Chesapeake Bay Inshore Trip

NEW Deale, MD 1 - 6 People 4 - 8 Hours From $595 Trip #10406
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin

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.

Climb aboard with Captain Thomas for a Chesapeake Bay fishing trip that blends family-friendly fun with generations of local expertise. Based out of a private dock in Shady Side, Maryland, this hands-on experience is perfect for anglers of all ages—and a great way to create lasting memories with your crew on one of the East Coast’s most iconic fisheries.

Captain Thomas is a fifth-generation waterman who grew up fishing these exact waters, and he brings...

About Your Trip

Climb aboard with Captain Thomas for a Chesapeake Bay fishing trip that blends family-friendly fun with generations of local expertise. Based out of a private dock in Shady Side, Maryland, this hands-on experience is perfect for anglers of all ages—and a great way to create lasting memories with your crew on one of the East Coast’s most iconic fisheries.

Captain Thomas is a fifth-generation waterman who grew up fishing these exact waters, and he brings a deep knowledge of the Chesapeake Bay to every trip. Whether you're an experienced angler or bringing the kids out for their very first catch, Capt. Tom will tailor the day to suit your group’s skill level and goals.

You’ll fish aboard a clean, well-equipped 42’ Provincial powered by a reliable 450 HP diesel engine. This boat is outfitted with top-of-the-line gear from trusted brands like Shimano, Okuma, and Penn, along with a live bait well (often full and ready when you arrive), a Fishfinder to help locate schools, an ice box to keep your catch fresh, and a clean onboard toilet for added comfort during longer outings. There’s room for up to six passengers, making this a perfect choice for families or small groups.

Offering half-day, 3/4-day, or full-day trips, you’ll target seasonal favorites like Striped Bass (Rockfish), Bluefish, Spanish Mackerel, White Perch, and more. Depending on conditions and time of year, Captain Thomas may use light tackle, trolling, jigging, or drift fishing to get the rods bending. His specialty is light tackle fishing, and he’s always happy to walk you through the techniques and help you get the most out of your time on the water.

All trips include everything you need for a successful outing: rods, reels, tackle, lures, live bait, fishing licenses, and even fish cleaning at the end of the day. A friendly and experienced first mate will be onboard to assist throughout your trip—15–20% gratuity is customary and appreciated for their hard work.

Just bring your favorite snacks and drinks, and Captain Thomas will take care of the rest. Whether you're chasing your first Rockfish or simply looking to spend a day on the water with friends and family, this Chesapeake Bay trip is all about enjoying the experience, learning a few tricks from a true local, and taking home fresh fish—and even better stories.
Amenities

Water Type

Inshore

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.

Flexible Cancelation

This trip can be canceled up to 14 days before the trip.

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
$595.00
$750.00
$850.00
2 People
$595.00
$750.00
$850.00
3 People
$595.00
$750.00
$850.00
4 People
$595.00
$750.00
$850.00
5 People
$595.00
$750.00
$850.00
6 People
$595.00
$750.00
$850.00
Pay 15% of the price as a deposit today, with the balance due on the day of the trip.
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About Your Guide

Thomas H.

Independent Guide
Captain Thomas is a 5th generation local fisherman. He has 42 years of fishing experience and previously worked in the commercial fishing industry. He now runs family friendly charters on Chesapeake Bay from April through November.

About Your Guide

Thomas H.

Independent Guide
Captain Thomas is a 5th generation local fisherman. He has 42 years of fishing experience and previously worked in the commercial fishing industry. He now runs family friendly charters on Chesapeake Bay from April through November.
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Start Location & Lodging Options

Deale, Maryland
Areas Fished

About Your Boat

Boat photo for Chesapeake Bay Inshore Trip
Boat Type
Pilothouse
Boat Manufacturer
Provincial
Year Built
2004
Boat Length
42'

About Your Boat

Boat Type
Pilothouse
Boat Manufacturer
Provincial
Year Built
2004
Boat Length
42'
Boat Restroom
Yes
Engine Manufacturer
Diesel
Total Horsepower
450
Number of Engines
1
Additional Amenities
Fishfinder, Live Bait Well, Ice Box
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Trip Details & Amenities

Water Type

Inshore

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.

Flexible Cancelation

This trip can be canceled up to 14 days before the trip.

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 »
  • 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

  • Bottom Fishing
  • Light Tackle Fishing

Everything Else to Know

All gear is included, but we also recommend bringing sunglasses, sunscreen, weather-appropriate clothing, and anything else you might want 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 14 days before the trip and receive credit back to your account. Cancelling within 14 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.
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