The Chesapeake Bay is waking up for the season — and so are the fish! As the water warms and spring settles in across Virginia, the Bay becomes a playground for anglers, families, and outdoor lovers alike. It’s the perfect time to grab your crew, hop aboard a fishing boat, and make memories that last far beyond the day’s catch.
Whether you’re craving an exciting weekday adventure in May or planning a summer outing the whole family will love, Captain Hogg’s Charter Service is here to help you create an unforgettable experience on the water.
Why Fish the Chesapeake Bay in May?
Fishing in May offers a unique combination of factors that make it one of the best times to book your Chesapeake Bay charter. Here’s why:
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Fewer Boats on the Water
Before the peak summer season, the waterways are quieter — which means you get more space, less competition, and a peaceful setting to enjoy your time on the Bay. -
Mild Weather Conditions
May offers comfortable temperatures, low humidity, and calmer seas — making it easier to relax, focus on fishing, and stay comfortable throughout the day. -
Early-Season Action
As the water begins to warm, species like black drum, sheepshead, Spanish Mackerel, bluefish, and croaker become more active. You’re hitting the start of peak fishing season, which means your chances of a productive day are high. -
Weekday Availability
If your schedule allows for a weekday trip, you’ll not only avoid weekend crowds — you’ll also have more flexibility in booking and more time with the captain to ask questions, learn, and enjoy a slower pace.
Whether you’re a seasoned angler or brand new to fishing, May charters offer the perfect blend of excitement and serenity. It’s an excellent time to get ahead of the summer rush and reel in early-season success.
A Chesapeake Bay Charter for Everyone — Not Just the Pros
Think fishing charters are only for hardcore fishermen? Think again.
At Captain Hogg’s Charter Service, we believe fishing should be fun, approachable, and accessible for everyone — from seasoned anglers to curious beginners to families with young kids. We’ve built our charter experiences around making everyone feel welcome and excited to be part of the day.
Here’s what sets us apart:
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Kid-Friendly Trips
Our crew is patient, encouraging, and great with kids. We turn every trip into a hands-on experience where young anglers can learn to bait hooks, cast lines, identify different fish, and celebrate their very first catch. -
Safe & Comfortable Vessels
We keep safety a top priority while also making sure everyone is comfortable. Our boat is spacious, clean, and equipped for both short and long outings — with shade, seating, and everything you need to have a great time. -
Customizable Trips
Want to keep it short and sweet for little ones? We offer half-day fishing trips. Looking to spend a full day on the water with a group of friends or extended family? We can do that too. Every charter is tailored to your group’s needs and goals.
What Can You Catch?
One of the best parts of fishing in the Chesapeake Bay is the diversity of species you might encounter on a single trip. While there are no guarantees (that’s part of the fun!), some of the most common catches during this time of year include:
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Bluefish – Feisty and fun to catch, especially for beginners.
- Black drum – Great for those looking to battle something hefty.
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Croaker – Great for kids and families because they’re active and often abundant.
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Flounder – A tasty prize if you’re lucky enough to land one.
- Sheepshead – One of the more challenging and rewarding fish to catch.
- Spanish Mackrel – A favorite among anglers of all skill levels!
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Spot, Speckled Trout, and Red Drum – Depending on the time of season, you might reel in one of these too.
Because the Chesapeake Bay is such a dynamic and ever-changing ecosystem, no two trips are the same — and that’s part of the magic.
Not Just a Fishing Trip — A Memory in the Making
At Captain Hogg’s, we don’t just take people fishing. We help families and groups create memories.
Some people book a charter as a birthday surprise. Others make it an annual tradition. We’ve had groups of friends reunite for a weekend getaway and parents bring their kids out for their very first time on a boat.
Beyond the fish, here’s what people say they love most:
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Unplugging from the Daily Grind
No screens, no meetings — just sunshine, salty air, and the sound of water lapping against the boat. -
Quality Time Together
Fishing brings people together in a way few things can. Whether it’s the shared excitement of a catch or the laughter between casts, it’s a bonding experience like no other. -
Scenic Beauty
The Chesapeake Bay is one of the most stunning waterways on the East Coast. You’ll see birds, shoreline views, and maybe even a dolphin or two along the way.
So whether you’re celebrating something special or just want to try something new, a day on the water is always time well spent.
What to Expect When You Book
Booking a trip with us is simple and stress-free. Here’s how it works:
- Choose Your Date – Contact us to see what’s available (especially if you’re looking at weekdays in May – they go quickly!).
- Select Your Experience – Half-day or full-day, beginners or pros – we tailor the trip to fit your goals.
- Show Up and Fish – We provide all the gear, bait, and licenses. You just bring your crew, a cooler, and your sense of adventure.
And if you’re not quite sure what you want yet? We’re happy to talk through options and make recommendations based on your group.
Ready to Book Your Chesapeake Bay Fishing Trip?
Don’t wait until the summer rush hits. May is one of the best-kept secrets for incredible Chesapeake Bay fishing – and our calendar fills up fast.
Whether you’re coming from Williamsburg, Virginia Beach, Norfolk, or the greater Hampton Roads area, we’re conveniently located and ready to host your next adventure.
Call 757-876-1590 to book your Chesapeake Bay charter fishing adventure today!
