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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 Trip

Water Type

Deep Sea

Skill Levels

Beginner, Intermediate, Advanced

Weather

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

About Your Trip

Head offshore from Islamorada for a true Florida Keys deep-sea fishing adventure aboard a spacious 39' Contender built to cover water and chase some of the Atlantic's most exciting gamefish.

Depending on the season and conditions, Dylan and the crew may have you hunting Mahi Mahi, Blackfin Tuna, Sailfish, Wahoo, Kingfish, Snapper, Grouper, Amberjack, and other offshore species. The exact game plan changes with the bite, with the crew paying attention to current, water color, temperature breaks, bait, and seasonal fish movements to find productive water.

Throughout the day, you may troll open water, work live baits, jig, or drop down to productive structure depending on what's biting. With more time to cover ground, this trip gives the crew the flexibility to make longer runs and explore different depths when the fish aren't close to home.

You'll fish aboard a 39' Contender powered by triple Yamaha 425s. The boat combines speed and offshore capability with plenty of fishing room, cushioned forward seating, T-top shade, Garmin electronics, multiple livewells, insulated fish boxes, and a console head.

Rods, reels, tackle, bait, fishing licenses, bottled water, and ice are provided. Whether you're looking to put some quality fish in the box or experience the speed and power of a pelagic bite, Dylan and his team will build the day around the conditions and your group's goals.

Amenities

Water Type

Deep Sea

Skill Levels

Beginner, Intermediate, Advanced

Tackle

All rods, reels, and tackle are included.

Fish Cleaning

This guide will clean your catch for you.

Beer

Feel free to enjoy responsibly, but please no glass.

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.

Kid Friendly

This trip can cater to small children.

Flexible Cancelation

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

Disability Friendly

This trip is not suited for those with disabilities.

Lunch

Please provide your own food / snacks.

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Pricing Matrix

	4 hours	6 hours	8 hours
1 Person	$1,300.00	$1,600.00	$1,900.00
2 People	$1,300.00	$1,600.00	$1,900.00
3 People	$1,300.00	$1,600.00	$1,900.00
4 People	$1,300.00	$1,600.00	$1,900.00
5 People	$1,350.00	$1,650.00	$1,950.00
6 People	$1,400.00	$1,700.00	$2,000.00

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

About Your Guide

Dylan M.

Outfitter

About Your Guide

Dylan M.

Outfitter

Captain Dylan and his team invite you to experience the incredible variety of fishing that makes Islamorada one of the most celebrated destinations in the Florida Keys. Alongside Dylan, the team includes Captains Travis and Peter, experienced inshore captains who help cover the backcountry, flats, and surrounding waters of Islamorada.

These guys spend their time fishing the local waters and understand that a successful day starts with being flexible. Tides, currents, bait movement, water color, weather, and the season all play a role in determining where they'll fish and what they'll target. Instead of sticking to the same routine every day, the crew builds each trip around what's happening on the water.

Their trips cover everything from shallow backcountry and Florida Bay fishing to reef fishing and offshore runs into blue water. Depending on the adventure you choose, you might find yourself casting around mangroves for Snook and Tarpon, working the flats for Redfish and Trout, dropping baits over a productive reef for Snapper and Grouper, or heading offshore in search of Mahi Mahi, Tuna, Sailfish, and Wahoo.

The fleet gives Dylan, Travis, and Peter plenty of flexibility. Their 26' Pathfinder is a versatile hybrid bay boat capable of working shallow backcountry water or heading offshore, while the 39' Contender provides the speed, space, and offshore capability needed for serious reef and deep-sea fishing.

Most importantly, Dylan and the crew want the experience to fit the anglers onboard. Whether you're an experienced fisherman looking to chase a specific species, bringing the family out for a fun day, or wetting a line in the Florida Keys for the first time, they'll work to make your time on the water comfortable, engaging, and memorable.

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Start Location & Lodging Options

Islamorada, Florida

Areas Fished

Florida Keys

About Your Boat

Boat photo for Offshore Deep Sea Fishing - 39'

Boat Type: Center Console
Boat Manufacturer: Contender
Year Built: 2023
Boat Length: 39'

About Your Boat

Boat Type: Center Console
Boat Manufacturer: Contender
Year Built: 2023
Boat Length: 39'
Boat Restroom: Yes
Engine Manufacturer: 1,275
Total Horsepower: 1275
Number of Engines: 3
Additional Amenities: Advanced Garmin electronics, multiple livewells, insulated fish boxes, cushioned forward seating, leaning posts, console head, T-top shade

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Trip Details & Amenities

Water Type

Deep Sea

Skill Levels

Beginner, Intermediate, Advanced

Tackle

All rods, reels, and tackle are included.

Fish Cleaning

This guide will clean your catch for you.

Beer

Feel free to enjoy responsibly, but please no glass.

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.

Kid Friendly

This trip can cater to small children.

Flexible Cancelation

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

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 » View Recent Islamorada Fishing Reports »

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

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.

This trip is managed by an outfitter. Dylan will be your point of contact and you will go out with one of their guides.

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.

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First Time Booking with Us?

Captain Experiences is home to thousands of quality, vetted fishing, hunting, and other outdoor sports 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, 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.