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Against The Wind Fishing 

4.8
(16 reviews)
 467 East Lake Drive, Montauk, NY 11954, United States–
+17
+14

Against The Wind Fishing 

Montauk, NY, United States
–
25 ft
4
4.8
(16 reviews)
Trips & prices
Targeted species
Boat info
What's biting
What's included
Contact captain
Trips & prices
What's included
Targeted species
Boat info
Reviews
Contact captain

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Against The Wind Fishing bids you a warm welcome to Montauk, New York. Come over and explore the inshore waters and their reefs and wrecks and have lots of fun chasing many different species prized both for taste and good fight. Captain Derrick Northcote will see that you have a safe, enjoyable, and successful trip, so join him and have a great time fishing!

The boat you'll use is a 25' Steiger Craft 255 Chesapeake pilothouse with space for 3 guests. It runs on a 225 HP Suzuki DF225 engine, uses full-featured modern technology for navigation and locating fish, and features a portable toilet. Also, there's a livewell to provide live bait, and an ice-box to store your food and drinks.

The species you can target include Black Seabass, Little Tunny, Cod, Flounder, Weakfish, Scup, Tautog, and more. Using light tackle, you'll be bottom fishing, trolling, spinning, jigging, popping, as well as drift fishing. You can keep the fish you catch and you're welcome to bring kids aboard.

All the fishing gear, bait, and licenses will be provided by Captain Derrick. If you wish, he can also clean and fillet your catch at no extra charge. Yours is just to bring your favorite food and drinks.

Visit Against The Wind Fishing and enjoy a lovely day on the water!

Against The Wind Fishing bids you a warm welcome to Montauk, New York. Come over and explore the inshore waters and their reefs and wrecks and have lots of fun chasing many different species prized both for taste and good fight. Captain Derrick Northcote will see that you have a safe, enjoyable, and successful trip, so join him and have a great time fishing!

The boat you'll use is a 25' Steiger Craft 255 Chesapeake pilothouse with space for 3 guests. It runs on a 225 HP Suzuki DF225 engine, uses full-featured modern technology for navigation and locating fish, and features a portable toilet. Also, there's a livewell to provide live bait, and an ice-box to store your food and drinks.

The species you can target include Black Seabass, Little Tunny, Cod, Flounder, Weakfish, Scup, Tautog, and more. Using light tackle, you'll be bottom fishing, trolling, spinning, jigging, popping, as well as drift fishing. You can keep the fish you catch and you're welcome to bring kids aboard.

All the fishing gear, bait, and licenses will be provided by Captain Derrick. If you wish, he can also clean and fillet your catch at no extra charge. Yours is just to bring your favorite food and drinks.

Visit Against The Wind Fishing and enjoy a lovely day on the water!

Derrick Northcote
Captain
Derrick Northcote
11 years of experience
ID & credentials verified
Popular features
Fishing license
Live bait
You keep catch
Catch cleaning & filleting
Toilet
Popular features
Fishing license
Live bait
You keep catch
Catch cleaning & filleting
Toilet

Select date to see availability

Trip date:
Group Size:
October 2026
SuMoTuWeThFrSa
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Group Size
2 adults • 0 children
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Half Day Trip – Inshore
FREE Cancellation 1 day notice
4 hour trip starts at 7:00 AM
Seasonal trip
(Sat, Sun)
US $600
Entire boat: up to 4 people
Half Day Trip – Inshore (PM)
FREE Cancellation 1 day notice
4 hour trip starts at 4:30 PM
Seasonal trip
May 1 - Nov 1
US $700
Entire boat: up to 4 people
5 Hour Trip – Striped Bass
FREE Cancellation 1 day notice
5 hour trip starts at 6:00 PM
US $700
Entire boat: up to 4 people
Full Day Trip – Inshore
FREE Cancellation 1 day notice
8 hour trip starts at 7:00 AM
Seasonal trip
(Sat, Sun)
US $900
Entire boat: up to 4 people

Customer reviews

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Rating

4.8
16 reviews
4.7
Boat & equipment
4.9
Captain & crew
4.8
Fishing Experience

Anglers' gallery (16)

All reviews (16)

Frequently mentioned
Showing 1 – 5 of 16 reviews
Scott Nastahowski
Scott Nastahowski
Repeat angler
us
New York, US
Member since 2024
4 trips
5.0
Verified
great trip!
Half Day Trip – Inshore on June 6, 2026 • 2 adults

got put on to some very nice stripe bass. caught an assortment of fish. will go again!

