Discover the top things to do in Chesapeake Bay for unforgettable adventures. Explore sailing, fishing, and wildlife encounters in this stunning destination.

Things To Do

Things To Do In Chesapeake Bay

Get your Maryland fishing license hassle-free with our comprehensive guide. Find all the info you need to start reeling in the big ones today!

Fishing License

Get Your Valid Maryland Fishing License

Striped Bass

Good Day Fishing

Experience the thrill of reeling in a striper bass in the serene waters of Chesapeake Bay. Join us for an unforgettable fishing adventure and feel the rush of the catch!

Striped Bass Fishing

Spent the day out on the water chasing those elusive striped bass! The thrill of the hunt and the satisfaction of a big catch make every fishing trip unforgettable.

Read expert Fishing articles, travel insights, and local stories from Fish 'N Party II in Chesapeake Bay. Stay informed and inspired for your next adventure.

Chesapeake Bay Fishing Articles & Insights | Fish 'N Party II

Experience the thrill of fishing in the picturesque waters of Maryland's Chesapeake Bay with Fish 'N Party II, your gateway to an unforgettable angling adventure. Situated in Chestertown, MD, this top-tier fishing charter service is led by the seasoned expertise of Captain Lenny Fletcher, who boasts years of experience navigating these pristine waters. When it comes to creating lasting memories and reeling in the catch of a lifetime, Fish 'N Party II is your trusted companion. Fish 'N Party Charters offers exclusive private fishing trips designed to accommodate up to six individuals, ensuring an intimate and personalized journey. Setting sail on a meticulously maintained 28' boat, you'll have access to the latest cutting-edge technology to elevate your fishing experience.&nbsp; Fish 'N Party II caters to a wide spectrum of angler preferences, offering inshore fishing charters. ur specialized trips are designed to target Striped Bass. The Chesapeake Bay holds the promise of unexpected and exciting Rockfish catches! Captain Lenny Fletcher goes beyond being a mere skipper; he is your mentor on the water. He will impart his extensive knowledge, teaching you the best techniques to hook your desired fish and ensuring your success.&nbsp; Worried about gear? There's no need to be. Fish 'N Party II provides everything you require, from top-quality rods and reels to bait and tackle. Your only task is to step aboard with enthusiasm and an appetite for adventure. Fish 'N Party Charters extends a warm welcome to anglers of all skill levels. Whether you're a novice eager to learn the ropes or an experienced angler with dreams of conquering the deep wrecks for a personal best catch, Captain Lenny Fletcher and his crew are eager to welcome you aboard Fish 'N Party II. Don't miss the opportunity to embark on an incredible fishing adventure in Maryland's Chesapeake Bay with Fish 'N Party II. Secure your spot today and create memories that will last a lifetime. Whether you're seeking a thrilling day on the water with friends or a peaceful solo escape, the pristine beauty of Chesapeake Bay awaits, and Fish 'N Party II is your ticket to an unforgettable angling experience. Cast your line, make your reservation, and let the adventure begin!

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Group of six people fishing in Chestertown.

Group of 6 people enjoying a fishing trip in Chestertown

Striped bass fish caught in Maryland while fishing

Seven striped bass caught while fishing in MD

Eight striped bass caught while fishing in MD

Group of 5 people enjoying fishing in Chestertown

Seven striped bass caught during fishing trip in MD

Experience the thrill of reeling in a striper bass in the serene waters of Chesapeake Bay. Join us for an unforgettable fishing adventure and feel the

Reel in Memories with Chesapeake Bay Fishing Charter

Don't let this opportunity slip away! Join Captain Lenny Fletcher aboard the Fish 'N Party II for an unforgettable fishing adventure in Chesapeake Bay,. Embrace your passion, reel in big catches, and create memories that will last a lifetime – book now before all spots are gone!

Fish 'N Party II offers an exceptional Chesapeake Bay fishing charter experience with expert guides who are familiar with the best fishing spots in the area. Whether you’re a first-time angler or a seasoned fisherman, our trips cater to all skill levels. Chesapeake Bay is known for its diverse species such as striped bass, bluefish, and spot, making it one of the top locations for sports fishing. With our charter, you'll gain access to prime fishing areas and receive expert guidance to ensure a successful outing. Our fishing charters go beyond just a day on the water, providing everything you need for a memorable experience. From high-quality gear to knowledgeable captains, we ensure a comprehensive and enjoyable trip. Our charters are perfect for families, groups of friends, or experienced anglers looking to sharpen their skills. Join us at 8601 Pippin Hill Ln, Chestertown, MD, for a top-tier fishing adventure on the Chesapeake Bay. Book your trip today and experience the best of what the Bay has to offer.&nbsp;

