Gray Willow Charters 

5.0/5 (15 reviews)
 211 East Main Street, Gloucester, MA 01930, United States

Gray Willow Charters 

5.0/5 (15 reviews)
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211 East Main Street
Gloucester, MA, United States
You may qualify for a Loyalty Program discount with Gray Willow Charters. To check if you can use a Loyalty Program discount for your selected dates, please sign in.

Gray Willow Charters is located in Gloucester and offers to show you a memorable time in these waters.

Capt. Ryan will do his best to make sure you have a fun day full of fishing. This involves 6 to 12-hour trips, mainly fishing for Haddock, Tuna, Bass, Cod, Bluefish, and Mackerel, depending on the season and conditions on the day. On these trips, you can expect to use techniques such as light tackle, heavy tackle, bottom fishing, trolling, fly fishing, drift fishing, jigging, kite fishing, popping, and spinning.

Your fishing adventure starts on a 35’ Duffy boat that can safely take up to 6 anglers. This boat comes with a toilet, ac, and an ice-box.

All rods, reels, and terminal tackle are included in the price so you can focus on what really matters, fishing. Your trip will include all the necessary fishing licenses for the day.

Book your trip now and hit the water with Gray Willow Charters.

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Customer reviews

Rating summary

5.0/5
out of 5 stars from 15 reviews
Boat
5.0/5
Crew
5.0/5
Experience
5.0/5

Photos & videos by reviewers (21)

600 pound 112" Bluefin Tuna
600 pound 112" Bluefin Tuna
600 pound 112" Bluefin Tuna
+18

Angler rating

14
0
0
0
0

Anglers claimed

Good experience

100%

Appropriate for children

100%

Friendly captain

100%

Satisfied with the boat

100%

Recommend this charter

93%

Caught fish

100%

Showing 1 - 5 of 15 reviews
Showing: 5 of 15 reviews
Ryan Mcshera
Ryan Mcshera
Waltham, Massachusetts
5.0
Tuna Excursion!
12 Hour Trip – Giant Bluefin Tuna on July 16, 2025
We had an amazing time with Captain Ryan on the Willow Gray! My company chartered a full day tuna fishing trip for three clients. Including Captain, there were five of us on the boat. We arrived to the dock and the boat was clean, rigged and ready to go. Ryan oriented us to the boat and we were off on our adventure. We steamed out of harbor and Ryan put us right on the fish. None of us had much experience with this kind of fishing. Once we hooked up to the tuna Ryan was super calm and his directions were easy to follow. An hour and a half later we had a 450 pound tuna tied up to the side of the boat. The experience far exceeded expectations! Planning the trip with Ryan was easy. He responded quickly to messages and answered all our questions. If you're looking to book a saltwater fishing trip in the waters surrounding Massachusetts, I would highly recommend you reach out to Ryan and get on the Willow Gray.
Reported Catch:
Bluefin Tuna
Atlantic Mackerel
0
Joey Solomon
Joey Solomon
Islip, New York
5.0
Full day giant tuna
12 Hour Trip – Giant Bluefin Tuna on July 16, 2025
Had a great day catching a giant with Capt Ryan! The vibe was relaxed, though he was on top of everything, and made sure we had everything we needed. He wasn’t concerned with burning fuel, and after a long stream we immediately got tight to a big fish. It was on the deck an hour and a half later and Capt Ryan did a great job providing instruction and making sure everyone got involved throughout the fight. All expected safety equipment was on board and the boat and all equipment were in good shape. Hope to fish with Capt Ryan again soon!
Reported Catch:
Bluefin Tuna
0
James Dudas
James Dudas
5.0
Verified
Awesome day
Full Day Ground Fishing (6 AM) on June 29, 20246 adults
I’ve been going to Gloucester for five years fishing for a father and sons trip this is ultimately the best trip I’ve had in five years going to Gloucester hanging out with these two guys. Ryan and Ben were the most awesome guys to spend your day with. I couldn’t say anymore they made our trip amazing they were awesome. They worked hard. They caught us a lot of fish, they were the bomb and I’m thinking I’m going back in August. I will fish with them any day of the week so fantastic people to spend your day with with your sons fathers daughters even I mean I can’t say anymore does the best I highly recommend them book a chart with them you will not be disappointed , I’m getting ready to book another one and I never do two in one year but I’m ready to book another one in August
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Reported Catch:
Haddock
0
SCOTT SMITH
SCOTT SMITH
Lincoln, NE
5.0
Verified
12 FOOTER!!! Sharking with Ryan was the Right Move
10 Hour Trip – Shark on July 9, 20233 adults1 child
My family and I had a phenomenal time with Ryan. He's very inviting and down to earth. I think at one point we all were napping except for wife who was reading a book as we waited for the sharks and tuna, all the while Captain Ryan chummed the water and kept an eye out for fish. (Allegedly wife and Ryan saw whales while I napped... the jury is still out "they were too far away to get a video" my wife says. Lol) We brought in two sharks one was about 12 feet long and is without a doubt a once in a lifetime opportunity. We kept busy fishing for bait fish while we waited for the big guys. Family estimated we caught over 75 of them. Ryan worked like a dog the entire time working the water and fishing gear to make our experience as great as possible. When we decide to come back to Boston we're going to hit up Ryan for a trip. Further, Ryan also did a great job about explaining the local land marks and some history. We talked about the fishing industry and what fisherman and the government are doing to help preserve the fish for future generations. Ryan's attitude reflects that of a person who wants to continue to improve his skill and make sure the best possible experience is had. Ryan is quick to respond to messages and was clear in helping me navigate what I need and want out of the trip. This fishing trip will be the trip that my children will tell their grandkids about long after I'm gone.
Review media 0
Review media 1
1
James Alba
James Alba
5.0
Verified
1/2 Day Fishing Trip
Half Day Ground Fishing on June 15, 20245 adults
Captain Ryan and his mate Colby were hands down the best private charter I ever been on. Very knowledgeable and a great guy! There were 5 of us in our charter and as soon as Captain Ryan drove to the spot. We all started to catch fish; it was so surreal. We caught over 20 fish. We will enjoy these memories forever! Thank you. We will be back!
Review media 0
0

