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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

Inshore, Nearshore

Skill Levels

Beginner, Intermediate, Advanced

Weather

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

About Your Trip

Join Captain Rob for an unforgettable fishing adventure around the beautiful waters of Key West, where endless mangrove islands, shallow backcountry flats, and winding channels create one of the most unique fisheries in the world. This trip is the perfect way to experience the natural beauty and incredible wildlife that make the Florida Keys such a legendary fishing destination.

Depending on your trip length, you can choose between a half-day or full-day charter, both offering excellent opportunities to explore productive backcountry waters aboard a 24-foot Yellowfin Bay Boat. This versatile platform allows access to shallow, fish-rich areas where larger boats simply cannot go, giving you a true edge when targeting local species.

The backcountry of Key West is home to an exciting mix of game fish, and every trip offers something different depending on conditions and time of year. Anglers may have the chance to target Tarpon, Sharks, Barracuda, Jacks, Permit, Grey Snapper, and other local species. From powerful surface strikes to hard-fighting runs in shallow water, the action in these waters is always engaging and unpredictable.

Captain Rob brings over 33 years of experience in the Keys, along with a deep knowledge of the tides, structures, and seasonal patterns that drive this fishery. His expertise helps ensure that each trip is tailored to current conditions, giving you the best possible shot at success while enjoying a relaxed and fun day on the water.

In addition to the fishing, this trip offers an incredible opportunity to see the natural beauty of the mangrove islands and the wildlife that thrives throughout the backcountry ecosystem. Dolphins, birds, and other marine life are commonly spotted along the way, adding even more excitement to your experience.

Whether you're a seasoned angler or new to saltwater fishing, Captain Rob is ready to show you the best of Key West on a trip filled with adventure, scenery, and memorable catches.

Amenities

Water Type

Inshore, Nearshore

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.

Music

You can play your own bluetooth music.

Live Bait

Live bait is included for this trip.

Location

This guide can be flexible with the departure location.

Weather

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

Flexible Cancelation

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

Physicality

This trip requires an average level of physical activity.

Boat Restroom

No, this boat does not have a bathroom on board.

Kid Friendly

This trip is not suited for small children.

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	$700.00	$850.00	$1,000.00
2 People	$700.00	$850.00	$1,000.00
3 People	$700.00	$850.00	$1,000.00
4 People	$700.00	$850.00	$1,000.00
5 People (two boats)	$1,400.00	$1,700.00	$2,000.00
6 People (two boats)	$1,400.00	$1,700.00	$2,000.00
7 People (two boats)	$1,400.00	$1,700.00	$2,000.00
8 People (two boats)	$1,400.00	$1,700.00	$2,000.00

Pay $500 as a deposit today, with the balance due on the day of the trip.

About Your Guide

Rob D.

Independent Guide

Talkative

Instructional

Beginner Oriented

Laid-back

Adventurous

Quality

Capt. Rob has over 30 years of fishing and boating experience. His father Ralph was a champion tournament angler, and he passed his passion and experience down to Rob. Captain Rob holds a few IGFA World Record. The top IGFA World Record is for a 38lbs, 12oz King Mackerel on 4lbs. test line! The angler's name was Jerry Mathews. If you're looking for an awesome charter fishing experience in Key West, book a trip with...

About Your Guide

Rob D.

Independent Guide

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Rapid Fire Guide Q & A

What’s the biggest fish you’ve caught?

1154lbs Bluefin Tuna on stand up tackle.

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

Snapper and Grouper

Rapid Fire Guide Q & A

What’s the biggest fish you’ve caught?

1154lbs Bluefin Tuna on stand up tackle.

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

Snapper and Grouper

What’s your favorite band?

Scorpion

What’s your favorite movie?

StarWars series

What’s your favorite sports team?

UFC

What’s your drink of choice?

Monster Zero Ultra

What was your last halloween costume?

Unicorn security guard

What do you want for Christmas this year?

Another Year!!!

How did you get started guiding?

Father

What makes you different from other guides?

We take pride in keeping our boat in the best shape.

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Start Location & Lodging Options

Your guide can be flexible with your start location.

You can work with your guide after booking to set a more specific start location in the area.

