Tailing Edge Sportfishing 

4.9
(6 reviews)
Recent reports
 20411 Harbor Road, Nanticoke, MD 21840, United States–

Tailing Edge Sportfishing 

Nanticoke, MD, United States
–
24 ft
4
4.9
(6 reviews)

Spend the day with Tailing Edge Sportfishing and see what's biting in Nanticoke!

These waters are known for Striped Bass, Redfish, Speckled Trout, Cobia, Sheepshead, and more – with any luck, it won't take long to hook into some. Depending on the species you’re after, you may find yourself spinning, bottom fishing, or maybe something more specialized in this area. Capt. Jacob also offers fly fishing, but you may need to bring your own fly gear.

Thinking of bringing the whole family? Kids are absolutely welcome! If you don't have a child-sized life vest of your own, be sure to ask if there's one on board. Also remember to bring snacks to ward off any mid-trip fatigue!

Capt. Jacob will bring you aboard a 24' Romarine pilothouse with capacity for 4 passengers. It comes with all the essentials. There's a toilet on board for your convenience. Your captain will provide rods and reels, as well as lures. Live bait is available, but you should ask the captain whether you'll be catching it yourself.

You'll have the help of a First Mate to put you on fish. Mates often work for tips and it's customary to offer them a 10–20% tip.

The charter boat covers your fishing license, so all you have to do is look forward to your trip! Be mindful that some species may have special rules or limited seasons. Simply ask and your captain can tell you more.

It's recommended to bring sunglasses, sunblock (non-spray), and a hat. There will be some drinks on offer, but let the captain know if you wish to bring your own. Alcohol is allowed in moderation, but you should avoid hard liquor as well as glass bottles.

Go ahead and treat yourself to a day on the water with Tailing Edge Sportfishing.

Spend the day with Tailing Edge Sportfishing and see what's biting in Nanticoke!

These waters are known for Striped Bass, Redfish, Speckled Trout, Cobia, Sheepshead, and more – with any luck, it won't take long to hook into some. Depending on the species you’re after, you may find yourself spinning, bottom fishing, or maybe something more specialized in this area. Capt. Jacob also offers fly fishing, but you may need to bring your own fly gear.

Thinking of bringing the whole family? Kids are absolutely welcome! If you don't have a child-sized life vest of your own, be sure to ask if there's one on board. Also remember to bring snacks to ward off any mid-trip fatigue!

Capt. Jacob will bring you aboard a 24' Romarine pilothouse with capacity for 4 passengers. It comes with all the essentials. There's a toilet on board for your convenience. Your captain will provide rods and reels, as well as lures. Live bait is available, but you should ask the captain whether you'll be catching it yourself.

You'll have the help of a First Mate to put you on fish. Mates often work for tips and it's customary to offer them a 10–20% tip.

The charter boat covers your fishing license, so all you have to do is look forward to your trip! Be mindful that some species may have special rules or limited seasons. Simply ask and your captain can tell you more.

It's recommended to bring sunglasses, sunblock (non-spray), and a hat. There will be some drinks on offer, but let the captain know if you wish to bring your own. Alcohol is allowed in moderation, but you should avoid hard liquor as well as glass bottles.

Go ahead and treat yourself to a day on the water with Tailing Edge Sportfishing.

Jacob Michelsen
Captain
Jacob Michelsen
16 years of experience
ID & credentials verified
responds within an hour

Select date to see availability

Trip date:
Group Size:
October 2026
SuMoTuWeThFrSa
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Group Size
2 adults • 0 children
Change
Almost there...
3 Hour Trip – Evening Rockfish
FREE Cancellation 3 days notice
3 hour trip starts at 3:00 PM
Seasonal trip
Sep 1 - Nov 1
Bass (Striped)
Speckled Trout
US $300
Entire boat: up to 4 people
4 Hour Trip
FREE Cancellation 3 days notice
4 hour trip multiple starting times (8:00 AM, 1:00 PM)
Bass (Striped)
Black Drum
Sheepshead
Speckled Trout
+1
US $400
Entire boat: up to 4 people
5 Hour Trip – Red Drum
FREE Cancellation 3 days notice
5 hour trip starts at 3:00 PM
Seasonal trip
May 1 - Sep 15
Redfish
US $550
Entire boat: up to 4 people
8 Hour Trip
FREE Cancellation 3 days notice
8 hour trip starts at 8:00 AM
Bass (Striped)
Redfish
Sheepshead
Speckled Trout
US $800
Entire boat: up to 4 people
8 Hour Trip – Cobia
FREE Cancellation 3 days notice
8 hour trip starts at 8:00 AM
Seasonal trip
Jun 15 - Sep 15
Cobia
Redfish
Sheepshead
US $1,000
Entire boat: up to 4 people

Customer reviews

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Rating

4.9
6 reviews
5.0
Boat & equipment
5.0
Captain & crew
4.8
Fishing Experience

Anglers' gallery (17)

Reviews (6)

  • Richard Kraft
    Richard Kraft
    us
    Florida, US
    Member since 2023
    5.0
    Verified
    New

