What To Expect

Your Charter Fishing Adventure Awaits

Your day with Whiptail Adventure starts at Spring Point Marina. When all are aboard we’ll all take off for one of the Captain’s favorite fishing spots.  These spots can be close to shore for some fish, and as far out as 35 miles from shore for others.  On the way out and back, you will pass historic forts and scenic lighthouses that you can hardly make out from shore. This is the time to sit back, relax, and get ready for an unforgettable Charter fishing experience! 

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You will get your fill of nautical adventure as you spend your day sport fishing for various species of shark, striped bass, mackerel. Maybe you would rather test your angling skills and fish for “ground fish” like haddock, halibut, pollack, and cod. If you’re after an ultimate offshore charter fishing experience and want to catch them all, you can book a custom charter that scratches just about any fishing itch.

All our charter fishing trips come inclusive with everything you need to make a great catch possible. You will be provided with rods, reels, tackle, bait, and a license for your party. Captain Jason Eaton will send your catch home cleaned and fileted, ready to go straight into the frying pan. Just remember to bring your own drinks and some snacks, these adventures are hungry work!

Whiptail Adventure Fishing

When is shark season / When’s the best time for a shark fishing charter?

The Shark fishing season in Portland, ME is from mid July to the end of October.  The peak of the season is August.  For the best chance to catch a real prize winner, we suggest booking your shark charter in August.  If you want to know how the sharks are biting right now, reach out to us!

Can my whole family go on a fishing charter?

Definitely, yes! Not every charter is ideal for the whole family though.  We suggest one of our shorter duration charters for family excursions.  Alsom, if you just want to spend time on the water with your family, we do offer Casco Bay harbor tours.

What is your cancellation policy?

The Captain of your charter reserves the right to cancel a trip due to weather conditions at the time of the trip.  If this happens, the customer will be refunded their original $100 deposit. If a customer cancels a trip within 48hrs of scheduled departure they are still required to pay for the trip in full.  If you cancel before this window, we will keep the initial deposit, but you will not need to pay for the full trip.

What's the difference between your different fishing charters?

Our charters vary by what we’re trying to catch.  Different fish live and gather in different areas.  Some charters require fairly long travel times to find a good fishing spot.  This extra time requirement affects their minimum length of duration.  Additionally, some fish require more skill than others to catch.  There is a lot more physicality to catching a shark than catching a Mackerel!

How old should kids be for a fishing charter?

While there isn’t a strict minimum because all children mature differently, we strongly suggest that kids be at least 8 years old for a charter, and that they have some experience with easy, kid-friendly fishing before trying to go out on a more serious fishing charter.

Can I keep my catch?

It depends on what kind of fishing charter you’re booking, but in most cases we practice catch and release.  This is because many of the fish we catch serve important roles in the ecosystem, most especially sharks who are very important to a healthy harbor.  The exception is Ground Fishing where you can keep your catch and are likely to go home with an ice chest of filets.

What should I bring for a fishing charter?

The boat covers all fishing licenses, bait, and tackle, so all you need to bring is food and something to drink.  We recommend bringing along a light jacket on morning trips because it can be surprisingly chilly. Remember, the water is a lot cooler than the land is in summer, and the wind off the water can be biting in the early hours.

What if I want to do a fishing charter that isn't listed?

While we feel the adventures we feature are fantastic, we know there are a lot of fish in the sea! If you are interested in a different charter, please just inquire about the possibility.  There’s a good chance we can accommodate your custom charter idea.  As an example, we often do a combination ground fish and shark trip.

Our Boat, “Whiptail”


Whiptail is a Steiger 28 Miami with twin Suzuki 250 engines that provide the power and speed needed to fish offshore safely. The boat has a 10 ft beam and an 80 sq. ft. cockpit, as well as a 200-gallon fuel capacity that allows it to have a range of over 400 miles. It is equipped with top-of-the-line electronics and all the required safety equipment to ensure a smooth and worry-free fishing experience.

The 28 Miami is designed with several fishing-specific features, including tackle storage throughout the boat, a large in-deck fish locker (120 Gal) for storing caught fish, overhead rocket launchers, recessed gunnel weight draws and rod storage, and generous storage beneath the port-side couch. It also has two (100 Gallon) insulated fish wells for storing live bait and keeping caught fish fresh.

The hull of the 28 Miami is made of hand-laid fiberglass and features an “I-Beam” grid system that adds durability and reduces flex in rough waters. The boat has a spacious cabin with a manual porcelain head, a stainless sink, a V-birth for two people, and three opening portholes for ventilation. The 28 Miami has a length of 28 ft, a beam of 10 ft, a weight of 8400 lbs, and a draft of 25 inches. In addition, unlike many other charters, the 28 Miami has a bathroom for added convenience.

Whiptail Boat

Our Captain, Jason Eaton

Captain Jason Eaton is an avid angler and a full-time registered Maine State Guide. He enjoys sharing his wealth of local knowledge with his customers and friends. Jason specializes in Groundfish, Striper, and Shark fishing out of Maine. His main goal is to provide his clients with the best sportfishing experience and come back home with an ice chest full of memories and filets. 

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Our captain isn’t just a skilled navigator, though, he is a proven tournament winning Guide.  He placed 1st in the 2018 Spring Point Shootout fishing competition for Striped Bass and 1st in the 2019 Spring Point Shootout for Shark. Jason learned to fish in Portland as a youngster, and has been up and down the New England coast to New York, and New Jersey to fish for Stripers.  So not only will you benefit from a great tour guide deeply familiar with the local seascape, you’ll be working with a real fishing pro who has been fishing these waters for decades!

Jason has lived all over the country, but now lives full time in Portland with his wife of 22 years, Michelle, and his daughter who is currently attending USM.  An avid outdoorsman, when he isn’t busy leading fishing adventures, Jason is probably fishing for pleasure, hunting for deer, or taking his Wirehaired Pointing Griffon, Sadie, birding.

Whiptail Adventure Jason Eaton

The Mission 

The purpose of Whiptail Adventures is to bring the joy and thrill of competitive fishing to the people of Portland, Maine, whether they’re local or visiting. We thrive on sharing the energy and excitement fishing brings into our lives with our clients.

We value the challenges and joys that offshore and inshore fishing provides both to us and our clients, and our ultimate goal is to help you form incredible memories about your time on the water in Maine.