(617)755-3740 jason@littlesister1.com




About the Captain

Fish with “Capt. Jason Colby”, a man who for many years made his living catching fish with a rod and reel.

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)

We fish from a 31 foot Contender fish catching machine with dual 300hp Yamahas and an electric motorized Minn-Kota anchor to hold us on GPS spots (called “Spot-Lock”) without having to put down a traditional anchor – which is much more bottom friendly and doesn’t spook the fish. The Minn Kota is also far more accurate than an anchor for targeting small pieces of structure that are seldom fished. Bait and tackle is included aboard but you are always welcome to bring your own.

*Note that space is very limited. Bring sunglasses, your smartphone camera, sunblock and anything you want to eat. Keep in mind there is no working head on the boat.*

That is a fine looking bird (and captain!)…

“Bird” has been aboard for 11 years now! He is mostly seen aboard while flounder fishing in and around Quincy Bay. He has a mate (“LadyBird”) and they nest on a nearby island. Bird is the Alpha Male Blackback Gull in the Quincy Bay area and he is not shy, often walking around the boat like he owns it. The only thing Bird really lets everyone know he does not like is kids. He doesn’t even like his own kids, much less anyone elses. Bird is the ultimate “herring gobbler”, often arriving on Little Sister just to keep us company and too full to eat another bite. When there are lots of herring around (like in June), Bird uses the boat as a place to watch for schools of the things while he calculates how much room he has in his belly so he knows when to grab some more! At these times he often gets angry if anyone tries to feed him because he has all the food he wants without any help.

2024 Prices

“Night Striped Bass”

The striped bass fishing has changed a lot over the past couple of years, mostly due to new regulations regarding circle hooks being required for using bait so most night striper trips will only involve casting plugs unless someone for some reason “needs to” fish with live eels. For that the only requirement would be enough time to get the eels but note that they can be very difficult to deal with and we catch plenty of fish on the plugs.
Night trips can go from 3-6am or 8-11pm. Three people are $350.



The boat gets launched in Quincy early in the month and we start right off with haddock. The fishing has been great and “easy limits” have been the norm on most trips. The regulations allow for 15 haddock per person and in some years we can keep a cod or two. Dress warm and bring gloves, just in case.


The haddock fishing stays strong all month and the flounder fishing gets better by the day. By mid May the flounder fishing is reaching it’s peak with the biggest flounder near the end of the month.


As the water warms the haddock move off to deeper, cooler water while early in the month the flounder fishing is still very strong and it is at this time of year we typically get our biggest flounder. Three, four and even 5 pound flounder (up to 5 pounds, 9 ounces)  have been caught on Little Sister in past Junes. About June 16th the boat hops aboard her trailer for the ride to Westport, Ma where she spends the rest of the season. There, in the latter part of June we get right into monster stripers along with schoolies and “slot fish” if anyone wants to bring home fillets. Late June is also the time for fluke and sea bass just outside the Westport River. Don’t forget the scup!

July and August

Sea bass! Lots of sea bass;…”easy limits” of jumbo sea bass are expected on most trips with lots of “catch and release” as well. These trips often see bluefish breaking on the surface and we always have rods ready to cast when we see them. Bonito and false albacore mix in with the blues as the summer wears on.  Cod are on The Hills and Coxes Ledge and as the surface temps rise, mahi can be had on these trips as well. Throughout the summer there can be good fishing for fluke off Newport and/or Noman’s Island but note that 2021 was not good at all for fluke.

Also, if you want to fill a cooler with scup, it is a great way to introduce kids to fishing as the action can be very fast paced!


Striped Bass are available in good numbers and sizes through mid October at least. Sea bass fishing shuts down in the second week of September and we start to concentrate on blackfish more and more. By mid October and through until mid November when we pull the boat for the season, it becomes “all blackfish” with some true monsters being hooked each year. Many of these fish break people off and some of them make it to the boat. Blackfish are strong! Are you stronger?


Capt Leo Chomen - Waterford, CT

This is my second year in a row making the trek up to “Little Sister” and Jason.The first year the fishing was tough all around but Jason kept working at it to scrap together a catch.Even though he does it day in and day out the enthusiasm is never lost and being a fisherman who logged a lot of hours on boats including my own I know when the captain is thinking and burning wood and he thinks out every move ,knows where to drift and in what wind and has plenty of backup plans in case. That is the sign of a great captain.

This year by the way we pounded them, not quite like the old days, but fairly close as our memories may sometimes not be totally accurate in the fishing world. Jason is a Captain in his environment and I highly suggest a trip with him to give you the best odds and fish with someone who thinks out every move and always works hard for success.

After 49 years of saltwater fishing,which started with flounder,I have learned alot from him in 2 trips!

Karmen M. - Old Lyme, CT

This is my 3rd year fishing with Captain Jason Colby of Little Sister Charters. I also grew up flounder fishing in Long Island Sound, back in the day when we would come home with a bushel basket of fish to clean. Jay knows flounder like no one else I’ve fished with. He consistently puts his customers on fish, and he’s a great teacher, explaining technique, habitat, conservation (he tells some pretty funny jokes, too). Our annual flounder trip is a family affair and I’ve also fished with Jay from his Westport location for some great bottom fishing. His prices are reasonable, and he will work his butt off to put you on fish. And oh yeah, he’s got a pretty hot hand when he gets to fish, too, consistently hooking to contribute to the catch, when he’s not assisting customers.

