Whiptail Adventures
Whiptail Adventures
Whiptail Adventures offers an incredible sport fishing experience on the waters out of South Portland, Maine. Join their experienced captain and head out in pursuit of Striped Bass, Groundfish and Shark. Plus, there is also a great chance to spot a whale on your way to the fishing trip! Fishing trips are tailored for 4 anglers in most situations depending on conditions and type of fishing. We can take 5 people but 4 is more comfortable for fishing
Step onboard the ‘Whiptail’, a 28’ Steiger Craft Pilothouse boat. She is a clean, seaworthy fishing machine with twin 250 HP Suzuki engines. The Whiptail can comfortably accommodate up to four anglers. She was built with comfort in mind. The Whiptail is outfitted with top-notch navigational and fishfinding electronics, as well as other professional accessories. There is also a toilet on board - a much-needed thing when spending your day on the water. Whiptail is ready to provide you with a fabulous trip!
Your day with Whiptail Adventures will begin when you cruise out of Spring Point Marina. The captain’s fishing spots are located 1-35 miles offshore. On your way there and back, you will pass historic forts and lighthouses. Just sit back, relax, and get ready for an unforgettable experience.
Spend your day targeting various types of sharks, including Mako, Thresher, Porbeagle, and Blue Shark. Test your angling skills and fish for Haddock, Halibut, Pollack, and Cod. And if you’re after an ultimate offshore experience and want to catch them all, book a Combo trip. Don’t miss the season!
All 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. The captain will send your catch home cleaned and filleted, ready to go straight into the frying pan. Just bring your own drinks, some snacks, and the desire to catch fish!
Customer reviews
Rating summary
Photos & videos by reviewers (132)
+129Angler rating
Anglers claimed
Good experience
96%
Appropriate for children
93%
Friendly captain
100%
Satisfied with the boat
100%
Recommend this charter
97%
Caught fish
93%
Aug 27, 2025
8hr Striped Bass trip 7AM
Killer Striper Guide!
We went out for an eight hour striped bass fishing trip with Captain Jason in Portland, Maine. It was our first ever charter and we had an absolute blast. Jason is incredibly knowledgeable about the area and really takes his time sharing his skills with you. It felt like Jason personalized our trip just for us, which is what lots of other reviewers have said too. We started the morning fishing for mackerel for bait, then we drove on to an amazing fishing spot while Jason pointed out several landmarks. It felt like a sightseeing cruise and fishing charter all in one, which made my wife very happy. She got lots of pictures of light houses, seals, and other wildlife. We caught 11 huge striped bass and one was keeper size, which Jason filleted for us. He even gave lots of helpful cooking recommendations. Whether you are a complete beginner or experienced, you really can't do better than a charter with Captain Jason!
We went out for an eight hour striped bass fishing trip with Captain Jason in Portland, Maine. It was our first ever charter and...
Captain repliedMark review as helpful
Mark review as helpful
Jul 14, 2025
6 Hour Trip – Striped Bass 7AM
Great Captain, nice boat, beautiful area
We had a great time on our trip with Jason. The boat is well equipped and Jason knows the area very well . The ones that were new to fishing on our trip had a blast catching the mackerel for bait, four at a time . They also enjoyed pulling up one of Jason’s lobster pots, and seeing the lobster , and hearing about the lobster fishery in Maine. Fishing was a bit slow this day, but Jason stuck with it and switched up spots a number of times, and we did catch a 28 inch striper. And Casco Bay scenery is beautiful. Will definitely give it another try with Jason when we are back up in the area again.
We had a great time on our trip with Jason. The boat is well equipped and Jason knows the area very well . The ones that were...
Captain repliedMark review as helpful
Mark review as helpful
Jun 22, 2025
4 Hour Trip – Striped Bass - 12PM
Early season striper fishing produces three landings.
Despite the unusually cold water conditions Jason put our group of four into a position to land three stripers (one each for three fishermen). Two of those landed were very, very (did I say very?) close to being keepers, but our group wasn't altogether disappointed to release them for someone else to enjoy catching them again. The captain was good company and gave us the benefit of his knowledge of fishing for all species of fish, conditions (weather, tides, wind, and bottom structure), and some Casco Bay history too. I look forward to booking another charter with Whiptail Adventures in the future.
Despite the unusually cold water conditions Jason put our group of four into a position to land three stripers (one each for three...
Captain repliedMark review as helpful
Mark review as helpful
Aug 28, 2025
8 Hour Trip – Combo
A day well spent!
Jason was a great captain and the day was one I won’t forget. Being on the water is so relaxing and even though the ground fishing wasn’t what we hoped for the day we went out, Jason tried his best to find what we could. Toward the last few minute of the trip my son got the chance to hook onto a shark! The smiles and excitement were just what we all needed.
Jason was a great captain and the day was one I won’t forget. Being on the water is so relaxing and even though the ground fishing...
Captain repliedMark review as helpful
Mark review as helpful
Aug 17, 2025
4 Hour Trip – Striped Bass 7AM
Nothing Short of Amazing
This is an experience that everyone needs to try and will be unforgettable. It was easy to book and an absolute amazing time with Captain Jason Eaton.
