Chesapeake Bay Fly Fishing Charters

The best out of 40 charter fishing deals in Chesapeake Bay - enter dates to check availability

Top Fly Fishing in Chesapeake Bay

Showing top 10 charters

Angler's choice

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54 ft

up to 20

 
Virginia Beach
When it comes down to fishing the mighty Atlantic Ocean, AquaMan Sportfishing knows it all. If you are looking for a fast action trip in the inshore waters, you have found the right place. Enjoy your adventure aboard the "Game On", a 54’ C
Trips from
US $675
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46 ft

up to 17

“Lucky Strike Charters” welcomes all angling enthusiasts to experience the thrill of fishing the Chesapeake Bay and Potomac River! We launch out of a few different marinas through out the season depending where the best fishing locations are.
Trips from
US $750
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30 ft

up to 6

 
Virginia Beach
6hr inshore
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+8
Reel Release offers sport fishing out of Virginia Beach, VA. Their number one goal is customer service, and they promise to provide the best fishing experience possible. Cruising out of Lynnhaven Inlet, Captain Robbie will take you fishing the Chesapeake
Instant Confirmation
Price for up to 6 people
US $900
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53 ft

up to 6

 
Virginia Beach
Top Notch Charters has a new 58’ Sportfisherman built in 2023. The boat is equipped with 3 a/c units, large salon and two large outside raised couches set in the shade. Go in First Class style and comfort aboard the largest charter boat in Virginia
Trips from
US $700
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50 ft

up to 6

 
Cape Charles
Tuna/ Mahi/ Marlin Blue / White
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+3
Join Top Dog Charters and discover just how amazing Virginia fishing can be! The Chesapeake Bay is one the most productive fishing grounds in the country and Captain Neil Lessard knows exactly what to do to get you on the hottest bite. Join him on his cus
Price for up to 6 people
US $2,300
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46 ft

up to 20

Whether you’re looking for a memory-making family vacation, a day with fishing buddies, or a business outing, Hot Pursuit Charter Fishing offers an exceptional angling experience for guests of all ages and skill levels. Located in Edgewater, MD, thi
Instant Confirmation
Trips from
US $600

Angler's choice

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27 ft

up to 6

 
Chesapeake Beach
Spring Trophy Bull Redfish
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Join us April – May 2025 “down south" near Virginia Beach and the Chesapeake Bay Bridge tunnel for some EXCITING BULL REDFISH ACTION. Capt. Giovanni has been fishing the spring migration for years and has some great locations that these migrating fish LOVE. Want to catch a BULL RED on your fly rod…This is the shot!! Trip is 5+ hours Lots of sight fishing and we will be all over the electronics finding fish. We can also have some Giant bluefish and striped bass show up.
Price for up to 2 people
US $995
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28 ft

up to 6

 
Leonardtown
Bottom fishing
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+5
Bottom fishing for anything you can put in the cooler and take home to eat. Can customize trip to meet your expectations and desires.
Instant Confirmation
Price for up to 6 people
US $800

Angler's choice

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30 ft

up to 6

Solo Fly-Fishing Trip
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+3
This is a one angler and guide trip. Great opportunity to “tune up” your casting and fly-fishing skills. You will be the only one fishing and have the boat to yourself. We will be fishing our Hewes 21 Redfisher. It is equipped with Garmin electronics (Hummingbird side scan coming this spring), a 300HP Yamaha and a Motor Guide trolling motor. Rod holders…GOT THEM!!! Room for 8 fly rods plus tons of storage. Bring you own equipment or use all our latest ORVIS rods.
Price for up to 1 person
US $595

Angler's choice

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29 ft

up to 6

6 Hour Trip "AM ONLY"
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The 6-hour trip is the suggested trip for those looking for a complete Chesapeake Bay experience. It allows enough time to catch plenty of fish even if we have to run far to get them. This trip allows you the best bang for your buck especially if you want to target Striped Bass. Note: The trip departure time may vary depending on weather, tides, and sunrise times. Captain will confirm times prior to trip. Fishing techniques depends on season, and fish species that will be targeted.
Instant Confirmation
Price for up to 4 people
US $800

Recent Fly catches in Chesapeake Bay

Stella Charters LLC
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Stella Charters LLC
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Stella Charters LLC
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Stella Charters LLC
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Stella Charters LLC
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Stella Charters LLC
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Fish w/Rock On Charter Fishing!!!
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Mikey’s Guide Service
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Capt. Brian with Thomason Tradition
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Stella Charters LLC
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Fly Fishing in Chesapeake Bay

The Chesapeake Bay is a fishing goldmine for saltwater and freshwater anglers alike. With more than 150 rivers and creeks that flow into the bay, its aquatic habitat gives life to hundreds of amazing species. Its diversity allows for many different types of fishing techniques, but when it comes to fly fishing in the Chesapeake Bay, there’s really nothing else quite like it.

