Whiptail Adventures is the most reviewed boat in the Portland deep sea fishing fleet, a versatile operation that Captain Jason runs out of South Portland on a 28 foot center console. It fishes three ways, striped bass and bluefish inshore, ground fishing for haddock, cod, and pollock on the closer grounds, and a shark trip in summer, and it carries a 4.9 rating across more than a hundred trips. For an angler who wants a flexible day and a captain who tailors the trip to the group, it is one of the strongest and most booked options in the port.
The verdict and where it ranks
At 8.0 Whiptail is a strong choice and third in the southern Maine field. It earns the spot on a deep, consistent review record, the largest in the Portland fleet, and a captain who reviewers single out for knowledge and for personalizing the trip. What holds it back on a deep sea page is the format. The 28 foot boat is the smaller end for the long run to the deep ledges, and its ground fishing works the grounds about 45 to 60 minutes from shore rather than the 20 to 30 mile push to Jeffreys Ledge, with the menu split between inshore striped bass and offshore species. Book it for a flexible, well run day. For a dedicated deep ledge groundfish run, the Kristin K and the LiveLiner fish farther out.
The boat
The Whiptail is a 28 foot center console that takes up to 6 anglers. It is a quick, capable boat for striped bass and bluefish in Casco Bay and for ground fishing the closer grounds, and the open layout suits light tackle and casting. The honest limit for a deep sea page is the size and range: a 28 footer is well suited to the nearer water but is the smaller end of the fleet for a long day on the deep ledges in a chop, which is why its ground fishing stays closer in than the dedicated groundfish boats. For the trips it runs, the boat is the right tool, and reviewers do not report issues with its condition or gear.
The fishing and what you target
Whiptail’s range is its selling point. Inshore, it fishes striped bass and bluefish through the warmer months, the bread and butter of Casco Bay. The ground fishing runs to the closer grounds, about 45 to 60 minutes out, for haddock, cod, and pollock, with haddock the keeper under the 2026 limits and cod mostly released. In summer it adds a shark trip. Reviewers describe Captain Jason putting groups on a wide mix of species in a day, which is the appeal of a versatile boat: you can shape the trip to what is biting rather than commit to one fishery. For the deep ledge bottom fishing, though, the longer running boats reach better groundfish water.
Trips and prices
Whiptail books by the boat through FishingBooker, private only, from about $400 for a striped bass trip, with the longer ground fishing and shark trips priced higher on the listing. We list the entry price rather than a full table, since the operator prices the trips through the platform; confirm the rate for the specific trip you want when you book. The boat takes up to 6 anglers, so it works out per head with a full group. Our cost guide sets these numbers against a shared head boat seat and the bigger private charters.
The crew
The crew is the strongest part of the operation. Captain Jason draws consistent praise across more than a hundred reviews for his knowledge of the water, his patience, and the way he personalizes the trip, with anglers reporting double digit species counts on a good day. A 4.9 rating over that many trips is the deepest clean record in the Portland fleet, which is the clearest signal of consistency a small operation can carry. The booking platform record also means the reviews come from anglers who actually fished the boat, so the rating is well tested.
Booking and what to know
Book through the FishingBooker listing, which carries the rates and the cancellation terms, and book ahead in summer, since the boat’s popularity fills its dates. It leaves from South Portland, so arrive early to park and load. No license is needed on the charter, the crew handles the catch, and you bring food, drinks, and layers. If the deep ledge ground fishing is the goal, ask how far out the trip runs when you book, since Whiptail fishes closer in than the dedicated groundfish boats.
How we scored it
Whiptail scores 8.0, third in the southern Maine port. Track record, service and booking, and captain and crew are its strongest factors, on the deepest review record in the fleet and a captain who tailors the trip. It is marked down for a deep sea ranking on trips and access, because the ground fishing works the closer grounds and the menu leans inshore, and on boat and equipment for a smaller hull than the long range groundfish boats. See how we scored this boat for the full rubric, and compare it against the rest of our southern Maine rankings.