Damn Good Flounder Fishing Charters In Chesapeake Bay

Check real-time availability and compare rates on Chesapeake Bay flounder fishing trips. Confidently book your next day on the water.

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Recently Booked Flounder 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
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore Fishing in Norfolk

Virginia Inshore Trips

100% (1)
28 ft 1 - 6 People From $750
Fishing in Destin
Fishing in Destin
Fishing in Destin

Nearshore Fishing in Virginia Beach

Cobia Fishing Charter

75% (4)
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 Annapolis

Annapolis Fishing Trips

80% (5)
46 ft 1 - 30 People From $650

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

Other Captain Experiences Trips 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
Hot Trip
people are viewing this trip.
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore Fishing in Rock Hall

Chesapeake Half-Day Rockfish Trip

100% (14)
46 ft 1 - 18 People From $840
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
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore Fishing in Stevensville

Full Day Trip

100% (3)
32 ft 1 - 6 People From $540
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Nearshore Fishing in Wanchese

6-8 Hour Fishing Trip

100% (4)
30 ft 1 - 6 People From $850
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
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore Fishing in Deale

Half Day (6 Hours)

100% (2)
46 ft 1 - 17 People From $750
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 Deale

Spring Catfish Trip

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

Inshore, Nearshore, River in Rock Hall

1/2 Day Trip – Rockfish Season

100% (1)
35 ft 1 - 10 People From $700
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Nearshore, River in Oxford

Chesapeake Bay Fishing Adventure

NEW
40 ft 1 - 6 People From $750
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore Fishing in Middle River

4-8 Hour Inshore Trip

NEW
30 ft 1 - 6 People From $425

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 Chesapeake Bay flounder fishing charter

What are the best flounder fishing charters in Chesapeake Bay?

The best flounder fishing charters in Chesapeake Bay are:

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

Our Damn Good Guides currently offer 4 flounder trips in Chesapeake Bay, and the most popular trips in the area are Chesapeake Bay Half & 3/4 Day Trips guided by John, Virginia Inshore Trips guided by Damani, and Cobia Fishing Charter guided by Kaleb.

Our guides in Chesapeake Bay are rated a 4.14 out of 5 based on 9584 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 flounder guides / fishing lessons in Chesapeake Bay? Check out our beginner and family friendly flounder guides in Chesapeake Bay.

What types of flounder fishing charters are common in Chesapeake Bay?

Inshore fishing is the most popular type of fishing for flounder in Chesapeake Bay as well as nearshore fishing.

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

How much do Chesapeake Bay flounder fishing charters cost?

Prices for flounder in Chesapeake Bay can range anywhere from about $884 to $2,905, but the average price for a half day trip for flounder in Chesapeake Bay is $1,503. The average price for a full day trip for flounder in Chesapeake Bay is $1,881.

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 flounder fishing in Chesapeake Bay?

The most popular season for flounder fishing in Chesapeake Bay is summer, and most anglers book their trips 25 days in advance.

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

See here for more information on flounder fishing licenses in Chesapeake Bay, flounder bag limits, and fishing season regulations for flounder in Chesapeake Bay. When in doubt, your guide will always know all the relevant flounder rules and regulations in Chesapeake Bay.

Recent Reviews

  • ★★★★★
    We had a great time with Captain Damani! He made sure we were comfortable, had fun and we had a big haul of Spanish Mackeral! First mate Frank was great too! He was knowledgeable and so helpful! We can’t wait to do this again!

    Kim B. | August 30, 2026

    Trip: Virginia Inshore Trips

  • ★★★★★
    Great boat and great first mate!

    Mike S. | August 29, 2026

    Trip: Annapolis Fishing Trips

  • ★★★★★
    What a personable and knowledgeable man Kaleb is. Everything was clean and smooth running. We will be hoping to go to sea with him in the future. 5 of 5 really.

    Gwendolyn J. | August 23, 2026

    Trip: Cobia Fishing Charter

  • ★★★★★
    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: October 22, 2026

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