Gray Willow Charters
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.
Customer reviews
Rating summary
Photos & videos by reviewers (21)
+18Angler rating
Anglers claimed
Good experience
100%
Appropriate for children
100%
Friendly captain
100%
Satisfied with the boat
100%
Recommend this charter
93%
Caught fish
100%
Waltham, Massachusetts
Jul 16, 2025
12 Hour Trip – Giant Bluefin Tuna
Tuna Excursion!
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.
We had an amazing time with Captain Ryan on the Willow Gray! My company chartered a full day tuna fishing trip for three clients....
Islip, New York
Jul 16, 2025
12 Hour Trip – Giant Bluefin Tuna
Full day giant tuna
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!
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...
Jun 29, 2024
Full day ground fish
Awesome day
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
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...
Lincoln, NE
Jul 9, 2023
10 Hour Trip – Shark
12 FOOTER!!! Sharking with Ryan was the Right Move
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.
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...
Jun 15, 2024
Half day ground fishing
1/2 Day Fishing Trip
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!
Captain Ryan and his mate Colby were hands down the best private charter I ever been on. Very knowledgeable and a great guy!...
Trip availability and prices
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Customer reviews
Rating summary
Photos & videos by reviewers (21)
+18Angler rating
Anglers claimed
Good experience
100%
Appropriate for children
100%
Friendly captain
100%
Satisfied with the boat
100%
Recommend this charter
93%
Caught fish
100%
Waltham, Massachusetts
Experience:
Boat
Crew
Overall
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.
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...
Islip, New York
Experience:
Boat
Crew
Overall
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!
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...
Experience:
Boat
Crew
Overall
Awesome day
Full day ground fish on June 29, 2024
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
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...
Lincoln, NE
Experience:
Boat
Crew
Overall
12 FOOTER!!! Sharking with Ryan was the Right Move
10 Hour Trip – Shark on July 9, 2023
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.
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...
Experience:
Boat
Crew
Overall
1/2 Day Fishing Trip
Half day ground fishing on June 15, 2024
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!
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!
FAQs about Gray Willow Charters
The fish you can target
What is the boat like?
