Toby Ann Charters
Toby Ann Charters
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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.
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.
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Trip availability and prices
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Customer reviews
Rating
Anglers' gallery (156)
What anglers say
Reviews (146)
David Douglas•
Massachusetts, USMember since 20265.0Verifiedour trip was everything we had hoped for!
6 Hour Haddock and Cod PM on August 16, 2026 • 6 adultsI took my 5 kids ages 24-14 for our first deep sea advnture. Captain Brian prior to our trip kept good communication with us in regards to questions I had. He offered to change the departure time to better acomodate us and was at the dock precisely at our new agreed time where he met us with a smile and " hop aboard". We were instantly comfortable with Brian. My kids have never fished deep and Capt Brian gave us lessons and assistance . By the end he had everyone tuned in and catching fish. we caught lots of fish, had. beautiful day and we for sure wil b booking again yearly and are planning a striper trip in another month! THANKS AGAIN , BRIAN! Douglas Family Fishing Trip 2026....
Ryan Shaw•Arizona, USMember since 20265.0VerifiedIncedible Family Trip
6 Hour Trip – Haddock on July 3, 2026 • 5 adults • 3 childrenwe had an amazing time with Captain Brian. my wife and I and our 3 boys went out for a 6 hour charter with Toby Ann, and it was their first charter. Captain Brian was amazing with our boys, and is just a great host all sround. Good conversation, and he clearly knows where to go in Gloucester to give you the nest chance to be on the fish. Highly recommend this charter to anyone who’s looking to charter a boat out of Gloucester… my family and i will be back out with Captain Brian!
David AbbottRepeat angler•California, US•Member since 20252 trips5.0VerifiedNewFantastic trip for striped bass
4 Hour Trip – Striped Bass AM on August 30, 2026 • 4 adultsWhat a fantastic morning of fishing! Capt. Brian was great with my boys and we landed several big guys. We were catch-and-release but we had a bunch of keepers for sure - could have filled a cooler. Would definitely recommend this great boat and captain! We will be back!
Anthony FratoniRepeat angler•Massachusetts, US•Member since 20262 trips5.0VerifiedNewstriper fishing
4 Hour Trip – Striped Bass AM on September 12, 2026 • 2 adults • 1 childthis is the second time I have been on the Toby Inn and it was a great experience. We caught 10 stripes two keepers. It was a great day. The Captain is great with children. Very knowledgeable. Boat was great. I would recommend it to anybody.
- Anthony FratoniRepeat angler•Massachusetts, US•Member since 20262 trips5.0VerifiedNew
first trip on Toby Ann Charters
4 Hour Trip – Striped Bass AM on August 26, 2026 • 2 adults • 1 childwe had a good time on the boat Captain Brian is a very nice person very knowledgeable. We caught nice fish overall great experience. I would recommend him if anybody’s looking to do any kind of saltwater fishing charters.
Jason MonniereRepeat angler•Vermont, US•Member since 20252 trips5.0VerifiedCrushed it!!!
8 Hour Trip – Striped Bass on June 23, 2026 • 2 adults2nd time with captain Brian and yet again he put us on the fish and filled our bags up! We will be bavk next year!! He worked his butt off amdvhis knowledge of ghe area is amazing. He will run the deck all day long but if you have a desire or experience he will let you get you hands dirty! Thanks captain see you next year!
Zhongzhu ChenRepeat angler•Massachusetts, US•Member since 20242 trips5.0VerifiedFishing with Brian
4 Hour Striped Bass PM on August 21, 2026 • 4 adults • 1 childHad a great day fishing with the captain! We caught two striped bass while the other boats around us didn’t have much luck. The captain was very experienced and knew exactly where to go. Great trip, and we would definitely recommend him!
Evelyn Doherty•Massachusetts, USMember since 20264.7Verifiedamazing fishing experience. great captain
4 Hour Striped Bass PM on July 20, 2026 • 6 adults • 4 childrenCaptain Brian was so patient, kind, and went out of his way to make our 7-year-old and friends have the best experience. The quality of fish was more than the quality, but the captain was determined to find us some beauties. We had to move 4 times, but we caught a 31, 32, and 38-inch bass. Everyone had a blast. Highly recommend.
Melanie PfefferRepeat angler•Michigan, US•Member since 20224 trips5.0VerifiedWe had a great time, caught lots of fish and enjoyed a beautiful day!
