Connecticut Striper Fishing Charters & More

Call Captain Sam for daily striper fishing charters & more out of Old Saybrook, CT.

Charter options

At Twenty4seven Guide Service, we specialize in Connecticut striper fishing charters as well as a variety of trip types to target all the different species Long Island Sound (and surrounding waters) has to offer. Twenty4Seven is based out of Old Saybrook, CT – a perfect location to call home for CT striper fishing. Amongst all the species in Long Island Sound, striped bass are the primary targeted species. The combination of power, agility, and beauty makes the striped bass a popular species of choice for most saltwater anglers on the east coast.

Early in the year, there is no better sight than watching a striped bass roll up on live bait and eat it on the surface right before your very eyes. While these fish are edible and pretty tasty, catch and release is practiced as the population has been dwindling over the years. Other species in the spring include aggressive bluefish, bottom fishing for porgy and black sea bass, and fluke.

During the fall season, water temperatures drop and introduce a whole new population of fish. Blackfishing season begins on October 10th, a fan favorite for many New Englanders. Blackfish taste great and provide an excellent bite, and a fantastic fight. False albacore also begins showing up in September, as well as the fall run of striped bass. Personally, the Fall is my favorite time of year to fish!

Food and drinks can be provided for an additional cost.

Charters can accommodate up to 4 anglers and are offered in 3, 5, or 7-hour sessions.

Local Striped Bass

Best Times: Mid May – August, October – November

7 Hour: $750, 5 Hour: $600, 3 Hour: $400

Here is your chance at chasing beautiful local Long Island striped bass! Local striped bass charters are fully customizable to best fit our client – whether it be free-swimming live bait in shallow water to hear and see the unmistakable noise a striped bass makes when coming up to annihilate a live bunker, or throwing massive plugs to girthy striped bass looking for a quick snack cruising on the surface.

Captain Sam will recommend times based on tidal and weather conditions to provide clients with the best opportunity at catching one of these gorgeous species the Long Island Sound has to offer. The best times to target these fish are often early in the morning or late at night, as these fish tend to feed the best when the sun is just rising, or just setting.

*Most of the Striped Bass fishing we do is CATCH AND RELEASE! The Striped Bass fishery has dwindled over many years of heavy fishing. We try to do our part by releasing the fish for it to continue to grow!

Block Island Trips

Best Times: June – September

Full Day: $1,000 (Half Day Not Available)

If you are in search of a once in a lifetime trophy striped bass, the Twenty4seven Block Island fishing charter is where you need to be! Block Island, Rhode Island is known to be one of the best regulated striped bass fisheries in the world. Due to its location being right in the middle of the Atlantic ocean, it is far enough off the coasts to inhabit many different forms of life, and a breeding ground for massive striped bass.

Block island charters are run late at night/early in the morning, leaving the dock at varying hours depending on weather, tide, and captain’s decision. This trip involves boarding the vessel and running about 40 miles to the fishing grounds off of Block Island. Fishing style includes 3-waying live eels on the bottom, or appetizing hungry bass with an enticing rubber eel. When the light comes up in the morning, large striped bass can be caught casting large spooks, poppers, or swimbaits depending on condition and feeding style. There is no better feeling then holding up a 40+ lb striped bass for the camera!

Bottom Fishing

Best Times: June – September

7 Hour: $750, 5 Hour: $600

Although most anglers flock to Long Island Sound in search for trophy Striped Bass, these waters also offer a great variety of bottom fishing, operational almost all summer long. Species that can be caught while bottom fishing include but are not limited too fluke, black seabass, porgy, and the occasional striped bass or bluefish coming down to the bottom for a squid strip appetizer.

For those clients that are looking to get out on a family trip or put some meat in the cooler, the bottom fishing trip is the charter for you.

False Albacore

Best Times: September – November

7 Hour: $750, 5 Hour: $600

For a very limited time during the Fall months of September, October, and November, the False Albacore show up, hot and heavy! Get your chance to catch one of this elusive little tuny. False Albacore/ Bonito are in the tuna family. Although they don’t make for as good table fare as a bluefin tuna, they make up for it with their high rate of speed and agile body.

False albacore rapidly chase little baitfish on the surface, creating a white water effect on the surface known to many anglers as “the washing machine”. These fast fish make rods bend and reel scream, keeping a smile on any anglers face.

Catching False Albacore can be done on a fly rod set up, or spinning set up. The main strategy for catching these fish is reeling metal-epoxy jigs across the surface of the water. This makes for visually satisfying topwater explosions and enough adrenaline to keep you coming back for more! Make sure to book your false albacore trips early, as spots run out quickly when the bite is hot!


Best Times: October 10 – November 28

7 Hour: $750, 5 Hour: $600

During the fall beginning on October 10th, the fan-favorite blackfish season begins! Blackfish are one of the strangest creatures in long island sound- They are easily identifiable by the ugly teeth poking out of their mouth, and their colors! Blackfish can change from various shades of black to white depending on conditions such as their habitat, migration pattern, diet, and many more known variables.

Do not be fooled by the size of these fish! Blackfish are one of the strongest fighting fish pound-for-pound long island sound has to offer. Nothing beats the excitement of pulling a big blackfish from the rocks beneath and landing him for some quality pictures and excitement onboard. Not only do Blackfish fight hard, but they make great tablefare too! Blackfish are often times referred too as “poor mans lobster” because of their light and flaky white meat. Make sure to bring a cooler to transport fresh fish home!

Trip Details

What’s Included

Each charter comes with an experienced and friendly captain, along with top-of-the-line fishing rods, reels, and tackle provided by Captain Sam. Additionally, we can arrange food for the charter at an additional cost.

What To Bring & Not To Bring

When preparing for your fishing trip, remember to bring along essentials such as a camera for capturing memories, sunscreen, a hat, sunglasses, and plenty of drinks and snacks to keep you fueled throughout the day. Our charters accommodate up to 4 anglers, so feel free to bring along friends or family to share in the experience.

However, please refrain from bringing glass bottles, liquor, drugs, GPS devices, or spray sunscreen. Additionally, ensure that any coolers brought aboard are of a reasonable size to allow ample space for food and drinks, as larger coolers may be difficult to accommodate on the boat.

Cancellation Policy

Upon booking a trip, a $100 payment will be made to secure your trip. If you are unable to make your scheduled time slot, please reach out more than 24 hours in advance to reschedule your charter.

Request Availability

Thanks for your interest in fishing with Twenty4Seven Guide Service! We’re happy to answer any questions you may have ahead of booking. Please complete the form with your preferred trip date.