Little Sister Charters

Westport, Massachusetts
Book Now Meet Your Guide
Ocean Charter (1/2 to 5 miles out)

About Your Guide

Jason Colby

Independent Guide
Meet Captain Jason—a seasoned angler who spent years making his living with a rod and reel. His experience speaks for itself, including 24 striped bass over 50 pounds and a personal best topping 64 pounds. When it comes to targeting big fish, he knows what it takes.

You’ll fish from a 31’ Contender powered by twin 300 HP Yamahas, equipped with a Minn Kota Spot-Lock system for precise positioning over small, productive pieces of structure—without dropping a traditional anchor or spooking fish. All bait and tackle are provided, though you’re welcome to bring your own favorites.

Whether you’re chasing your first striper or hunting a personal best, Captain Jason offers a knowledgeable, high-confidence day on the water.

About Your Guide

Jason Colby

Independent Guide
Meet Captain Jason—a seasoned angler who spent years making his living with a rod and reel. His experience speaks for itself, including 24 striped bass over 50 pounds and a personal best topping 64 pounds. When it comes to targeting big fish, he knows what it takes.

You’ll fish from a 31’ Contender powered by twin 300 HP Yamahas, equipped with a Minn Kota Spot-Lock system for precise positioning over small, productive pieces of structure—without dropping a traditional anchor or spooking fish. All bait and tackle are provided, though you’re welcome to bring your own favorites.

Whether you’re chasing your first striper or hunting a personal best, Captain Jason offers a knowledgeable, high-confidence day on the water.
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Ocean Charter (1/2 To 5 Miles Out)

NEW Westport, MA 1 - 12 People 5 - 6 Hours From $600
Ocean Charter (1/2 to 5 miles out)
Ocean Charter (1/2 to 5 miles out)
Ocean Charter (1/2 to 5 miles out)
Ocean Charter (1/2 to 5 miles out)
Ocean Charter (1/2 to 5 miles out)
Ocean Charter (1/2 to 5 miles out)
Ocean Charter (1/2 to 5 miles out)
Ocean Charter (1/2 to 5 miles out)
Ocean Charter (1/2 to 5 miles out)
Ocean Charter (1/2 to 5 miles out)
Ocean Charter (1/2 to 5 miles out)
Ocean Charter (1/2 to 5 miles out)
Ocean Charter (1/2 to 5 miles out)
Ocean Charter (1/2 to 5 miles out)
Ocean Charter (1/2 to 5 miles out)
Ocean Charter (1/2 to 5 miles out)

About Your Trip

Water Type

Nearshore

Skill Levels

Beginner, Intermediate, Advanced

Weather

You won’t lose your deposit if the trip is canceled due to weather

I don't carry a mate (I've thrown them all overboard). I don't have a bathroom (but I do have a bucket).

The trip includes bait, tackle, license and fish cutting (except for scup, I don't clean scup!). We mostly catch (a lot of) sea bass, stripers, blues, fluke, tog, scup and flounder, depending on the time of year. Night fishing (striped bass) trips available too!

Please be at least 5 minutes early, the parking is...

About Your Trip

I don't carry a mate (I've thrown them all overboard). I don't have a bathroom (but I do have a bucket).

The trip includes bait, tackle, license and fish cutting (except for scup, I don't clean scup!). We mostly catch (a lot of) sea bass, stripers, blues, fluke, tog, scup and flounder, depending on the time of year. Night fishing (striped bass) trips available too!

Please be at least 5 minutes early, the parking is free but sometimes "confusing". The trip to the fishing is an average of 20-25 minutes. Bring your own food, drink, camera, sunscreen, etc. Hotels nearby as well as a friends Air BnB. Just ask for details if you need them.
Amenities

Water Type

Nearshore

Skill Levels

Beginner, Intermediate, Advanced

Tackle

All rods, reels, and tackle are included.

Fish Cleaning

This guide will clean your catch for you.

Beer

Feel free to enjoy responsibly, but please no glass.

Music

You can play your own bluetooth music.

