Looking for an unforgettable day on the Chesapeake Bay? Whether you’re into sport fishing, leisurely sailing, or sunset cruising, Rock Hall, Maryland is home to a variety of charter boat experiences for every kind of traveler. From seasoned anglers to families looking for a weekend adventure, here are the top charter boat options in Rock Hall, MD.
Sailing Charters in Rock Hall, Maryland
Blue Crab Chesapeake Charters
Relaxing Day Sails and Sunset Cruises
Operating for over 25 years, Blue Crab Chesapeake Charters offers 90-minute sails aboard their 43-foot sailboat, Island Girl. Departing from Waterman’s Crab House, their sailing charters are perfect for small groups wanting a personalized sailing experience.
- Private & shared sailing options
- Sunset cruises available
Shardana Sailing Charters
Custom Sailing Experiences on a Catalina 425
Departing from Osprey Point Marina, Shardana offers fully customizable charters including half-day, full-day, and multi-day sailing trips. Great for learning the ropes or just kicking back.
- Great for beginners and experienced sailors
- Ideal for small private groups
Fishing Charters in Rock Hall, MD
Miss Carolyn II Charters
Large Group Fishing on a 42-Foot Boat
With over 50 years on the water, Captain Fletcher offers full-service fishing trips for groups up to 26 people aboard the Miss Carolyn II. This charter is ideal for corporate outings or family reunions.
- Trolling, live lining & bottom fishing
- Clean, well-equipped vessel
Rock Bottom Fishing Charters
Large-Group Fishing Trips with a Seasoned Captain
Led by Captain Jimmy Price, who brings over 30 years of experience on the Chesapeake Bay, Rock Bottom Fishing Charters offers memorable fishing adventures departing from Rock Hall Harbor. Their 46-foot custom-built Chesapeake Bay fishing boat is Coast Guard approved for up to 26 passengers, making it ideal for larger groups seeking a comfortable and successful day on the water. The vessel features a spacious cabin, canopy, comfortable seating, and a bathroom for your convenience.
Whether you’re planning a corporate outing, family reunion, or a day out with friends, Rock Bottom Fishing Charters provides a top-notch experience tailored to your group’s needs.
Rockaholic Fishing Charters
Chesapeake Bay Sportfishing Adventures
Rockaholic offers flexible, family-friendly fishing charters with all gear included. Great for first-timers and seasoned anglers alike.
- Customizable half-day & full-day trips
- All licenses and gear provided
Unique Charter Boat Experiences
Rock Hall Tiki Boat
Floating Tiki Bar Cruises on the Bay
Celebrate with friends aboard this tropical-themed tiki boat. Whether it’s a birthday, bachelorette party, or just a sunset cruise, this experience is as fun as it is Instagram-worthy.
- BYOB welcome
- Private group bookings available
Plan Your Chesapeake Bay Charter in Rock Hall Today
Whether you’re chasing rockfish, sailing under the sunset, or floating with friends on a tiki boat, charter boats in Rock Hall, Maryland offer something for everyone. With calm waters, friendly captains, and beautiful Chesapeake Bay views, there’s no better place to set sail.
Pro Tips for Booking a Rock Hall Charter:
- Book early during spring and summer weekends
- Ask about what’s included (gear, licenses, food, etc.)
- Bring sunscreen, soft-soled shoes, and a cooler if allowed
Looking to live near the water or plan your next waterfront weekend? Reach out—we’d love to help you explore Rock Hall from land or sea.
