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!



Select date to see available trips and rates:

  • Private trip
    Half Day Trip – Inshore
    FREE Cancellation 1 day notice
    4 Hour Trip, starts at 7:00 AM
    Seasonal trip (Sat, Sun)
    US $600
    Striped Bass fishing around the best part of the tide, and or bottom fishing for Fluke, Seabass, and Porgy.
  • Private trip
    Half Day Trip – Inshore (PM)
    FREE Cancellation 1 day notice
    4 Hour Trip, starts at 4:30 PM
    US $600
    You'll get 4 and a half hours of inshore fishing around the best tide for Striped Bass, as well as all other species in season. The trip starts at 4:30 p.m. and includes all the rods, reels, tackle, bait, as well as fishing licenses.
  • Private trip
    5 Hour Trip – Striped Bass
    FREE Cancellation 1 day notice
    5 Hour Trip, starts at 6:00 PM
    US $700
    Starting at 6:00 p.m., you and the captain will be fishing for Striped Bass at night using live eels. The trip lasts for 5 hours and includes all the fishing gear, live bait, lures, as well as fishing licenses. What you should bring are only your snacks and drinks.
  • Private trip
    Full Day Trip – Inshore
    FREE Cancellation 1 day notice
    8 Hour Trip, starts at 7:00 AM
    Seasonal trip (Sat, Sun)
    US $1,100
    This is an 8-hour trip that will see you fish for all inshore species in season. You and the captain will depart at 7:00 a.m. and he'll take care of all the rods, reels, tackle, live bait, lures, as well as fishing licenses. Just bring some snacks and drinks and your adventure can begin.
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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 $600 per group - Half Day Trip – Inshore (PM) (4 hours)
  • US $700 per group - 5 Hour Trip – Striped Bass (5 hours)
  • US $1,100 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
  • Cod
  • Flounder
  • Little Tunny (False Albacore)
  • Scup (Porgy)
  • Seabass (Black)
  • Tautog
  • Weakfish

Meet the Captain

Derrick Northcote
Montauk, New York, United States
ID & license verified
12 Customer reviews
Response time 5 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.

About this listing

Targeted species

Bass (Striped) Striped Bass
Bluefish Bluefish
Cod Cod
Flounder Flounder

Boat specs

Steiger Craft (Pilothouse) originally built in 2006. Powered by a 225HP Suzuki engine, with a maximum cruising speed of 30 knots.

Length
25 ft
Capacity
4 persons

Types of fishing

Inshore Fishing
Reef Fishing
Wreck Fishing

Fishing techniques

Light Tackle
Bottom Fishing
Trolling
Spinning
Jigging
Popping
Drift Fishing

Amenities

Toilet
GPS
Fishfinder
Live Bait Well
Ice Box
Radar

Trip includes

Rods, reels & tackle
Live Bait
Lures
Catch cleaning & filleting
Fishing License

Cancellation policy

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.

Listing policies

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

Payment

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

Montauk Fishing Calendar

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Customer reviews

Rating summary
Excellent
4.8 / 5
out of 5 stars from 12 reviews
Boat
Excellent
4.6 / 5
Crew
Excellent
4.9 / 5
Experience
Excellent
4.8 / 5
Photos & videos by reviewers (10)
May fishing trip
May fishing trip
My youngest graduation gift
+7
Angler rating
6
2
0
0
0
Anglers claimed
Good experience
100%
Friendly captain
100%
Recommend this charter
67%
Appropriate for children
50%
Satisfied with the boat
100%
Caught fish
100%
Sort by:
Featured  
Showing:
5 of 12 reviews
Joseph S.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

May fishing trip

VERIFIED   Half Day Trip – Inshore (PM) on May 19, 2023
Joseph S. recommends Against The Wind Fishing
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Joseph S. recommends Against The Wind Fishing
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Herve S.
East Hampton, New York
Very good
3.7 / 5
Experience:
Good
3.0 / 5
Boat
Very good
4.0 / 5
Crew
Very good
4.0 / 5
Overall

Fishing with Derrick

VERIFIED   Half Day Trip – Inshore (PM) on July 3, 2023
Herve S. recommends Against The Wind Fishing
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Herve S. recommends Against The Wind Fishing
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Lisa P.
East Meadow, NY
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

My youngest graduation gift

VERIFIED   5 Hour Trip – Striped Bass on July 29, 2022
Derrick was awesome my 3 sons said and would definitely recommend as well as return for another trip
Lisa P. recommends Against The Wind Fishing
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Lisa P. recommends Against The Wind Fishing
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John S.
New York, New York
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Rough day made great

VERIFIED   Half Day Trip – Inshore (PM) on October 16, 2021
CPT Derrick is fantastic. Despite some tough conditions he pulled it out for us. Great guy who was willing to make sure we...
John S. recommends Against The Wind Fishing
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John S. recommends Against The Wind Fishing
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Scott S.
Westfield, NJ
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

October fishing trip

VERIFIED   5 Hour Trip – Striped Bass on October 11, 2022
Scott S. recommends Against The Wind Fishing
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1 person finds this review helpful
You and 1 other person found this review helpful
Scott S. recommends Against The Wind Fishing
Mark review as helpful
1 person finds this review helpful
You and 1 other person found this review helpful