About Your Guide

A Certified Damn Good Guide is someone who goes above and beyond to show you an incredible experience on your trip. Guides earn this badge through quality reviews, quick and responsive communication, and low cancellation rates.

Kaleb Underwood

Certified Damn Good Guide

Independent Guide

Talkative

Laid-back

Instructional

Quality

Expert Oriented

Adventurous

Captain Kaleb is a skilled and passionate Virginia Beach fishing guide with a deep love for the water and years of experience chasing local species. Known for his friendly, hands-on approach, Kaleb delivers fun, high-energy trips tailored to anglers of all skill levels—whether you're a seasoned pro or casting a line for the first time.

He specializes in light tackle, sight fishing, bottom fishing, and trolling, targeting Cobia, Drum, Sheepshead, Mackerel, Spadefish, Trophy Striper, and even Bluefin Tuna in the right season. With his sharp instincts and local know-how, Kaleb consistently puts clients on the fish while keeping the vibe relaxed and fun.

From teaching kids the basics to guiding hardcore anglers to their next trophy, Captain Kaleb is all about creating memorable, personalized fishing experiences—every single trip.

About Your Guide

Kaleb Underwood

Certified Damn Good Guide

Independent Guide

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Rapid Fire Guide Q & A

What’s the biggest fish you’ve caught?

To stay relevant to the fish I now chase as a guide, My biggest cobia was an estimated 90+ pound fish. We caught it in the summer of 2021 and it remains the biggest to this day. Since then, I've caught a handful of 60, 70 pound class fish with clients on board!

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

My best friend makes a very simple dish that is blackened cobia over a bed of lemon butter pasta...so good

What’s your favorite band?

I'm really in to some 80s and 90s rock when im on the boat, cant put my finger on one specifically!

What’s your favorite movie?

Interstellar

Rapid Fire Guide Q & A

What’s the biggest fish you’ve caught?

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

My best friend makes a very simple dish that is blackened cobia over a bed of lemon butter pasta...so good

What’s your favorite band?

I'm really in to some 80s and 90s rock when im on the boat, cant put my finger on one specifically!

What’s your favorite movie?

Interstellar

What’s your favorite sports team?

Alabama and THE Dallas Cowboys

What’s your drink of choice?

water, but if I had an alcoholic beverage of choice, it'd be a John Daly!

What was your last halloween costume?

Slinky!

What do you want for Christmas this year?

More fishing gear

How did you get started guiding?

I have been mating since high school on multiple boats. Once I started my career out of college, I took the leap and purchased the boat I use now for trips. Immediately got my 6 pack captains license and here we are!

What makes you different from other guides?

I'm personable when it comes to fishing. I never had anyone close to me growing up who was into fishing like I was. I know how it feels to not really have a good idea on how to target a species, because the fishing community can be very secretive. I pride myself in being able to provide a wealth of knowledge that I've learned over the years to help the client become a better fisherman once they get off my boat. No question is dumb, ask away and I'm happy to provide my expertise. That's what I think separates me from others.

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Nauti Dog Sportfishing Trips

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Damn Good

Certified Damn Good Guides offer 10/10 trips. Guides earn this badge through quality reviews, quick and responsive communication, and low cancellation rates.

Nearshore Fishing in Virginia Beach

Cobia Fishing Charter

67% (3) Guided by Kaleb

24 ft 1 - 8 People From $650

Damn Good

Certified Damn Good Guides offer 10/10 trips. Guides earn this badge through quality reviews, quick and responsive communication, and low cancellation rates.

Nearshore Fishing in Virginia Beach

10 Hour Wreck Trip

67% (3) Guided by Kaleb

24 ft 1 - 8 People From $1,250

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Recent Reviews of Nauti Dog Sportfishing