Captain Lenny Fletcher brings a lifetime of experience and a deep passion for fishing to every trip aboard Fish 'N Party II. His connection with Chesapeake Bay is built on years of fishing, and his extensive knowledge of the local waters makes him a standout guide. For Captain Lenny, fishing is much more than a hobby—it’s a way of life, and he is dedicated to sharing his expertise with every angler he takes on the water. His enthusiasm is contagious, creating a positive and engaging atmosphere for all guests. Over the years, Captain Lenny has honed his skills, learning the ins and outs of Chesapeake Bay's waters. His ability to read the water and predict fish movements, particularly for prized species like Striped Bass, allows him to offer a targeted and successful experience for all anglers. Captain Lenny’s approach is patient and educational, taking the time to ensure guests not only catch fish but also understand the sport and its finer details. His passion for fishing and teaching is evident throughout each trip. Captain Lenny’s commitment to providing an exceptional fishing experience is matched only by his love for the sport. He brings a wealth of local knowledge to every outing, making him an invaluable guide for both seasoned anglers and beginners alike. Whether you're looking to learn or just enjoy the day on the water, Captain Lenny’s expertise ensures that every trip is both rewarding and memorable. The Fish 'N Party II is a meticulously restored 28' Century Center Console, powered by two robust 700HP Caterpillar engines that allow the boat to reach speeds of up to 28 knots. This powerful vessel offers both speed and stability, ensuring smooth navigation through Chesapeake Bay’s waters. With a comfortable capacity for up to six guests, Fish 'N Party II provides ample space for everyone to enjoy the day, making it the perfect boat for a memorable fishing adventure. Its high-performance design ensures that guests can spend more time fishing and less time getting to the best spots, all while enjoying a safe and enjoyable ride.

Chesapeake Bay Fishing Locations

Meet Captain Lenny Fletcher and Fish 'N Party II

Book a full-day inshore fishing trip for Striped Bass in Chesapeake Bay. Expert guides, prime spots, up to 6 anglers. Reserve now!

Bay Reels

Premium Chesapeake Bay Fishing with Fish 'N Party II

Book a premium inshore fishing trip for monster striped bass in Chesapeake Bay. Morning, afternoon, and night options available.

Bay Catch

Top-Rated Chesapeake Bay Striped Bass Charters

Learn inshore fishing basics on this 8-hour Chestertown charter. Perfect for beginners, all gear provided. Book now!

Striper Intro

Learn Striped Bass Fishing in Chesapeake Bay

Book an inshore fishing trip in Chestertown, MD for trophy Striped Bass. 8 hours of expert-guided angling awaits!

Striped Pro

Advanced Striped Bass Charter in Chesapeake Bay

Book a premium 8-hour family fishing trip in Chesapeake Bay. Catch striped bass with expert guides. Reserve now!

Family Bass Fun

Expert-Guided Striped Bass Charters in Chestertown

Common Questions: What is the best bait for the Chesapeake Bay?The go-to baits for fishing in the Chesapeake Bay are earthworms/nightcrawlers, blood worms, and grass shrimp.&nbsp;You can enhance your fishing experience with these baits on the Fish 'N Party II, a premier choice for Chesapeake Bay fishing charters in Maryland. Where is the best striper fishing in the Chesapeake Bay?The Chesapeake Bay Bridge and Tunnel, Eastern Bay, Poplar Island, and the Hampton Roads Bridge-Tunnel are among the hot spots for striper fishing in the Chesapeake Bay.&nbsp;You can explore these prime fishing locations aboard the Fish 'N Party II, a premier choice for Chesapeake Bay fishing charters in Maryland. Can you fish in the Chesapeake?Yes, the Chesapeake Bay is a prolific fishing destination, home to a variety of fish including trout, catfish, flounder, bass, and spadefish.&nbsp;You can explore these abundant waters aboard the Fish 'N Party II, a premier choice for Chesapeake Bay fishing charters in Maryland. What types of fishing charters are offered by Fish 'N Party II in Chesapeake Bay?Fish 'N Party II offers a variety of fishing charters in Chesapeake Bay, including private inshore fishing trips. You can enjoy half-day or full-day excursions, with a focus on targeting Striped Bass and other exciting species. Captain Lenny Fletcher customizes each trip to match your preferences and the best seasonal opportunities. What is included in a typical fishing charter with Fish 'N Party II?A typical charter with Fish 'N Party II includes a guided fishing experience aboard a well-maintained 28-foot boat, all necessary fishing gear, bait, and tackle. Captain Lenny Fletcher provides expert guidance and ensures a comfortable and enjoyable trip with refreshments and safety equipment included. Are Fish 'N Party II charters suitable for beginners?Yes, Fish 'N Party II charters are ideal for anglers of all skill levels, including beginners. Captain Lenny Fletcher offers hands-on instruction and shares his extensive knowledge to help new anglers learn the ropes and enhance their fishing skills throughout the trip. What fish species can I expect to catch on a charter with Fish 'N Party II?On a fishing charter with Fish 'N Party II, you can target a range of species including Striped Bass, also known as Rockfish, and occasionally other species like Bluefish. Captain Lenny Fletcher will tailor your trip to focus on the most active and sought-after species during your visit. How do I prepare for a fishing charter with Fish 'N Party II?To prepare for your charter, wear comfortable, weather-appropriate clothing and bring sunscreen, sunglasses, and a hat. Fish 'N Party II provides all necessary fishing gear, so you only need to bring your enthusiasm and a valid fishing license if required. What is the best time of year for fishing in Chesapeake Bay with Fish 'N Party II?The best times for fishing in Chesapeake Bay are typically spring and fall, when the fish are most active. However, Captain Lenny Fletcher can provide excellent fishing experiences year-round by adjusting your trip to seasonal conditions and target species. Can I book a charter with Fish 'N Party II for a special event or group outing?Absolutely! Fish 'N Party II accommodates special events and group outings. Whether you’re planning a corporate event, a family reunion, or a birthday celebration, Captain Lenny Fletcher will work with you to customize the trip and ensure a memorable experience for everyone.

