Toby Ann Charters
Toby Ann Charters runs angling trips out of Gloucester and offers to show you what the local fishery is all about.
Capt. Brian is here to get you on some fish, and to make sure you have fun doing it. You’ll be using techniques like bottom fishing, trolling, jigging, and spinning, depending on what you’re going after. As part of their 3 to 12-hour trips, you can target species like Haddock, Tuna, Bass, and Cod, depending on the current season and weather conditions.
Your boat for the day will be a 36’ Calvin Beal that fits up to 6 anglers at any one time. The boat comes with an ice box. The price of your trip includes all the rods, reels, and terminal tackle you’ll need for a productive day on the water. Your trip will include all the necessary fishing licenses for the day. You’re welcome to keep all legal species caught during the trip.
This is a children-friendly charter, so you’re welcome to bring your kids on for a fun fishing adventure.
Book your trip now and hit the water with Toby Ann Charters.
Customer reviews
Rating summary
Photos & videos by reviewers (97)
+94Angler rating
Anglers claimed
Good experience
98%
Appropriate for children
98%
Friendly captain
100%
Satisfied with the boat
100%
Recommend this charter
99%
Caught fish
98%
Jul 5, 2025
5 Hour Striped Bass PM
Great fun on the ocean! Five Stars isn't Enough!
Our group of five booked Toby Ann Charters for an afternoon striped bass trip and had a blast! Captain Brian somehow managed to juggle setting up all of the fishing rods, driving the boat, and being all-around entertaining all while showing us the best spots to find the fish. Everyone in our group caught at least one striper, thanks to Captain Brian's guidance. Highly recommend for anyone looking for some fun and some fish! Rob, Phill, Tyler, Justin, and Max.
Our group of five booked Toby Ann Charters for an afternoon striped bass trip and had a blast! Captain Brian somehow managed...
Jun 21, 2025
6 Hour Trip – Striped Bass
Hardest working captain out there!!!
Brian is just a machine! His knowledge of the area and experience is over the top. I booked a 6 hour charter for my son and I to get stripers . The day before a storm came through dropping the water temp enough to drive the fish to new grounds. Brian changed the game plan on a moments notice and wasn’t taking no for an answer! He found them and we had an amazing trip! He is just the coolest captain out there! If I could give him 10 stars I would. We will be back!! Jason and Sam
Brian is just a machine! His knowledge of the area and experience is over the top. I booked a 6 hour charter for my son and I...
Jun 22, 2025
4 Hour Trip – Striped Bass AM
What a great time we had!!!!
Excellent captain on a great boat! Captain Brian was very down to earth, and super nice so nice that he didn’t even curse once! He was out early looking around for fish b4 we even got there, and he got us on a hotspot within 10 mins and the fun started, fish after fish and the rest is history. Guy is a seasoned fisherman who’s been at the game 30yrs plus so don’t worry you will be in good hands. Can’t wait to go back out with captain Brian.Thanks
Excellent captain on a great boat! Captain Brian was very down to earth, and super nice so nice that he didn’t even curse once!...
Oct 14, 2024
5 Hour Striped Bass PM
Exceptional Experience with Captain Brian
We recently visited the area from Indiana had the pleasure of an afternoon fishing trip with Captain Brian, and despite the rainy, windy October weather, it turned out to be a fantastic experience. We spent the first hour catching live bait, and Captain Brian's expertise made it enjoyable and productive. Once we moved into the bay, the action was fast-paced. In just two hours, we landed 12 striped bass, with our first four casts resulting in four catches! We kept four and released the rest, all thanks to Captain Brian's skill and knowledge of the area. We highly recommend Captain Brian for anyone looking to fish in the area, and I’ll definitely be reaching out directly to him again on our next visit!
We recently visited the area from Indiana had the pleasure of an afternoon fishing trip with Captain Brian, and despite the rainy,...
Aug 10, 2024
6 Hour Trip – Striped Bass
5 Stars for our Captain Brian⭐️⭐️⭐️⭐️⭐️
We maxed out! But that is not why he got 5 stars. Brian is a great captain and he connected with our family right out of the port. He is a Gloucester native and knows the waters and the history and the fish & birds too! If you search for the shiny new boat with a crew of three - don’t fool yourself. Brian was solo and worked like four people. Keeping it light and committed to our overall experience. Even when one of us was a little queasy due to the swells, he readjusted his plan to take a smooth route but a successful one. 🐟🐟🐟🐟🐟 Thanks Captain Brian👍🏼
We maxed out! But that is not why he got 5 stars. Brian is a great captain and he connected with our family right out of the...
Trip availability and prices
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Customer reviews
Rating summary
Photos & videos by reviewers (97)
+94Angler rating
Anglers claimed
Good experience
98%
Appropriate for children
98%
Friendly captain
100%
Satisfied with the boat
100%
Recommend this charter
99%
Caught fish
98%
Experience:
Boat
Crew
Overall
Great fun on the ocean! Five Stars isn't Enough!
