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Little Sister Charters

  • Quincy, Massachusetts 02169
  • Vendor Type: Charters / Boats
  • Fishing Type: Saltwater
  • Fishing Style: Spin / Bait Casting
  • Amenities: Please bring drinks, food, sunscreen, ice/cooler, wear soft-soled shoes and don’t forget your camera. Artificial baits. Live bait if needed and available.
  • Targets: Striped Bass, Flounder, Fluke, Sea Bass, Black Cod, Bluefish, Blackfish
  • Phone: (617) 755-3740
  • Website: www.littlesister1.com


Little Sister Charters 

Little Sister Charters are based in Quincy, Massachusetts. Quincy, MA is located just south of Boston. Little Sister Charters fishes inside Boston Harbor (approximately 50 square miles) May, July, July for flounder and striped bass. Inside the harbor the seas are calm and the catch is strong. In August, September the boat moves port to Westport, Massachusetts. There Little Sister fishes inshore for stripers, sea bass, bluefish and toutog. In October, November the boat fishes 1-5 miles offshore Westport, MA for blackfish. The sea’s off Westport, Massachusetts can be a little rough on the fishing charter, some passengers find it helpful to have ‘patches’ or ‘pills’ for seasick relief.

You will spend the day fishing aboard a 26’ center console boat, a reliable and safe vessel that offers a dry, quick ride. Its wide and spacious deck can comfortably accommodate up to six anglers, plus crew and there is a t-top for shade. Little Sister is powered by a 300HP Yamaha outboard motor, and comes equipped with GPS, fishfinder, VHF radio and all necessary safety equipment. Fishing equipment, bait/lures are all top notch and change with species targeted, all are included with your charter fee. Anglers, please bring your own food, drink and your camera. All fish can be cleaned, filleted and bagged at no additional cost (please bring a separate cooler to tote home.)


Your Captain


Captain Jason Colby holds certification from the US Coast Guard: USCF OUPV. With over 15 years of commercial fishing experience he is sure to put you on the fish. There are two 5 hours trips per day (6-11AM and 12-5PM) and these fill up fast! Book today with Little Sister Charters and tell Jason you found him on Sportsmens Compass.



Both an avid surf caster and boat fisherman, Jason grew up on Long Island fishing the beaches and back bays while working on charter and commercial boats. Now residing in Massachusetts, Jason Colbyhe has seen both the commercial and recreational side of the picture. Jason wrote his first article for The Fisherman in 1978 and has been a contributor ever since, he also writes The Conservation Corner for the New England edition of The Fisherman each month.



Guide Cast


Meet Jason Colby – Captain/owner of Little Sister Fishing Charters

Fun Fact: Capt. Jason has personally caught 24 Striped Bass over 50 lbs and took a Striper that topped the scales at 64 1/4 lbs. (personal best)

Member Reviews


by Rob | Overall Rating:

Oct 20, 2016

I have fished with Jason Colby many times. Not only for flounder, but for tautog, stripers as well as Black Sea Bass. Jason has patience not only with the clients but in waiting for the bite. His many decades of experience shows and I really appreciate the guidance he has...

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Cpt. Jason will put you on the fish(es).

by Brian | Overall Rating:

Oct 01, 2016

Though I've fished with Captain Colby more than a dozen times, this was my first time casting eels at night. We had action almost the whole time with fish to 38", tossing back both keepers and shorts. A few bluefish made it in the boat as a bonus. Whether it...

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fishing on the little sister

by Michael | Overall Rating:

Oct 01, 2016

I always have a good time fishing with Captain Jason Colby. This man really knows his stuff. He made the trip fun which is always a good thing. I have been fishing on the Little Sister for quite a few years and I can honestly say I have not had...

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Striped bass fishing with jason colby

by kevin | Overall Rating:

Apr 05, 2016

I have been fishing with Capt Jason for a number of years. This is the was first time I brought my family. He was very understanding and professional in engaging my family members to fish. Even though there was a language barrier he was very engaging. Everyone on the boat...

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Request Booking/Information

Call today (802) 347- 4550 or fill out the form below to plan your next fishing adventure:

The Fish


Things really come alive with Flounder (Limit on Flounder is 8 per angler) and Striped Bass becoming more numerous and larger with each passing day.


Flounder are abundant and Striped Bass Fishing is at it’s best with  a good shot of fish over 30 lbs!


Flounder become scarce and you have to travel for Cod, but Striped Bass are very hot with some of the BIGGEST fish of the year.


Little Sister heads to Westport the 1st and there it is a mixture of stripers, sea bass, bluefish, scup, fluke, trigger fish, tuna, sharks and whatever else we can get! This fishing is pure fun as you will never know for sure what will bite next..


Good Bass Fishing, day and night. Fluke move out and tautog (blackfish) move in.


Bass fade out, blackfish take over


All Black Fish !

The Boat

26 foot Center Console

Little Sister Charters 5



Fishing News from Captain Jason/Little Sister Charters

Flounder fishing BostonFishing Boston

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