About Your Trip

Water Type

Deep Sea, Nearshore

Skill Levels

Beginner, Intermediate, Advanced

Weather

You won’t lose your deposit if the trip is canceled due to weather.

About Your Trip

Are you ready for your next fishing adventure? Captain Jack and his experienced crew are here to offer a luxurious, fun-filled day on the water, perfect for both passionate anglers and families looking to create lasting memories. With over 30 years of expertise, Captain Jack knows exactly how to guide you toward the catch of your dreams, whether you’re a seasoned pro or just starting out.

Step aboard the 36’ Everglades center console, a state-of-the-art vessel designed for up to six anglers of all skill levels. Powered by triple 350 HP Yamaha engines, this boat is built for both comfort and performance. It features ample seating, an electric reel, expanded live wells, and even a private toilet to ensure a smooth and enjoyable ride. Modern technology such as GPS, radar, fishfinders, and outriggers adds to the excitement, making your trip both productive and thrilling.

Each trip with Captain Jack is a full-day adventure, allowing you the time and flexibility to tailor your experience to your goals. Whether you choose a half-day, 3/4 day, or full-day trip, the possibilities are endless. Target popular species like Mahi Mahi, Red Snapper, Wahoo, and Black Grouper, or go offshore to chase Tuna, Amberjack, and Kingfish. The adventure is yours to shape.

The boat is equipped with all the amenities you need for an incredible day, including a live bait well, tuna tubes, refrigerator, multimedia system, and ice box to keep your catch fresh. Captain Jack takes care of the details, providing fishing licenses, rods, reels, tackle, live bait, and lures, as well as cleaning and filleting your catch so it’s ready to take home. All you need to bring is food, drinks, sun protection, and plenty of enthusiasm. A 20% gratuity for the hardworking First Mate is recommended to show your appreciation.

This is more than just a fishing trip—it’s your chance to level up your skills, catch a trophy fish, and spend quality time with your loved ones. Whether you’re drawn to inshore, offshore, reef, or wreck fishing, Captain Jack and his team are ready to create an experience you’ll never forget. Book your trip today and get ready for the adventure. Welcome aboard!

Amenities

Water Type

Deep Sea, Nearshore

Skill Levels

Beginner, Intermediate, Advanced

Tackle

All rods, reels, and tackle are included.

Fish Cleaning

This guide will clean your catch for you.

Boat Restroom

This boat has a restroom.

Live Bait

Live bait is included for this trip.

Weather

You won’t lose your deposit if the trip is canceled due to weather.

Flexible Cancelation

This trip can be canceled for a refund up to 3 days before the trip.

Beer

No beer allowed.

Kid Friendly

This trip is best for adults.

Disability Friendly

This trip is not suited for those with disabilities.

Lunch

Please provide your own food / snacks.

Scroll for more

Pricing Matrix

	4 Hours	6 Hours	8 Hours
1 Person	$1,100.00	$1,400.00	$1,700.00
2 People	$1,100.00	$1,400.00	$1,700.00
3 People	$1,100.00	$1,400.00	$1,700.00
4 People	$1,100.00	$1,400.00	$1,700.00
5 People	$1,100.00	$1,400.00	$1,700.00
6 People	$1,100.00	$1,400.00	$1,700.00

Pay 15% of the price as a deposit today, with the balance due on the day of the trip.

You're in good hands

Book your trip with confidence — We only work with the best local guides that know where to put you on fish.

Reserve Your Trip

Total

NEW

Select a date to view pricing. The date you selected is no longer available. Please select another date.

Date

Select a group size to view pricing.

Select a duration to view pricing.

Select a start time to check out.

You won't be charged yet

Total

Browse Similar Trips

You're in good hands

Book your trip with confidence — We only work with the best local guides that know where to put you on fish.

About Your Guide

Jack N.

Independent Guide

Quiet

Intense

Instructional

Beginner Oriented

Adventurous

Quality

About Your Guide

Jack N.

Independent Guide

Captain Jack and his experienced friendly Jesse James crew welcome you aboard for a great day on the water in beautiful Islamorada, also known as the Fishing Capital of the World.
Jesse James is a versatile state of the art Everglades 365 vessel comfortably equipped for 6 anglers at all levels. With ample seating, electric reel and expanded live wells, for bait and catch, we can take the hard-core fisherman to a new level. We excel in hands on guidance and instruction to catch Mahi, Wahoo, Sailfish, Tuna, as well as deeper drop (300ft to 600ft) for Vermillion Snapper and Snowy Grouper, as well as, other deep water fish species. Every deep water outing brings the possibility of wrangling a SWORD Fish, Marlin, Sharks, Cobia or other Sport Fish. We are committed to making your Sport Fishing trip as productive as possible, taking into account that adverse weather and No fish in area can limit catch quantity. We troll the Reef and Gulf Stream for the best fishing opportunities each day to target your personalized outing. Jesse James is a powerful luxury ride with a knowledgeable crew making us equally versatile for both sport fishing and/or family charter for the novice angler and occasional cruiser. Captain Jack has 40 years of experience on the Atlantic coastal waters. He likes nothing more than sharing his love of boating and passion for the sport, all making for a memorable day and guaranteed bucket list experience!

Scroll for more

Rapid Fire Guide Q & A

What’s the biggest fish you’ve caught?

Swordfish

If you were cooking for all your friends what would you cook?

