TOP 30 Chesapeake bay in Annapolis, Maryland

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Island Chill Yacht Charters (ICYC) is a travel agency located at 1444 Shore Drive in Edgewater, Maryland, United States. We specialize in creating the 'Relaxing Excitement of the Islands' on private sail and powerboat cruises for families, friends, and couples. Conveniently situated in historic Londontowne, we are close to Washington D.C. and Baltimore, just 6 miles south of Annapolis - the 'Sailing Capital of America!' Our cruises are perfect for hot summer days and chill sunsets, making them ideal for birthdays, anniversaries, bachelorette parties, corporate retreats, national holidays, and special events. Choose from our 43-foot sailboat (Therapy), 34-foot powerboat (Irie Vibes), or 20-foot bow-rider powerboat (Tallawah) for captained cruises along the South and Rhode Rivers, Chesapeake Bay, and Thomas Point Shoal Lighthouse. Enjoy swimming, paddle boarding, floating lily pads, sunbathing, beaches, sandbars, islands, kayaking, and fishing options.

Schooner Woodwind Sailing Cruises offers an unforgettable experience for visitors looking to explore the waters of Annapolis, Maryland. Located at 80 Compromise Street, this tourist attraction and travel agency provides guests with the opportunity to sail on a beautiful schooner while taking in the stunning views of the Chesapeake Bay. Whether you're a seasoned sailor or a first-time cruiser, Schooner Woodwind Sailing Cruises offers a range of tours and experiences to suit every preference. Set sail with them for a memorable adventure on the water.

Ohana Charters is a travel agency located at 500 Piney Narrows Road in Chester, Maryland, United States. Specializing in Annapolis Charter, Catamaran Charter, Sailing Charter, and more, Ohana offers a luxurious and unique sailing experience on the Chesapeake Bay. Guests can enjoy stunning sunsets, delicious food, and the opportunity to enhance their sailing skills. Whether celebrating a special occasion like an anniversary, birthday, or graduation, or simply looking for a relaxing getaway, Ohana Charters provides a memorable and unforgettable experience on the water. With the option for overnight stays, intimate family reunions, or exclusive events, Ohana Charters offers a variety of packages to suit every need. Experience romance, relaxation, and adventure aboard Ohana Charters for an unparalleled sailing experience.

Picture Perfect Sailing is a premier sailing institution located at 980 Awald Road in Annapolis, Maryland, United States. Escape the hustle and bustle of everyday life and enjoy quality time with family and friends on the beautiful Chesapeake Bay. Whether you are looking for a day sail or an overnight adventure, our experienced skippers will take you on a memorable journey. Choose from a variety of sailing charters, starting at $650 for 2 guests on weekdays. Your charter includes a skipper, snacks, and beverages. For a longer experience, opt for our all-day sailing or overnight options. Sail to destinations such as Baltimore or Saint Michaels and create memories that will last a lifetime.

Down Time Sportfishing Charters is a premier institution offering light tackle sportfishing charters on the Chesapeake Bay. Located at 1000 Fairwinds Drive in Annapolis, Maryland, United States, we specialize in bottom fishing, trolling, and crabbing excursions. Our experienced captain, Frank Tuma, has over 40 years of experience on the Bay, ensuring a memorable and successful fishing trip for you and your group. Whether you're targeting rockfish, bluefish, perch, or catfish, we have the equipment and knowledge to make your fishing adventure a success. Private group and family charters are welcome, so be sure to book your trip early to secure the best dates. In addition to fishing charters, we also offer family crabbing excursions, allowing you to catch your own Maryland Blue Crab in the morning. With convenient access to the best sportfishing areas from Annapolis to Baltimore, Down Time Sportfishing Charters is your go-to choice for an unforgettable Chesapeake Bay fishing experience.

Liberte, The Schooner is a renowned travel agency located at 222 Severn Avenue in Annapolis, Maryland, United States. Specializing in luxury sailing experiences, Liberte offers guests the opportunity to explore the stunning Chesapeake Bay aboard their beautiful schooner. With experienced crew members and top-notch amenities, guests can relax and enjoy the breathtaking views while sailing the waters of the East Coast. Whether you're looking for a romantic sunset cruise or a unique corporate event venue, Liberte, The Schooner is the perfect choice for a memorable and unforgettable sailing experience.

