TOP 30 Sailboats in Maryland

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Sea Baltimore Sailboat Charters is a premier travel agency located at 951 Fell Street in Baltimore, Maryland. We offer unforgettable sailing experiences on the beautiful waters of the Chesapeake Bay. Our fleet of luxury sailboats are fully equipped and ready to take you on a relaxing cruise or an exciting adventure. Whether you're looking for a romantic sunset sail, a team-building corporate event, or a fun day out with friends and family, Sea Baltimore Sailboat Charters has the perfect charter for you. Come sail with us and experience the beauty of the bay like never before.

Boat Baltimore offers exclusive private boat charters in the heart of Baltimore, Maryland. Located at 321 East Cromwell Street, our travel agency provides intimate sailing yacht cruises, large group charters, and fishing adventures. As Baltimore's only locally owned private boat charter, you'll never have to share the boat with strangers. Our 45ft sailing yacht, SAEDA, offers private two-hour cruises for up to six passengers departing from the Baltimore Peninsula four times a day. Kids sail for free!

Sail Alyosha is a premier travel agency located at 12817 Harbor Road in Ocean City, Maryland. Specializing in providing unforgettable sailing experiences, Sail Alyosha offers a wide range of services including sunset cruises, private charters, and sailing lessons. Whether you are looking to explore the beautiful waters of the Atlantic Ocean or simply relax and enjoy the stunning views, Sail Alyosha has something for everyone. With experienced captains and top-of-the-line sailboats, you can trust that your sailing adventure will be both safe and enjoyable. Book your next sailing excursion with Sail Alyosha and create memories that will last a lifetime.

BaySail School of Sailing, located at 100 Bourbon Street in Havre de Grace, Maryland, is an accredited American Sailing Association (ASA) school. Our institution offers professional instruction ranging from Introduction to Sailing to Advanced Sailing Classes. Conveniently situated just off I-95, we are only an hour away from Philadelphia and 45 minutes from Baltimore. Join us at BaySail School of Sailing to embark on a journey of learning and mastering the art of sailing.

Coastal Conversions, located on Hanover Pike in Hampstead, Maryland, is a one-stop shop for all your van conversion needs. Whether you're looking for a weekend getaway vehicle, a road trip companion, a family vacation van, or a permanent home on wheels, Coastal Conversions has got you covered. With over 20 years of experience in remodeling hotels, homes, commercial buildings, and restaurants, as well as working on high-end vessels like yachts and sailboats, Coastal Conversions is a trusted name in the industry. They offer two customizable floor plans that can be tailored to your specific requirements, ensuring that you get the van of your dreams.

Solomon Yacht Restoration, LLC is a premier car repair institution located at 3774 Beach Drive Boulevard in Edgewater, Maryland, United States. With a team of highly skilled technicians and state-of-the-art equipment, we specialize in restoring and repairing yachts to their former glory. Whether you need routine maintenance, cosmetic upgrades, or major repairs, our experts are here to provide top-notch service and ensure your yacht is in pristine condition. Trust Solomon Yacht Restoration, LLC for all your yacht repair needs.

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.

Chesapeake Bay Charter Services is a premier travel agency located at 910 Kentmorr Road in Stevensville, Maryland, United States. Specializing in charter services for exploring the beautiful Chesapeake Bay, they offer a wide range of customizable packages for fishing trips, sightseeing tours, and private cruises. With experienced captains and top-of-the-line equipment, Chesapeake Bay Charter Services guarantees a memorable and enjoyable experience on the water. Whether you're a seasoned angler or just looking to relax and take in the scenic views, this institution has everything you need for an unforgettable adventure on the Chesapeake Bay.

elax on a Chesapeake Bay sailing tour with Sail Selina II in St. Michaels, Maryland. Located at 101 North Harbor Road, this tourist attraction and travel agency offers relaxing sailboat rides and sightseeing boat trips. Join the friendly crew on a comfortable, well-maintained historic sailboat as you learn about St. Michaels and enjoy the outdoor scenery. Experience a romantic sunset cruise with Champagne or wine, or a moonlight cruise with free Champagne. For those looking to learn about wine tasting, Sail Selina II offers a wine cruise with Captain Iris and her crew. Enjoy a fun and refreshing beer tasting experience with Maryland Craft breweries aboard the sailboat. Embark on a sailing adventure with the experienced team to learn new skills and build confidence on the water.

Chesapeake Windsail Cruises Corporation is a premier travel agency located at 4160 Mears Avenue in Chesapeake Beach, Maryland. Specializing in unforgettable sailing experiences, they offer a variety of cruises along the beautiful Chesapeake Bay. Whether you're looking for a romantic sunset sail, a family-friendly adventure, or a corporate team-building event, Chesapeake Windsail Cruises Corporation has something for everyone. Their experienced crew and top-of-the-line sailboats ensure a safe and enjoyable experience for all guests. Book your next sailing excursion with Chesapeake Windsail Cruises Corporation for a truly memorable journey on the water.

