A Whiptail Adventure offers incredible sport fishing experience on the waters out of South Portland, Maine. Join their experienced captain and head out in pursuit of Groundfish and Shark. Plus, there is also a great chance to spot a whale on your way to the fishing trip!

Step onboard the ‘Whiptail’, a 27’ Sailfish 2660 center console. She is a clean, seaworthy fishing machine with twin 150 HP Yamaha 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 fish finding 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. The Whiptail is ready to provide you with a fabulous trip!

Your day with A Whiptail Adventure will begin when you cruise out of Spring Point Marina. The captain’s fishing spots are located 12-35 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 non-alcoholic drinks, some snacks, and the desire to catch fish!



Select date to see available trips and rates:

  • Private trip
    4 Hour Trip – Striped Bass
    FREE Cancellation 3 days notice
    4 Hour Trip, starts at 7:00 AM
    Seasonal trip May 15 - Oct 15
    $550
    Striped Bass fishing in Casco Bay.
  • Private trip
    4 Hour Trip – Striped Bass - PM
    FREE Cancellation 3 days notice
    4 Hour Trip, starts at 12:00 PM
    Seasonal trip May 15 - Oct 15
    $550
    Striped Bass fishing in Casco Bay.
  • Private trip
    4 Hour Trip – Striped Bass PM
    FREE Cancellation 3 days notice
    4 Hour Trip, starts at 2:00 PM
    Seasonal trip Sep 9 - Sep 9 (Fri)
    $550
    Striped Bass fishing in Casco Bay.
  • Private trip
    6 Hour Trip – Striped Bass
    FREE Cancellation 3 days notice
    6 Hour Trip, starts at 7:00 AM
    Seasonal trip May 15 - Oct 15
    $700
    Striped Bass fishing in Casco and Saco Bay.
  • Private trip
    6 Hour Trip – Striped Bass - PM
    FREE Cancellation 3 days notice
    6 Hour Trip, starts at 12:00 PM
    Seasonal trip May 15 - Oct 15
    $700
    Striped Bass fishing in Casco and Saco Bay.
  • Private trip
    8hr Striped Bass trip
    FREE Cancellation 3 days notice
    8 Hour Trip, starts at 7:00 AM
    Seasonal trip May 15 - Oct 15
    $800
    Explore Casco bay and experience a full tide swing chasing Stripers. Great full day experience fishing multiple spots and techniques.
  • Private trip
    6 Hour Trip – Groundfishing
    FREE Cancellation 3 days notice
    6 Hour Trip, starts at 7:00 AM
    Seasonal trip Jun 1 - Oct 15
    $950
    This trip is ideal for any angler. Target Cod, Haddock, Pollack and Halibut. Don't miss the bite when it's hot!
  • Private trip
    8 Hour Trip – Combo
    FREE Cancellation 3 days notice
    8 Hour Trip, starts at 7:00 AM
    Seasonal trip Jun 1 - Oct 15
    $1,200
    This is a combo trip. Target Groundfish and Shark with all the necessary equipment provided.
  • Private trip
    8 Hour Trip – Groundfishing
    FREE Cancellation 3 days notice
    8 Hour Trip, starts at 7:00 AM
    Seasonal trip May 20 - Oct 15
    $1,200
    If you want a few more hours on the water, this is your trip. Your targeted species will include Cod, Haddock, Pollack, and Halibut.
  • Private trip
    8 Hour Trip – Shark Fishing
    FREE Cancellation 3 days notice
    8 Hour Trip, starts at 7:00 AM
    Seasonal trip Jul 1 - Oct 15
    $1,200
    If you want to fight the monsters, look no further. Target Mako, Thresher, Porbeagle, and Blue Sharks.
There is 1 person looking at this charter.

About the Captain

Jason Eaton
South Portland, Maine, United States
ID & License verified
25 Customer reviews
Response time 2 hours
Member since September 2017
Captain Jason Eaton is an avid angler and a 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 sport fishing experience and come back home with an ice-chest full of memories.

About this listing

Targeted species

Bass (Striped) Striped Bass
Cod Cod
Haddock Haddock
Halibut Halibut

Boat specs

Sailfish 2660 (Center console) originally built in 2011. Powered by 2 150HP Yamaha engines, with a maximum cruising speed of 35 knots.

Length
27 ft
Capacity
4 persons

Types of fishing

Inshore Fishing
Offshore Fishing

Fishing techniques

Light Tackle
Heavy Tackle
Bottom Fishing
Spinning
Jigging
Drift Fishing
Deep Sea Fishing

Amenities

Toilet
Small Head for emergencies
GPS
Raymarine Axiom
Fishfinder
Raymarine Axiom Chirp
Live Bait Well
Radar
Raymarine

Trip includes

Rods, reels & tackle
Live Bait
Lures
Catch cleaning & filleting
Fishing License

Cancellation policy

Free cancellation up to 3 days prior to trip

You can cancel or modify your booking up to 3 days days before the trip date, free of charge. If you cancel or modify your booking later, or fail to show up, you'll forfeit 100% of what you've paid.

