The Best Chesapeake bay cruises in Baltimore, Maryland

Sea Baltimore Sailboat Charters is a premier travel agency located at 951 Fell Street in Baltimore, Maryland. We offer unforgettable sailing experiences on the beautiful waters of the Chesapeake Bay. Our fleet of luxury sailboats are fully equipped and ready to take you on a relaxing cruise or an exciting adventure. Whether you're looking for a romantic sunset sail, a team-building corporate event, or a fun day out with friends and family, Sea Baltimore Sailboat Charters has the perfect charter for you. Come sail with us and experience the beauty of the bay like never before.

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!

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.

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.

Baltimore's Finest Charters is a premier charter service located at 730 Riverside Drive in Essex, Maryland. With a fleet of top-of-the-line boats and experienced captains, we offer unforgettable fishing and sightseeing excursions on the beautiful waters of Maryland. Whether you're looking to reel in a big catch or simply relax and enjoy the scenic views, Baltimore's Finest Charters has something for everyone. Book your adventure with us today and experience the best that Baltimore has to offer 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.

The Seven Foot Knoll Lighthouse is a historic maritime landmark located at Pier 5 in Baltimore, Maryland, United States. This charming lighthouse, standing at seven feet tall, dates back to 1855 and has served as a beacon for sailors navigating the waters of the Chesapeake Bay for over a century. Today, it is a popular tourist attraction where visitors can learn about the rich maritime history of the region and enjoy stunning views of the harbor. The Seven Foot Knoll Lighthouse is a must-visit destination for history buffs and maritime enthusiasts alike.

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.

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.