    Awesome Captain and Mate

    8 Hour Trip on October 10, 2026 • 2 adults

    First time using Fishing Booker. Jacob was one of the best captains i have fished with and i have chartered many trips over the years. i own a boat and am new to the area and wanted to meet a local guide turned out to be a great fit. He is local and very knowledgeable and is not afraid to show you around. My wife was very impressed as well and they helped cater to her!!!! a big plus in my book. We caught our limit of fish for dinner and left them chewing at the end of the day. Not by the capains choice but ours. i highly recommend Tailing Edge Charters

  • Stacey Michelsen
    Stacey Michelsen
    Member since 2026
    5.0

    Red Drum

    5 Hour Trip – Red Drum on August 21, 2026

    If you are looking for an unforgettable experience on the water, I can’t recommend Tailing Edge Sportfishing enough! Jacob is extremely knowledgeable, professional, and is dedicated to making sure his customers have a great experience. He knows the area extremely well, puts safety first, and goes above and beyond to make the trip enjoyable and memorable. If you are looking for an amazing fishing adventure then book your trip today! You won’t be disappointed!!

  • Taylor Kellerman
    Taylor Kellerman
    us
    Connecticut, US
    Member since 2026
    5.0
    Verified
    New

    Great trip!

    3 Hour Trip – Evening Rockfish on October 3, 2026 • 2 adults

    The Captain Jacob and Dakota are fantastic guides! They are highly knowledgeable about the Bay, incredibly patient, and made sure everyone on board was having a good time and catching fish. I 100% recommend booking with Tailing Edge Fishing!

  • Nathan Harper
    Nathan Harper
    Member since 2026
    5.0

    Full Day trip with Captain Jacob

    8 Hour Trip on August 8, 2026

    Thankfully got to reschedule due to weather. Boy was it worth it. Caught 3 sheepshead and 2 red drum. Highly recommend. Beautiful day on the water 10/10

  • Will Goslee
    Will Goslee
    Member since 2026
    5.0

    Fishing with Jacob

    5 Hour Trip – Red Drum on May 16, 2026

    proofs in the pictures….. book the trip

  • Seth Owens
    Seth Owens
    Member since 2026
    4.7

    Fishing with Jacob

    5 Hour Trip – Red Drum on August 21, 2026

Rating

4.9
6 reviews
5.0
Boat & equipment
5.0
Captain & crew
4.8
Fishing Experience

Anglers' gallery (17)

All reviews (6)

Showing 1 – 5 of 6 reviews
Richard Kraft
Richard Kraft
us
Florida, US
Member since 2023
5.0
Verified
New
Awesome Captain and Mate
8 Hour Trip on October 10, 2026 • 2 adults

First time using Fishing Booker. Jacob was one of the best captains i have fished with and i have chartered many trips over the years. i own a boat and am new to the area and wanted to meet a local guide turned out to be a great fit. He is local and very knowledgeable and is not afraid to show you around. My wife was very impressed as well and they helped cater to her!!!! a big plus in my book. We caught our limit of fish for dinner and left them chewing at the end of the day. Not by the capains choice but ours. i highly recommend Tailing Edge Charters

Reported catch:
Striped Bass
Jacob Michelsen
Response from Captain

Thank you for the kind words, Richard! It was a pleasure having you and your wife aboard and sharing a great day of fishing. I’m glad you both felt well taken care of, and I appreciate your recommendation. Looking forward to fishing with you again!

Stacey Michelsen
Stacey Michelsen
Member since 2026
5.0
Red Drum
5 Hour Trip – Red Drum on August 21, 2026

If you are looking for an unforgettable experience on the water, I can’t recommend Tailing Edge Sportfishing enough! Jacob is extremely knowledgeable, professional, and is dedicated to making sure his customers have a great experience. He knows the area extremely well, puts safety first, and goes above and beyond to make the trip enjoyable and memorable. If you are looking for an amazing fishing adventure then book your trip today! You won’t be disappointed!!

Reported catch:
Black Drum
Taylor Kellerman
Taylor Kellerman
us
Connecticut, US
Member since 2026
5.0
Verified
New
Great trip!
3 Hour Trip – Evening Rockfish on October 3, 2026 • 2 adults

The Captain Jacob and Dakota are fantastic guides! They are highly knowledgeable about the Bay, incredibly patient, and made sure everyone on board was having a good time and catching fish. I 100% recommend booking with Tailing Edge Fishing!

Reported catch:
Speckled Trout
Nathan Harper
Nathan Harper
Member since 2026
5.0
Full Day trip with Captain Jacob
8 Hour Trip on August 8, 2026

Thankfully got to reschedule due to weather. Boy was it worth it. Caught 3 sheepshead and 2 red drum. Highly recommend. Beautiful day on the water 10/10