Top Target Species

Fishermen from all over the country visit the Chesapeake Bay to get a cut of the action. Whether you’re going after Spanish Mackerel, Bluefish, Cobia, Redfish, Trout, or Stripers, this area holds some of the hottest fishing grounds for fly fishermen.

Striped Bass

Striped Bass, also locally known as Rockfish, is hands down the most popular species to target on fly. If you’re fly fishing for Stripers in the Chesapeake Bay, you’re working with a pretty good time frame. Striped Bass show up in April and stick around until Thanksgiving. However, when fly fishing for Stripers, you’ll need to switch up your technique, depending on the season and location.

Historically, Stripers have dominated the bay, but their numbers have been dwindling over recent years due to overfishing. Today, the largest schools of Rockfish are over towards the mouth of the Eastern Bay, so your best bet is to visit the Maryland side.

Speckled and Gray Trout

Speckled Trout is a relatively new species to target by fly, but if you’re fishing in shallower parts of the bay, it’s an excellent choice. Weakfish, or Gray Trout, is also a top target.

The bay’s tidal creeks and marshes produce excellent fly fishing conditions for Trout. The best time to target Gray and Speckled Trout is between May and October, especially on the eastern side of the bay, between the Choptank River and Tangier Sound.

Redfish

Chesapeake Bay Redfish are on the rise. Due to conservation efforts from southern states, as well as warming water temperatures, Red Drum’s range has expanded north. Targeting a “Chessie Red” on a fly is extremely challenging and they’re known for being hard fighters. Redfishing in the Chesapeake Bay really starts to heat up around June and begins to taper off in October. July and August will give you the highest likelihood of catching a Bull Red.

Need to Know

Maryland and Virginia saltwater charters are licensed to cover everyone aboard, so you won’t need to purchase one separately. However, anglers 16 and older who plan on fishing alone need to buy a license before fishing.

Many charters provide fly gear, but some require you to bring your own, so check with your captain before heading out. Additionally, you might want to pack extra layers, as well as rain gear and sun protection, depending on the weather.

You’re now one step closer to planning your fly fishing adventure in the Chesapeake Bay. Pick your spot, choose a captain, and get ready to fish one of the most productive estuaries of North America!

Chesapeake Bay

4.8/5
Based on 29,146 reviews by FishingBooker anglers

What anglers said about Fly Fishing in Chesapeake Bay

Don L.
Don L.
Reviewed Chesapeake Bay Afternoon Trip
1/2 day trip with Captain Jeff on upper Chesapeake Bay TUE MAY 16, 2023
5/5
light tackle & fly fishing fun- casting lures & flies - reeling in 100+ Rock fish on an AM charter with Captain Jeff mid May. Been fishing with Jeff every year since the spring of 2001 (20+ years). Jeff works hard, family friendly, patient, attentive, and simply an joy to fish with! Can't wait till my next trip!!
Wendy H.
Wendy H.
Reviewed Half Day Trip – Inshore (AM)
Fishing with Bob
5/5
We had a great experience with Captain Bob for our half day trip. Both the captain and first mate were extremely knowledgeable and friendly, easy to be around. We caught 19 mackerel and saw some dolphins too! Captain was very flexible in moving our trip to the day after it was scheduled due to bad conditions as well. Would highly recommend!
Jeff H.
Jeff H.
Reviewed 3 Hour Bottom Fishing Trip
Great Day on Water
5/5
Chris provided us a great day on the water. We caught plenty of fish and toured the bay. Had great conversations and felt like we have known him for years. Will definitely rebook with Chris for future trips.
Charles B.
Charles B.
Reviewed 2 Hr Ocean Trip AM
2 HOUR MORNING FISH
5/5
Had a great experience. Took 4 young teenage boys...inexpierienced, easily bored, and not super interested. Our captian was very knowledgeable, personable, and made this a trip of a lifetime. All the boys had a great time, caught lots of fish, and seen a lot of dolphin, too. Thanks for a great time. Would highly recommend!
J.J. K.
J.J. K.
Reviewed 4 Hour Trip – Inshore (PM)
Great day on the water!
5/5
Booked a trip for our boys birthday present and it was awesome. Capital Chuck was very accommodating with our 3 boys, none of them had been on an ocean fishing trip before. Both Chuck and mate Conner where great answering all our boys questions and worked hard to get them on the fish. Would highly recommend Captain Chuck!