The 30 Best Private sailing charters in Maryland

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.

Sundance Sailing Charters is a premier travel agency located at 78 George Street in Georgetown, Maryland, United States. Specializing in unforgettable sailing adventures, they offer a variety of charter options for exploring the beautiful waters of the Chesapeake Bay and beyond. Whether you're looking for a relaxing day on the water or a week-long sailing excursion, Sundance Sailing Charters has you covered. Their experienced crew and top-of-the-line vessels ensure a safe and enjoyable experience for all passengers. Book your next sailing adventure with Sundance Sailing Charters and create memories that will last a lifetime.

Watermark Tours, Charters, Cruises is a premier tourist attraction and travel agency located at 1 Dock Street in the charming city of Annapolis, Maryland, United States. Offering a variety of tours, private charters, and scenic cruises, visitors can explore the historic waterfront and iconic sites of Annapolis from the water. With knowledgeable guides, luxurious vessels, and unforgettable experiences, Watermark Tours, Charters, Cruises is the perfect destination for those seeking to discover the beauty and history of this picturesque city. Whether you're looking for a relaxing cruise, a private charter for a special occasion, or a guided tour of Annapolis, this institution has something for every traveler.

Located at 951 Fell Street in Baltimore, Maryland, Bay Dream Sailing is a premier tourist attraction and travel agency that offers unforgettable boat tours along the stunning waters of the Chesapeake Bay. Whether you're celebrating a special occasion like a birthday or anniversary, or simply looking for a unique way to explore the city, a boat tour with Bay Dream Sailing is a must-do activity in Baltimore. With private cruises available, you can enjoy a personalized and intimate experience on the water with your loved ones. Our experienced Captain, who is also the Commodore of the Sassafras River Yacht Club, has spent 25 years navigating the Chesapeake and is excited to share his passion for the waterways with you.

Annapolis Sailing Adventures is a premier travel agency located in Annapolis, Maryland, United States. We offer a variety of sailing experiences, including private charters, sunset cruises, and sailing lessons. Our experienced captains will take you on a memorable journey on the beautiful Chesapeake Bay. Whether you are a seasoned sailor or a beginner looking to learn the ropes, Annapolis Sailing Adventures has something for everyone. Come aboard and experience the thrill of sailing in one of the most scenic locations in the United States.

Darling Charters is a premier travel agency located at 1 Dock Street in Annapolis, Maryland. Specializing in luxury yacht charters and personalized travel experiences, our team of experienced professionals is dedicated to creating unforgettable vacations for our clients. Whether you're looking to explore the Chesapeake Bay or sail to exotic destinations around the world, Darling Charters is here to make your travel dreams a reality. Contact us today to start planning your next adventure!

Seas the Bay Private Sailing Charters is a premier travel agency located in Annapolis, Maryland, United States. Specializing in private sailing charters, they offer unforgettable experiences on the beautiful Chesapeake Bay. Whether you're looking for a romantic sunset cruise, a fun day out on the water with friends, or a corporate team-building event, Seas the Bay has you covered. Their experienced crew will ensure a safe and enjoyable journey as you take in the stunning views and relax on the open water. Book your private sailing charter today and make memories that will last a lifetime.

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!

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.

Reflections DC - Private Sailing Cruises offers unforgettable experiences on the water, allowing guests to explore the stunning waters of the Chesapeake Bay. Located at 4817 Woods Wharf Road in Shady Side, Maryland, this travel agency specializes in private sailing cruises, providing a luxurious and intimate setting for guests to relax and enjoy the beauty of the surrounding landscape. Whether you're looking for a romantic sunset cruise or a fun-filled day on the water with friends and family, Reflections DC - Private Sailing Cruises has something for everyone. Book your sailing adventure today and create lasting memories on the open seas.

My Girl Charters is a premier travel agency located at 1048 Turkey Point Road in Edgewater, Maryland, United States. Specializing in luxury yacht charters, we offer unforgettable experiences on the water for our clients. Whether you're looking for a romantic sunset cruise, a fun-filled day out with friends, or a corporate event with a touch of elegance, My Girl Charters has you covered. Our experienced crew and top-of-the-line vessels ensure a safe and enjoyable journey every time. Book your next adventure with us and create lasting memories on the beautiful waters of Maryland.

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.

Marauder Charters is a premier school and travel agency located at 255 Alexander Lane in Solomons, Maryland, United States. Our institution specializes in providing top-notch education and hands-on training in the field of maritime travel and adventure. Whether you are looking to learn how to navigate the open seas or book an unforgettable sailing experience, Marauder Charters has you covered. Join us for an exciting journey into the world of boating and exploration.

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.

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.

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.

Sailing Center Chesapeake is a premier sailing institution located in Lexington Park, Maryland, United States. Offering a wide range of sailing programs and courses for all skill levels, from beginners to advanced sailors, the center provides a unique opportunity to learn and improve sailing skills on the beautiful waters of Chesapeake Bay. With experienced instructors, top-of-the-line equipment, and a welcoming atmosphere, Sailing Center Chesapeake is the perfect place to embark on your sailing journey. So come and experience the thrill of sailing with us at Sailing Center Chesapeake!