Trip availability and prices

Trip Date:
Days:
Group Size:
Select date to see availability
November 2025
SuMoTuWeThFrSa
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Number of days
1
Group Size
2 adults • 0 children
Change
Almost there...
Half Day Ground Fishing
Low rate deposit non-refundable
5 Hour Trip, starts at 8:00 AM
Seasonal trip May 1 - Jul 1
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US $750 
Entire boat: up to 6 people
Night Bass
Low rate deposit non-refundable
6 Hour Trip, starts at 8:00 PM
Seasonal trip Jun 10 - Aug 20
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US $750 
Entire boat: up to 6 people
10 Hour Trip – Shark
Low rate deposit non-refundable
10 Hour Trip, starts at 6:00 AM
Seasonal trip Jun 15 - Nov 1
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US $1,100 
Entire boat: up to 6 people
Full Day Ground Fishing (6 AM)
Low rate deposit non-refundable
8 Hour Trip, starts at 6:00 AM
Seasonal trip May 1 - Jul 1
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US $1,100 
Entire boat: up to 6 people
Full Day Ground Fishing (7 AM)
Low rate deposit non-refundable
9 Hour Trip, starts at 7:00 AM
Seasonal trip May 1 - Jul 1
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US $1,100 
Entire boat: up to 6 people
12 Hour Trip – Giant Bluefin Tuna
Low rate deposit non-refundable
12 Hour Trip, starts at 4:00 AM
Seasonal trip Jun 15 - Dec 1
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US $1,400 
Entire boat: up to 6 people

Customer reviews

Rating summary

5.0/5
out of 5 stars from 15 reviews
Boat
5.0/5
Crew
5.0/5
Experience
5.0/5

Photos & videos by reviewers (21)

600 pound 112" Bluefin Tuna
600 pound 112" Bluefin Tuna
600 pound 112" Bluefin Tuna
+18

