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Against The Wind Fishing
Captain

Against The Wind Fishing

Montauk, United States
10+ reviews
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.

Charter

Rating

4.8
16 reviews
4.7
Boat & Equipment
4.9
Captain & Crew
4.8
Fishing Experience

All reviews (16)

Showing 1 – 5 of 16 reviews
  • Scott Nastahowski
    Scott Nastahowski
    Repeat angler
    us
    New York, US
    •
    Member since 2024
    •
    3 trips
    5.0
    Verified

    great trip!

    Half Day Trip – Inshore • 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 • 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) • 4 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 • 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) • 1 adult

Real catches shared by our community

  • Against The Wind Fishing
    Against The Wind FishingMontauk, NY
    Night time stripers
    Michael G.
    Michael G.
  • Against The Wind Fishing
    Against The Wind FishingMontauk, NY
    awesome time
    Daniel G.
    Daniel G.
  • Against The Wind Fishing
    Against The Wind FishingMontauk, NY
    May fishing trip
    Joseph S.
    Joseph S.
  • Against The Wind Fishing
    Against The Wind FishingMontauk, NY
    My youngest graduation gift
    Lisa P.
    Lisa P.
  • Against The Wind Fishing
    Against The Wind FishingMontauk, NY
    Night Time Bass Fishing with Derrick
    Neil G.
    Neil G.

What's biting with Against The Wind Fishing in Montauk

As some of the crowds die down, the action inshore heats up. This is prime time for another of Montauk's specialities: surf fishing for Stripers. Don't miss the Montauk Surf Classic!

Top catches for September

Fishing reports

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.

Great Striped Bass fishing with diamond

Mar 23, 2026 • Montauk
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!
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Angler proudly displaying a large Striped Bass while fishing on a boat in open water.

Diamond jigging striped bass and bluefis

May 24, 2025 • Montauk
May and June have been excellent for diamond jigging striped bass and bluefish in Montauk!!
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