4.0

based on 3 reviews

Alex

Verified Review

Alex

Verified Review

I like Kaleb, he and his mate were super friendly, but this was a boring disaster of a trip and it was not worth $1000 ($800 plus a mandatory $20% tip) for six hours. We were going for cobia, and even though it grew increasingly obvious that that was not going to happen, we kept at it anyway and did not get a single bite in the entire time. Neither I nor anyone in our group even touched a fishing pole. I know that this is a possible outcome, but I basically paid two guys to fish for me and find nothing. The reason you hire a guide is to ensure that you participate and walk away with something. My fondest memory of the trip was the nap I took as we made the 60 minute trip back to the dock. Kaleb, you’re a nice guy, but you don’t understand your core customers quite yet, and you need to work that. Look at the promised experience posted, with all of those different fish we could have tried for, compare that to what you delivered, and ask yourself if you really earned your fees and tips. None of us even touched a rod and reel. Not once. How is that a $1000 fishing charter? Kaleb has no skin in the game - if he fails and repeatedly makes poor decisions, *you* pay for that risk. Just be aware that's what you are paying for when you book one of these. EDIT: to clarify something, Kaleb did not keep is out "longer" at no additonal charge. We were scheduled to leave at 8, we got there earlier but could not find the boat and had a hard time working the logistics, so we got off a little late, but Kaleb assured us that the clock started when we left and not to sweat it. We disembarked at 8:20AM, and we actually got back almost exactly 6 hours later at 2:25PM. I have a receipt from The Back Deck, where we had lunch afterwards that I closed out at 3:00PM, so I think it was Kaleb's honest intention to stay out longer, and he said that he was going to earlier, it's just that he didn't actually do that, he brought us in when he did. Those are the facts.

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Response from Kaleb:

I'm genuinely sorry the fishing didn't work out the way we all hoped. No one wanted to see you catch fish more than I did, and I worked every option I could think of to make it happen. Unfortunately, that's the reality of fishing—some days the fish simply don't cooperate, despite our best efforts. I made every call possible in an attempt to target another species, but it was just one of those days where nearly every charter boat was given a bad hand. Not just us.
I would like to clarify a couple of points for anyone reading this review. The trip was $800, not $1,000, and I actually kept everyone on the water longer than the scheduled trip at no additional charge because I wanted to give the group every possible opportunity to catch fish.
I understand it's frustrating to come home empty-handed, and I respect that you were disappointed. My goal on every charter is to provide the best experience possible, and while I can guarantee hard work, local knowledge, and giving it everything I've got, I can't guarantee that fish will bite.
I appreciate you giving us the opportunity, and I wish the outcome had been different.

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Anna

Verified Review

Anna

Verified Review

My husband, brother-in-law, and father had an incredible time with Kaleb! I planned the trip as a Father’s Day outing, and they all had an absolute blast. They haven’t stopped talking about it and are already asking when they can book their next trip with him!

Kaleb was personable, accommodating, and communicative from the moment the trip was booked. He made everyone feel comfortable and ensured they had an unforgettable experience on the water. His knowledge, professionalism, and laid-back personality made for the perfect day. If you’re looking for a fun, memorable fishing charter with a captain who truly cares about his guests having a great time, I highly recommend booking with Kaleb. We’ll definitely be back!

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Response from Kaleb:

Thanks, Anna! What a crew, we had a great time with them. Hussein catching his first cobia was a moment I won't soon forget!!

Response from Kaleb:

Thanks, Anna! What a crew, we had a great time with them. Hussein catching his first cobia was a moment I won't soon forget!!

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Ryan

Verified Review

Had the pleasure of having Kaleb as our guide and would highly recommend him. He put my son on to his first few cobia and he had a blast.

Kaleb was friendly, knowledgeable and put in max effort to put us on the fish.

Ryan

Verified Review

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Response from Kaleb:

Thanks, Ryan! Always love to be a part of someones first cobia!!

Response from Kaleb:

Thanks, Ryan! Always love to be a part of someones first cobia!!

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Potential Target Species

Color-coded seasonality below is based on .

View Full Species Seasonality Chart » View Recent Virginia Beach 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

Artificial Lure Fishing

Type of Fishing

Nearshore

Recent Fishing Reports

Early July 2026

Had a great windmill trip sunday, limit of flounder and cobia, with some seabass as well. The cobia are starting to act normal after spawning through the past few weeks, with good catches (5+ fish per day) the past few days. Triggers and flounders are also starting to heat up inshore for us.

Early June 2026

The preseason Cobia bite remains on fire. 10 days left until harvest season opens. We've caught double digit fish for the past few days straight!
Have a seabass trip tomorrow. Bite for them is still great. Flounder have shown up so we should be on a good flounder bite as well