Windfish Private Tours and Fishing Charters 

5.0/5 (27 reviews)
 2 Commercial Street, Gloucester, MA 01930, United States

Windfish Private Tours and Fishing Charters 

Gloucester, MA, United States
25 ft
4
5.0/5 (27 reviews)

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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).

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).

Daniel Sanfilippo
Captain
Daniel Sanfilippo
10 years of experience
responds within an hour

Select date to see availability

Trip availability and prices

Trip Date:
Group Size:
August 2026
SuMoTuWeThFrSa
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Group Size
2 adults • 0 children
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Almost there...
Half Trip (AM) – Inshore
FREE Cancellation 3 days notice
3 hour trip starts at 7:00 AM
Seasonal trip
May 23 - Oct 31
Bass (Striped)
Bluefish (Tailor)
Cod
Haddock
+3
US $480
Entire boat: up to 4 people
Half Trip (PM) – Inshore
FREE Cancellation 3 days notice
3 hour trip starts at 12:00 PM
Seasonal trip
May 23 - Oct 31
Bass (Striped)
Bluefish (Tailor)
Cod
Pollock
+4
US $480
Entire boat: up to 4 people
Full Trip – Inshore or Deep Sea
FREE Cancellation 3 days notice
7 hour trip starts at 7:00 AM
Seasonal trip
May 23 - Oct 31
Bass (Striped)
Bluefish (Tailor)
Cod
Pollock
+4
US $810
Entire boat: up to 4 people
There are 12 people looking at this charter.

Customer reviews

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Rating

5.0
27 reviews
4.9
Boat & equipment
5.0
Captain & crew
5.0
Fishing Experience

Anglers' gallery (21)

All reviews (27)

Frequently mentioned
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Showing 15 of 27 reviews
Tim Kane
Tim Kane
us
New York, US
Member since 2026
5.0
Verified
New
Three Pointer at the Buzzer
Half Trip (PM) – Inshore on July 28, 20264 adults

What a day! It all started with good conditions all along the coastline for Striped Bass. Calm waters presented numerous good spots with even some hits but no fish in the boat after several hours. Then an unexpected storm stirred up the water creating less than desirable conditions. With a little more than an hour left Captain Dan went into fast and furious mode hitting several spots as we went back toward shore. But still no fish. As we entered the harbor to end the trip Dan had one last play: fishing underneath a pier minutes away from docking. All of a sudden,when hope was really fading, bingo!! A 14-pound keeper emerged from the waters to save the day thanks to Dan's determination. A great shot with no time left on the clock. What a day!!

Reported catch:
Striped Bass
Daniel Sanfilippo
Response from Captain

Thanks for being such a great crew on a slower afternoon! I'm glad we finally found some action to cap off such a pleasant trip and one to take home for dinner to boot! Thanks again and hope to see you all again next time you're out this way. All the best, Cpt Dan

Michael Disa
Michael Disa
us
Massachusetts, US
Member since 2026
5.0
Verified
New
Perfect day on the water
Half Trip (AM) – Inshore on August 8, 20262 adults

My son and I had a beautiful sunny calm day fishing on the water with Captain Dan. We went to a few different spots before we got our first bite, but Capt Dan neber gave up and was motivated by finding us a spot where the fish were biting. Did he ever?!!After that, every cast we attempted, hooked us a big striper. So much fun! Thanks Capt Dan for making great memories for my son and me.

John Lamar
John Lamar
Repeat angler
us
New York, US
Member since 2025
2 trips
4.7
Verified
New
Great trip!
Half Trip (PM) – Inshore on August 12, 20261 adult2 children

Captain was awesome! He worked hard to keep us busy. the Bass fishing was slow, but we had a great time catching mackerel and pollock. My son asked captain Daniel if he had lobster traps and the captain took us to check all his traps. He let my son pull the traps and take out the lobsters. He showed him how to determine if the lobsters were keepers and how to band the claws. It made my dons dat. pous he let us keep the lobsters! we will definitely be back!

Reported catch:
Pollock
Atlantic Mackerel
Lobster
Ada Ates
Ada Ates
us
Ohio, US
Member since 2026
5.0
Verified
Literally best experience ever!
Half Trip (AM) – Inshore on June 28, 20262 adults

I booked this trip mostly for my dad as he loves to go fishing. I didn’t expect much from this experience but Captain Daniel was amazing! He made the experience very enjoyable and made sure I also caught a fish. He helped me with the equipment and showed me tricks. We caught plenty of mackerels and two huge striped bass! My dad and I can’t wait to go back. Highly recommend!

