TOP Cruise destinations in Annapolis, Maryland

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.

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.

Annapolis Tours by Watermark is a premier tourist attraction and travel agency located at 1 Dock Street in Annapolis, Maryland, United States. Offering a variety of guided tours and experiences, visitors can explore the historic city of Annapolis by land and by water. Discover the rich history, charming architecture, and picturesque waterfront views that make Annapolis a must-visit destination. Whether you're interested in a scenic boat tour, a walking tour of the city's historic sites, or a customized itinerary, Annapolis Tours by Watermark has something for everyone. Experience the beauty and charm of Annapolis with expert guides and exceptional service.

The Annapolis Waterfront Hotel, Autograph Collection is a luxurious lodging option located at 80 Compromise Street in the charming city of Annapolis, Maryland, United States. Situated right on the waterfront, this hotel offers stunning views of the Chesapeake Bay and the historic city skyline. With upscale amenities, elegant decor, and personalized service, guests can enjoy a relaxing and memorable stay in this picturesque setting. Perfect for both leisure and business travelers, the Annapolis Waterfront Hotel is the ideal choice for those looking for a unique and unforgettable experience in the heart of Annapolis.

Annapolis Water Taxi by Watermark offers a convenient and scenic way to explore the charming city of Annapolis, Maryland. Located at 1 Dock Street, this institution provides water taxi services for locals and tourists alike. Whether you're looking to enjoy a leisurely cruise on the water or need a quick and reliable transportation option, Annapolis Water Taxi by Watermark has you covered. Sit back, relax, and take in the stunning views of the city's historic waterfront as you travel from one destination to another. With experienced captains and a fleet of well-maintained boats, you can trust that your journey will be both safe and enjoyable. Don't miss the opportunity to experience Annapolis from a unique perspective with Annapolis Water Taxi by Watermark.

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!

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!

Susan Campbell Park is a charming waterfront park located on Dock Street in Annapolis, Maryland. This picturesque park offers stunning views of the harbor and sailboats gliding by, making it a popular spot for locals and tourists alike. Visitors can relax on the grassy lawn, enjoy a picnic, or simply take in the sights and sounds of the bustling harbor. With its convenient location near downtown Annapolis, Susan Campbell Park is a must-visit destination for anyone looking to experience the beauty and charm of this historic city.

Knapp’s Narrows Marina & Inn is a waterfront lodging institution located on Maryland’s Eastern Shore in Tilghman Island. With a full-service boatyard, 1000-foot floating dock, swimming pool, and 20-room waterfront inn, guests can enjoy stunning views of the Chesapeake Bay from their own balcony or patio. The marina also offers lighthouse tours, fishing charters, and a taste of Chesapeake culture and history in the town of Tilghman. Environmentalists and bird watchers will appreciate the wildlife and expansive views, including sightings of Eagles, egrets, herons, and Monarch butterflies. Sunset sailboat cruises, lighthouse tours, and professional fishing charters are also available for guests to enjoy. Knapp’s Narrows Marina & Inn is the perfect destination for special events, family reunions, conferences, and more. Conveniently located within a day trip from Annapolis, St. Michael's, and other nearby cities, it is the ideal getaway for those looking to experience the beauty of the Chesapeake Bay.

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!

Naptown Tiki Club is the ultimate destination for a unique and unforgettable experience in Annapolis, Maryland. Located at 655 Americana Drive, this travel agency offers the first and only tiki boat bar in the city. With a capacity of up to 16 passengers, this BYOB private floating tiki bar is perfect for friends, families, and colleagues looking to enjoy a fun and safe cruise on the water. Embark on a private boat charter from Nautilus Point Marina and cruise for an hour and a half while sipping on your favorite drinks, snacking on delicious foods, and dancing to your favorite music. The marina offers free parking for passengers, making it convenient for all guests.

Spa Creek Galley is a charming waterfront restaurant located at 314 6th Street in Annapolis, Maryland. With stunning views of Spa Creek, this institution offers a unique dining experience in a picturesque setting. Specializing in delicious seafood dishes and American cuisine, Spa Creek Galley is the perfect spot for a romantic dinner or a casual lunch with friends. The cozy atmosphere and friendly staff make it a popular choice among locals and tourists alike. Come and enjoy a memorable meal at Spa Creek Galley in the heart of historic Annapolis.

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.

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.

Lilly Sport Boats is a premier store located in Arnold, Maryland, United States, specializing in a wide range of high-quality sport boats. Our store offers a variety of top-of-the-line boats for all water enthusiasts, from fishing and watersports to leisure cruising. With expert staff on hand to provide guidance and assistance, Lilly Sport Boats is the go-to destination for anyone looking to purchase a reliable and stylish watercraft. Visit us at 1193 Baltimore Annapolis Boulevard to explore our selection and start your next aquatic 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.