Listing policies

Pickup not included
Transfer to/from departure site is not included in trip rates.
Child Friendly
12yrs or older for offshore trips
No Alcohol
You Keep Catch
Catch and Release Allowed

Payment

Book with 10% deposit, pay rest to captain

When the captain confirms your trip, FishingBooker charges your credit card a 10% deposit to guarantee your reservation.

The remaining balance is to be paid directly to the charter operator on or prior to your trip date in one of the following payment methods:

Cash
Visa
Mastercard
American Express
PayPal

Customer reviews

Rating Summary
Excellent
4.9 / 5
out of 5 stars from 25 reviews
Boat
Excellent
5.0 / 5
Crew
Excellent
4.9 / 5
Experience
Excellent
4.8 / 5
Photos & videos by reviewers (46)
4 hour trip
4 hour trip
Fishing with Jason
+43
Angler Rating
24
0
1
0
0
Anglers Claimed
Good experience
95%
Friendly captain
100%
Recommend this charter
96%
Appropriate for children
95%
Satisfied with the boat
100%
Catch intended fish
90%
Sort By:
Featured  
Showing:
5 of 25 reviews
Ronald L.
Souderton, PA
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

6 hour trip with Captain Jason Eaton

VERIFIED   6 Hour Trip – Striped Bass on September 7, 2022
Hands down best fishing trip we have ever experienced. Captain Jason is the best charter Captain we have ever met. His knowledge...
Ronald L. recommends Whiptail Adventures
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  Jason Eaton Captain replied

Wayne S.
Stowe, VT
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Half day trip with captain Jason

VERIFIED   4 Hour Trip – Striped Bass on August 28, 2022
Captain Jason was fantastic. The boat was very comfortable and perfectly designed for fishing. We caught two nice Stripers...
Wayne S. recommends Whiptail Adventures
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You found this review helpful
  Jason Eaton Captain replied

Dave J.
Billings, MT
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

What a day

VERIFIED   4 Hour Trip – Striped Bass on August 29, 2022
I’m so pleased that we were privileged to fish with Jason. The day went exactly as he predicted. It was a great experience...
Dave J. recommends Whiptail Adventures
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  Jason Eaton Captain replied

John W.
Minot, ND
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

8 hour ground fishing

VERIFIED   8 Hour Trip – Groundfishing on July 20, 2022
Had a great day on the water with my 3 son-in-laws and caught fish until our arms ached. Jason runs a top notch operation and...
John W. recommends Whiptail Adventures
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  Jason Eaton Captain replied

Sarah M.
Waban, Massachusetts
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

4 hour trip

VERIFIED   4 Hour Trip – Striped Bass - PM on October 15, 2022
Booked a trip for my daughters birthday. The captain was great with communicating in timely manner and great with my Daughter...
Sarah M. recommends Whiptail Adventures
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You found this review helpful
  Jason Eaton Captain replied

FAQs about Whiptail Adventures

Whiptail Adventures offers the following trips to customers:
  • $550 per group - 4 Hour Trip – Striped Bass (4 hours)
  • $550 per group - 4 Hour Trip – Striped Bass - PM (4 hours)
  • $550 per group - 4 Hour Trip – Striped Bass PM (4 hours)
  • $700 per group - 6 Hour Trip – Striped Bass (6 hours)
  • $700 per group - 6 Hour Trip – Striped Bass - PM (6 hours)
  • $800 per group - 8hr Striped Bass trip (8 hours)
  • $950 per group - 6 Hour Trip – Groundfishing (6 hours)
  • $1,200 per group - 8 Hour Trip – Combo (8 hours)
  • $1,200 per group - 8 Hour Trip – Groundfishing (8 hours)
  • $1,200 per group - 8 Hour Trip – Shark Fishing (8 hours)

When you book a trip with Whiptail Adventures, you can expect the following amenities onboard:
  • Toilet Small Head for emergencies
  • GPS Raymarine Axiom
  • Fishfinder Raymarine Axiom Chirp
  • Live Bait Well
  • Radar Raymarine

Trips booked with Whiptail Adventures include:
  • Rods, reels & tackle
  • Live Bait
  • Lures
  • Catch cleaning & filleting
  • Fishing License

Whiptail Adventures offers the following types of fishing:
  • Inshore Fishing
  • Offshore Fishing

Whiptail Adventures offers the following fishing techniques:
  • Light Tackle
  • Heavy Tackle
  • Bottom Fishing
  • Spinning
  • Jigging
  • Drift Fishing
  • Deep Sea Fishing

Top targeted fish species with Whiptail Adventures include:
  • Bass (Striped)
  • Cod
  • Haddock
  • Halibut
  • Pollock
  • Shark (Blue)
  • Shark (Mako)
  • Shark (Porbeagle)
  • Shark (Thresher)