This is an experience that everyone needs to try and will be unforgettable. It was easy to book and an absolute amazing time with...
Captain repliedMark review as helpful
Mark review as helpful
Trip availability and prices
| Su | Mo | Tu | We | Th | Fr | Sa | |
|---|---|---|---|---|---|---|---|
Customer reviews
Rating summary
Photos & videos by reviewers (132)
+129Angler rating
Anglers claimed
Good experience
96%
Appropriate for children
93%
Friendly captain
100%
Satisfied with the boat
100%
Recommend this charter
97%
Caught fish
93%
Experience:
Boat
Crew
Overall
Killer Striper Guide!
8hr Striped Bass trip 7AM on August 27, 2025
We went out for an eight hour striped bass fishing trip with Captain Jason in Portland, Maine. It was our first ever charter and we had an absolute blast. Jason is incredibly knowledgeable about the area and really takes his time sharing his skills with you. It felt like Jason personalized our trip just for us, which is what lots of other reviewers have said too. We started the morning fishing for mackerel for bait, then we drove on to an amazing fishing spot while Jason pointed out several landmarks. It felt like a sightseeing cruise and fishing charter all in one, which made my wife very happy. She got lots of pictures of light houses, seals, and other wildlife. We caught 11 huge striped bass and one was keeper size, which Jason filleted for us. He even gave lots of helpful cooking recommendations. Whether you are a complete beginner or experienced, you really can't do better than a charter with Captain Jason!
We went out for an eight hour striped bass fishing trip with Captain Jason in Portland, Maine. It was our first ever charter and we had an absolute blast. Jason is incredibly knowledgeable about the area and really takes his time sharing his skills with you. It felt like Jason personalized our trip just for us, which is what lots of other reviewers have said too. We started the morning fishing for mackerel for bait, then we drove on to an amazing fishing spot while Jason pointed out several...
Mark review as helpful
Experience:
Boat
Crew
Overall
Great Captain, nice boat, beautiful area
6 Hour Trip – Striped Bass 7AM on July 14, 2025
We had a great time on our trip with Jason. The boat is well equipped and Jason knows the area very well . The ones that were new to fishing on our trip had a blast catching the mackerel for bait, four at a time . They also enjoyed pulling up one of Jason’s lobster pots, and seeing the lobster , and hearing about the lobster fishery in Maine. Fishing was a bit slow this day, but Jason stuck with it and switched up spots a number of times, and we did catch a 28 inch striper. And Casco Bay scenery is beautiful. Will definitely give it another try with Jason when we are back up in the area again.
We had a great time on our trip with Jason. The boat is well equipped and Jason knows the area very well . The ones that were new to fishing on our trip had a blast catching the mackerel for bait, four at a time . They also enjoyed pulling up one of Jason’s lobster pots, and seeing the lobster , and hearing about the lobster fishery in Maine. Fishing was a bit slow this day, but Jason stuck with it and switched up spots a number of times, and we did catch a 28 inch striper. And Casco Bay...
Mark review as helpful
Experience:
Boat
Crew
Overall
Early season striper fishing produces three landings.
4 Hour Trip – Striped Bass - 12PM on June 22, 2025
Despite the unusually cold water conditions Jason put our group of four into a position to land three stripers (one each for three fishermen). Two of those landed were very, very (did I say very?) close to being keepers, but our group wasn't altogether disappointed to release them for someone else to enjoy catching them again. The captain was good company and gave us the benefit of his knowledge of fishing for all species of fish, conditions (weather, tides, wind, and bottom structure), and some Casco Bay history too. I look forward to booking another charter with Whiptail Adventures in the future.
Despite the unusually cold water conditions Jason put our group of four into a position to land three stripers (one each for three fishermen). Two of those landed were very, very (did I say very?) close to being keepers, but our group wasn't altogether disappointed to release them for someone else to enjoy catching them again. The captain was good company and gave us the benefit of his knowledge of fishing for all species of fish, conditions (weather, tides, wind, and bottom structure), and...
Mark review as helpful
Experience:
Boat
Crew
Overall
A day well spent!
8 Hour Trip – Combo on August 28, 2025
Jason was a great captain and the day was one I won’t forget. Being on the water is so relaxing and even though the ground fishing wasn’t what we hoped for the day we went out, Jason tried his best to find what we could. Toward the last few minute of the trip my son got the chance to hook onto a shark! The smiles and excitement were just what we all needed.
Jason was a great captain and the day was one I won’t forget. Being on the water is so relaxing and even though the ground fishing wasn’t what we hoped for the day we went out, Jason tried his best to find what we could. Toward the last few minute of the trip my son got the chance to hook onto a shark! The smiles and excitement were just what we all needed.
Mark review as helpful
Experience:
Boat
Crew
Overall
Nothing Short of Amazing
4 Hour Trip – Striped Bass 7AM on August 17, 2025
This is an experience that everyone needs to try and will be unforgettable. It was easy to book and an absolute amazing time with Captain Jason Eaton.
This is an experience that everyone needs to try and will be unforgettable. It was easy to book and an absolute amazing time with Captain Jason Eaton.
Mark review as helpful
FAQs about Whiptail Adventures
The fish you can target
What is the boat like?
