TOP 10 Sailing adventures 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.

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.

Pirate Adventures on the Chesapeake, located at 311 Third Street in Annapolis, Maryland, is a top tourist attraction and travel agency offering a unique and exciting experience for families. Guests rave about the high-energy and memorable adventures provided by the enthusiastic pirate crew. From searching for sunken treasure to firing water cannons, kids of all ages are sure to have a blast on this pirate cruise. The institution is highly recommended for parents of young children, as well as for school field trips. With activities like pirate dress up, face-painting, and interactive storytelling, Pirate Adventures on the Chesapeake is a must-visit destination for families looking for outdoor fun and entertainment. Don't miss out on this unforgettable experience – book your reservation today and set sail for a day filled with laughter and exploration!

American Sailing Tours is a premier travel agency located at 400 Key Highway in Baltimore, Maryland. We offer unforgettable sailing experiences along the beautiful waters of the United States. Our expert guides will take you on a journey through stunning landscapes and provide you with a unique perspective of the American coastline. Whether you're a seasoned sailor or a first-time adventurer, American Sailing Tours has something for everyone. Book your tour today and set sail with us for an unforgettable experience on the open sea.

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.

Blue Crab Chesapeake Sailing Charters is a premier travel agency located in Rock Hall, Maryland, United States. Offering scenic sailing charters along the beautiful Chesapeake Bay, this institution provides guests with unforgettable experiences on the water. Whether you're looking for a relaxing sunset cruise or a thrilling sailing adventure, Blue Crab Chesapeake Sailing Charters has something for everyone. With experienced captains and top-notch service, you can trust that your time on the water will be both safe and enjoyable. Book your next sailing excursion with Blue Crab Chesapeake 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!

Chesapeake Sailing Tours is a premier travel agency located in Annapolis, Maryland. We offer unforgettable sailing experiences on the beautiful Chesapeake Bay, providing guests with the opportunity to explore the stunning waterways and historic landmarks of the area. Our knowledgeable captains and crew are dedicated to providing a safe and enjoyable sailing experience for all guests. Whether you are looking for a relaxing sunset cruise or a thrilling day of sailing, Chesapeake Sailing Tours has something for everyone. Join us at 1117 Skyway Drive for an unforgettable adventure on the water.

Shardana Sailing Charters is a premier travel agency located at 20786 Rock Hall Avenue in Rock Hall, Maryland, United States. Specializing in sailing charters, they offer unforgettable experiences on the open water for individuals and groups alike. With a fleet of top-of-the-line boats and experienced captains, Shardana Sailing Charters provides a safe and luxurious way to explore the stunning waters of the Chesapeake Bay. Whether you're looking for a romantic sunset cruise or a day of adventure with family and friends, Shardana Sailing Charters has something for everyone. Book your next sailing excursion with them and create memories that will last a lifetime.

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.

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.

Das Boot Sailing Charters is a premier travel agency located at 4883 Church Lane in Galesville, Maryland, United States. Specializing in unforgettable sailing experiences, Das Boot offers a wide range of charter options for those looking to explore the beautiful waters of the Chesapeake Bay and beyond. Whether you're a seasoned sailor or a first-time adventurer, Das Boot's experienced crew will ensure a safe and enjoyable journey. Book your next sailing excursion with Das Boot Sailing Charters for an unforgettable experience on the open water.

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.

Cool Breeze Sailing Charters LLC is a premier travel agency located at 1900 Thames Street in Baltimore, Maryland. Specializing in sailing charters, they offer unforgettable experiences on the water for individuals, couples, and groups. Whether you're looking for a relaxing day cruise or a multi-day sailing adventure, Cool Breeze Sailing Charters LLC has the expertise and resources to make your nautical dreams a reality. With a fleet of well-maintained boats and experienced captains, you can trust that you'll have a safe and enjoyable voyage every time. Book your next sailing excursion with Cool Breeze Sailing Charters LLC and let the wind carry you to new and exciting destinations.

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.

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.

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.

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!

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.

Jackalope is a unique institution located at 52 White Sail Circle in Ocean Pines, Maryland. This establishment is a one-stop shop for all things related to bicycles, clothing, and more. Whether you're in need of a new bike, trendy apparel, or accessories for your outdoor adventures, Jackalope has you covered. Visit us today and experience the excellent selection and top-notch service that sets us apart from the rest.

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.

West Marine is a well-known clothing store located at 8226 Ocean Gateway in Easton, Maryland, United States. Specializing in marine-themed apparel and accessories, West Marine offers a wide selection of high-quality clothing for boating enthusiasts and outdoor adventurers. Whether you're looking for stylish nautical-inspired clothing or durable gear for your next water-based adventure, West Marine has you covered. Visit their store today to browse their extensive collection and find the perfect outfit for your next maritime excursion.

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.