Whiptail Adventures

4.9/5 (107 reviews)

Spring Point Drive, South Portland, ME 04106, United States–

Whiptail Adventures

4.9/5 (107 reviews)

Spring Point Drive

South Portland, ME, United States

Trips & prices Targeted species Boat info What's biting What's included Contact captain

Trips & prices What's included Targeted species Boat info Reviews Contact captain

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!

Popular features

Fishing license

Live bait

You keep catch

Catch cleaning & filleting

Toilet

Popular features

Fishing license

Live bait

You keep catch

Catch cleaning & filleting

Toilet

Rating

4.9

107 reviews

4.9

Boat & equipment

4.9

Captain & crew

4.8

Fishing Experience

Anglers' gallery (135)

What anglers say

96%

Great experience

93%

Family friendly

100%

Friendly captain

100%

Good boat

97%

Recommended

93%

Caught fish

All reviews (107)

Filter

Sort by: Featured

Showing 1 – 5 of 107 reviews

Tim Evan

Texas, US

•

Member since 2026

5.0

Verified

New

Excellent trip

4 Hour Trip – Striped Bass - 12:00 PM on May 26, 2026 • 3 adults

Captain Jason was awesome. he was extremely knowledgeable about the area and the waters. I had my 2 boys with me (19 and 17), and none of us had done any ocean fishing. Jason was extremely patient in teaching everyone the proper techniques. I’d definitely recommend Whiptail to others and would go out on the water with Jason again.

Response from Captain

May 28, 2026

had a great tome with you guys!  

David Nassif

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!

Reported catch:

Response from Captain

August 28, 2025

thank you for the kind words!  had a great time with you guys!  hope we can do it again!

Robert Farrell

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.

Response from Captain

July 26, 2025

I had a great time!   Thanks

Cameron M. Brown

Maine, US

•

Member since 2025

5.0

Verified

Early season striper fishing produces three landings.

4 Hour Trip – Striped Bass - 12:00 PM on June 22, 2025 • 4 adults

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.

Response from Captain

June 25, 2025

I had a great time with you guys

Karen Rancourt

Maine, US

•

Member since 2026

5.0

Verified

New

16th birthday

4 Hour Trip – Striped Bass on May 23, 2026 • 3 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.

Response from Captain

May 23, 2026

had a great time with the guys.  thanks

Trip availability and prices

Trip Date:

Days:

Group Size:

Select date to see availability

June 2026

Su	Mo	Tu	We	Th	Fr	Sa

Number of days

Group Size

2 adults • 0 children

Change

Almost there...

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

US $400

Entire boat: up to 6 people

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

US $600

Entire boat: up to 6 people

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

US $600

Entire boat: up to 6 people

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

US $800

Entire boat: up to 6 people

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

US $950

Entire boat: up to 6 people

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

US $1,050

Entire boat: up to 6 people

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

US $1,300

Entire boat: up to 6 people

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

US $1,300

Entire boat: up to 6 people

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

US $1,300

Entire boat: up to 6 people

US $1,300

Entire boat: up to 6 people

There are 22 people looking at this charter.

Rating

4.9

107 reviews

4.9

Boat & equipment

4.9

Captain & crew

4.8

Fishing Experience

Anglers' gallery (135)

What anglers say

96%

Great experience

93%

Family friendly

100%

Friendly captain

100%

Good boat

97%

Recommended

93%

Caught fish

All reviews (107)

Filter

Sort by: Featured

Showing 1 – 5 of 107 reviews

Tim Evan

Texas, US

Member since 2026

5.0

Verified

New

Excellent trip

4 Hour Trip – Striped Bass - 12:00 PM on May 26, 2026 • 3 adults

Captain Jason was awesome. he was extremely knowledgeable about the area and the waters. I had my 2 boys with me (19 and 17), and none of us had done any ocean fishing. Jason was extremely patient in teaching everyone the proper techniques. I’d definitely recommend Whiptail to others and would go out on the water with Jason again.

Response from Captain

May 28, 2026

had a great tome with you guys!  

David Nassif

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!

Reported catch:

Response from Captain

August 28, 2025

thank you for the kind words!  had a great time with you guys!  hope we can do it again!

Robert Farrell

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.

Response from Captain

July 26, 2025

I had a great time!   Thanks

Cameron M. Brown

Maine, US

Member since 2025

5.0

Verified

Early season striper fishing produces three landings.

4 Hour Trip – Striped Bass - 12:00 PM on June 22, 2025 • 4 adults

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.

Response from Captain

June 25, 2025

I had a great time with you guys

Karen Rancourt

Maine, US

Member since 2026

5.0

Verified

New

16th birthday

4 Hour Trip – Striped Bass on May 23, 2026 • 3 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.

Response from Captain

May 23, 2026

had a great time with the guys.  thanks

FAQs about Whiptail Adventures

The fish you can target

What is the boat like?

Boat category

Cabin cruisers

Capacity

6 persons

Boat length

28 ft

Year built

2009

Boat manufacturer

Steiger craft

Boat type

Pilothouse

Engine model

Suzuki

2 x 250HP

Max cruising speed

35 knots

Whiptail Adventures

Rating

Anglers' gallery (135)

What anglers say

All reviews (107)

Trip availability and prices

Rating

Anglers' gallery (135)

What anglers say

All reviews (107)

FAQs about Whiptail Adventures

The fish you can target

What is the boat like?

What’s biting in South Portland right now

Compare similar fishing charters