Schooner Woodwind Offsite Business Office is a travel agency located at 1930 Lincoln Drive in Annapolis, Maryland. Our office is dedicated to providing exceptional service and assistance to our clients in planning their travel adventures on the Schooner Woodwind sailboats. Whether you are looking to book a private charter, a team building event, or a unique corporate outing, our experienced team is here to help create a memorable and enjoyable experience for you and your group. Contact us today to start planning your next sailing adventure on the beautiful waters of Annapolis.

Granmar Sailing is a premier travel agency located at #8 Randall Street in Annapolis, Maryland, United States. Specializing in sailing adventures, Granmar Sailing offers a variety of packages for individuals and groups looking to explore the open waters. Whether you are a seasoned sailor or a beginner looking to learn the ropes, Granmar Sailing has something for everyone. With experienced captains and top-of-the-line equipment, you can trust that your sailing experience with Granmar Sailing will be safe, enjoyable, and unforgettable. Book your next sailing adventure with Granmar Sailing and set sail for an experience of a lifetime.

Chesapeake Bay Charters offers an unforgettable family sailing adventure at their location in Solomons, Maryland. This institution is a school, tourist attraction, and travel agency all rolled into one, providing a unique opportunity for families to experience the beauty of the Chesapeake Bay from the deck of a sailboat. Whether you're a seasoned sailor or a complete novice, their experienced instructors will guide you through the waters, teaching you the ropes and ensuring a safe and enjoyable journey. Come aboard and create lasting memories with your loved ones on a Chesapeake Bay Charter adventure.

Chronic Sailing is a premier sailing school located at 7082 Bembe Beach Road in Annapolis, Maryland, United States. Our institution offers top-notch sailing instruction for all skill levels, from beginners to advanced sailors. Whether you're looking to learn the basics of sailing or improve your racing techniques, our experienced instructors are here to help you achieve your goals on the water. Join us at Chronic Sailing and experience the thrill of sailing in one of the most beautiful locations on the East Coast.

St. Michaels Sailing Charters is a premier tourist attraction located at 23672 Mount Pleasant Landing Circle in the picturesque town of Saint Michaels, Maryland, United States. Offering unforgettable sailing experiences on the beautiful waters of the Chesapeake Bay, visitors can enjoy a variety of charter options including private cruises, sunset sails, and sailing lessons. With experienced captains, top-notch vessels, and stunning views, St. Michaels Sailing Charters is the perfect destination for those looking to explore the bay in style. Whether you're a seasoned sailor or a first-time visitor, this institution promises a memorable and relaxing maritime adventure.

Susan Campbell Park is a charming waterfront park located on Dock Street in Annapolis, Maryland. This picturesque park offers stunning views of the harbor and sailboats gliding by, making it a popular spot for locals and tourists alike. Visitors can relax on the grassy lawn, enjoy a picnic, or simply take in the sights and sounds of the bustling harbor. With its convenient location near downtown Annapolis, Susan Campbell Park is a must-visit destination for anyone looking to experience the beauty and charm of this historic city.

Luxe Dental Care is a premier dental institution located at 352 Thompson Creek Mall in Stevensville, Maryland, United States. Situated on the tranquil shores of Chesapeake Bay, our dedicated team of dental professionals, led by our expert dentist, is committed to providing the most comfortable and compassionate care possible. Whether you're in need of a routine check-up or a complete smile makeover, we'll work with you every step of the way to ensure you achieve the dazzling smile you've always wanted. At Luxe Dental Care, we believe that visiting the dentist should never be a stressful experience. Our gentle approach to dentistry allows you to relax and enjoy the journey towards a healthier, more beautiful smile. Whether it's routine cleanings, cosmetic treatments, or emergency procedures, we're here to assist you every step of the way.

The Seven Foot Knoll Lighthouse is a historic maritime landmark located at Pier 5 in Baltimore, Maryland, United States. This charming lighthouse, standing at seven feet tall, dates back to 1855 and has served as a beacon for sailors navigating the waters of the Chesapeake Bay for over a century. Today, it is a popular tourist attraction where visitors can learn about the rich maritime history of the region and enjoy stunning views of the harbor. The Seven Foot Knoll Lighthouse is a must-visit destination for history buffs and maritime enthusiasts alike.

Located at 2015 Turkey Point Road in Essex, Maryland, Charly's Sue Creek is a charming food institution that offers a delightful dining experience for all. Whether you're looking to enjoy a meal with friends, celebrate a special occasion, or venture out on the water with Sue Creek Rentals, Charly's has something for everyone. Indulge in delicious and organic American seafood and pub fare, from baked salmon to fresh salads made with chickpeas, arugula, herbs, and olives. Our Events Team is available to help plan additional dining options for rehearsal dinners, corporate events, or any celebration you have in mind.

