TOP 10 Sailing packages 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.

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!

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.

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.

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.

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.

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.

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!

2118 Sail Inn is a cozy bar located at 2118 Lincoln Avenue in Sparrows Point, Maryland. This waterfront establishment offers a relaxed and friendly atmosphere for patrons to enjoy a wide selection of drinks, including craft beers, cocktails, and wines. The bar also features live music and events throughout the week, making it a popular spot for locals and visitors alike. Whether you're looking to unwind after a long day or catch up with friends, 2118 Sail Inn is the perfect place to kick back and enjoy good company.

P.F. Chang's in Annapolis, Maryland is a popular restaurant offering delicious Asian-inspired cuisine for dine-in, takeout, and delivery. Located at 307 Sail Place, this institution provides a variety of options for individual meals, catering packages, and build-your-own feasts. From chopsticks to dessert, everything you need is available for pickup or delivery right to your door. In addition to food, P.F. Chang's offers a selection of exclusive apparel, accessories, and cookware, making it a great place to find a unique gift for any occasion. Whether you're looking to make a reservation or place an online order for delivery, takeout, or catering, P.F. Chang's in Annapolis has you covered.

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.

Carnival Cruise Line is a renowned travel agency located in Baltimore, Maryland, United States. Offering a wide range of exciting cruise experiences, Carnival Cruise Line is known for its fun-filled vacations at sea. With top-notch amenities, delicious dining options, and thrilling onboard activities, Carnival Cruise Line is the perfect choice for travelers looking to explore the world in style. Whether you're looking to relax on a tropical beach or embark on an adventure-filled journey, Carnival Cruise Line has something for everyone. Book your dream cruise today and set sail with Carnival Cruise Line for an unforgettable vacation experience.

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.

Salisbury Cruise Club is a premier travel agency located at 3911 5 Friars Road in Salisbury, Maryland, United States. We specialize in creating unforgettable cruise experiences for our clients, offering a wide range of cruise packages to destinations all around the world. Our team of experienced travel experts is dedicated to providing personalized service and helping you plan the perfect cruise vacation tailored to your preferences and budget. Whether you're looking for a relaxing Caribbean getaway or an adventurous Alaskan expedition, Salisbury Cruise Club has you covered. Book your dream cruise with us today and set sail on the vacation of a lifetime.

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!

Located on 48th Street Bayside in Ocean City, Maryland, 48th Street Watersports is the ultimate destination for all your water sports and beach activities. Whether you're looking to sail, wind surf, paddle board, kayak, or simply relax on the water, we have everything you need for a day of fun in the sun. Our prime location behind the Princess Bayside offers a peaceful escape from the summer crowds, allowing you to enjoy the sparkling waters of the Isle of Wight Bay. With options for eco-tours, yoga classes, sunset paddles, and even night paddles, there's something for everyone at 48th Street Watersports. Plus, we offer free delivery of kayaks for those looking to explore beyond our midtown location. Come experience the best of Ocean City's water sports with our experienced and friendly staff at 48th Street Watersports.

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.

Cruises Plus is a premier travel agency located at 100 West Road in Towson, Maryland, United States. Specializing in luxury cruises and vacation packages, Cruises Plus offers a wide range of options for travelers seeking unforgettable experiences on the high seas. With a dedicated team of travel experts, exceptional customer service, and competitive pricing, Cruises Plus is your go-to destination for all your cruise vacation needs. Book your dream getaway today and set sail with Cruises Plus!

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.

Ambassador Cruises is a premier travel agency located at 3169 Eutaw Forest Drive in Waldorf, Maryland. Specializing in luxury cruises, Ambassador Cruises offers a wide range of travel packages to exotic destinations around the world. With a team of experienced travel experts, Ambassador Cruises provides personalized service and attention to detail to ensure an unforgettable vacation experience for every client. Whether you're looking for a romantic getaway, a family vacation, or a group trip, Ambassador Cruises has the perfect package for you. Book your dream cruise today and set sail on the adventure of a lifetime with Ambassador Cruises.

Tall Timbers Marina is a charming waterfront institution located at 18521 Herring Creek Road in Tall Timbers, Maryland, United States. This multi-faceted establishment offers a variety of amenities including a restaurant, store, and marina services. Visitors can enjoy delicious food while taking in picturesque views of the water or browse the store for unique gifts and souvenirs. The marina also provides convenient access to the water for boating and fishing enthusiasts. With its scenic location and array of offerings, Tall Timbers Marina is a must-visit destination for locals and tourists alike.

Annapolis Watersports is a premier water sports store located in Edgewater, Maryland. We offer a wide range of equipment and gear for all your water adventures, including kayaking, paddleboarding, sailing, and more. Our knowledgeable staff are passionate about water sports and are dedicated to helping you find the perfect equipment for your needs. Whether you're a seasoned pro or a beginner looking to get started, Annapolis Watersports has everything you need to make the most of your time on the water. Visit us at 2830 Solomons Island Road and let us help you gear up for your next aquatic adventure!

Huntingfield Corporation is a unique lodging institution located at 4928 Eastern Neck Road in Rock Hall, Maryland, United States. The institution, known as The Inn at Huntingfield Creek, offers a tranquil and picturesque retreat on the Maryland Eastern Shore. Guests can choose from five beautifully appointed guest rooms in the Manor House or seven private cottages, each offering a different experience. The inn also features a spacious vacation rental in downtown Rock Hall for those looking for a more urban setting. With 70 acres of land, a farmhouse, and a crystal barn, Huntingfield Corporation can accommodate a variety of events and group sizes. The property boasts stunning sunsets, fragrant gardens, a romantic pond, and a bayside dock, making it a popular choice for weddings, parties, and special events.

Landon Marine, Inc. is a full-service marine institution located at 8110 Brices Mill Road in Chestertown, Maryland. Our range of services includes repairs, maintenance, repowers, installations, electronics, bottom painting, detailing, winterization, storage, restoration, and on-lift/travel maintenance. As a Platinum Level Certified Evinrude Etec Dealer, we offer a showroom where you can find your new engine today. Founded by Bill Landon, who has always had a passion for the water, Landon Marine has become a trusted name in the marine industry. We offer repair services for all types of boats, including inboards, outboards, diesel, jet boats, pontoon boats, sail boats, jet skis, and more. Our experienced technicians can handle everything from oil changes to full engine rebuilds, as well as trailer repairs and maintenance.