Chesapeake Bay Fly Fishing Charters
40 Fishing Charters
The best out of 40 charter fishing deals in Chesapeake Bay - enter dates to check availability
- Home
- United States
- Chesapeake Bay
- Fly Fishing in Chesapeake Bay
Top Fly Fishing in Chesapeake Bay
Showing top 10 charters
Prince Frederick
Half Day Trip (AM)




+3
Hop on board the Reel Time and explore Maryland's Chesapeake Bay with Capt. James. He will take you to all the best spots where you will get the most bites using live bait. On this trip, you will target a wide range of beautiful species including, Cobia, Redfish, Striped Bass, Black Drum, Spanish Mackerel and many more. Book a trip today and enjoy a productive day of fishing out on the bay!
Price for up to 4 people
US $540
Gloucester Point
Full Day Trip
An 8-hour trip gives you the chance to explore a range of different fishing grounds in and near the Chesapeake Bay. Head up to 45 minutes offshore and battle it out with monster Cobia and fish the shallow waters nearshore waters to fill the boat with plenty of delicious creatures to take home for a well-deserved dinner. Bottom fish to entice the bite of Flounder, Drum, Spadefish, and many more, before using all your skills to keep them on the line and hooking 'em aboard.
Price for up to 5 people
US $950
Crisfield
8 Hour Trip – Inshore Fishing
Embark on an 8-hour fishing adventure covering the inshore waters of the Chesapeake Bay, Tangier Sound, and Pocomoke Sound. During our extended trips we often encounter and target multiple species. You can expect opportunities at Striped Bass, Speckled Trout, Flounder, Bluefish, Drum, and Spanish Mackerel depending on the time of year and seasonal temperatures. Bring your Lunch or breakfast and hop onboard for a fun filled day on the water. We look forward to spending the day with you.
Price for up to 3 people
US $800
Madison
Half Day Trip (AM)
Enjoy a morning on the water chasing fish. You and Captain Tony will be leaving from either Madison, MD or Cambridge, MD. The captain will take care of all the fishing equipment, licenses, as well as catch cleaning. The trip starts at 5:00 a.m.
Instant Confirmation
Price for up to 5 people
US $600
Chesapeake Beach
Full Day Trip–Cobia, Redfish, Trout




Conditions are sensitive but when the stars come together, Maryland is home to some of the best Cobia fishing on the planet. The crew lives for this time of the year. Here’s a summary of a typical day. Depart at first light and run down the bay at blistering speed till you're in the area. You'll get on the front casting deck waiting for the crew to call out a fish. You cast, work the bait, then BAM! Fish on! That’s what sight fishing for giant Cobia, Redfish, and Trout is all about. Captain's favorite!
Price for up to 4 people
US $1,095
Leonardtown
8 Hour Trip – Red Drum and cobia




Chasing the huge Red Drum , cobia , bluefish, and spanish mackeral. Red drum and cobia are
The hardest fighting fish in the bay. Usually, starting around early July through early September. Max of 5 anglers.
Instant Confirmation
Price for up to 6 people
US $1,000
Annapolis
Redfish/Cobia




+1
We are one of only a few who truly target these fish!
The Bay is home to some of the biggest Cobia in the world! We do not catch small fish on this trip. It’s hardcore fishing & fun!
Here’s a summary of a typical day. Depart at first light and run down the bay at a smooth 40mph. You'll get on the front casting deck waiting for the crew to call out a fish. You cast, work the bait, then BAM! Fish on! That’s what sight fishing for giant Cobia and Redfish is about!
Price for up to 4 people
US $1,095
Pasadena
6 Hour Trip "AM ONLY"



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
Fly Fishing in Chesapeake Bay
Chesapeake Bay
4.8/5