Last Hurrah Charter Fishing LLC is located at 487 New York Avenue in Pasadena, Maryland, United States. We pride ourselves on offering one of the best charter fishing experiences on the Chesapeake Bay. Our full-service operation is perfect for anglers of all skill levels, from beginners to advanced. Owned and operated by USCG Master Captain Scott Singleton, Last Hurrah Charters runs fishing trips for up to 6 passengers on the custom-built 35-foot Markley boat. We are based at Atlantic Marina on the Magothy, conveniently located less than 30 minutes from Annapolis and Baltimore, and an hour from Washington D.C.

Classic Sail Charters is a premier sailing school located in Annapolis, Maryland, offering private sailing adventures for up to six passengers. With world-class sailing yachts, experienced captains, and top-notch service, we ensure that your charter experience is truly unforgettable. Our charters are exclusively for private parties, allowing you to customize your adventure. Join us at 980 Awald Road for a unique and luxurious sailing experience on the beautiful Siena yacht. With Captain Nate, Payton, and Tony at the helm, you can relax, learn some sailing skills, and enjoy the stunning views of the West River. Whether you're looking for a romantic engagement shoot, a family outing, or a relaxing day on the water, Classic Sail Charters has something for everyone. Book your trip today and set sail for an unforgettable experience on the Chesapeake Bay.

Lafayette Waterfront Park is a picturesque park located at 199 Lafayette Avenue in Annapolis, Maryland. Situated along the waterfront, this park offers stunning views of the Chesapeake Bay and provides a peaceful escape from the hustle and bustle of city life. Visitors can enjoy leisurely strolls along the waterfront promenade, relax on the grassy lawns, or have a picnic with family and friends. The park also features playgrounds for children, picnic areas, and walking trails, making it a perfect destination for outdoor recreation and relaxation. Whether you're looking to unwind by the water or explore the natural beauty of the area, Lafayette Waterfront Park is a must-visit destination in Annapolis.

Amos Garrett Waterfront Park is a picturesque park located at 101 Spa View Avenue in Annapolis, Maryland, United States. This charming waterfront park offers stunning views of the Chesapeake Bay and is a popular tourist attraction in the area. Visitors can enjoy leisurely strolls along the waterfront promenade, relax on the grassy lawns, or have a picnic while taking in the beautiful scenery. The park is also a great spot for birdwatching and is a perfect place to unwind and escape the hustle and bustle of city life. With its serene atmosphere and breathtaking views, Amos Garrett Waterfront Park is a must-visit destination for nature lovers and outdoor enthusiasts.

Horn Point Park is a beautiful waterfront park located on Chesapeake Avenue in Annapolis, Maryland. This serene park offers stunning views of the Chesapeake Bay and is a popular spot for picnics, walking, and enjoying the outdoors. Visitors can relax on the grassy lawns, take a stroll along the shoreline, or watch the boats go by. With its peaceful atmosphere and scenic surroundings, Horn Point Park is the perfect place to escape the hustle and bustle of city life and connect with nature.

The Flounder Pavilion Beach Front at Sandy Point State Park in Annapolis, Maryland, is a stunning 786-acre park located along the Chesapeake Bay. Known for its scenic water views and sandy beaches, the park offers a variety of activities and services for guests to enjoy. From fishing and boat rentals to picnic areas and playgrounds, there is something for everyone to enjoy at this beautiful state park. Please note that the South Beach area will be closed for construction from mid-September 2024 until Summer 2025 for a restoration project. For more information and to check park hours, visit the Maryland Department of Natural Resources website. Come and experience the beauty of Sandy Point State Park on the shores of the Chesapeake Bay.

Jonas Green Park Beach is a beautiful waterfront park located in Annapolis, Maryland, United States. Situated along the shores of the Chesapeake Bay, this park offers stunning views of the water and plenty of opportunities for outdoor recreation. Visitors can enjoy swimming, sunbathing, picnicking, and fishing at this family-friendly destination. The park also features walking and biking trails, as well as a playground for children. With its peaceful atmosphere and scenic surroundings, Jonas Green Park Beach is the perfect spot for a relaxing day by the water.

Sandy Point Beach Parking Lot is a convenient parking area located on South Beach Road in Annapolis, Maryland, United States. Situated near the beautiful Sandy Point State Park, this parking lot provides easy access to the sandy shores of the Chesapeake Bay. Visitors can enjoy a day of swimming, sunbathing, picnicking, and beachcombing at this popular recreational spot. With ample parking spaces available, guests can relax and unwind in the natural beauty of the park without worrying about finding a place to park. Whether you're looking to spend a peaceful day by the water or enjoy some outdoor activities with family and friends, Sandy Point Beach Parking Lot is the perfect starting point for your beach adventure.

