TOP 10 Romantic sailing getaways 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.

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.

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.

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.

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.

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.

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.

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 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.

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.

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.

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.

Liberte, The Schooner is a renowned travel agency located at 222 Severn Avenue in Annapolis, Maryland, United States. Specializing in luxury sailing experiences, Liberte offers guests the opportunity to explore the stunning Chesapeake Bay aboard their beautiful schooner. With experienced crew members and top-notch amenities, guests can relax and enjoy the breathtaking views while sailing the waters of the East Coast. Whether you're looking for a romantic sunset cruise or a unique corporate event venue, Liberte, The Schooner is the perfect choice for a memorable and unforgettable sailing experience.

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.

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.