About Your Guide

Kaleb Underwood

Independent Guide
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

Independent Guide
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.
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Virginia Beach Inshore Fishing

NEW 1 - 4 People 6 - 8 Hours From $750
Virginia Beach Inshore Fishing
Virginia Beach Inshore Fishing
Virginia Beach Inshore Fishing
Virginia Beach Inshore Fishing
Virginia Beach Inshore Fishing
Virginia Beach Inshore Fishing
Virginia Beach Inshore Fishing
Virginia Beach Inshore Fishing
Virginia Beach Inshore Fishing
Virginia Beach Inshore Fishing
Virginia Beach Inshore Fishing
Virginia Beach Inshore Fishing
Virginia Beach Inshore Fishing
Virginia Beach Inshore Fishing
Virginia Beach Inshore Fishing
Virginia Beach Inshore Fishing
Virginia Beach Inshore Fishing

About Your Trip

Water Type

Inshore

Skill Levels

Beginner, Intermediate, Advanced

Weather

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

Join Captain Kaleb for a private 6 to 8-hour inshore fishing adventure along the beautiful coastal waters of Virginia Beach—a perfect blend of hands-on action, local expertise, and laid-back fun. Whether you're a first-timer learning the ropes or a seasoned angler chasing your next personal best, Captain Kaleb customizes each trip to match your pace, skill level, and fishing goals.

You'll target a variety of exciting species depending on the season. During the summer, expect...

About Your Trip

Join Captain Kaleb for a private 6 to 8-hour inshore fishing adventure along the beautiful coastal waters of Virginia Beach—a perfect blend of hands-on action, local expertise, and laid-back fun. Whether you're a first-timer learning the ropes or a seasoned angler chasing your next personal best, Captain Kaleb customizes each trip to match your pace, skill level, and fishing goals.

You'll target a variety of exciting species depending on the season. During the summer, expect
to hook into Cobia, Black Drum, Redfish, Spanish Mackerel, Sheepshead, Spadefish, and more using a mix of techniques like sight fishing, trolling, and bottom fishing with both live bait and lures. In the winter months (December through mid-February), the action shifts to chasing Striped Bass, with plenty of opportunities for light tackle thrills and cooler-season strategy.

Your trip will be powered by top-tier gear and guided by a captain and mate who know these waters inside and out. From spotting cruising Cobia on the surface to working structure for Sheepshead and Drum, Captain Kaleb's local knowledge and friendly instruction make it easy to get hooked up, no matter your experience level.

Everything you need is included—rods, reels, tackle, bait, and expert guidance—so all you need to bring is your Virginia fishing license, your favorite snacks and drinks, and a cooler to bring home your catch. The boat is fully equipped for comfort and performance, ensuring a smooth ride and productive day on the water.

Captain Kaleb also specializes in family-friendly trips, making this an excellent option for parents looking to introduce their kids to fishing in a safe, engaging, and exciting environment. Whether it’s a family memory-maker or a hardcore angling mission, you’re in great hands.

Book your Virginia Beach inshore fishing trip today, and let Captain Kaleb show you why these waters are a local favorite and a coastal treasure!
Amenities

Water Type

Inshore

Skill Levels

Beginner, Intermediate, Advanced

Tackle

All rods, reels, and tackle are included.

Beer

Feel free to enjoy responsibly, but please no glass.

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 14 days before the trip.

Fish Cleaning

No cleaning service provided.

Boat Restroom

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

Live Bait

Live bait is not used on this trip.

Disability Friendly

This trip is not suited for those with disabilities.

Lunch

Please provide your own food / snacks.

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About Your Boat

Boat photo for Virginia Beach Inshore Fishing
Boat photo for Virginia Beach Inshore Fishing
Boat Type
Center Console
Boat Manufacturer
Key West
Year Built
2022
Boat Length
24'

About Your Boat

Boat Type
Center Console
Boat Manufacturer
Key West
Year Built
2022
Boat Length
24'
Boat Restroom
No
Engine Manufacturer
Suzuki
Total Horsepower
300
Number of Engines
1
Additional Amenities
Bait Tank, GPS, VHF Radio
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Potential 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

Cut Bait Fishing
Light Tackle Fishing
Trolling

Type of Fishing

Need a Place to Stay?

Nauti Dog Sportfishing Photo Gallery

Virginia Beach Inshore Fishing
October 23rd, 2025
Exmore, Virginia
Virginia Beach Inshore Fishing
October 23rd, 2025
Exmore, Virginia
Virginia Beach Inshore Fishing
October 23rd, 2025
Exmore, Virginia
Virginia Beach Inshore Fishing
October 23rd, 2025
Exmore, Virginia
Virginia Beach Inshore Fishing
October 23rd, 2025
Exmore, Virginia
Virginia Beach Inshore Fishing
October 23rd, 2025
Exmore, Virginia
Virginia Beach Inshore Fishing
October 23rd, 2025
Exmore, Virginia
Virginia Beach Inshore Fishing
October 23rd, 2025
Exmore, Virginia
Virginia Beach Inshore Fishing
October 23rd, 2025
Exmore, Virginia
Virginia Beach Inshore Fishing
October 23rd, 2025
Exmore, Virginia
Virginia Beach Inshore Fishing
October 23rd, 2025
Exmore, Virginia
Virginia Beach Inshore Fishing
October 23rd, 2025
Exmore, Virginia
Virginia Beach Inshore Fishing
October 23rd, 2025
Exmore, Virginia
Virginia Beach Inshore Fishing
October 23rd, 2025
Exmore, Virginia
Virginia Beach Inshore Fishing
October 23rd, 2025
Exmore, Virginia
Virginia Beach Inshore Fishing
October 23rd, 2025
Exmore, Virginia
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