Reported catch:
Striped Bass
Atlantic Mackerel
Daniel Sanfilippo
Response from Captain

Thanks for a great trip, guys! Hope to have you aboard again soon. Best of luck next semester and a safe trip back to Turkey! All the best, Cpt Dan

Ryan Beckner
Ryan Beckner
us
Massachusetts, US
Member since 2026
5.0
Verified
captain Dan is the Man!
Full Trip – Inshore or Deep Sea on June 14, 20263 adults

Captain Dan is amazing. He keeps you entertained the whole trip. Extremely nice. he works his butt off to make sure you have a good time. this is our second time out with him and we will definitely be back. Thanks for the great experience!

Reported catch:
Pollock
Atlantic Mackerel
Lobster

FAQs about Windfish Private Tours and Fishing Charters

Windfish Private Tours and Fishing Charters offers the following trips to customers:
  • US $480 per group - Half Trip (AM) – Inshore (3 hours)
  • US $480 per group - Half Trip (PM) – Inshore (3 hours)
  • US $810 per group - Full Trip – Inshore or Deep Sea (7 hours)
When you book a trip with Windfish Private Tours and Fishing Charters, you can expect the following amenities onboard:
  • Toilet Camping toilet and cabin privacy. No built-in head
  • GPS
  • Fishfinder
  • Live bait well
  • Outriggers
  • Ice box
  • Radar
Trips booked with Windfish Private Tours and Fishing Charters include:
  • Rods, reels & tackle
  • Live bait
  • Lures
  • Catch cleaning & filleting
  • Snacks
  • Drinks
  • Fishing license
Windfish Private Tours and Fishing Charters offers the following types of fishing:
  • Inshore fishing
  • Nearshore fishing
  • Offshore fishing
Windfish Private Tours and Fishing Charters offers the following fishing techniques:
  • Light tackle
  • Bottom fishing
  • Trolling
  • Jigging
  • Drift fishing
  • Deep sea fishing
Top targeted fish species with Windfish Private Tours and Fishing Charters include:
  • Bass (Striped)
  • Bluefish (Tailor)
  • Cod
  • Haddock
  • Kingfish (Southern)
  • Lobster
  • Mackerel (Atlantic)

Your captain

Daniel Sanfilippo
Daniel Sanfilippo
Daniel Sanfilippo

Gloucester, Massachusetts, United States

27 Customer reviews
Typical response within an hour
Member since March 2024

Deep-rooted Gloucester native with a lifetime of seafaring and fishing experience. In depth knowledge of local species, fishing techniques, and history. UMass Lowell Engineering Alum. Fully insured and licensed USCG Captain.

27 Customer reviews
Typical response within an hour
Member since March 2024

Deep-rooted Gloucester native with a lifetime of seafaring and fishing experience. In depth knowledge of local species, fishing techniques, and history. UMass Lowell Engineering Alum. Fully insured and licensed USCG Captain.

The fish you can target

Striped Bass
Striped Bass
Bluefish (Tailor)
Bluefish (Tailor)
Cod
Cod
Haddock
Haddock
Southern Kingfish
Southern Kingfish
Lobster
Lobster
Atlantic Mackerel
Atlantic Mackerel
Striped Bass
Striped Bass
Bluefish (Tailor)
Bluefish (Tailor)
Cod
Cod
Haddock
Haddock
Southern Kingfish
Southern Kingfish

Real catches by this captain

  • August fishing trip
    John W.
    John W.
  • Kids loved it!!
    Brian S.
    Brian S.
  • Literally best experience ever!
    Ada A.
    Ada A.
  • Capt Dan!!!!!
    Edward L.
    Edward L.
  • September fishing trip
    Suzanne A.
    Suzanne A.
  • Great fishing trip
    Keith K.
    Keith K.
  • A great trip
    Sean S.
    Sean S.

What is the boat like?

Boat image
Boat category
Cabin cruisers
Capacity
4 persons
Boat length
25 ft
Year built
1997
Boat manufacturer
Parker
Boat type
Pilothouse
Engine model
Volvo Penta
Powered by
1 x 350HP
Max cruising speed
28 knots

What kind of fishing will you do?

Inshore Fishing
Nearshore Fishing
Offshore Fishing

Which fishing techniques you can try

Light Tackle
Bottom Fishing
Trolling
Jigging
Drift Fishing
Deep Sea Fishing

Which amenities are available onboard

Toilet
Camping toilet and cabin privacy. No built-in head
GPS
Fishfinder
Live bait well
Outriggers
Ice box
Radar
What's included in the trip price
Rods, reels & tackle
Live bait
Lures
Catch cleaning & filleting
Snacks
Drinks
Fishing license

How cancellations work

Free cancellation up to 3 days prior to trip

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.

More details

What the listing policies are

Pickup not included

Transfer to/from departure site is not included in trip rates.

Child friendly
You keep catch
Catch and release allowed

How you can pay

Book with 20% deposit, pay rest to captain

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

 Bank transfer

What’s biting in Gloucester right now

Bass (Striped)Bass (Striped)
Bluefish (Tailor)Bluefish (Tailor)
CodCod
HaddockHaddock
Mackerel (Atlantic)Mackerel (Atlantic)

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