Daniel Gross
Daniel Gross
us
New York, US
Member since 2024
5.0
Verified
awesome time
Half Day Trip – Inshore on September 7, 2024 • 4 adults

I had a great trip with three friends from college on Captain Derrick’s boat. He was very knowledgeable about where the best Fishing was and showed us all the technique we needed. We brought home a striped bass, black bass and Porgies 10 times out of 10 would recommend and will book with him again in the future.

Reported catch:
Striped Bass
Bluefish (Tailor)
Scup (Porgy)
Black Seabass
Arna Zohlman
Arna Zohlman
us
New York, US
Member since 2024
5.0
Verified
Great trip!
Half Day Trip – Inshore (PM) on August 24, 2024 • 3 adults • 1 child

Captain Derrick was terrific! He was patient with the kids (ages 13 and 11) and did everything he could to help everyone catch some fish! We will definitely be back.

Reported catch:
Bluefish (Tailor)
Black Seabass
Michael Genzano
Michael Genzano
Repeat angler
us
Connecticut, US
Member since 2025
3 trips
4.7
Verified
Night time stripers
5 Hour Trip – Striped Bass on June 7, 2025 • 3 adults

Great night time trip

Reported catch:
Striped Bass
Joseph Schappert
Joseph Schappert
Repeat angler
us
New York, US
Member since 2023
2 trips
5.0
Verified
May fishing trip
Half Day Trip – Inshore (PM) on May 19, 2023 • 1 adult

FAQs about Against The Wind Fishing

Against The Wind Fishing offers the following trips to customers:
  • US $600 per group - Half Day Trip – Inshore (4 hours)
  • US $700 per group - 5 Hour Trip – Striped Bass (5 hours)
  • US $700 per group - Half Day Trip – Inshore (PM) (4 hours)
  • US $900 per group - Full Day Trip – Inshore (8 hours)
When you book a trip with Against The Wind Fishing, you can expect the following amenities onboard:
  • Toilet
  • GPS
  • Fishfinder
  • Live bait well
  • Ice box
  • Radar
Trips booked with Against The Wind Fishing include:
  • Rods, reels & tackle
  • Live bait
  • Lures
  • Catch cleaning & filleting
  • Fishing license
Against The Wind Fishing offers the following types of fishing:
  • Inshore fishing
  • Reef fishing
  • Wreck fishing
Against The Wind Fishing offers the following fishing techniques:
  • Light tackle
  • Bottom fishing
  • Trolling
  • Spinning
  • Jigging
  • Popping
  • Drift fishing
Top targeted fish species with Against The Wind Fishing include:
  • Bass (Striped)
  • Bluefish (Tailor)
  • Cod
  • Flounder
  • Little Tunny (False Albacore)
  • Scup (Porgy)
  • Seabass (Black)
  • Tautog
  • Weakfish

Your captain

Derrick Northcote
Derrick Northcote
Montauk, New York, United States
2 Fishing Reports
ID & license verified
16 Customer reviews
Typical response within 3 hours
Member since July 2021
Captain Derrick was a deckhand/mate for Captain James Joseph for 10 years, a part-time mate/captain for Viking Fleet for 4 years, as well as a mate/captain for Grand Slam Charter boat for 5 years.
Derrick Northcote
Derrick Northcote
Fully verified
2
reports
16
reviews
2021
member since
~3h
response
Captain Derrick was a deckhand/mate for Captain James Joseph for 10 years, a part-time mate/captain for Viking Fleet for 4 years, as well as a mate/captain for Grand Slam Charter boat for 5 years.