Weather

You won’t lose your deposit if the trip is canceled due to weather

Kid Friendly

This trip can cater to small children.

Flexible Cancelation

This trip can be canceled up to 7 days before the trip.

Physicality

This trip requires an average level of physical activity.

Boat Restroom

No, this boat does not have a bathroom on board.

Live Bait

Live bait is not used on this trip.

Disability Friendly

This trip is not suited for those with disabilities.

Lunch

Please provide your own food / snacks.

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About Your Boat

Boat photo for Ocean Charter (1/2 To 5 Miles Out)
Boat photo for Ocean Charter (1/2 To 5 Miles Out)
Boat Type
Center Console
Boat Manufacturer
Contender
Year Built
2001
Boat Length
31'

About Your Boat

Boat Type
Center Console
Boat Manufacturer
Contender
Year Built
2001
Boat Length
31'
Boat Restroom
No
Engine Manufacturer
Yamaha
Total Horsepower
600
Number of Engines
2
Additional Amenities
Spotlock!
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Potential Target Species

Color-coded seasonality below is based on .
View Full Species Seasonality Chart »
  • Get it while it's HOT!
  • This species is in play.
  • You might get lucky (as long as things are in-season).
  • Couldn't tell ya! (no data)

Techniques

Bottom Fishing
Drift Fishing
Jigging

Type of Fishing

Nearshore

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Little Sister Charters Photo Gallery

Ocean Charter (1/2 to 5 miles out)
Ocean Charter (1/2 To 5 Miles Out)
March 27th, 2025
Westport, Massachusetts
Ocean Charter (1/2 to 5 miles out)
Ocean Charter (1/2 To 5 Miles Out)
March 28th, 2025
Westport, Massachusetts
Ocean Charter (1/2 to 5 miles out)
Ocean Charter (1/2 To 5 Miles Out)
March 27th, 2025
Westport, Massachusetts
Ocean Charter (1/2 to 5 miles out)
Ocean Charter (1/2 To 5 Miles Out)
March 28th, 2025
Westport, Massachusetts
Ocean Charter (1/2 to 5 miles out)
Ocean Charter (1/2 To 5 Miles Out)
March 27th, 2025
Westport, Massachusetts
Ocean Charter (1/2 to 5 miles out)
Ocean Charter (1/2 To 5 Miles Out)
March 27th, 2025
Westport, Massachusetts
Ocean Charter (1/2 to 5 miles out)
Ocean Charter (1/2 To 5 Miles Out)
March 27th, 2025
Westport, Massachusetts
Ocean Charter (1/2 to 5 miles out)
Ocean Charter (1/2 To 5 Miles Out)
March 27th, 2025
Westport, Massachusetts
Ocean Charter (1/2 to 5 miles out)
Ocean Charter (1/2 To 5 Miles Out)
March 27th, 2025
Westport, Massachusetts
Ocean Charter (1/2 to 5 miles out)
Ocean Charter (1/2 To 5 Miles Out)
March 27th, 2025
Westport, Massachusetts
Ocean Charter (1/2 to 5 miles out)
Ocean Charter (1/2 To 5 Miles Out)
March 27th, 2025
Westport, Massachusetts
Ocean Charter (1/2 to 5 miles out)
Ocean Charter (1/2 To 5 Miles Out)
March 27th, 2025
Westport, Massachusetts
Ocean Charter (1/2 to 5 miles out)
Ocean Charter (1/2 To 5 Miles Out)
March 27th, 2025
Westport, Massachusetts
Ocean Charter (1/2 to 5 miles out)
Ocean Charter (1/2 To 5 Miles Out)
March 27th, 2025
Westport, Massachusetts
Ocean Charter (1/2 to 5 miles out)
Ocean Charter (1/2 To 5 Miles Out)
March 27th, 2025
Westport, Massachusetts
Ocean Charter (1/2 to 5 miles out)
Ocean Charter (1/2 To 5 Miles Out)
March 27th, 2025
Westport, Massachusetts
Book Now