Jan S. - Quincy, MA

If you are looking for a fun and exciting fishing charter in the Quincy area, there is none better than Little Sister Charter. Captain Jason couldn’t be any more accommodating and knowledgeable of our beautiful waters and flounders galore! Always a great time and look forward to more trips with Captain Jason!

Mike M. - Arlington, VA

I have been flounder fishing with Capt. Jason Colby for the past two seasons. I crew with my old buddies from NY.

It is a 467 mile one-way drive for me as I live in Arlington, VA. The fact that I have done this multiple times is a testament to the fine job Jason does and the good time had by all on our trips. I have limited on all the trips and have had a blast doing it. We’ve caught fish in the sun, rain and wind; but, it’s all good.
If you are looking to do some quality (fish are LARGE) flounder fishing and have a good time while doing it, Little Sister Charter is your boat.

Corey B. - Quincy, MA

Flounder fishing in Quincy and adjoining areas….

Simply put….It does not get any better than Capt Jason Colby and his boat Little Sister.

He is the undisputed KING of Flounder…and not to mentioned other fish…..in the Quincy/Boston region. Not only does he run a solid (and very reasonably priced) charter service in Quincy…he runs a top-notch service out of Tripp’s Marina in Westport, MA starting in August of every year. There he is the KING of Tautog (blackfish) and other groundfish including fluke (Summer flounder) and hump heads (black sea) bass. A repeated state record holder…you are in good hands with Capt. Jason…FIVE STARS!!!

Rich M. - Attleboro, MA

Had a great time flounder fishing last year with Little Sister. We caught plenty and he writes about his trips and informs everyone on how well he is doing each time he goes out. Looking forward to my next adventure

Kevin K. - Hull, MA

If there are ten fish (no matter species) in a select spot, Colby knows where 9 of them are.

Barry F. - New Port Richey, FL

I have been fishing with Captain Jason for at least 10 years – every summer I would book Jason for Quincy Striper Fishing (I live in Florida) – at least twice a summer. When he added Westport to his list of ports – I made a special effort to visit in the fall for EXCELLENT bottom fishing – TAUTOG and Sea Bass. I took my 2 grandnephews fishing in Quincy for flounder (their FIRST TIME FISHING) and Capt Jason showed them how to fish – I think I learned too. Obviously, my 5 STARS summarize how good/excellent LITTLE SISTER CHARTER is.

Capt Carl C. - Roscoe, NY

Jason Colby is one of the best bottom fishermen in the trade. His ability to provide quality as well as quantity of targeted species makes him my first choice when considering a charter in his area.

Being a retired Montauk Charter Captain myself – I feel right at home when fishing with on the Little Sister.

Catch em up !

John H. - Hollis, NH

I have fished with Captain Colby for 10 years, and have always been more than pleased with his skill, knowledge and mostly his effort to put us on fish, help u catch them and make our trip enjoyable and productive.  He goes more than the extra mile in working to find fish those few times when they were not cooperating.

The fishing changes over the years…10 years ago it was half cod and half flounder, now it is awesome flounder without a cod to be seen,  but his effort, and great attitude is always top notch.
I have gone on charters with “the guys” as well as with a teenage daughter and son and he accommodates each group based on their skill and what they want to catch.

I caught my personal best flounder with him  2 years ago( 4 lb 7 oz) and a friend caught his personal best ( 4 lb 11 oz) with Captain Colby this season.   He knows where and how to catch the big ones, as well as the numbers of fish.

He takes time to teach both the rookie and the old timers so everyone learns as well as catches fish while having fun.
Do not hesitate to charter this boat!

John D. Silva - New England Outdoor Freelance

As a an outdoor writer I’ve been out with many charter captains and guides over the years. Almost all of them are gruff in one way or another, but that’s not necessarily a bad thing. Some of them will spend 5 hours barking orders at you and treating you like you’re an idiot. Others drone on and on for hours about how great they are and how bad other guides are. Some are more concerned about you marking up their shiny new boats than how much fun you have. And then there are just some GWB’s (guys with boats) trying to pay their gas and mooring fees with your money.

Capt Jason Colby however is A TRUE FISHERMAN. He is a throwback, a salty-blooded charter captain with a long track record of trophy catches and commercial fishing success. This is a guy that made his living and reputation on the water. He won’t boast or talk about himself, (although he may share a few silly jokes), so just do a little research and you’ll see for yourself. His experience and past successes are well documented.

If you want to catch fish AND have a good time, give Captain Jason a call. He’s not about “fancy” gear and complicated techniques. He won’t just pop two wire rods in the transom and drive around for 6 excruciatingly boring hours. He’ll work for you. He puts you on fish and puts a rod in your hand and lets you enjoy the whole experience. When you go with Jason, YOU are doing fishing, not the boat. When you see Lil Sister for the first time, you’ll know right away that this guy catches fish, (and don’t worry, he won’t yell at you for putting a mark on the paint job).

And just wait till you see him work a fillet knife. No one is better…