Angler rating

14
0
0
0
0

Anglers claimed

Good experience

100%

Appropriate for children

100%

Friendly captain

100%

Satisfied with the boat

100%

Recommend this charter

93%

Caught fish

100%

Showing 1 - 5 of 15 reviews
Showing: 5 of 15 reviews
Ryan Mcshera
Ryan Mcshera
Waltham, Massachusetts
5.0
Tuna Excursion!
12 Hour Trip – Giant Bluefin Tuna on July 16, 2025
We had an amazing time with Captain Ryan on the Willow Gray! My company chartered a full day tuna fishing trip for three clients. Including Captain, there were five of us on the boat. We arrived to the dock and the boat was clean, rigged and ready to go. Ryan oriented us to the boat and we were off on our adventure. We steamed out of harbor and Ryan put us right on the fish. None of us had much experience with this kind of fishing. Once we hooked up to the tuna Ryan was super calm and his directions were easy to follow. An hour and a half later we had a 450 pound tuna tied up to the side of the boat. The experience far exceeded expectations! Planning the trip with Ryan was easy. He responded quickly to messages and answered all our questions. If you're looking to book a saltwater fishing trip in the waters surrounding Massachusetts, I would highly recommend you reach out to Ryan and get on the Willow Gray.
Reported Catch:
Bluefin Tuna
Atlantic Mackerel
0
Joey Solomon
Joey Solomon
Islip, New York
5.0
Full day giant tuna
12 Hour Trip – Giant Bluefin Tuna on July 16, 2025
Had a great day catching a giant with Capt Ryan! The vibe was relaxed, though he was on top of everything, and made sure we had everything we needed. He wasn’t concerned with burning fuel, and after a long stream we immediately got tight to a big fish. It was on the deck an hour and a half later and Capt Ryan did a great job providing instruction and making sure everyone got involved throughout the fight. All expected safety equipment was on board and the boat and all equipment were in good shape. Hope to fish with Capt Ryan again soon!
Reported Catch:
Bluefin Tuna
0
James Dudas
James Dudas
5.0
Verified
Awesome day
Full Day Ground Fishing (6 AM) on June 29, 20246 adults
I’ve been going to Gloucester for five years fishing for a father and sons trip this is ultimately the best trip I’ve had in five years going to Gloucester hanging out with these two guys. Ryan and Ben were the most awesome guys to spend your day with. I couldn’t say anymore they made our trip amazing they were awesome. They worked hard. They caught us a lot of fish, they were the bomb and I’m thinking I’m going back in August. I will fish with them any day of the week so fantastic people to spend your day with with your sons fathers daughters even I mean I can’t say anymore does the best I highly recommend them book a chart with them you will not be disappointed , I’m getting ready to book another one and I never do two in one year but I’m ready to book another one in August
Review media 0
Review media 1
Review media 2
Review media 3
Review media 4
Reported Catch:
Haddock
0
SCOTT SMITH
SCOTT SMITH
Lincoln, NE
5.0
Verified
12 FOOTER!!! Sharking with Ryan was the Right Move
10 Hour Trip – Shark on July 9, 20233 adults1 child
My family and I had a phenomenal time with Ryan. He's very inviting and down to earth. I think at one point we all were napping except for wife who was reading a book as we waited for the sharks and tuna, all the while Captain Ryan chummed the water and kept an eye out for fish. (Allegedly wife and Ryan saw whales while I napped... the jury is still out "they were too far away to get a video" my wife says. Lol) We brought in two sharks one was about 12 feet long and is without a doubt a once in a lifetime opportunity. We kept busy fishing for bait fish while we waited for the big guys. Family estimated we caught over 75 of them. Ryan worked like a dog the entire time working the water and fishing gear to make our experience as great as possible. When we decide to come back to Boston we're going to hit up Ryan for a trip. Further, Ryan also did a great job about explaining the local land marks and some history. We talked about the fishing industry and what fisherman and the government are doing to help preserve the fish for future generations. Ryan's attitude reflects that of a person who wants to continue to improve his skill and make sure the best possible experience is had. Ryan is quick to respond to messages and was clear in helping me navigate what I need and want out of the trip. This fishing trip will be the trip that my children will tell their grandkids about long after I'm gone.
Review media 0
Review media 1
1
James Alba
James Alba
5.0
Verified
1/2 Day Fishing Trip
Half Day Ground Fishing on June 15, 20245 adults
Captain Ryan and his mate Colby were hands down the best private charter I ever been on. Very knowledgeable and a great guy! There were 5 of us in our charter and as soon as Captain Ryan drove to the spot. We all started to catch fish; it was so surreal. We caught over 20 fish. We will enjoy these memories forever! Thank you. We will be back!
Review media 0
0

FAQs about Gray Willow Charters

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The fish you can target

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What is the boat like?

Boat Image
Boat category
Cabin cruisers
Capacity
6 persons
Boat length
35 ft
Year built
2000
Restored in
2010
Boat manufacturer
Duffy
Boat type
Downeast

Engine model
Cummins
Powered by
1 x 450HP
Max cruising speed
16 knots
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