July 17, 2025
Fishing

Marathon, FL
$300 - $1,000 price range
Updated Date: September 8, 2025

Summary

Join Captain Bill for a half-day guided fishing trip in beautiful Islamorada. You'll head out on a well-equipped boat with up to 3 guests, making it perfect for small groups or families. Captain Bill knows these waters inside and out, and he's an expert at finding bonefish, permit, and the prized tarpon. Whether you're new to fishing or have years of experience, he'll tailor the trip to your skill level. All the gear you need is provided, including quality rods and reels. As you cruise the crystal-clear flats, keep an eye out for your next catch while taking in the stunning views. It's a great way to spend a morning or afternoon on the water, with personalized attention from a knowledgeable local guide. Remember, deposits can't be refunded, so plan accordingly. Get ready for some serious sport fishing in one of Florida's top spots!

Key West's Premier Night Fishing Charters

Rods, Reels, and Catches

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Hop Aboard Islamorada Fishing Charters!

Reel in the Big Ones: Half-Day Islamorada Fishing

Get ready to chase some of the most prized gamefish in the Florida Keys on this action-packed half-day trip with Bill Fish Sportfishing. We'll be hitting the flats and backwaters around Islamorada, targeting bonefish, permit, snook, and the mighty silver king – tarpon. Whether you're a seasoned angler or just getting your feet wet, Captain Bill's got you covered with top-notch gear and local know-how that'll have you hooked up in no time.

What to Expect on the Water

We'll meet up at the marina bright and early, load up the boat with ice-cold drinks and snacks, and head out to where the fish are biting. Captain Bill's custom flats boat is perfect for sneaking up on those spooky bonefish and permit in the shallows. With room for up to 3 anglers, you'll have plenty of space to cast and fight fish without getting tangled up. The boat's decked out with all the latest safety gear, so you can focus on the fishing while we take care of the rest.

Techniques That Land Fish

Depending on what's running and where they're feeding, we might be sight-casting to tailing bonefish, flipping live bait for snook around the mangroves, or setting up on the edge of a flat to intercept cruising permit. For tarpon, we often use heavy spinning gear with live crabs or mullet – when one of these silver missiles hits, hold on tight! Captain Bill's always happy to show you the ropes if you're new to these techniques, or swap tips if you're an old hand. Either way, you're in for some world-class inshore fishing.

Species You'll Want to Hook

Bonefish: These "grey ghosts" of the flats are lightning-fast and notoriously spooky. Averaging 4-6 pounds, with some monsters pushing 10+, bonefish will test your casting accuracy and give you a blistering run when hooked. They're most active in the warmer months, tailing on the flats during high tides.

Permit: The holy grail for many flats anglers, permit are strong, smart, and downright picky eaters. These disc-shaped bruisers can top 30 pounds and will put your tackle and patience to the test. Spring and fall are prime permit seasons in the Keys, but you can find them year-round if conditions are right.

Snook: These ambush predators love to hang around mangrove shorelines and bridge pilings. Known for their acrobatic jumps and hard-charging runs, snook put up a great fight on light tackle. They're most active in the warmer months, with the bite really heating up as they prepare to spawn in the summer.

Tarpon: The "silver king" is the ultimate gamefish for many anglers. These prehistoric beasts can top 150 pounds and are famous for their gill-rattling jumps and endurance-testing fights. While the big migratory tarpon show up in spring and early summer, resident fish can be found year-round in the backcountry.

Why Anglers Keep Coming Back

Islamorada isn't called the "Sportfishing Capital of the World" for nothing. The variety of species and fishing opportunities here is hard to beat anywhere else. One minute you're sight-casting to a tailing bonefish, the next you're battling a tarpon that's trying to jump into the next zip code. Captain Bill's years of experience mean you're not just fishing, you're getting an education in the local ecosystem and the habits of these incredible gamefish. Plus, with all the gear provided and the flexibility to adapt to conditions and your skill level, it's a hassle-free way to experience some of the best inshore fishing the Keys have to offer.

