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Guides > Captain James Grindey

4th Generation Fishing Charters

5 4 reviews Identity VerifiedIdentity Verified

33036 FL

Guidesly Guarantee
Guides > Captain James Grindey

4th Generation Fishing Charters

location33036 FL

Guidesly Guarantee
5 4 reviews

Your Captain

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James Grindey

Identity Verified

James Grindey, Captain at 4th Generation Fishing Charters

4th Generation Fishing Charters, helmed by Captain James Grindey, a fourth generation florida fishing guide. is all about excitement and adventure in the vibrant Florida keys. Prepare yourself for an action packed experience like no other as you delve into the world of light tackle, bottom fishing, drift fishing, heavy tackle, spinning, and deep-sea fishing techniques. 


Captain James Grindey, a true master of the trade, possesses an insatiable passion for the ocean and a profound understanding of the local fish species. With his expertise and unwavering enthusiasm, he guarantees an unforgettable fishing expedition that will leave you breathless with anticipation.


Embark on an inshore fishing adventure, where you'll feel the rush of adrenaline as you chase after elusive flounder, redfish, and snook. Test your skills against the powerful hogfish, snapper, and grouper during reef fishing trips, where the underwater kingdoms come alive with vivid colors and bustling marine life. If you're seeking a thrilling challenge, offshore fishing will take you to the deep waters where trophy-sized king mackerel, bull sharks, and goliath grouper lurk. Brace yourself for an exhilarating battle as you pit your strength against these formidable creatures of the deep. Wreck fishing enthusiasts will have the opportunity to explore sunken treasures, discovering the hidden habitats of gag grouper and other majestic species that call these artificial reefs home. Nearshore fishing ventures will allow you to target a diverse range of species, including the acrobatic tarpon and the prized mangrove snapper.


No matter which fishing experience you choose, rest assured that Captain Grindey has you covered. The charter provides all the necessary amenities to ensure a worry-free trip. Your fishing license, refreshing drinks, high-quality lures, live bait, top-notch rods, reels, and tackle are all included.


What makes 4th Generation Fishing Charters even more extraordinary is its commitment to inclusivity. Families and children are warmly welcomed aboard the 23' Privateer, a sleek center console boat originally built in 2000. Powered by a formidable 150HP Honda engine, this vessel boasts a maximum cruising speed of 34 knots, ensuring you reach the prime fishing spots swiftly and comfortably. Accommodating up to four persons, it is the perfect vessel for an intimate and thrilling fishing adventure.


Prepare yourself for an action-packed journey that will leave you with lifelong memories.

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Upcoming Availability

July 2025
August 2025

Expertise & Attributes

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fishing

fishing

Good with FamiliesGood with FamiliesGood with KidsGood with KidsGood with New AnglersGood with New AnglersLive BaitLive BaitSaltwater FishingSaltwater Fishing

Fishing Techniques

Heavy TackleLight TackleDeep Sea / Bottom FishingDrift Boat Fishing

What's Included

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Keep your Catch

Keep your Catch

This guide offers trips that you are able to take home your catch.

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Good to Knows

Good to Knows

Your Guide has some important details about your trip with them.

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License

License

Read about the licensing details that is / is not covered in the below trips.

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Nature / Wildlife Views

Nature / Wildlife Views

This guide offers trips with nature and wildlife views.

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Cancellation Policy

Cancellation Policy

When you book your fishing trip, you will need to first put down a deposit to hold the reservation.

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What's Included

Keep your Catch

Keep your Catch

This guide offers trips that you are able to take home your catch.

Show More

Good to Knows

Good to Knows

Your Guide has some important details about your trip with them.

Show More

License

License

Read about the licensing details that is / is not covered in the below trips.

Show More

Nature / Wildlife Views

Nature / Wildlife Views

This guide offers trips with nature and wildlife views.

Show More

Cancellation Policy

Cancellation Policy

When you book your fishing trip, you will need to first put down a deposit to hold the reservation.

Show More

Trips Available with 4th Generation Fishing Charters

Islamorada Fishing Charters | 4 Hour
Islamorada Fishing Charters | 4 HourTop-Rated
Islamorada Fishing Charters | 4 HourInstant Booking
Islamorada Fishing Charters | 4 HourFishing - Inshore
Islamorada Fishing Charters | 4 Hour

Privateer23'Privateer (Center console) Max 4 guests (base trip price includes 4 guests)

Islamorada Fishing Charters | 4 Hour

Set off on an unforgettable 4-hour fishing adventure in the stunning waters of Islamorada, where a thrilling angling experience awaits. Target a variety of prized fish species, including the speedy mackerel, the elusive snook, the acrobatic tarpon, the powerful cobia, the spirited redfish, and the tasty snapper. All the essential fishing gear will be provided, allowing you to focus solely on the excitement of reeling in your dream catch. As you cast your line and the thrill builds, don't forget to bring along some snacks and drinks to keep your energy up. Book your trip today!