The Baltimore Yacht Club is a prestigious institution located at 800 Baltimore Yacht Club Road in Essex, Maryland, United States. Established in [insert year], the club offers a range of amenities and services for boating enthusiasts, including a marina, sailing programs, social events, and dining options. With its beautiful waterfront location and welcoming atmosphere, the Baltimore Yacht Club is the perfect destination for those who love the sea and all things nautical. Whether you're a seasoned sailor or just looking to relax by the water, this club has something for everyone. Come experience the charm and elegance of the Baltimore Yacht Club today!

The Annapolis Yacht Club is a prestigious and historic institution located at 2 Compromise Street in Annapolis, Maryland. With a rich maritime tradition dating back to its founding in 1886, the club offers members and guests a wide range of amenities and activities, including sailing races, social events, dining options, and access to a beautiful waterfront setting. Boasting a welcoming and inclusive atmosphere, the Annapolis Yacht Club is a cherished destination for boating enthusiasts and community members alike.

Chesapeake Boating Club, located at 213 Eastern Avenue in Annapolis, Maryland, is a unique institution that offers sail and power boat charters and rentals. Founded in 1992 in the Historic Eastport section of Annapolis, the club prides itself on providing flexible, fun, and affordable boating experiences. With a variety of boats ranging from 17' to 36' in length, members can choose the right vessel for any adventure on the Chesapeake Bay. In addition to boat rentals, the Chesapeake Boating Club also offers instruction in sailing and powerboating. The club's experienced J World coaches provide online educational seminars during the off-season to help members enhance their boating skills.

Chesapeake Canvas Shop is a furniture and home goods store located at 26661 Medders Road in Still Pond, Maryland. Specializing in upholstery and marine canvas, they offer a wide range of products and services for customers in the area. From the Bay Bridge to Bohemia Bay, Chesapeake Canvas is your go-to destination for all your upholstery and canvas needs. Contact them at (410) 708 4559 or email [email protected] for more information. Visit Chesapeake Canvas Shop today for top-quality products and excellent customer service.

Bufflehead Nautical Home is a charming home goods store located at 1628 Postal Road in Chester, Maryland. Specializing in nautical-themed decor and furnishings, this store offers a wide selection of items to help you bring a touch of the sea into your home. From coastal-inspired furniture to beachy accents and accessories, Bufflehead Nautical Home has everything you need to create a relaxing and stylish seaside retreat in any room. Whether you're looking to redecorate your beach house or simply add a little coastal flair to your current home, this store is the perfect destination for all your nautical decor needs.

Body Reset System & Dr. Brenda Shaeffer, Physical Therapy is a health institution located at 166 Defense Highway in Annapolis, Maryland, United States. Dr. Brenda Shaeffer, a licensed Physical Therapist since 1978, offers intelligent physical therapy solutions for workplace, athletic, and home tasks. With a focus on interactive education, the institution aims to help individuals reach their fitness goals, prevent and remove pain and injury, and achieve optimal performance in work, sports, and life. Dr. Brenda Shaeffer, who holds a Doctorate of Physical Therapy and a Bachelor of Science, has over 40 years of experience in treating athletes at all levels and providing post-surgical rehabilitation, performance training, and neurological disease care. As a former elite gymnast and national sailboat racer, Dr. Shaeffer brings a unique perspective to her practice, emphasizing realism, compassion, and measurable results.

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.

The Annapolis School of Seamanship is a renowned institution located at 410 Severn Avenue in Annapolis, Maryland, United States. As a leading school specializing in seamanship, the institution offers a wide range of courses and programs designed to educate and train individuals in the art of sailing and boating. With experienced instructors, state-of-the-art facilities, and a hands-on approach to learning, students can expect to receive top-notch education and practical skills that will prepare them for a successful career in the maritime industry. Whether you are a beginner looking to learn the basics or an experienced sailor seeking to enhance your skills, the Annapolis School of Seamanship is the perfect place to achieve your goals.

Blown Away Sailing LLC is a premier sailing institution located at 20880 Rock Hall Avenue in Rock Hall, Maryland, United States. We offer a range of sailing experiences, from beginner lessons to advanced courses, all taught by experienced and certified instructors. Our fleet of sailboats is well-maintained and equipped with the latest safety features, ensuring a smooth and enjoyable sailing experience for all participants. Whether you're looking to learn the basics of sailing or hone your skills on the open water, Blown Away Sailing LLC has something for everyone. Come join us for an unforgettable sailing adventure!

The Sailing Academy is a premier institution located at 411 Deale Road in Tracys Landing, Maryland, United States. Our academy offers top-notch sailing education and training programs for individuals of all skill levels, from beginners to experienced sailors. Our experienced instructors provide hands-on instruction in a safe and supportive environment, ensuring that students receive the highest quality education. Whether you are looking to learn the basics of sailing or improve your skills, The Sailing Academy is the perfect place to embark on your sailing journey. Join us and discover the thrill of sailing on the beautiful waters of Maryland.

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.