Old-School Classic Trip

Starting at $350 | 2 - 6 Hours | Inshore, Nearshore | 6 People

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.

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About Your Boat

Boat Type
Cuddy Cabin
Boat Manufacturer
Boston Whaler
Year Built
Boat Length
Engine Manufacturer
Total Horsepower
Number of Engines
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

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.

Start Location

180 Scranton Avenue, Falmouth, MA 02540, United States

Amenities and Information

Water Type

Inshore, Nearshore

Skill Levels

Advanced, Beginner, Intermediate


All rods, reels, and tackle are included.

Fish Cleaning

This guide will clean your catch for you.


Feel free to enjoy responsibly, but please no glass.

Boat Restroom


Live Bait

Yes, Included


You will get a refund if the trip is canceled due to weather.


No meal provided.


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


Bottom Fishing, Drift Fishing, Jigging, Light Tackle Fishing

Gear & Packing

Fishing License, Ice Box with Water, Rods, reels & tackle
At an Additional Rate
No added costs.
Recommended Packing
Nothing required, we always recommend sunglasses, sunscreen, water, and weather-appropriate clothing.
Required Items
A valid fishing license.

Things To Keep In Mind

Payment & Tipping
After paying the deposit, a QR Code will be emailed to you. On the day of the trip, your guide will scan your QR code to automatically transfer the remaining balance. The only cash needed is for a customary tip (we recommend 20%).
Cancellation/Refund Policy
Yes, cancel for free up to 1 day before the trip.

Where to Buy a Fishing License

Find out more about licenses here.

Pricing & Availability

To check pricing, please select a trip date, duration, group size and start time.

Free Cancellation

Rest easy with free cancellation up to 1 day before the trip.

100% Weather Protection

Receive a full refund in the event of inclement weather.


Susan B.


October 23, 2021

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.


October 18, 2021

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, ...Read More

Ashley M.


September 4, 2021

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 ...Read More

First Time Booking with Us?

Captain Experiences is the home of over 1000 Damn Good fishing and hunting guides. Our mission is to unlock the outdoors for everyone, and we want to help you get out there through our no-hassle online booking experience and our team of outdoors experts.
We vet our guides to make sure they are the best of the best. We want guides who not only put you on 'em, but show you a great time, keep you safe, and give you a memorable experience with your group.
Once you've paid your deposit at checkout, we'll send you a QR code (like a mobile boarding pass). Just show your guide your QR code on the day of the trip, they'll scan it, the remaining balance will transfer automatically, and you'll be all set to get out there. Just make sure you bring a cash tip for the guide!
In the case of inclement weather, our guides will make the call and we'll work with you to reschedule your trip or issue a full refund. Your safety is our top concern.
Once you book the trip, we will connect you directly with the guide to go over any additional details. In the meantime, our location specialists are always available to answer your questions via email, text, chat, or call!