VA Guided Fly Fishing Charters

Guided Fly Fishing Trips | Options & Rates

There are essentially three different guided fly fishing trips to choose from:
  • Lower Chesapeake Bay and Ocean off Virginia Beach fishing for cobia, red drum, stripers, black drum, blues or spanish mackerel in the Boston Whaler 320 Outrage
  • Inshore/Flats for redfish, speckled trout and stripers in the Triton 220 LTS
  • Adventure: custom trip
Charter Length Bay / Ocean
(BW Outrage 320)
Inshore / Flats
{Triton 220 LTS}
Full Day 8-hour+ $950 $800
¾ day 6-hour $750 $650
½ day 4-hour $650 $550
Dusk or Dawn 3-hour / Optimal Fishing Time $450
Adventure Custom One to multiple days: price agreed upon prior to trip


Spring and summer cobia sight fishing trips usually start at 8:00 am (to allow the sun to get up for sight fishing) and end at 4pm. Trips will start earlier with a long run to the fishing grounds.

Fall (mid-August to mid-September) cobia trips usually start at day break and end at 3:30, as early structure fishing can be very productive.

Spring, fall and winter flats trips are scheduled around optimal fishing times, with tide, current, light, wind and moon phase all contributing to that equation. Full day trips are always available, but frequently tides call for fishing a shorter window when water depth allows for successful fishing. Trip charges are reflective of time on the water.

Capt. Wayne can pick you up at your hotel or meet at the ramp. After booking, there will be plenty of text/talk/email the day(s) before your trip to get those details ironed out.

Cobia fishing: The lower portion of the Chesapeake Bay and near-shore ocean off Virginia Beach is a massive body of water, 17 miles wide in some places with depths over 100 feet. Winds in excess of 10 knots make fly and light tackle casting difficult and winds greater than 15 knots are unfishable. We also need sun to sight fish. East winds usually bring heavy cloud cover over the bay; warm west winds usually bring sun on the bay, even when there are clouds over land.

Capt. Wayne will typically cancel windy or cloudy days. If there are flats opportunities with clouds or winds, he will offer them and you can decide.

Full refunds are provided for weather cancelations. If the day is only partially fishable due to weather, the cost of the day will be reduced according to the hours of the day fished.

Flats fishing: Winds are not as problematic and we can generally find the lee and productive fishing somewhere in Hampton Roads. Having said that, the whole goal is to have a pleasant fun day, so the weather policy is very liberal! If the wind is blowing 15+ knots or if it is raining hard, we can cancel with a full refund.

Chesapeake Bay Fishing charters require a $200 deposit per day made concurrently with the reservation. Deposits can be paid online through our Booking Calendar after you contact us and we set a date. Final payment is due at completion of service and should be paid in cash, check or credit card. The client may cancel the reservation up to 21 days prior to the reserved date and receive a full refund of the deposit.

The deposit may be forfeited, at the captain’s discretion, if the reservation is canceled by the client less than 21 days prior to the reserved date. The captain reserves the right to cancel the reservation anytime due to weather or other unforeseen circumstance; in which case, the client may choose to reserve a new date or receive a full refund of the deposit.

Please consider tipping for a job well done or better yet, please send a check to one of these organizations:

  • Boys and Girls Club of the Peninsula
  • VersAbility Resources, Inc.
  • W&M Tribe Club
  • Arc of Williamsburg


  • “Amber color lens” polarized sun glasses
  • Tackle is provided (both fly and spin) but most anglers like using their own tackle. That’s why you bought it!
  • 10, 11 & 12 wt. rods for cobia and big red drum.
  • WF floating lines with plenty of backing for June-July and floating and 300-450gr sink lines for late summer/fall cobia fishing. We may use both floating and sinking lines in the same trip.
  • 7,8 & 9wt. rods for the redfish, stripers and specks on the flats
  • WF floating or IS lines in spring, summer and fall, fast sinking lines in winter. Bring both floating and sinking line spools if you have them.
  • Rain gear (tops & pants) (better safe than sorry!)
  • A lightweight cap to keep sun out of your eyes.
  • Notify captain before trip of any special accommodations you may require
  • Any medications you may need while on board
  • Sun protection: long sleeve shirt, balaclava, hat with brim
  • Food and beverages. Bring a standard size cooler if you like: there is plenty of room on both boats.
  • Fishing license is provided for all aboard

Whatever you want!

This could be running off-shore to the Virginia Beach windmills for dolphin on fly, trailering to new places when reports come in that fishing is fantastic, or fishing multiple days from a specific port. If you want to explore new areas and you like my Tidewater on the Fly program, let’s discuss it and put a plan in place.

Please note that I am a Virginia captain with reciprocity in Maryland. Outside these states, I am not licensed to offer guide services. Contacting a local guide familiar with the area you are interested in fishing is strongly encouraged.