Reported catch:
Sheepshead
Redfish
Will Goslee
Will Goslee
Member since 2026
5.0
Fishing with Jacob
5 Hour Trip – Red Drum on May 16, 2026

proofs in the pictures….. book the trip

Reported catch:
Redfish
Speckled Trout

FAQs about Tailing Edge Sportfishing

Tailing Edge Sportfishing offers the following trips to customers:
  • US $300 per group - 3 Hour Trip – Evening Rockfish (3 hours)
  • US $400 per group - 4 Hour Trip (4 hours)
  • US $400 per group - 4 Hour Trip - 1:00 PM (4 hours)
  • US $550 per group - 5 Hour Trip – Red Drum (5 hours)
  • US $800 per group - 8 Hour Trip (8 hours)
  • US $1,000 per group - 8 Hour Trip – Cobia (8 hours)
When you book a trip with Tailing Edge Sportfishing, you can expect the following amenities onboard:
  • Toilet There is a porta potty available in the cabin
  • GPS
  • Fishfinder
  • Wireless trolling motor
  • Ice box
Trips booked with Tailing Edge Sportfishing include:
  • Rods, reels & tackle
  • Live bait (Live spot is sometimes used)
  • Lures
  • Drinks (Alcohol is permitted in moderation. I will provide waters for everybody on board, but if you would like anything specific, bring it along!)
  • First mate (When booking full day, cobia and often times red drum trips there will be a mate to help assist and make fishing easier for you.)
  • Fishing license (All fishing licenses are included)
Tailing Edge Sportfishing offers the following types of fishing:
  • Inshore fishing
  • Reef fishing
  • Wreck fishing
  • Flats fishing
  • Backcountry fishing
Tailing Edge Sportfishing offers the following fishing techniques:
  • Light tackle
  • Bottom fishing
  • Spinning
  • Fly fishing
Top targeted fish species with Tailing Edge Sportfishing include:
  • Bass (Striped)
  • Black Drum
  • Cobia
  • Redfish
  • Sheepshead
  • Speckled Trout

Your captain

Jacob Michelsen
Jacob Michelsen
Nanticoke, Maryland, United States
2 Fishing Reports
ID & license verified
6 Customer reviews
Typical response within an hour
Member since August 2026
Capt. Jacob Michelsen is your guide to an unforgettable fishing adventure in the waters of Nanticoke, Maryland. Explore these waters teeming with Red Drum, Sheepshead, Rock fish, Speckled Trout and Cobia under Jacob’s expert guidance. The only way to learn is to join them on the water.
Our Team
Jacob M.
Jacob M.
Captain
Jacob Michelsen
Jacob Michelsen
Fully verified
2
reports
6
reviews
2026
member since
~1h
response
Capt. Jacob Michelsen is your guide to an unforgettable fishing adventure in the waters of Nanticoke, Maryland. Explore these waters teeming with Red Drum, Sheepshead, Rock fish, Speckled Trout and Cobia under Jacob’s expert guidance. The only way to learn is to join them on the water.
The crew
Jacob M.
Jacob M.
Captain

The fish you can target

Striped Bass
Striped Bass
Black Drum
Black Drum
Cobia
Cobia
Redfish
Redfish
Sheepshead
Sheepshead
Speckled Trout
Speckled Trout
Striped Bass
Striped Bass
Black Drum
Black Drum
Cobia
Cobia
Redfish
Redfish
Sheepshead
Sheepshead

Real catches by this captain

  • Awesome Captain and Mate
    Richard K.
    Richard K.
  • Great trip!
    Taylor K.
    Taylor K.

What is the boat like?

Boat image
Boat category
Cabin cruisers
Capacity
4 persons
Boat length
24 ft
Year built
1991
Restored in
2026
Boat manufacturer
Romarine
Boat type
Pilothouse
Engine model
Suzuki
Powered by
1 x 225HP
Max cruising speed
40 knots

What kind of fishing will you do?

Inshore Fishing
Reef Fishing
Wreck Fishing
Flats Fishing
Backcountry Fishing

Which fishing techniques you can try

Light Tackle
Bottom Fishing
Spinning
Fly Fishing

Which amenities are available onboard

Toilet
There is a porta potty available in the cabin
GPS
Fishfinder
Wireless trolling motor
Ice box
What's included in the trip price
Rods, reels & tackle
Live bait
Live spot is sometimes used
Lures
Drinks
Alcohol is permitted in moderation. I will provide waters for everybody on board, but if you would like anything specific, bring it along!
First mate
When booking full day, cobia and often times red drum trips there will be a mate to help assist and make fishing easier for you.
Fishing license
All fishing licenses are included

How cancellations work

Free cancellation up to 3 days prior to trip
You can cancel or modify your booking up to 3 days before the trip date, free of charge. If you cancel or modify your booking later, or fail to show up, you'll forfeit 100% of what you've paid.
More details

What the listing policies are

Pickup not included
Transfer to/from departure site is not included in trip rates.
Child friendly
Children that are 4+ years old are welcome aboard! just make sure to bring all essentials for them
You keep catch
Catch and release allowed

How you can pay

Pay online in full
Pay online in full through FishingBooker and save on credit card fees at the dock.
No additional fees.
Book with 15% deposit, pay rest to captain
When the captain confirms your trip, FishingBooker charges your credit card a 15% deposit to guarantee your reservation.
The remaining balance is to be paid directly to the charter operator on or prior to your trip date in one of the following payment methods:
 Cash
 Visa
 Mastercard
 American Express
When paying the remaining balance with a credit card, an additional 3.5% charge will apply.

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