TOP 10 Family sailing trips 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!

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.

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.

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!

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.

The Duckaneer Pirate Ship is a thrilling travel agency located at 311 Talbot Street in Ocean City, Maryland, United States. Step aboard this unique pirate ship and set sail on an unforgettable adventure on the high seas. With interactive pirate-themed activities, live entertainment, and scenic views of the coast, The Duckaneer Pirate Ship promises an exciting experience for all ages. Join the crew and embrace your inner pirate as you embark on a voyage unlike any other. Get ready to make memories that will last a lifetime at The Duckaneer Pirate Ship.

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!

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!

Travel Dream Weaver is a travel agency located at 6081 Otterbein Lane, Ellicott City, Maryland, United States. Whether you are planning a simple trip or a milestone celebration, Travel Dream Weaver can make your travel experience a breeze. They offer free VIP treatment with preferred partners, exclusive perks, and upgrades. With industry resources at their fingertips, Travel Dream Weaver can plan trips anywhere in the world and find the best available rates on accommodations. Their booking services are completely free, with the only fee charged for full day-to-day itinerary planning if requested.

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.

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.

The Town of St. Michaels, Maryland is a charming and historic waterfront community located at 300 Mill Street in Saint Michaels, Maryland, United States. Known for its picturesque harbor, quaint shops, and rich maritime history, the town offers visitors a unique blend of small-town charm and coastal beauty. With its vibrant arts scene, delicious seafood restaurants, and scenic views of the Chesapeake Bay, the Town of St. Michaels is a must-visit destination for anyone looking to experience the best of the Eastern Shore.