The fish you can target

Striped Bass
Striped Bass
Bluefish (Tailor)
Bluefish (Tailor)
Cod
Cod
Flounder
Flounder
Little Tunny (False Albacore)
Little Tunny (False Albacore)
Scup (Porgy)
Scup (Porgy)
Black Seabass
Black Seabass
Tautog
Tautog
Weakfish
Weakfish
Striped Bass
Striped Bass
Bluefish (Tailor)
Bluefish (Tailor)
Cod
Cod
Flounder
Flounder
Little Tunny (False Albacore)
Little Tunny (False Albacore)

Real catches by this captain

  • A selection of freshly caught striped bass laid out on a cleaning table at the dock, with a fishing boat in the background on a foggy morning.
    Fish 1
    Striped Bass
    Michael and his crew had a great afternoon of Striped Bass fishing on diamond jigs, catching their limit and releasing many more up to 40lbs!
  • Angler proudly displaying a striped bass while fishing on a foggy day, showcasing the excitement of a successful catch.
    Fish 1
    Striped Bass
    Michael G.
    Michael G.
    Great night time trip
  • A young angler proudly displaying a large striped bass while seated on a boat, enjoying a sunny day on the water.
    Fish 1
    Striped Bass
    May and June have been excellent for diamond jigging striped bass and bluefish in Montauk!!
  • Angler proudly displaying a large Striped Bass while fishing on a charter boat.
    Fish 1
    Fish 2
    Striped Bass
    Daniel G.
    Daniel G.
    I had a great trip with three friends from college on Captain Derrick’s boat. He was very knowledgeable about where the best Fishing was and showed us all the technique we needed. We brought home a striped bass, black bass and Porgies 10 times out of 10 would recommend and will book with him again in the future.
  • Adult angler holding a striped bass on a center-console boat offshore.
    Fish 1
    Striped Bass
    Joseph S.
    Joseph S.
  • Three anglers proudly displaying their catch of striped bass on a fishing boat at night.
    Fish 1
    Striped Bass
    Lisa P.
    Lisa P.
    Derrick was awesome my 3 sons said and would definitely recommend as well as return for another trip
  • Two adult anglers pose aboard a boat at night while holding a large elongated fish.
    Fish 1
    Fish 2
    +2
    Striped Bass
    Neil G.
    Neil G.
    My father in-law, brother in-law and I caught so many fish we had to start throwing them back. Excellent experience with a knowledgeable captain. Highly recommend.

What is the boat like?

Boat image
Boat category
Cabin cruisers
Capacity
4 persons
Boat length
25 ft
Year built
2006
Boat manufacturer
Steiger Craft
Boat type
Pilothouse
Engine model
Suzuki
Powered by
1 x 225HP
Max cruising speed
30 knots

What kind of fishing will you do?

Inshore Fishing
Reef Fishing
Wreck Fishing

Which fishing techniques you can try

Light Tackle
Bottom Fishing
Trolling
Spinning
Jigging
Popping
Drift Fishing

Which amenities are available onboard

Toilet
GPS
Fishfinder
Live bait well
Ice box
Radar
What's included in the trip price
Rods, reels & tackle
Live bait
Lures
Catch cleaning & filleting
Fishing license

How cancellations work

Free cancellation up to 1 day prior to trip
You can cancel or modify your booking up to 1 day 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 agreed upon reservation
Transfer to/from departure site may be available and included in price depending on your location and distance from the dock.
Child friendly
You keep catch
Catch and release allowed

How you can pay

Book with 20% deposit, pay rest to captain
When the captain confirms your trip, FishingBooker charges your credit card a 20% 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
 PayPal
 Checks

What’s biting in Montauk right now

Bass (Striped)Bass (Striped)
Bluefish (Tailor)Bluefish (Tailor)
CodCod
FlounderFlounder
Little Tunny (False Albacore)Little Tunny (False Albacore)
Scup (Porgy)Scup (Porgy)
Seabass (Black)Seabass (Black)
TautogTautog
WeakfishWeakfish

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Against The Wind Fishing
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