Broadneck Grill & Cantina is a vibrant and welcoming restaurant located in Annapolis, Maryland. Situated at 1364 Cape Saint Claire Road, this establishment offers a diverse menu of delicious dishes that are sure to satisfy any craving. From mouthwatering grilled steaks to flavorful Mexican-inspired cuisine, there is something for everyone at Broadneck Grill & Cantina. The laid-back atmosphere and friendly staff make it the perfect spot for a casual meal with friends or family. Whether you're looking for a hearty dinner or a refreshing cocktail, this restaurant has it all. Come dine with us and experience the flavors of Broadneck Grill & Cantina.

The Bayside Grill is a charming waterfront restaurant located in Annapolis, Maryland, United States. This popular eatery offers a diverse menu featuring fresh seafood, grilled meats, and delicious cocktails. With its stunning views of the bay and relaxed atmosphere, The Bayside Grill is the perfect spot for a casual meal with friends or a romantic dinner for two. Come and enjoy a taste of the Chesapeake Bay at The Bayside Grill.

The Choptank is a vibrant and modern seafood restaurant located in the heart of Annapolis, Maryland. Situated at 110 Compromise Street, this institution offers a unique and flavorful dining experience that celebrates the rich culinary heritage of the Chesapeake Bay region. With a focus on fresh, locally sourced ingredients and expertly crafted dishes, The Choptank is a must-visit destination for seafood lovers and food enthusiasts alike. Whether you're craving Maryland crab cakes, oysters on the half shell, or a perfectly grilled fish fillet, The Choptank has something to satisfy every palate. Come and enjoy a taste of the Chesapeake Bay at this renowned restaurant in Annapolis.

Level a small plates lounge is a popular establishment located at 69 West Street in Annapolis, Maryland, United States. This unique venue combines the elements of a bar, cafe, food destination, night club, and restaurant all in one. The concept of small plates has been a hit across the country, and Level has embraced this trend with a menu that features dishes meant to be shared, drawing inspiration from both the Chesapeake region and international cuisine. At Level, you will find a welcoming atmosphere that prioritizes the local community while also being inclusive to all. The handcrafted cocktails are a highlight, with options like Gimlets, Angels & Demons, Bourbonapolis, and a selection of wines available at happy hour prices.

Beacon Waterfront is a charming restaurant located at 2020 Chesapeake Harbour Drive East in Annapolis, Maryland. Situated right on the waterfront, this institution offers breathtaking views of the Chesapeake Bay while you enjoy delicious food and drinks. Whether you're looking for a romantic dinner for two or a fun gathering with friends, Beacon Waterfront provides a welcoming atmosphere and top-notch service. Come and experience a memorable dining experience at this hidden gem in Annapolis.

Eastport Yacht Club is a premier sailing and social club located at 317 First Street in Annapolis, Maryland, United States. With a rich history dating back to 1982, the club offers a vibrant community of boating enthusiasts, sailors, and social members. Situated on the picturesque shores of the Chesapeake Bay, Eastport Yacht Club provides top-notch facilities and amenities for its members, including a marina, clubhouse, and a full calendar of events and activities. Whether you're a seasoned sailor or just looking to connect with fellow water lovers, Eastport Yacht Club is the perfect place to enjoy the beauty of the bay and foster a love for all things nautical.

Located at 7153 Lake Shore Drive in North Beach, Maryland, Ketch 22 is a charming restaurant offering a fantastic dining experience with beautiful views of the water. Owned by Bobby and Julie Jones, who have over 25 years of experience in the hospitality industry, the restaurant prides itself on using fresh, locally sourced ingredients from the Chesapeake Bay region. With a menu that constantly changes to reflect the seasons and availability of ingredients, Ketch 22 offers a wide variety of delicious dishes and handcrafted cocktails. The large windows overlooking the water, expansive outdoor deck and bar, and friendly atmosphere make it the perfect place to enjoy a meal with friends and family.

Severn Sailing Association, located at 311 First Street in Annapolis, Maryland, is a premier sailing institution that hosts over a dozen fleets and a vibrant junior program. Whether you are a seasoned sailor or just starting out, SSA offers top-notch competition and a welcoming community of fellow sailors. Join us for exciting races, camaraderie, and the thrill of sailing on the beautiful waters of the Chesapeake Bay.

The Chesapeake Bay Yacht Racing Association (CBYRA) is a prestigious institution located at 821 Chesapeake Avenue in Annapolis, Maryland, United States. CBYRA is dedicated to promoting and supporting the sport of yacht racing in the Chesapeake Bay region. With a rich history and strong community of sailors, CBYRA organizes races, events, and educational programs to foster a love of sailing and competition. Join us at CBYRA and experience the thrill of racing on the beautiful waters of the Chesapeake Bay.