Fish Scampi with Pasta

Rapid Fire Guide Q & A

What’s the biggest fish you’ve caught?

Swordfish

If you were cooking for all your friends what would you cook?

Fish Scampi with Pasta

What’s your favorite band?

Eclectic

What’s your favorite movie?

Die Hard

What’s your favorite sports team?

Yankees

What’s your drink of choice?

Red wine

What was your last halloween costume?

Clown

What do you want for Christmas this year?

Peace and harmony world wide

How did you get started guiding?

Followed my grandfathers foot steps

What makes you different from other guides?

I respect people and enjoy sharing my knowledge and experience

Scroll for more

Start Location & Lodging Options

Islamorada, Florida

About Your Boat

Boat photo for Islamorada Fishing Adventure

Boat Type: Center Console
Boat Manufacturer: Everglades 365
Year Built: 2016
Boat Length: 36'

About Your Boat

Boat Type: Center Console
Boat Manufacturer: Everglades 365
Year Built: 2016
Boat Length: 36'
Engine Manufacturer: Yamaha F300 4.2L V6
Total Horsepower: 1050
Number of Engines: 3
Additional Amenities: GPS, Fishfinder, Live Bait Well, Refrigerator, Multimedia System, Outriggers, Tuna Tubes, Ice Box, Radar

Scroll for more

Trip Details & Amenities

Water Type

Deep Sea, Nearshore

Skill Levels

Beginner, Intermediate, Advanced

Tackle

All rods, reels, and tackle are included.

Fish Cleaning

This guide will clean your catch for you.

Boat Restroom

This boat has a restroom.

Live Bait

Live bait is included for this trip.

Weather

You won’t lose your deposit if the trip is canceled due to weather.

Flexible Cancelation

This trip can be canceled for a refund up to 3 days before the trip.

Beer

No beer allowed.

Kid Friendly

This trip is best for adults.

Disability Friendly

This trip is not suited for those with disabilities.

Lunch

Please provide your own food / snacks.

Target Species

Color-coded seasonality below is based on .

View Full Species Seasonality Chart »

Get it while it's HOT!
This species is in play.
You might get lucky (as long as things are in-season).
Couldn't tell ya! (no data)

Techniques

Artificial Lure Fishing
Bottom Fishing
Heavy Tackle Fishing
Jigging
Light Tackle Fishing
Live Bait Fishing
Trolling

Everything Else to Know

All rods, reels, and tackle are included, but we also recommend bringing sunglasses, sunscreen, weather-appropriate clothing, and any gear of your own you want to use on the trip.

You're all set! You don't need to buy a license for this trip.

We use a cashless autopay system. We'll send you a boarding pass, and on the day of the trip, your guide will scan your boarding pass to automatically transfer the remaining balance. The only cash needed is to tip your guide (we recommend 20%).

Cancel for free up to 3 days before the trip and receive credit back to your account. Cancelling within 3 of the trip will forfeit your deposit to the guide. Day-of cancellations and no-shows will be charged the full balance of the trip to their card.

In the event of inclement weather you'll be covered by out 100% Weather Guarantee and will not lose your deposit.

Recent Reviews of Captain Experiences

Danyel

Verified Review

Super cool and nice had a great time.

Danyel

Verified Review

Super cool and nice had a great time.

Scroll for more

Trip: In or Near Shore Experience

James

Verified Review

EXCELLENT!!!Will be booking again!

James

Verified Review

EXCELLENT!!!Will be booking again!

Scroll for more

Trip: Ledges and Reef Run

Ali

Verified Review

Fun, educational and exactly what we were looking for! Highlight of our vacation.

Ali

Verified Review

Fun, educational and exactly what we were looking for! Highlight of our vacation.

Scroll for more

Trip: Inshore Fishing with Kaleb

Jamie

Verified Review

Great trip on short notice

Jamie

Verified Review

Great trip on short notice

Scroll for more

Trip: Gulfbound Glory: Emerald Coast

Randolph

Verified Review

Awesome trip! Great guys, great communication. Will definitely book again.

Randolph

Verified Review

Awesome trip! Great guys, great communication. Will definitely book again.

Scroll for more

Trip: Afternoon Surf Fishing For Sharks

First Time Booking with Us?

Captain Experiences is home to 1,600+ quality, vetted fishing and hunting guides across the US and beyond. Our mission is to Unlock the Outdoors by making it quick and easy to book the trip of a lifetime every time with our Damn Good Guides.

We vet our guides and only partner with the best of the best. Our guides do their very best to keep you safe, show you a great time, and send you home with a memorable experience shared with family and friends.

Once you've paid your deposit at checkout, we'll send you a QR Code boarding pass. Just show your guide your boarding pass on the day of the trip, they'll scan it, the remaining balance will transfer automatically, and you'll be all set to get out there. Just make sure you bring a cash tip for the guide!

In the event of inclement weather, our guides will check the conditions and make the final call on whether its safe to go on the trip. If they decide the trip needs to be postponed, we'll work closely with you to reschedule or provide a credit for the full deposit, which can be applied to any of our trips in the US and beyond.

Each trip's price is determined by the guide and reflects all associated costs. A significant factor in pricing is often the type of boat and the corresponding fuel expenses. Additional costs may include leases, marina or slip fees, bait, and the expenses involved in providing and maintaining the necessary gear for your trip.

After booking your trip, we'll connect you directly with your guide to discuss additional details. In the meantime, our team is here to answer any questions via email, text, or phone.