Boston Whaler: 4
Triton: 3

Cobia arrive in May and usually leave the bay and ocean near Virginia Beach in late September. They are strong fighters and excellent table fare. We only sight fish for cobia. Conventional and fly opportunities are available and can be performed concurrently.

Striped bass: our striped bass fishery is year-round. I concentrate low-light times for stripers in shallow water and sight fish for very large stripers in the spring. Small schoolie stripers are available in the summer and fall months.

Red drum/redfish: also a year-round fishery, our reds vary from small “pups”, “slots and over slots” and massive “drum”. Sight fishing makes up about 50% of our fishing; the other 50% is blind casting structure. Redfishing can be both easy and challenging at times.

Speckled trout: available fall to spring, we usually have lots of small specks in the system each fall, which makes excellent new angler fishing. Trophy specks are available in late fall through early spring. Winter months in Norfolk, Virginia Beach and Chesapeake can be fantastic fishing for trophy fish.

Bluefish: we generally target blues in the summer month; they can be great new angler targets as they will readily eat a fly or small lure.

Spanish mackerel: a late spring, summer and fall fish, Spanish are excellent table fare but can be challenging on fly and caught in large numbers trolling.

Mahi mahi: also called dolphin fish, mahi are available off the coast of Virginia Beach, including the wind mills and nearby buoys.

Spadefish: spadefish are plentiful at the islands of the CBBT. If you are interested in catching spadefish on the fly, TOTF can provide that opportunity.

More Info

There is nothing more satisfying for a fly fishing guide than a new (saltwater) fly angler learning fly casting and fishing skills and catching multiple fish on fly. Catching lots of small fish on fly is a great way to learn fly fishing skills, and summer striper and blues and fall speckled trout and white perch offer these opportunities. If you are a new fly angler and want to learn fly fishing skills, these are great days. If you are a new fly angler, let me know and we will schedule casting instruction and target more typically cooperative species.

I specialize in teaching three types of fly fishing casting:

• New Fly Angler Casting
• Distance blind casting (including hauling and double hauling)
• Power sight casting (distance line shooting with as few false casts as possible)

There are redfish and speckled trout wade fishing opportunities throughout Hampton Roads, including spots in Virginia Beach, Norfolk, Hampton, Newport News and Poquoson. Let me know if you want to wade fish. Depending on the time of year, we can usually make that happen.

As an IGFA captain, I support the mission of the International Game Fish Association, including the focus on sustainable fisheries and the rigorous criteria IGFA applies to the world record application process. Chasing world records can make your fishing experience more fun and rewarding IF you keep it in perspective. Chasing a world record is about the 3 P’s: process, practice and procedures. Obtaining a WR is not about ego, it is affirmation that the work and discipline resulted in a positive result. Chasing a WR defines the day and makes fishing more enjoyable. I encourage you to join and support the IGFA.

There are a number of world records that are “gettable” in tippet class weight, fly length and junior length records. If you have an interest in a world record, let’s talk about it and make a plan.

Cobia fly fishing is one of the most difficult fisheries in the world.

Renown North Carolina fly guide Capt. Brian Horsley admits, “Sight fishing for cobia (on fly) is hard no way around it. It has humbled me.” My guess is more fly anglers have caught permit on fly than cobia on fly. That makes it an exciting challenge for an experienced or aspiring saltwater fly angler. To be successful, being able to see surface cobia and cast 50’ or more to a sighted cobia with three or less false casts are important. Maintaining control of your fly line, feeding fish and strip setting are also necessary skills.

On a typical day, we will sight enough cobia (usually 10-25 and some days many more) to get a fly angler some good shots, but there are days when cobia are not on the surface, are swimming fast in transportation mode, or just won’t cooperate. This fishery can be a lot like permit fishing in the Keys, or tarpon fishing in off-season months. I will do everything I can to get you shots include making long runs, but keep in mind there will be days when there are no viable shots, even for an advanced saltwater fly angler.

A 2017 VIMS study (McGrath & Hilton, Temperature selectivity and movement patterns of speckled trout) concluded that most small speckled trout leave the Chesapeake Bay in late November each year and big speckled trout take the opposite approach, pushing up into the lower Bay and Virginia Beach and Chesapeake river systems, wintering in shallow mud flats in close proximity to deeper holes. These wintertime speckled trout movements provide a truly world-class opportunity to catch Virginia citation and world record size speckled trout. But…these opportunities come with a cost: all the smaller specks that make up those 50-fish autumn days are gone so it can be painfully slow fishing! I compare it to musky fishing: the successful angler is persistent and willing to blind cast for long periods of time to enjoy the short periods when the “bite” is on. During the 2022-23 winter, TOTF clients caught 22 Virginia speckled trout on fly and set two pending IGFA world records but this came with a lot of nothing and some shut out days. My goal is to meet or exceed expectations and I may not have set appropriate expectations in the past.