Damn Good Chesapeake Bay Fishing Charters

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

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4.54/5 Average Rating

Recently Booked Fishing Charters In Chesapeake Bay

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
Hot Trip
people are viewing this trip.
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, Flats Fishing in Saluda

Half Day Trip – Backcountry

NEW
26 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 Hampton

Chesapeake Bay Shark Fishing

100% (1)
44 ft 1 - 19 People From $1,000
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

Top Types of Trips in Chesapeake Bay

What makes Captain Experiences Damn Good?

Damn Good Guides

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

Damn Good Guides

Experts Available 24/7

Our US-based team is available 24/7 to help you with any questions or concerns.

Experts Available 24/7

100% Weather Guarantee

We want to keep everyone safe, so if the weather is bad we'll work with you to reschedule at no cost.

100% Weather Guarantee

4.9 / 5 Average Rating

We hand pick our Damn Good Guides, and our network spans across North America and beyond.

4.9 / 5 Average Rating

“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

Top Species for Fishing in Chesapeake Bay

More Fishing Charters In Chesapeake Bay

Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, River Fishing in Crisfield

Delmarva Tidal/Nontidal Fishing

NEW
20 ft 1 - 2 People From $450
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore Fishing in Norfolk

Inshore Fishing Trip

100% (1)
21 ft 1 - 4 People From $600
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

Nearshore Fishing in Virginia Beach

8 Hour Bay Trip

100% (1)
27 ft 1 - 4 People From $1,000
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.
Fishing in Destin
Fishing in Destin
Fishing in Destin

Nearshore Fishing in Virginia Beach

Cobia Fishing Charter

67% (3)
24 ft 1 - 8 People From $650
Hot Trip
people are viewing this trip.
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Nearshore Fishing in Virginia Beach

Virginia Beach Inshore/Nearshore

100% (5)
32 ft 1 - 6 People From $650

Didn't Find What You Were Looking For?

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.

The proof is in the pudding, and we’re incredibly proud of our 4.9 / 5 average review score. Hit the button below to see more trip options:

Everything to Know About Booking a Fishing Charter in Chesapeake Bay

What are the best fishing charters in Chesapeake Bay?

The best fishing charters in Chesapeake Bay are:

Why should I book a fishing charter in Chesapeake Bay with Captain Experiences?

Our Damn Good Guides currently offer 31 trips in Chesapeake Bay, and the most popular trips in the area are Flyfish The Eastern Shore guided by Denny, Full Day Fishing Trip - 40’ Evans guided by Buck, and Half Day Trip – Backcountry guided by Doug.

Our guides in Chesapeake Bay are rated a 4.54 out of 5 based on 8383 verified reviews on Captain Experiences.

All guides on Captain Experiences are vetted by our team. You can access their reviews, click through trip photos, read bios to get to know them, and preview trip details like species, techniques, group sizes, boat specs and more.

Looking for kid friendly charters / fishing lessons in Chesapeake Bay? Check out our beginner and family friendly charters in Chesapeake Bay.

What types of fishing charters are common in Chesapeake Bay?

Inshore fishing is the most popular type of fishing in Chesapeake Bay as well as nearshore fishing, river fishing, and flats fishing.

The most commonly sought after species in Chesapeake Bay are: 1. striped bass, 2. redfish, 3. bluefish, 4. spanish mackerel, and 5. speckled trout.

The most common fishing techniques in Chesapeake Bay are light tackle fishing, bottom fishing, and trolling but live bait fishing and jigging are popular as well.

How much do Chesapeake Bay fishing charters cost?

Prices in Chesapeake Bay can range anywhere from about $651 to $2,538, but the average price for a half day trip in Chesapeake Bay is $1,310. The average price for a full day trip in Chesapeake Bay is $1,667.

Is booking a fishing guide worth the money?

Hiring a guide provides a number of benefits and many choose to book a fishing guide for a combination of experience, local knowledge, convenience, and cost-effectiveness.

Working with experienced fishing guides who know the best local spots and techniques can dramatically increase your odds of a great day. Having someone who is on the water every day and knows the area like the back of their hand is going to give you the best chances of success.

Booking a guide is also more cost effective, especially if you only get out a handful of times per year. When you consider all of the costs you would incur on your own such as the price of a boat, maintenance, insurance, gas, high-quality gear and tackle, repairs, and more, you’ll find that DIY is sometimes not worth the expense.

Even if you’ve got a great setup already in your home waters, booking a guide also provides a great opportunity to experience new techniques, new locations, or even a chance at a new target species to knock off the bucket list.

What month is best for fishing in Chesapeake Bay?

The most popular season for fishing in Chesapeake Bay is summer, and most anglers book their trips 59 days in advance.

Do I need a Chesapeake Bay fishing license and what are the bag limits in Chesapeake Bay?

See here for more information on fishing licenses in Chesapeake Bay, bag limits for target species, and fishing season regulations in Chesapeake Bay. When in doubt, your guide will always know all the relevant rules and regulations 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 trip! My kids enjoyed it.

    Kellie H. | July 1, 2026

    Trip: Virginia Beach Inshore/Nearshore

  • ★★★★★
    Aaron was a great guild!! He was very knowledgeable and knew all the greats spots to fish. We was very personable as well. Next time we’re in the OBX he will be our guy for a fishing trip! Thanks Aaron!!

    Noel H. | July 1, 2026

    Trip: 6-8 Hour Fishing Trip

  • ★★★★★
    Ripped me off!!!

    Michael M. | June 24, 2026

    Trip: Chesapeake Half-Day Rockfish Trip

  • ★★★★★
    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!

    Anna J. | June 21, 2026

    Trip: Cobia Fishing Charter

  • ★★★★★
    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 S. | June 3, 2026

    Trip: Cobia Fishing Charter

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Last updated: July 19, 2026

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