Damn Good Chesapeake Bay Fishing Charters

Check real-time availability and compare rates on Chesapeake Bay fishing trips. Inshore, Nearshore, Flats, and River trips available.

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5/5 Average Rating

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You will only find quality, vetted guides on Captain Experiences, and we know them all on a first-name basis

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Recently Booked Fishing Charters In Chesapeake Bay

Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Nearshore Fishing in Hampton

Chesapeake Bay Half & 3/4 Day Trips

100% (1)
44 ft 1 - 19 People From $770
Veteran Operated
This trip is managed by a veteran of the US armed forces.
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore Fishing in Rock Hall

Chesapeake Half-Day Rockfish Trip

100% (11)
46 ft 1 - 18 People From $770
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Flats, Eco Tour in Nanticoke

Crabbing And Casting Adventure!

NEW
23 ft 1 - 6 People From $455
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore Fishing in Norfolk

Inshore Fishing Trip

NEW
21 ft 1 - 4 People From $550
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore Fishing in Hampton

Fall Fishing Trip

100% (1)
44 ft 1 - 19 People From $990
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore Fishing in Edgewater

6 Hour Inshore Trip

NEW
32 ft 1 - 6 People From $700

Top Types of Trips in Chesapeake Bay

Top Species for Fishing in Chesapeake Bay

“Our Damn Good Guides go above and beyond, and we’ve handpicked every single one. We’re passionate about the outdoors and look forward to getting you out on the trip of a lifetime, every time.”

Jonathan and Attison   |   Co-founders   |   Austin, Texas

More Fishing Charters In Chesapeake Bay

Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Nearshore, River in Reedville

Full Day Fishing Trip - 40’ Evans

100% (5)
40 ft 1 - 6 People From $883
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Nearshore, River in Rock Hall

1/2 Day Trip – Rockfish Season

NEW
35 ft 1 - 10 People From $700
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore Fishing in Deale

Chesapeake Bay Inshore Trip

NEW
42 ft 1 - 6 People From $595
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore Fishing in Norfolk

Virginia Inshore Trips

NEW
28 ft 1 - 6 People From $650
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore Fishing in Deale

Spring Catfish Trip

NEW
42 ft 1 - 6 People From $700
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Flats Fishing in Oyster

Flyfish The Eastern Shore

NEW
20 ft 1 - 4 People From $600
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Everything to Know About Booking a Fishing Charter in Chesapeake Bay

What are the best fishing charters in Chesapeake Bay?

Overview of Chesapeake Bay

The Chesapeake Bay is a unique fishery that has a diversity of species and environments found nowhere else. People often separate the Bay into the Upper, Middle, and Lower Chesapeake Bay areas but you can divide this even further if you include the rivers and tributaries that feed into it. The Chesapeake Bay is a paradise for anglers with more spots to catch fish than you could ever explore.

Fishing in Chesapeake Bay Overview

Hit the Bay in early summer for black drum, perch, and spot fishing while late Summer into Fall is ideal for cobia, redfish, and even Spanish mackerel. If you love catching monster bull redfish or cobia Chesapeake bay needs to be on your bucket list. The shad run on the Virginia side can be particularly fun in the spring as well. The Chesapeake Bay is a gorgeous and inspiring place to visit that happens to have incredible fishing opportunities.

Trolling for Rockfish in the Bay

While the Chesapeake Bay is home to many species including bluefish, redfish, speckled trout, perch, and fluke, it is the striped bass(in the area commonly called rockfish) that takes the cake as the signature fish of the Bay. It is a state fish of both Maryland and Virginia because of its popularity among anglers for sport and food.

Trolling the Chesapeake Bay for rockfish is a great way for any angler to spend their day. Head out with an umbrella lure in the upper Bay during the May trophy season for your chance to land a beast. October (or Rocktober) is when the main season is firing on all cylinders and the fish go into a feeding frenzy when it starts to get colder. If trolling isn’t for you, rockfish arent too picky - you can fish with spoons as well, and many locals swear by nightcrawlers and bloodworms.

Recent Reviews

  • ★★★★★
    Great time

    Andrew S. | August 31, 2025

    Trip: Virginia Beach Inshore/Nearshore

  • ★★★★★
    We had a great time. The fish were not biting but our captain Muscles tried his hardest to put us on fish. The time of year was just not the best for fishing. We did catch a few nice size Rock fish. You can't beat a day on the water fishing with friends. The crew had good conversation and tried multiple spots to get the fish on hooks. We appreciated the effort and the atmosphere. Thank you Muscles, Scott and Wayne was with us in spirit.

    Solomon R. | October 21, 2024

    Trip: Chesapeake Half-Day Rockfish Trip

  • ★★★★★
    Highly knowledgeable guide and hard working mate. Capt. Buck and Rodney provided top notch guiding and service and, in spite of foul weather, kept us on the bite throughout the day. Highly recommended by a seasoned fisherman.

    William C. | July 31, 2023

    Trip: Full Day Fishing Trip - 40’ Evans

  • ★★★★★
    Captain and mate were really great, the fish was slow for everyone we met today but they never quit. We brought several home.

    Gerald J. | May 13, 2023

    Trip: VA Beach Nearshore Action

Top Targeted Fishing Species in Chesapeake Bay

Most Popular Tour Species in Chesapeake Bay

Top Fishing Techniques in Chesapeake Bay

Top Types of Fishing in Chesapeake Bay

Top Types of Tours in Chesapeake Bay

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Our guides are Damn Good Guides, which means they’re vetted by our team of outdoor experts who know them on a first-name basis. We hand pick each and every one of them, and our network spans all across the US and beyond.

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