Eastport Kitchen is a charming restaurant located at 923 Chesapeake Avenue in Annapolis, Maryland. This cozy eatery offers a diverse menu featuring a variety of delicious dishes made with locally sourced ingredients. Whether you're in the mood for a hearty breakfast, a light lunch, or a flavorful dinner, Eastport Kitchen has something for everyone. The warm and inviting atmosphere makes it the perfect spot for a casual meal with friends or a special night out with loved ones. Come experience the flavors of the Chesapeake Bay region at Eastport Kitchen.

Bassett Furniture is a furniture store and home goods store located at 1906 Towne Centre Boulevard in Annapolis, Maryland. As part of a strong network of Bassett stores and retail partners across the country, they offer a wide selection of custom furniture and finishing touches like lamps, rugs, and mirrors. Their design consultants are available to help you with your next design project, whether you're redecorating a whole room or just looking for the perfect accent piece. Located in the walkable Annapolis Town Center at Parole, Bassett Home Furnishings Annapolis is the dream design center of the Chesapeake Bay area. Visit them today for a refreshing take on your style and enjoy every step of the design process with their talented consultants. Schedule a virtual or in-store appointment or simply drop in to get started on creating the home of your dreams.

Rehab Care-Arbor at Baywoods is a health institution located at 7101 Bay Front Drive in Annapolis, Maryland, United States. Situated directly on the beautiful Chesapeake Bay and just minutes away from the historic city of Annapolis, BayWoods of Annapolis is the premier waterfront Continuing Care Retirement Community in Maryland. Established in 2003, our community offers gracious retirement living for discerning seniors with a variety of unique amenities. Residents at BayWoods enjoy the largest retirement apartments in the area, complete with covered parking spaces to shield them from the winter weather. As a resident-owned and resident-run cooperative community, residents have a say in the operations of the community.

R&R Charters and Sail School, located in Chester, Maryland, United States, is a professional institution dedicated to sharing the joy of sailing with students. Our experienced educators provide personalized instruction to help students master the knowledge and skills needed to feel confident on the water. Whether you prefer individual instruction or learning in a small group setting with friends and family, our maximum of four students per boat ensures that each student receives ample hands-on experience. Captain Penny encourages students to "Learn to sail; you might want to go somewhere."

Fish for a Cure (F4AC) is a renowned fishing tournament and fundraising challenge located at 2000 Medical Parkway in Annapolis, Maryland. Every year, we host an exciting fishing tournament on the Chesapeake Bay, followed by a lively Shore Party in Annapolis. All funds raised through F4AC directly support the Cancer Survivorship Program at Luminis Health Anne Arundel Medical Center’s Geaton and JoAnn DeCesaris Cancer Institute. The Legends League is for previous winners of the Paul C. Dettor Captain’s Challenge, while the Open League is open to all other registered boats. Join us at Safe Harbor Marina for an unforgettable experience and help make a difference in cancer care in our community.

Knapp’s Narrows Marina & Inn is a waterfront lodging institution located on Maryland’s Eastern Shore in Tilghman Island. With a full-service boatyard, 1000-foot floating dock, swimming pool, and 20-room waterfront inn, guests can enjoy stunning views of the Chesapeake Bay from their own balcony or patio. The marina also offers lighthouse tours, fishing charters, and a taste of Chesapeake culture and history in the town of Tilghman. Environmentalists and bird watchers will appreciate the wildlife and expansive views, including sightings of Eagles, egrets, herons, and Monarch butterflies. Sunset sailboat cruises, lighthouse tours, and professional fishing charters are also available for guests to enjoy. Knapp’s Narrows Marina & Inn is the perfect destination for special events, family reunions, conferences, and more. Conveniently located within a day trip from Annapolis, St. Michael's, and other nearby cities, it is the ideal getaway for those looking to experience the beauty of the Chesapeake Bay.

Blue Crab Cupcakes is a charming bakery located in Annapolis, Maryland, just a stone's throw away from the beautiful Chesapeake Bay. Specializing in delectable cupcakes inspired by the local blue crab, this quaint store offers a wide variety of flavors and designs to satisfy any sweet tooth. Whether you're in the mood for a classic vanilla cupcake or a unique crab-shaped treat, Blue Crab Cupcakes has something for everyone. Stop by their cozy shop at 1580 Whitehall Road and indulge in a delicious dessert that captures the essence of Maryland's famous crustacean.