About Your Trip

Water Type

Inshore, Nearshore, River

Skill Levels

Beginner, Intermediate, Advanced

Weather

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

About Your Trip

When you're in Oxford, MD, there’s no better way to experience the heart of Chesapeake Bay than with Captain Gary at the helm. With a lifetime of experience fishing these waters, Captain Gary knows every bend, shoal, and honey hole the Bay has to offer. Whether you're an experienced angler chasing a personal best or brand new to fishing, this trip offers something for everyone—relaxation, excitement, and the chance to reel in some serious fish.

Your day begins aboard a spacious 40’ Robbins commercial-style fishing boat, custom-built for comfort and performance. With a 500 HP Cummins engine pushing you along at speeds up to 32 knots, you’ll waste no time getting to the bite. The boat is decked out with the latest electronics, including GPS, radar, and fishfinder, and features a live bait well, trolling gear, outriggers, and even a fighting chair for when the big ones start pulling. The air-conditioned cabin, private restroom, and accessible layout also make this trip a great fit for anglers of all ages and abilities—including those using wheelchairs.

This 7-hour trip gives you the flexibility to chase a variety of Chesapeake Bay favorites. Depending on the time of year and what’s biting, you might target Striped Bass, Bluefish, Black Drum, Spanish Mackerel, Spotted Seatrout, White Perch, and Weakfish. Captain Gary brings a wide selection of rods, reels, and tackle to match your target species and skill level, so if you’re looking to try something new—be it light tackle casting, trolling, or bottom fishing—he’s ready to make it happen.

A professional First Mate is along for the ride to help keep things running smoothly. From baiting hooks to cleaning your catch, the Mate’s job is to make your day on the water easy and enjoyable. A 20% gratuity is customary and always appreciated for their hard work.

Your trip includes just about everything: fishing licenses, tackle, lures, live bait, cold bottled water, and fish cleaning at the end of the day. Just bring your favorite snacks, sun protection, and any additional drinks you’d like to enjoy while you’re out on the Bay.

From calm morning waters to an afternoon of chasing trophy Stripers, Captain Gary’s charter offers a classic Chesapeake Bay experience that blends comfort, adventure, and top-notch fishing. Don’t miss your chance to step aboard—book your trip today and see what makes Oxford one of the East Coast’s best kept fishing secrets.

Amenities

Water Type

Inshore, Nearshore, River

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.

Air Conditioning

This boat has air conditioning.

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 small children.

Flexible Cancelation

This trip can be canceled up to 3 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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Pricing Matrix

	7 hours
1 Person	$750.00
2 People	$750.00
3 People	$750.00
4 People	$750.00
5 People	$750.00
6 People	$750.00

Pay 15% of the price as a deposit today, with the balance due on the day of the trip.

You're in good hands

Book your trip with confidence — We only work with the best local guides that know where to put you on fish.

Reserve Your Trip

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You're in good hands

Book your trip with confidence — We only work with the best local guides that know where to put you on fish.

About Your Guide

Gary B.

Independent Guide

Captain Gary has been fishing with his dad since he was 3 years old. A connoisseur of many different fishing techniques, his favorites include live lining, trolling, chumming, and bottom fishing. The Chesapeake Bay is his personal playground and he looks forward to showing all of his guests the beauty of the waters.

About Your Guide

Gary B.

Independent Guide

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Start Location & Lodging Options

Oxford, Maryland

Areas Fished

About Your Boat

Boat photo for Chesapeake Bay Fishing Adventure

Boat Type: Pilothouse
Boat Manufacturer: Robbins
Year Built: 1987
Boat Length: 40'

About Your Boat

Boat Type: Pilothouse
Boat Manufacturer: Robbins
Year Built: 1987
Boat Length: 40'
Boat Restroom: Yes
Engine Manufacturer: Cummins
Total Horsepower: 500
Number of Engines: 1
Additional Amenities: Fighting Chair, GPS, Fishfinder, Live Bait Well, Refrigerator, Outriggers, Ice Box, Radar

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Trip Details & Amenities

Water Type

Inshore, Nearshore, River

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.

Air Conditioning

This boat has air conditioning.

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 small children.

Flexible Cancelation

This trip can be canceled up to 3 days before the trip.

Disability Friendly

This trip is not suited for those with disabilities.

Lunch

Please provide your own food / snacks.

Target Species

Color-coded seasonality below is based on .

View Full Species Seasonality Chart »

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
Heavy Tackle Fishing
Jigging
Light Tackle Fishing
Trolling

Everything Else to Know

All gear is included, but we also recommend bringing sunglasses, sunscreen, weather-appropriate clothing, and anything else you might want on the trip.

You're all set! You don't need to buy a license for this trip.

We use a cashless autopay system. We'll send you a boarding pass, and on the day of the trip, your guide will scan your boarding pass to automatically transfer the remaining balance. The only cash needed is to tip your guide (we recommend 20%).

Cancel for free up to 3 days before the trip and receive credit back to your account. Cancelling within 3 of the trip will forfeit your deposit to the guide. Day-of cancellations and no-shows will be charged the full balance of the trip to their card.

In the event of inclement weather you'll be covered by out 100% Weather Guarantee and will not lose your deposit.

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First Time Booking with Us?

Captain Experiences is home to thousands of quality, vetted fishing, hunting, and other outdoor sports guides across the US and beyond. Our mission is to Unlock the Outdoors by making it quick and easy to book the trip of a lifetime every time with our Damn Good Guides.

We vet our guides and only partner with the best of the best. Our guides do their very best to keep you safe, show you a great time, and send you home with a memorable experience shared with family and friends.

Once you've paid your deposit at checkout, we'll send you a QR Code boarding pass. Just show your guide your boarding pass 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 event of inclement weather, our guides will check the conditions and make the final call on whether its safe to go on the trip. If they decide the trip needs to be postponed, we'll work closely with you to reschedule or provide a credit for the full deposit, which can be applied to any of our trips in the US and beyond.

Each trip's price is determined by the guide and reflects all associated costs. A significant factor in pricing is often the type of boat and the corresponding fuel expenses. Additional costs may include leases, marina or slip fees, and the expenses involved in providing and maintaining the necessary gear for your trip.

After booking your trip, we'll connect you directly with your guide to discuss additional details. In the meantime, our team is here to answer any questions via email, text, or phone.

Chesapeake Bay Fishing Adventure

About Your Trip

About Your Trip

Pricing Matrix

You're in good hands

Reserve Your Trip

You're in good hands

About Your Guide

About Your Guide

Start Location & Lodging Options

About Your Boat

About Your Boat

Trip Details & Amenities

Target Species

Techniques

Everything Else to Know

Recent Reviews of Captain Experiences

First Time Booking with Us?