Fishing Charter Locations on  Chesapeake Bay

Air Fee

Bait Fee

Divemaster Fee

Mate's Fee

Nitrox Fee

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State Taxes

Trimix Fee

The spring striped bass run has been exceptional, and our 4-hour fishing trips have been successful! We've been targeting both keeper and jumbo striped bass, with some reaching up to 52 inches in length, offering our customers an unmatched fishing experience. With trips available every day—morning, afternoon, and night—you can choose the perfect time to join us on the water. Whether you're a seasoned angler or just looking to try your hand at fishing, our team is dedicated to making sure you have a productive outing. Don’t miss your chance to be part of this remarkable fishing season and reel in some impressive striped bass. *Deposits are non-refundable (Trips &amp; Rates Page).

Century (Center console)

4 hrs 

Half Day Striped Bass Fishing Trip - Chesapeake Bay

Enjoy a fantastic full-day fishing adventure in the beautiful Chesapeake Bay for only $800, tailored for groups of up to 6 people. Spend your day on the water targeting Striped Bass with the guidance of an experienced captain who knows the best fishing spots. The pristine waters of Maryland provide the perfect setting for a productive and enjoyable fishing experience. Whether you're a seasoned angler or a beginner, this trip is designed to offer an unforgettable time for all skill levels. Book your Striped Bass fishing trip in Chesapeake Bay today, and get ready to make lasting memories with your group. *Deposits are non-refundable (Trips &amp; Rates Page).

8 hrs 

Full Day Striped Bass Fishing Trip - Chesapeake Bay

Seasoned anglers, this 8-hour Striped Bass charter is built for you. Departing at 7:00 AM from Chestertown, MD, we’ll cover the most productive areas of Chesapeake Bay using advanced trolling, jigging, and live bait techniques. Your captain shares expert strategies to help you land trophy-sized Stripers while utilizing top-quality gear and electronics. This trip accommodates up to 6 guests and includes all necessary equipment. If you’re ready to take your fishing game to the next level, reserve your advanced Striped Bass experience today!

Full Day Advanced Striped Bass Fishing Trip - Chesapeake Bay

Perfect for newcomers, this 8-hour introductory charter makes Striped Bass fishing simple and fun. Departing from Chestertown at 7:00 AM, your captain will walk you through every step—rigging, casting, and reeling in your catch. Our calm, friendly approach ensures beginners of all ages feel confident and engaged. All rods, bait, and safety gear are provided, so just show up ready to fish! With space for up to 6 guests, this is an ideal trip to learn while enjoying the scenic Chesapeake Bay. Book now and discover how exciting Striper fishing can be!

Full Day Beginner-Friendly Striped Bass Fishing Trip - Chesapeake Bay

Gather the family for an 8-hour Striped Bass charter designed for anglers of all ages! Departing at 7:00 AM from Chestertown, this trip combines exciting fishing with a safe and comfortable environment. Our captain ensures kids and adults alike have a memorable day, providing easy-to-use gear, safety equipment, and plenty of guidance. Enjoy the stunning Chesapeake Bay while catching Stripers and creating lasting memories. Accommodates up to 6 guests for $800 total—book your family adventure today!