5 Hour Striped Bass PM on July 5, 2025
Our group of five booked Toby Ann Charters for an afternoon striped bass trip and had a blast! Captain Brian somehow managed to juggle setting up all of the fishing rods, driving the boat, and being all-around entertaining all while showing us the best spots to find the fish. Everyone in our group caught at least one striper, thanks to Captain Brian's guidance. Highly recommend for anyone looking for some fun and some fish! Rob, Phill, Tyler, Justin, and Max.
Our group of five booked Toby Ann Charters for an afternoon striped bass trip and had a blast! Captain Brian somehow managed to juggle setting up all of the fishing rods, driving the boat, and being all-around entertaining all while showing us the best spots to find the fish. Everyone in our group caught at least one striper, thanks to Captain Brian's guidance. Highly recommend for anyone looking for some fun and some fish! Rob, Phill, Tyler, Justin, and Max.
Experience:
Boat
Crew
Overall
Hardest working captain out there!!!
6 Hour Trip – Striped Bass on June 21, 2025
Brian is just a machine! His knowledge of the area and experience is over the top. I booked a 6 hour charter for my son and I to get stripers . The day before a storm came through dropping the water temp enough to drive the fish to new grounds. Brian changed the game plan on a moments notice and wasn’t taking no for an answer! He found them and we had an amazing trip! He is just the coolest captain out there! If I could give him 10 stars I would. We will be back!! Jason and Sam
Brian is just a machine! His knowledge of the area and experience is over the top. I booked a 6 hour charter for my son and I to get stripers . The day before a storm came through dropping the water temp enough to drive the fish to new grounds. Brian changed the game plan on a moments notice and wasn’t taking no for an answer! He found them and we had an amazing trip! He is just the coolest captain out there! If I could give him 10 stars I would. We will be back!! Jason and Sam
Experience:
Boat
Crew
Overall
What a great time we had!!!!
4 Hour Trip – Striped Bass AM on June 22, 2025
Excellent captain on a great boat! Captain Brian was very down to earth, and super nice so nice that he didn’t even curse once! He was out early looking around for fish b4 we even got there, and he got us on a hotspot within 10 mins and the fun started, fish after fish and the rest is history. Guy is a seasoned fisherman who’s been at the game 30yrs plus so don’t worry you will be in good hands. Can’t wait to go back out with captain Brian.Thanks
Excellent captain on a great boat! Captain Brian was very down to earth, and super nice so nice that he didn’t even curse once! He was out early looking around for fish b4 we even got there, and he got us on a hotspot within 10 mins and the fun started, fish after fish and the rest is history. Guy is a seasoned fisherman who’s been at the game 30yrs plus so don’t worry you will be in good hands. Can’t wait to go back out with captain Brian.Thanks
Experience:
Boat
Crew
Overall
Exceptional Experience with Captain Brian
5 Hour Striped Bass PM on October 14, 2024
We recently visited the area from Indiana had the pleasure of an afternoon fishing trip with Captain Brian, and despite the rainy, windy October weather, it turned out to be a fantastic experience. We spent the first hour catching live bait, and Captain Brian's expertise made it enjoyable and productive. Once we moved into the bay, the action was fast-paced. In just two hours, we landed 12 striped bass, with our first four casts resulting in four catches! We kept four and released the rest, all thanks to Captain Brian's skill and knowledge of the area. We highly recommend Captain Brian for anyone looking to fish in the area, and I’ll definitely be reaching out directly to him again on our next visit!
We recently visited the area from Indiana had the pleasure of an afternoon fishing trip with Captain Brian, and despite the rainy, windy October weather, it turned out to be a fantastic experience. We spent the first hour catching live bait, and Captain Brian's expertise made it enjoyable and productive. Once we moved into the bay, the action was fast-paced. In just two hours, we landed 12 striped bass, with our first four casts resulting in four catches! We kept four and released the rest,...
Experience:
Boat
Crew
Overall
5 Stars for our Captain Brian⭐️⭐️⭐️⭐️⭐️
6 Hour Trip – Striped Bass on August 10, 2024
We maxed out! But that is not why he got 5 stars. Brian is a great captain and he connected with our family right out of the port. He is a Gloucester native and knows the waters and the history and the fish & birds too! If you search for the shiny new boat with a crew of three - don’t fool yourself. Brian was solo and worked like four people. Keeping it light and committed to our overall experience. Even when one of us was a little queasy due to the swells, he readjusted his plan to take a smooth route but a successful one. 🐟🐟🐟🐟🐟 Thanks Captain Brian👍🏼
We maxed out! But that is not why he got 5 stars. Brian is a great captain and he connected with our family right out of the port. He is a Gloucester native and knows the waters and the history and the fish & birds too! If you search for the shiny new boat with a crew of three - don’t fool yourself. Brian was solo and worked like four people. Keeping it light and committed to our overall experience. Even when one of us was a little queasy due to the swells, he readjusted his plan to take...
FAQs about Toby Ann Charters
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