Morning Trip

Islamorada Fishing Charters | 4 HourMaximum 4 persons allowed
(base trip price includes 4 guests)
Islamorada Fishing Charters | 4 Hour4 Hours
Islamorada Fishing Charters | 4 Hour8:00 AM
$650

Pick Your Date

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Reef Fishing Florida Keys | 2 Hour
Best Price Guarantee
Reef Fishing Florida Keys | 2 HourTop-Rated
Reef Fishing Florida Keys | 2 HourInstant Booking
Reef Fishing Florida Keys | 2 HourFishing - Wrecks

Reef Fishing Florida Keys | 2 Hour

Kickstart an unforgettable fishing adventure in the Florida Keys, where the reefs surrounding Islamorada offer incredible fishing opportunities for anglers of all skill levels! Enjoy a 2-hour offshore fishing charter as we head out to the offshore reefs in search of yellowtail and mutton snapper, grouper, kingfish, and many more exciting species. These charters are the perfect way to dive into the thrilling world of offshore fishing, whether you're a beginner or a seasoned angler. With excellent reef fishing available year-round, you can experience the best of what Islamorada has to offer, no matter the season. We can't wait to share this amazing experience with you, so book your trip today!

Morning Trip

Reef Fishing Florida Keys | 2 HourMaximum 4 persons allowed
(base trip price includes 4 guests)
Reef Fishing Florida Keys | 2 Hour2 Hours
Reef Fishing Florida Keys | 2 Hour7:00 AM
$400

Pick Your Date

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Deep Sea Fishing Islamorada | 6 Hour
Deep Sea Fishing Islamorada | 6 HourTop-Rated
Deep Sea Fishing Islamorada | 6 HourInstant Booking
Deep Sea Fishing Islamorada | 6 HourFishing - Inshore
Deep Sea Fishing Islamorada | 6 Hour

Privateer23'Privateer (Center console) Max 4 guests (base trip price includes 4 guests)

Deep Sea Fishing Islamorada | 6 Hour

Set sail in the crystal-clear waters and get ready for an exhilarating adventure. With a variety of sought-after species, including Goliath Grouper, Red Grouper, King Mackerel, and many more, you're bound to have an action-packed experience. The trip provides high-quality rods, reels, tackle, and fishing licenses, ensuring you have all the necessary gear to reel in your prized catches. As you cast your line, take in the breathtaking views and feel the thrill of the chase. Don't forget to bring your favorite snacks and drinks to keep you energized throughout the day. Book now!

Morning Trip

Deep Sea Fishing Islamorada | 6 HourMaximum 4 persons allowed
(base trip price includes 4 guests)
Deep Sea Fishing Islamorada | 6 Hour6 Hours
Deep Sea Fishing Islamorada | 6 Hour8:00 AM
$900

Pick Your Date

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Vehicle

Privateer

Boat Type:

Boat Guest Capacity:

4

Boat Length:

23 ft

Manufacturer Name:

Privateer (Center console)

Model Year:

2000

Engine Manufacturer Name:

Honda

# of Engines:

1

Horsepower Per Engine:

150

Maximum Cruising Speed:

34

Features: Bait Tank Snorkelling Equipment Flybridge Fish Finder GPS

4th Generation Fishing Charters Privateer (Center console) Boat

The 23' Privateer is a center console boat that was originally built in 2000, offering a classic design and sturdy construction. Powered by a 150HP Honda engine, it boasts a maximum cruising speed of 34 knots, allowing for swift navigation on the water. It has a capacity to carry up to 4 guests.

Boat

4th Generation Fishing Charters Privateer (Center console) Boat image 0

Privateer

Boat Type:

Boat Guest Capacity:

4

Boat Length:

23 ft

Vehicle Details

FAQs about 4th Generation Fishing Charters

Reports and Expert Articles

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A Recap of Successful Fishing In Islamorada

We've got plenty of bait - good-sized shrimp at the marina and catchable pilchards around Islamorada. This time of year, getting bait is easy, making half the battle for a good fishing day already won. Our team fished the ocean side patches on the Atlantic side, small bits of coral reef in shallow waters from 10 to 30 feet. They caught a mix of fish like snappers (mangroves, and muttons), groupers, hogfish, and mackerel. The pilchards worked well for snappers and groupers, while hogfish preferred shrimp. Note that we can't keep hogfish this time of year. In a nutshell, with lots of bait options and a focus on ocean side patches, our anglers had a successful day, showing how different bait can attract different fish. The availability of bait continues to be a big plus for our fishing adventures.

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Fishing day

Guests had an absolute blast as they skillfully reeled in a diverse array of fish during their excursion. With plenty of laughter and thrilling battles, the experience was truly memorable. Join us in the stunning surroundings of Islamorada for your own unforgettable day out on the water.

Ratings & Reviews Summary

5.00
out of 5
Based on 4 ratings
100%
recommended
recommended
Based on 4 recommendations
5
4
4
3
2
1

July 12, 2025

Captain James put us on the fish for non stop action the entire trip! Great guy very friendly and personable. I will be back to fish with him again. šŸ’Æ

July 12, 2025

Capt. James was awesome! Booking was very easy. He was great with our 10 & 12yo boys explaining how to bait, cast & reel in very much a "big brother" like. This was our first fishing trip & fishing charter and we couldn't have asked for a better experience. We will definitely come back.

July 12, 2025

It was an amazing experience. Captain James was fantastic. We booked on very short notice, and he accommodated us without hesitation!

July 12, 2025

He performed exceptionally well in navigating away from adverse weather conditions, consistently catching fish throughout the entire day without pause. His precise knowledge of where to locate the fish proved accurate, and every prediction he made about our catch came to fruition. It was a fantastic experience with an outstanding captain who also happened to be a genuinely pleasant individual.

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