Cape Classic Charters in Falmouth, Massachusetts

Guided by Greg Penta

Inshore Nearshore

About Your 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.

Cape Classic Charters Trips

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. Read More

Inshore, Nearshore Fishing Charter in Falmouth

Old-School Classic Trip

100% (7)
27 ft 1 - 6 People From $58 / person

Recent Reviews of Cape Classic Charters

Catherine H.


First fishing trip!! It was great, thank you Greg!!

Giedrius G.


Greg was a great host and gave the kids simple, clear fishing instructions. We caught lots of fish and had fun as a family.



Captain Greg knows the right spots. We couldn’t drop a line without getting a bite. Must of pulled up 30+ between 2 poles in an hour. Started throwing everything back after the first 15 minutes.

Chris S.


We had the best time fishing with Captain Greg! He made sure we were catching fish the entire time! He was very kind, patient and did a great job explaining exactly what we had to do. We would for sure book with him again!

Susan B.


Knowledgeable, confidant, helpful, capt greg is as good with people as he is with fish. He knows what each fisherman needs before he asks and this makes fishing smooth and easy. Everyone broke a personal best that day and went home happy.

Michael P.


Took my son and a couple if his buddies out for a couple of hours. Capt. Greg was awesome and made us feel like real fishermen. (we’re not) Filled a bucket of porgies and threw back 3 seabass. (out of season) Great start to a great day. Thanks Captain Greg, we all had a blast.

Ashley M.


We had an amazing time fishing with Captain Greg! He made us feel comfortable and was very knowledgeable. He did a great job explaining to the kids what to do. This was such a fun time and I would highly recommend to anyone! We did use his back up boat and it was equipped with everything we needed. We will definitely be back!


Black Drum, Bluefish, Bonito, Scup, Striped Bass, Tautog


Bottom Fishing, Drift Fishing, Jigging, Light Tackle Fishing

Types of Fishing

Inshore, Nearshore

Start Location

180 Scranton Avenue, Falmouth, MA 02540, United States

Cape Classic Charters Photo Gallery

Book a Trip with Greg