Whiptail Adventures 

4.9
(126 reviews)
 Spring Point Drive, South Portland, ME 04106, United States–

Whiptail Adventures 

South Portland, ME, United States
–
28 ft
6
4.9
(126 reviews)

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!

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!

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Trip date:
Group Size:
November 2026
SuMoTuWeThFrSa
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Group Size
2 adults • 0 children
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Kids trip
FREE Cancellation 3 days notice
2 hour trip multiple starting times (7:00 AM, 12:00 PM, 5:00 PM)
Seasonal trip
Jun 1 - Sep 30
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US $400
Entire boat: up to 6 people
4 Hour Trip – Striped Bass
FREE Cancellation 3 days notice
4 hour trip multiple starting times (7:00 AM, 12:00 PM)
Seasonal trip
May 15 - Oct 15
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US $600
Entire boat: up to 6 people
4 Hour Trip – Striped Bass 2PM
FREE Cancellation 3 days notice
4 hour trip starts at 2:00 PM
Seasonal trip
Jun 1 - Oct 9
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US $600
Entire boat: up to 6 people
6 Hour Trip – Striped Bass
FREE Cancellation 3 days notice
6 hour trip multiple starting times (7:00 AM, 12:00 PM)
Seasonal trip
May 15 - Oct 15
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US $800
Entire boat: up to 6 people
8hr Striped Bass trip 7AM
FREE Cancellation 3 days notice
8 hour trip starts at 7:00 AM
Seasonal trip
May 15 - Oct 15
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US $950
Entire boat: up to 6 people
6 Hour Trip – Groundfishing
FREE Cancellation 3 days notice
6 hour trip starts at 7:00 AM
Seasonal trip
Jun 1 - Oct 15
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US $1,050
Entire boat: up to 6 people
8 Hour Trip – Combo
FREE Cancellation 3 days notice
8 hour trip starts at 7:00 AM
Seasonal trip
Jun 1 - Oct 15
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US $1,300
Entire boat: up to 6 people
8 Hour Trip – Groundfishing
FREE Cancellation 3 days notice
8 hour trip starts at 7:00 AM
Seasonal trip
May 20 - Oct 15
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US $1,300
Entire boat: up to 6 people
8 Hour Trip – Shark Fishing
FREE Cancellation 3 days notice
8 hour trip starts at 7:00 AM
Seasonal trip
Jul 1 - Oct 15
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US $1,300
Entire boat: up to 6 people

Customer reviews

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Rating

4.9
126 reviews
5.0
Boat & equipment
5.0
Captain & crew
4.8
Fishing Experience

Anglers' gallery (168)

What anglers say

96%
Great experience
92%
Family friendly
100%
Friendly captain
100%
Good boat
98%
Recommended
93%
Caught fish

Reviews (126)

  • Olivier Cloutier
    Olivier Cloutier
    Repeat angler
    ca
    Québec, Canada
    Member since 2023
    3 trips
    5.0
    Verified

    We’e going to be sore for the entire week!!

    8 Hour Trip – Groundfishing on August 15, 2026 • 5 adults

    We started the day with perfect weather and headed more than 15 miles offshore. We spent the first hour setting up a chum line, and the moment the sharks found it, the action was ON! We had an incredible morning with 7 shark battles, including a beautiful Mako that launched several feet into the air — absolutely incredible to see! 🤯🦈 Captain Jason barely sat down all day. From running the boat, changing lines, and constantly adding bait to the chum line, he was working nonstop to keep the action going. After noon, when the wind died down and we had pretty much caught all the sharks in the area, Jason suggested we put our strength and endurance to the test with some bottom fishing. The action was nonstop from start to finish, and needless to say, we’ll be feeling it in our muscles all week! It was a full day of action with a captain who wanted this trip to be just as successful as we did. Jason knows the fish and the waters around Portland, and his experience really showed. We found our guy for the years to come! 🎣🦈 A huge thank you to Captain Jason for an unforgettable day on the water. We’ll definitely be back for the next adventure!