Key West, Florida

Areas Fished

About Your Boat

Boat photo for Second Generation Bay Boat

1/3

Boat Type: Bay Boat
Boat Manufacturer: Yellowfin
Year Built: 2013
Boat Length: 24'

About Your Boat

Boat Type: Bay Boat
Boat Manufacturer: Yellowfin
Year Built: 2013
Boat Length: 24'
Boat Restroom: No
Engine Manufacturer: Yamaha
Total Horsepower: 300
Number of Engines: 1
Additional Amenities: Trolling motor, power poles, Live well

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Trip Details & Amenities

Water Type

Inshore, Nearshore

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.

Music

You can play your own bluetooth music.

Live Bait

Live bait is included for this trip.

Location

This guide can be flexible with the departure location.

Weather

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

Flexible Cancelation

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

Physicality

This trip requires an average level of physical activity.

Boat Restroom

No, this boat does not have a bathroom on board.

Kid Friendly

This trip is not suited for small children.

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 Key West 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

We have the ice and a cooler... just bring what you would like to eat and drink on your 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.

Reviews

4.9

based on 7 reviews

Kip

Verified Review

May 30

Everything about our trip was outstanding! The boat, the Captian, Captain Carlson was fantastic. He wanted fish for every one of us on the boat even more than we wanted to catch! He worked so hard to load the boat and that we did!!! One of the best charters I have even been one. We all can’t wait to come back again and do it all over again!

Kip

Verified Review

May 30

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Trip: Dry Tortugas Fishing Trip

Robert

Verified Review

May 19

Second Generation fisherman Rob was absolutely the best. He knew where to go close to the Harbor to put us on the fish. Highly recommended.

Robert

Verified Review

May 19

Second Generation fisherman Rob was absolutely the best. He knew where to go close to the Harbor to put us on the fish. Highly recommended.

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Jim

Verified Review

June 11

Captain Mason really did his best to put us on the fish. We came late on the season for Tarpon which unfortunately migrated early this year. We still got some great hits and the blacktip shark gave me the pull and dance around the boat that’s makes sport fishing so addictive. Nothing like feeling the power of these predators. I’d happily go back, but seasonal fishing is always a crapshoot.

Jim

Verified Review

June 11

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Jodie

Verified Review

October 7

The best

Jodie

Verified Review

October 7

The best

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Trip: Dry Tortugas Fishing Trip

Lee

Verified Review

July 5

Lee

Verified Review

July 5

We had an absolutely unforgettable day on the water with Captain Mason! Our family of six—ranging from more "seasoned" to children—was treated to a private fishing excursion that truly exceeded all expectations.

From the moment we stepped on the boat, the Mason made us feel completely at ease. He was incredibly accommodating, making sure each of us was comfortable, engaged, and having a great time. Whether it was adjusting for the kids' needs, helping with baiting hooks, or offering fishing tips to the beginners among us, his patience and positive energy never wavered.

What stood out the most was how safe and inclusive he made the entire experience. Every member of the family felt like part of the crew. He kept a watchful eye on everything while still creating a laid-back, fun atmosphere. We never once felt rushed or out of place—just fully present and enjoying every moment.

He also went above and beyond in every possible way—from extending our time a bit when the fish were biting to showing us local wildlife and secret spots only a seasoned pro would know. It truly felt like a one-of-a-kind adventure curated just for us.

Highly recommend this charter to anyone looking for a fun, family-friendly, and expertly guided day on the water. Can’t wait to book again next time we’re in town!

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Trip: Dry Tortugas Fishing Trip

Blaine

Verified Review

March 19

We had a great time with mason-fun day on the water

Blaine

Verified Review

March 19

We had a great time with mason-fun day on the water

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Trip: Dry Tortugas Fishing Trip

Patrick

Verified Review

May 27

Mason was phenomenal. Easy to talk to, engaging, great at teaching, and fun to be with… we got Mahi-Mahi and an exotic. We had a blast and will go fishing with Mason again soon!!!

Patrick

Verified Review

May 27

Mason was phenomenal. Easy to talk to, engaging, great at teaching, and fun to be with… we got Mahi-Mahi and an exotic. We had a blast and will go fishing with Mason again soon!!!

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Trip: Dry Tortugas Fishing Trip

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.