
Departing from Gloucester, Massachusetts, and servicing the Cape Ann Area, Windfish Private Tours and Fishing Charters offers trips for those seeking a diverse New England fishing experience. The friendly and knowledgeable Captains provide safe, informative marine navigation and strive to exceed your expectations!
Everyone has different interests, so Windfish offers a range of activities on the water that appeal to timid first-time mariners and experienced ocean-goers of all age groups. Whether your interest be in fishing, exploration, sightseeing, or education in wildlife, they strive to ensure everyone onboard has a full and satisfying experience! You can expect the focus to change mid-trip if a new opportunity arises or if the activity you pursued was accomplished or has grown stale. If time permits, feel free to ask the Captain to mix it up at any point in your trip!
You can expect to fish inshore, near shore, or offshore targeting your preference of
Mackerel, Striped Bass, Bluefish, Haddock, Cod, Whiting, Lobster, and more, depending on the time of year.
The Windfish is a comfortable and clean 25' Pilothouse with a capacity for 4 passengers and is equipped with all modern necessities for fishing and navigation. There's a camping toilet in the privacy of the cabin for your convenience (no built-in head). Bait, rods, reels, and tackle are provided, as well as lures, but feel free to bring your own.
You may bring any food or beverages you like. There are some snacks, water, and nausea remedies aboard as well. Beer/Wine/Seltzers are fine - No hard liquor or glass is permitted. Don't forget to dress and prepare appropriately for the weather and wear closed-toed shoes. No hard-body coolers or chairs are permitted - There is an ice chest and seating onboard. All capable ages are permitted aboard. Children under 12 must wear appropriately-fitting PFDs (2 child-sized PFDs are stored aboard).
Rating summary
Photos & videos by reviewers (12)


+9Angler rating
Anglers claimed
Good experience
100%
Appropriate for children
100%
Friendly captain
100%
Satisfied with the boat
100%
Recommend this charter
100%
Caught fish
100%
Jul 19, 2025
Half Trip (PM) – Inshore
We had an absolutely incredible experience with Captain Dan! From start to finish, everything was smooth, professional, and most importantly—fun. The captain was knowledgeable, friendly, and clearly passionate about what he does. He made sure everyone on board felt comfortable, whether you were a seasoned angler or a total beginner. The boat was clean, well-maintained, and fully equipped with all the gear we needed. We hit some great fishing spots, and he knew exactly where to go to find the action. We caught Striped Bass, and the excitement on board was contagious. Whether you’re looking for a serious fishing adventure or just a fun day on the water with family or friends, I highly recommend Captain Dan. I’ll definitely be booking with him again!
We had an absolutely incredible experience with Captain Dan! From start to finish, everything was smooth, professional, and most...
Sep 21, 2025
Half Trip (AM) – Inshore
First fish charter. We had two little guys with us, captain was patient with them and did his best to give the best experience which it was!!! We all had a blast. Kids said it was the best day ever! Would highly recommend and we’ll be back!
First fish charter. We had two little guys with us, captain was patient with them and did his best to give the best experience...


Jul 29, 2025
Half Trip (AM) – Inshore
Captain Dan was a true gentleman. We had so much on the water with him. From beginning to end it was a spectacular experience. He never gave up… and the icing on the cake was the striped bass we came home with. 🎣
Captain Dan was a true gentleman. We had so much on the water with him. From beginning to end it was a spectacular experience....
Sep 15, 2025
Half Trip (PM) – Inshore
the guys truly enjoyed their trip thank you so much for making it a Time To Remember. the weather was beautiful the area is beautiful. can't wait to come back and catch more fish
the guys truly enjoyed their trip thank you so much for making it a Time To Remember. the weather was beautiful the area is beautiful....

Aug 2, 2025
Half Trip (AM) – Inshore
Dan did a great job. Worked hard to find some fish and keep the lines in the water. His efforts were rewarded toward the end of the day when the stripers started hitting.
Dan did a great job. Worked hard to find some fish and keep the lines in the water. His efforts were rewarded toward the end of...
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Rating summary
Photos & videos by reviewers (12)


+9Angler rating
Anglers claimed
Good experience
100%
Appropriate for children
100%
Friendly captain
100%
Satisfied with the boat
100%
Recommend this charter
100%
Caught fish
100%
Experience:
Boat
Crew
Overall
Half Trip (PM) – Inshore on July 19, 2025
We had an absolutely incredible experience with Captain Dan! From start to finish, everything was smooth, professional, and most importantly—fun. The captain was knowledgeable, friendly, and clearly passionate about what he does. He made sure everyone on board felt comfortable, whether you were a seasoned angler or a total beginner. The boat was clean, well-maintained, and fully equipped with all the gear we needed. We hit some great fishing spots, and he knew exactly where to go to find the action. We caught Striped Bass, and the excitement on board was contagious. Whether you’re looking for a serious fishing adventure or just a fun day on the water with family or friends, I highly recommend Captain Dan. I’ll definitely be booking with him again!
We had an absolutely incredible experience with Captain Dan! From start to finish, everything was smooth, professional, and most importantly—fun. The captain was knowledgeable, friendly, and clearly passionate about what he does. He made sure everyone on board felt comfortable, whether you were a seasoned angler or a total beginner. The boat was clean, well-maintained, and fully equipped with all the gear we needed. We hit some great fishing spots, and he knew exactly where to go to find the...
Experience:
Boat
Crew
Overall
Half Trip (AM) – Inshore on September 21, 2025
First fish charter. We had two little guys with us, captain was patient with them and did his best to give the best experience which it was!!! We all had a blast. Kids said it was the best day ever! Would highly recommend and we’ll be back!
First fish charter. We had two little guys with us, captain was patient with them and did his best to give the best experience which it was!!! We all had a blast. Kids said it was the best day ever! Would highly recommend and we’ll be back!


Experience:
Boat
Crew
Overall
Half Trip (AM) – Inshore on July 29, 2025
Captain Dan was a true gentleman. We had so much on the water with him. From beginning to end it was a spectacular experience. He never gave up… and the icing on the cake was the striped bass we came home with. 🎣
Captain Dan was a true gentleman. We had so much on the water with him. From beginning to end it was a spectacular experience. He never gave up… and the icing on the cake was the striped bass we came home with. 🎣
Experience:
Boat
Crew
Overall
Half Trip (PM) – Inshore on September 15, 2025
the guys truly enjoyed their trip thank you so much for making it a Time To Remember. the weather was beautiful the area is beautiful. can't wait to come back and catch more fish
the guys truly enjoyed their trip thank you so much for making it a Time To Remember. the weather was beautiful the area is beautiful. can't wait to come back and catch more fish

Experience:
Boat
Crew
Overall
Half Trip (AM) – Inshore on August 2, 2025
Dan did a great job. Worked hard to find some fish and keep the lines in the water. His efforts were rewarded toward the end of the day when the stripers started hitting.
Dan did a great job. Worked hard to find some fish and keep the lines in the water. His efforts were rewarded toward the end of the day when the stripers started hitting.