  • Jamie Dorland
    Jamie Dorland
    Repeat angler
    us
    Colorado, US
    Member since 2022
    10 trips
    5.0
    Verified

    Great Afternoon On The Water

    4 Hour Trip – Striped Bass 2PM on August 1, 2026 • 4 adults • 2 children

    We had a great time with Captain Jason. The weather was warm, but he still got us on the fish. Also got to do some sightseeing and learn more about the area. The boat was comfortable, and he was great at helping our kids enjoy the experience.

  • Jeff Hardimon
    Jeff Hardimon
    Repeat angler
    us
    Pennsylvania, US
    Member since 2018
    2 trips
    5.0
    Verified

    Great father & son day!

    6 Hour Trip – Striped Bass - 12:00 PM on June 19, 2026 • 3 adults

    We couldn’t go deep-sea fishing because of 20+ knot winds and rough seas. Our captain adapted the trip and took us striped bass fishing in the back bays instead. We caught fish, brought home dinner, and made great memories.

  • Karen Rancourt
    Karen Rancourt
    us
    Maine, US
    Member since 2026
    5.0
    Verified

    16th birthday

    4 Hour Trip – Striped Bass on May 23, 2026 • 4 adults • 1 child

    Grandson wanted to try for his birthday. Three 16 year olds and one grandfather. Everyone reeled in something. They would like to try shark fishing next summer. Thoroughly enjoyed! Would definitely recommend this company and the captain.

  • Wesley Deisher
    Wesley Deisher
    Repeat angler
    us
    Texas, US
    Member since 2023
    2 trips
    5.0
    Verified

    Great Outing

    8 Hour Trip – Combo on August 27, 2026 • 2 adults

    An abdolute blast out on the water, and great conversation with Captain Jason. We caught several species of fish in a short amount of time. I would recommend to anybody in Portland who is looking to do some fishing!

  • Josh Benefield
    Josh Benefield
    Repeat angler
    us
    Georgia, US
    Member since 2026
    2 trips
    5.0
    Verified

    Fun Family Trip

    4 Hour Trip – Striped Bass on July 3, 2026 • 6 adults • 2 children

    Jason was a great captian. Got everyone involved!! 4 hour trip success. Had a heat wave so fish didnt act great but still caught several aoecies. Thanks!!

  • Mark Grab
    Mark Grab
    us
    Pennsylvania, US
    Member since 2026
    5.0
    Verified

    Awesome captain.

    4 Hour Trip – Striped Bass on June 4, 2026 • 3 adults

    Jason was an awesome captain. Caught fish and was like having a fishing excursion sightseeing tour all in one!

  • Damir Timirbaev
    Damir Timirbaev
    us
    Florida, US
    Member since 2026
    5.0
    Verified

    Fishing with Jason

    4 Hour Trip – Striped Bass on July 5, 2026 • 2 adults

    Everything was perfect. The Captain was very professional.

  • David Nassif
    David Nassif
    us
    New York, US
    Member since 2025
    5.0
    Verified

    Killer Striper Guide!

    8hr Striped Bass trip 7AM on August 27, 2025 • 3 adults

    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!

  • Robert Farrell
    Robert Farrell
    us
    Massachusetts, US
    Member since 2025
    5.0
    Verified

    Great Captain, nice boat, beautiful area

    6 Hour Trip – Striped Bass on July 14, 2025 • 5 adults

    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.

FAQs about Whiptail Adventures

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The fish you can target

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Real catches by this captain

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What is the boat like?

Boat image
Boat category
Cabin cruisers
Capacity
6 persons
Boat length
28 ft
Year built
2009
Boat manufacturer
Steiger craft
Boat type
Pilothouse
Engine model
Suzuki
Powered by
2 x 250HP
Max cruising speed
35 knots
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