Cape Classic Fishing Charters

Falmouth, Massachusetts
Old-School Classic Trip

About Your Guide

Greg Penta

Independent Guide
Captain Greg is a Falmouth resident who grew up spending his summers on the waters of Falmouth, the Vineyard, and Nantucket Sound. Greg is an avid boater and experienced fisherman who is familiar with the local waters and fishing “hot spots.” When he was a teenager, Greg worked as a deckhand on the charter boats "High Hopes" and "Double Eagle" from Falmouth Harbor. He also spent two years at the United States Coast Guard Academy, before graduating from Assumption College in 2002 with a dual major in economics and psychology. Greg is experienced working with children; he enjoys coaching youth basketball, introducing children to the marine environment, and has worked as a therapeutic mentor for at-risk youth at both Child & Family Services and Family Continuity in Hyannis, MA. A trip with Captain Greg is sure to be a memorable one; whether you're an experienced East Coast angler or a first-timer, you'll have a blast aboard his beautiful 1967 Mackenzie Cuttyhunk.

About Your Guide

Greg Penta

Independent Guide
Captain Greg is a Falmouth resident who grew up spending his summers on the waters of Falmouth, the Vineyard, and Nantucket Sound. Greg is an avid boater and experienced fisherman who is familiar with the local waters and fishing “hot spots.” When he was a teenager, Greg worked as a deckhand on the charter boats "High Hopes" and "Double Eagle" from Falmouth Harbor. He also spent two years at the United States Coast Guard Academy, before graduating from Assumption College in 2002 with a dual major in economics and psychology. Greg is experienced working with children; he enjoys coaching youth basketball, introducing children to the marine environment, and has worked as a therapeutic mentor for at-risk youth at both Child & Family Services and Family Continuity in Hyannis, MA. A trip with Captain Greg is sure to be a memorable one; whether you're an experienced East Coast angler or a first-timer, you'll have a blast aboard his beautiful 1967 Mackenzie Cuttyhunk.
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Old-School Classic Trip

NEW 1 - 6 People 2 - 8 Hours From $350
Old-School Classic Trip
Old-School Classic Trip
Old-School Classic Trip
Old-School Classic Trip
Old-School Classic Trip
Old-School Classic Trip
Old-School Classic Trip
Old-School Classic Trip
Old-School Classic Trip
Old-School Classic Trip

About Your Trip

Water Type

Inshore, Nearshore

Skill Levels

Beginner, Intermediate, Advanced

Weather

You won’t lose your deposit if the trip is canceled due to weather

Get out there with Captain Greg and see what's biting off of Falmouth, MA. With an awesome 27' Boston Whaler Cuddy Cabin and more than 30 years of experience fishing these waters, Captain Greg is ready to put together a perfect trip for anyone, whether you're an experienced angler, a first-time fisherman, or a family looking for a classic East Coast excursion. On this trip, you'll focus on inshore wrecks and underwater structure—perfect habitat for...

About Your Trip

Get out there with Captain Greg and see what's biting off of Falmouth, MA. With an awesome 27' Boston Whaler Cuddy Cabin and more than 30 years of experience fishing these waters, Captain Greg is ready to put together a perfect trip for anyone, whether you're an experienced angler, a first-time fisherman, or a family looking for a classic East Coast excursion.

On this trip, you'll focus on inshore wrecks and underwater structure—perfect habitat for
a variety of fish species, including Striped Bass, Black Seabass, Porgy, Bluefish, and Tautog. Chase these fish with a variety of techniques, from jigging to drifting to bottom fishing.

You will fish aboard his classic 27' Boston Whaler with twin outboard 250hp Yamaha motors for safety and redundancy. Over 10 feet wide, this vessel offers a comfortable and stable fishing platform that keeps side to side rocking to a minimum. Capable of making inshore and offshore runs with speed and safety, this model Boston Whaler is largely hailed as one of the finest hulls that Boston Whaler ever produced.

Captain Greg will come prepared with everything you need for a memorable fishing and boating experience. That includes rods, reels, bait, tackle, and most importantly, his expertise and skill. This is a captain who knows how to put you right on the fish, so everyone from Grandpa to Junior will be hooking up on a personal best! To maximize your experience on the water, make sure to bring proper clothing, a hat, polarized sunglasses, and sunscreen, then get out there and enjoy a beautiful day fishing in a classic craft.
Amenities

Water Type

Inshore, Nearshore

Skill Levels

Beginner, Intermediate, Advanced

Tackle

All rods, reels, and tackle are included.

Fish Cleaning

This guide will clean your catch for you.

Beer

Feel free to enjoy responsibly, but please no glass.

Boat Restroom

This boat has a restroom.

Live Bait

Live bait is included for this trip.

Weather

You won’t lose your deposit if the trip is canceled due to weather

Kid Friendly

This trip can cater to kids.

Flexible Cancelation

This trip can be canceled for a refund up to 1 days before the trip.

Disability Friendly

This trip is not suited for those with disabilities.

Lunch

Please provide your own food / snacks.

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About Your Boat

Boat photo for Old-School Classic Trip
Boat Type
Cuddy Cabin
Boat Manufacturer
Boston Whaler
Year Built
1967
Boat Length
27'

About Your Boat

Boat Type
Cuddy Cabin
Boat Manufacturer
Boston Whaler
Year Built
1967
Boat Length
27'
Engine Manufacturer
Yamaha
Total Horsepower
500
Number of Engines
2
Additional Amenities
Radar, GPS, Depth sounder / Fishfinder, Cruising Speed @ 30 knots, Rod, reels, bait and tackle provided, Safety Equipment (e.g. Life vests / EPIRB), Marine Head (Toilet in cabin for privacy), Canvas enclosure for protection from elements, Fish filleting, Ice Box with Bottled water
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Potential Target Species

Color-coded seasonality below is based on .
January February March April May June July August September October November December
Black Drum
Good
Good
Good
Great
Great
Great
Good
Good
Good
Good
Good
Good
Black Seabass
Good
Good
Good
Good
Good
Good
Good
Good
Good
Good
Good
Good
Bluefish
Good
Good
Good
Great
Great
Great
Great
Great
Great
Great
Good
Good
Bonito
Good
Good
Good
Good
Great
Great
Great
Great
Good
Good
Good
Good
Flounder
Good
Good
Good
Good
Great
Great
Great
Great
Good
Good
Good
Good
Scup
Not Ideal
Not Ideal
Not Ideal
Good
Great
Great
Good
Good
Great
Good
Good
Not Ideal
Striped Bass
Good
Good
Great
Great
Good
Not Ideal
Not Ideal
Not Ideal
Good
Great
Good
Good
Tautog
Good
Good
Great
Great
Great
Good
Good
Good
Good
Great
Great
Good
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  • Get it while it's HOT!
  • This species is in play.
  • You might get lucky (as long as things are in-season).
  • Couldn't tell ya! (no data)

Techniques

Bottom Fishing
Drift Fishing
Jigging
Light Tackle Fishing

Types of Fishing

Inshore
Nearshore

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Cape Classic Fishing Charters Photo Gallery

Old-School Classic Trip
November 10th, 2023
Falmouth, Massachusetts
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Old-School Classic Trip
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