Bay Princess is a charming lodging institution located at 110 81st Street in the beautiful coastal town of Ocean City, Maryland. Situated just steps away from the sandy shores of the Atlantic Ocean, Bay Princess offers guests a serene and relaxing retreat. The cozy rooms are tastefully decorated and equipped with modern amenities to ensure a comfortable stay. Guests can also enjoy stunning views of the ocean from the comfort of their rooms or take a leisurely stroll along the boardwalk. With its convenient location and warm hospitality, Bay Princess is the perfect choice for those looking to experience the best of Ocean City.

Sea Time North is a cozy lodging institution nestled in the heart of Ocean City, Maryland, United States. With its prime location just a stone's throw away from the beach, guests can enjoy breathtaking ocean views and easy access to the sandy shores. The institution offers comfortable accommodations, friendly staff, and a relaxing atmosphere perfect for a beach getaway. Whether you're looking for a weekend escape or a longer vacation, Sea Time North provides the perfect home away from home.

Ocean Princess is a charming lodging institution located at 11 134th Street in the beautiful coastal town of Ocean City, Maryland, United States. Situated just steps away from the sandy beaches and crashing waves of the Atlantic Ocean, Ocean Princess offers guests a serene and relaxing retreat by the sea. The cozy accommodations and friendly staff make for a truly unforgettable stay, with ocean views and easy access to all the attractions and amenities of Ocean City. Whether you're looking for a romantic getaway, a family vacation, or a solo adventure, Ocean Princess is the perfect choice for your next coastal escape.

River City Cruise Co. is a premier travel agency located at 10282 River Landing Road in Denton, Maryland, United States. Specializing in river cruises, our experienced team is dedicated to providing unforgettable travel experiences for our customers. Whether you're looking to explore local waterways or embark on a luxurious cruise vacation, River City Cruise Co. has you covered. Book your next adventure with us and set sail on a journey of a lifetime.

M/V Bay Breeze is a charming bar and travel agency located at 208 Bank Street in the picturesque town of Chesapeake City, Maryland, United States. This unique establishment offers a relaxing and inviting atmosphere where patrons can enjoy a drink while planning their next adventure. With a focus on providing exceptional service and personalized travel experiences, M/V Bay Breeze is the perfect destination for those looking to unwind and explore new destinations. Whether you're stopping in for a cocktail or booking your next vacation, M/V Bay Breeze is sure to leave a lasting impression.

Miss Ocean City Fishing is the premier bay fishing boat in Ocean City, Maryland. Our 52-foot boat is certified by the United States Coast Guard and offers a clean and comfortable experience for all passengers. With plenty of seating and a clean restroom onboard, our 3-hour bay fishing trips are perfect for both experienced anglers and those new to fishing. We prioritize the comfort of our guests by limiting our trips to a maximum of 33 passengers, ensuring a more personalized experience. Book your trip online using special codes and secure your spot on the best bay fishing boat in Ocean City!

The Captain's Cottage is a charming lodging located at 985 Awald Road in Annapolis, Maryland, United States. This cozy retreat offers a unique and inviting atmosphere for guests looking for a relaxing getaway. The cottage is tastefully decorated with a nautical theme, paying homage to the maritime history of the area. Guests can enjoy comfortable accommodations, modern amenities, and personalized service from the friendly staff. Whether you're in town for a weekend escape or a longer vacation, The Captain's Cottage is the perfect place to unwind and experience the beauty of Annapolis.

The Inn at Huntingfield Creek is a charming bed and breakfast located in Rock Hall, Maryland. Situated on 70 acres of peaceful land, our inn offers a variety of accommodations including guest rooms in the Manor House and private cottages. Guests can enjoy breathtaking sunsets, colorful gardens, and a romantic pond during their stay. With a focus on casual elegance, our inn provides a welcoming and relaxed atmosphere for guests to unwind and reconnect. Whether you're looking for a romantic getaway, a wedding venue, or a special event location, the Inn at Huntingfield Creek has everything you need.

Sea Seminars is a premier travel agency located at 1301 York Road in Timonium, Maryland, United States. Specializing in oceanic adventures and cruises, Sea Seminars offers a wide range of travel packages to exotic destinations around the world. With a team of experienced travel experts, Sea Seminars is dedicated to providing top-notch customer service and creating unforgettable travel experiences for all clients. Whether you're looking to explore tropical islands, embark on a luxury cruise, or discover underwater wonders, Sea Seminars has the perfect travel package for you. Book your next oceanic adventure with Sea Seminars and let the journey of a lifetime begin.

Z Flight Parasail and Watersports is a premier travel agency located at 300 Second Street in Annapolis, Maryland, United States. Offering the lowest price parasail flights in Marathon with no coupon code needed, Z Flight provides an unforgettable experience for guests. In Marathon, guests can enjoy scenic views of the island, wildlife, Sombreo Key Light, and more. In Annapolis, visitors can take in views of downtown Annapolis and the Naval Academy, with the option to venture out to the Thomas Point Lighthouse. With over 30 years of experience in the boating industry and a 100% safety record, Z Flight Watersports is the top choice for families and locals looking for a thrilling adventure on the water. Gift cards are available for purchase and can be used towards any Z Flight Watersports experience. Refunds are offered in case of trip cancellations due to weather or mechanical issues, with a 24-hour cancellation policy for individual bookings and a 7-day policy for group and private charters. Don't miss out on the opportunity to create cherished memories with Z Flight Parasail and Watersports.