4 Hour Striped Bass PM on July 9, 2026 • 2 adultsCaptain Bryan was awesome! We had a great time, caught lots of fish and enjoyed a beautiful day! Captain was very knowledgeable and we had a great time and would highly recommend this trip!
Steven Lindale•Delaware, USMember since 20265.0VerifiedAwesome
4 Hour Trip – Striped Bass AM on July 13, 2026 • 5 adultsCaptain Brian was awesome. He was very patient with everyone explaining the how and why at to way to fish. We had a great day on the water, we'll be back.
Rating
Anglers' gallery (156)
What anglers say
All reviews (146)
I took my 5 kids ages 24-14 for our first deep sea advnture. Captain Brian prior to our trip kept good communication with us in regards to questions I had. He offered to change the departure time to better acomodate us and was at the dock precisely at our new agreed time where he met us with a smile and " hop aboard". We were instantly comfortable with Brian. My kids have never fished deep and Capt Brian gave us lessons and assistance . By the end he had everyone tuned in and catching fish. we caught lots of fish, had. beautiful day and we for sure wil b booking again yearly and are planning a striper trip in another month! THANKS AGAIN , BRIAN! Douglas Family Fishing Trip 2026....
we had an amazing time with Captain Brian. my wife and I and our 3 boys went out for a 6 hour charter with Toby Ann, and it was their first charter. Captain Brian was amazing with our boys, and is just a great host all sround. Good conversation, and he clearly knows where to go in Gloucester to give you the nest chance to be on the fish. Highly recommend this charter to anyone who’s looking to charter a boat out of Gloucester… my family and i will be back out with Captain Brian!
All around, ouldnt have asked for a better experience! It was easy to park and board the boat, Captain Brian was clear with his communication before departure. He was excellent with our two kids, one of whom asked LOTS of questions. And best of all, we slayed stripped bass all day long! Would highly recommend!
What a fantastic morning of fishing! Capt. Brian was great with my boys and we landed several big guys. We were catch-and-release but we had a bunch of keepers for sure - could have filled a cooler. Would definitely recommend this great boat and captain! We will be back!
this is the second time I have been on the Toby Inn and it was a great experience. We caught 10 stripes two keepers. It was a great day. The Captain is great with children. Very knowledgeable. Boat was great. I would recommend it to anybody.
FAQs about Toby Ann Charters
- US $650 per group - 4 Hour Striped Bass PM (4 hours)
- US $650 per group - 4 Hour Trip – Striped Bass AM (4 hours)
- US $750 per group - 5 hour Striped Bass AM (5 hours)
- US $750 per group - 5 Hour Striped Bass PM (8 hours)
- US $850 per group - 6 Hour Haddock and Cod PM (6 hours)
- US $850 per group - 6 Hour Trip – Haddock (6 hours)
- US $850 per group - 6 Hour Trip – Striped Bass (6 hours)
- US $850 per group - Shark Charter (6 hours)
- US $1,050 per group - 8 Hour Trip – Striped Bass (8 hours)
- US $1,100 per group - Shark Charter (8 hours)
- US $1,450 per group - 10 Hour Trip – Bluefin Tuna (10 hours)
- US $1,750 per group - Bluefin Tuna Marathon Day (12 hours)
- Toilet Privy style toilet down below
- GPS
- Fishfinder
- Bed
- Live bait well
- Ice box
- Radar
- Rods, reels & tackle
- Live bait
- Catch cleaning & filleting
- Fishing license
- Inshore fishing
- Nearshore fishing
- Offshore fishing
- Light tackle
- Heavy tackle
- Bottom fishing
- Trolling
- Spinning
- Jigging
- Deep sea fishing
- Bass (Striped)
- Cod
- Haddock
- Tuna (Bluefin)
Your captain
Gloucester, Massachusetts, United States
Captain Brian Higgins is a passionate angler who looks forward to showing you a fun day out on the water.
Real catches by this captain
What is the boat like?
What kind of fishing will you do?
Which fishing techniques you can try
Which amenities are available onboard
How cancellations work
You can cancel or modify your booking up to 3 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.
What the listing policies are
Pickup agreed upon reservation
Transfer to/from departure site may be available and included in price depending on your location and distance from the dock.
How you can pay
When the captain confirms your trip, FishingBooker charges your credit card a 20% 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
PayPal
Checks
What’s biting in Gloucester right now
Bass (Striped)
Cod
Haddock
Tuna (Bluefin)Compare similar fishing charters
5.0(105)35 ftGroup size 1 - 61 - 6
+83 hour trip • 6 personsUS $579
