The 30 Best Cruise vacations in Annapolis, Maryland

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.

Cruises Come True LLC is a premier travel agency located at 849 Singing Hill's Court in Annapolis, Maryland. Specializing in luxury cruise vacations, our team of experienced travel experts is dedicated to making your dream cruise a reality. Whether you're looking for a romantic getaway, a family vacation, or an adventurous expedition, we can help you find the perfect cruise package tailored to your preferences. Contact us today to start planning your unforgettable cruise experience with Cruises Come True LLC.

Cruise Planners is a premier travel agency located in Annapolis, Maryland, United States. Specializing in planning unforgettable cruise vacations, our experienced team of travel experts are dedicated to providing personalized service and creating tailored itineraries to ensure a seamless and enjoyable travel experience for our clients. Whether you're looking to explore exotic destinations or relax on a luxury cruise ship, Cruise Planners has the knowledge and resources to make your dream vacation a reality. Contact us today to start planning your next adventure at sea!

Waypoints Annapolis is a premier travel agency located in the heart of Annapolis, Maryland. Situated at 222 Severn Avenue, our agency specializes in creating unforgettable travel experiences for our clients. Whether you're looking to plan a romantic getaway, a family vacation, or a business trip, our team of experienced travel experts is here to help. From booking flights and accommodations to arranging tours and activities, we take care of all the details so you can relax and enjoy your journey. Trust Waypoints Annapolis to guide you to your next adventure.

Cruise One is a premier travel agency located at 2731 Cabernet Lane in Annapolis, Maryland. Specializing in luxury cruises, our experienced team of travel agents will help you plan the perfect getaway on the high seas. Whether you're looking for a romantic honeymoon cruise, a family vacation, or a group adventure, Cruise One has the expertise to make your dream vacation a reality. Contact us today to start planning your next unforgettable cruise experience.

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!

Schooner Woodwind Offsite Business Office is a travel agency located at 1930 Lincoln Drive in Annapolis, Maryland. Our office is dedicated to providing exceptional service and assistance to our clients in planning their travel adventures on the Schooner Woodwind sailboats. Whether you are looking to book a private charter, a team building event, or a unique corporate outing, our experienced team is here to help create a memorable and enjoyable experience for you and your group. Contact us today to start planning your next sailing adventure on the beautiful waters of Annapolis.

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.

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.

Eastport Yacht Club is a premier sailing and social club located at 317 First Street in Annapolis, Maryland, United States. With a rich history dating back to 1982, the club offers a vibrant community of boating enthusiasts, sailors, and social members. Situated on the picturesque shores of the Chesapeake Bay, Eastport Yacht Club provides top-notch facilities and amenities for its members, including a marina, clubhouse, and a full calendar of events and activities. Whether you're a seasoned sailor or just looking to connect with fellow water lovers, Eastport Yacht Club is the perfect place to enjoy the beauty of the bay and foster a love for all things nautical.

Chesapeake Harbour Village Condo is a prestigious gated community located at 2014 Sams Way in Annapolis, Maryland. Residents of Chesapeake Harbour enjoy easy access to Annapolis, Baltimore, and Washington, DC, as well as the beautiful Chesapeake Bay for boating, fishing, cruising, and racing. This stunning home in Chesapeake Harbour has been extensively renovated since 2017, with a focus on perfection in every aspect, including the kitchen and bathrooms. The property offers unparalleled views of the marina and Chesapeake Bay, providing a vacation lifestyle for its residents.