Time to Book Your Spot

If you're itching to bend a rod and feel that heart-pounding rush of a big fish on the line, don't wait to book this trip. Half-days fill up fast, especially during peak seasons. Whether you're looking to check a species off your bucket list, improve your casting game, or just enjoy a morning on the water with a chance at some world-class fishing, Captain Bill's got you covered. Remember, the boat's limited to 3 anglers, so you'll get plenty of personalized attention and shots at fish. Grab your hat and sunscreen, and let's hit the flats – those fish aren't going to catch themselves!

Learn more about the species

Bonefish

Bonefish are the ghosts of the flats, usually 3-5 pounds but can reach 10-plus. You'll find them tailing in skinny water, often just inches deep. They feed with the tides, so time your trip right. Spring and fall are prime seasons here. Bones are lightning fast - hook one and it'll rip off 100 yards of line before you can blink. Sight fishing for them is addictive. Use a light spinning rod or an 8-weight fly setup. For flies, small shrimp patterns like Gotchas work great. When you spot a fish, lead it by a few feet and let the fly sink. Give it a small twitch as the bone approaches. Remember, they spook easily, so make your first cast count. A stealthy approach is key - sometimes I'll even get out and wade to avoid boat noise.

Permit

Permit are the holy grail of flats fishing. These silvery, disc-shaped fish usually run 15-30 pounds but can top 50. You'll find them tailing on shallow flats, often in just a foot or two of water. Spring and fall are best as they move in to feed on crabs. Permit are incredibly wary - spotting and stalking them is half the challenge. When you do hook one, they'll peel off 100 yards of line in seconds. For the best shot, use a small crab pattern fly or a live crab. Make a long, accurate cast well ahead of the fish. Let it sit until the permit gets close, then give it a twitch. Be ready for an incredibly hard fight if you manage to hook up. Just remember, a bad cast will spook them instantly, so take your time and wait for the right shot.

Snook

Snook are sleek predators that can reach 4-5 feet, but most run 1-2 feet. You'll find them around mangroves, docks, and other structure in shallow coastal waters. They love ambushing prey, so look for them lurking in shadows. Spring and fall are prime seasons as water temps change. Snook put up an incredible fight - they'll make blistering runs and leap clear out of the water. Their meat is prized, but most anglers practice catch and release to protect the fishery. When targeting snook, I like using live bait like pinfish or mullet rigged on a circle hook. Cast it right up against the mangroves and be ready for an explosive strike. Just be careful - snook are masters at cutting you off on structure.

Tarpon

Tarpon are the silver kings of the flats, growing up to 8 feet and 280 pounds. Most run 80-100 pounds though. You'll find them in shallow coastal waters, rolling on the surface. Spring and summer are prime, especially around the full moon. Tarpon give you the fight of your life - they'll jump 10 feet in the air and make blistering runs. It's all catch and release, so enjoy the battle. When you see a school of tarpon, lead them with your cast. Strip fast to trigger a strike. Use heavy tackle - at least a 10-weight fly rod or 30-pound spinning gear. Once hooked up, bow to the king when he jumps to avoid breaking off. Just remember, tarpon have bony mouths, so it takes practice to get a good hook set.

About the Billfish

Vehicle Guest Capacity: 3

Manufacturer Name: Yamaha

Maximum Cruising Speed: 35

Number of Engines: 1

Horsepower per Engine: 115

Hop aboard for a laid-back half-day fishing adventure in beautiful Islamorada. Captain Bill knows these waters like the back of his hand and will put you on the hottest spots for bonefish, permit, and other prized catches. His roomy boat has everything you need for a comfortable day out, including quality rods and reels. Whether you're new to fishing or have years of experience, the captain tailors the trip to your level. Soak in the views of the open sea between casts as you try your luck at landing the big one. With space for up to 3 guests, it's perfect for a small group outing. Just remember, deposits can't be refunded - so lock in your date and get ready for some serious Florida Keys fishing action.

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