Best Boat Charters in Baltimore

Why These Boat Charters?

Our goal is to connect people with the best local experts. We scored Baltimore Boat Charters on more than 25 variables across five categories, and analyzed the results to give you a hand-picked list of the best.

Reviewed Curated Top Picks 172 109 16

Our Selection Criteria:

  • 1. Availability

    Consistently approachable and responsive, so customers never feel ignored.

  • 2. Qualifications

    Building customer confidence with licensing, accreditations, and awards.

  • 3. Reputation

    A history of delighted customers and outstanding service.

  • 4. Experience

    Masters of their craft, based on years of practical experience and education.

  • 5. Professionalism

    Providing service with honesty, reliability, and respect.

Read more about our selection process

American Sailing Tours

American Sailing Tours, located in Baltimore, Maryland, provides elegant tours that are as informative and entertaining as they are authentic. They provide day sails and night sails, as well as private charters, daily charters, and Chesapeake Bay B&B Charters. During the summer, American Sailing Tours hosts a variety of other events, including firework dock parties, old city seaport festivals, and Fourth of July festivities. Tickets can be purchased online or over the phone.

Baltimore, MD 21202


Annapolis Bay Charters

Annapolis Bay Charters, located in Annapolis, Maryland, has an impressive fleet, and a well-seasoned crew with over 30 years of combined experience. They provide a variety of services, including bareboat charters, skippered charters, corporate regattas, itinerary planning, sailing training, and yacht sales. Annapolis Bay Charters is a member of Dream Yacht Charter, and they pride themselves on being one of the premier charter services in the area.

Annapolis, MD 21403


Annapolis Cartamaran Charters

Annapolis Catamaran Charters, located in Edgewater, Maryland, was established in 1997 by Susan and Jess Berndt. They are long-term sailors of the Chesapeake Bay area, and they are dedicated to providing exceptional customer service. Their philosophy is to keep things simple and to make the charters as enjoyable as possible. Their cruising catamaran has spacious accommodations, and is comfortable and luxurious. In the winter months, they travel south to the Bahamas.

Edgewater, MD 21037



Aquaventures, located in Cockeysville, Maryland, is a multi-faceted sailing company that provides many services and offers a variety of amenities. Some of the various water adventures they provide include coastal eco tours, guided snorkeling tours, diving courses, technical diving, boat chartering, and accommodations at their top-rated B&B. Boat chartering can be booked for corporate events, private events, diving and angling, survey inspection, and buoy placement. Booking can be done over the phone or online.

Cockeysville, MD 21030


Miss Grace Charters

Miss Grace Charters, located in Annapolis, Maryland, is a multi-faceted cruising and fishing company that can accommodate up to 40 passengers in a single trip. They can be chartered for events such as lighthouse tours, bachelor and bachelorette parties, fishing trips, anniversary celebrations, crab feasts, dinner destination trips, and burial ceremonies. Miss Grace Charters is a member of the Maryland Charter Boat Association, Upper Bay Charter Boat Association, the National Association of Charter Boat Operators, American Professional Captains Association, and the Annapolis chapter of Ducks Unlimited.

Annapolis, MD 21403


Sail the Pintita

Sail the Pintita, located in Annapolis, Maryland, is licensed to accommodate up to 20 people. The Pintita has many different amenities, including heating and air conditioning, and an enclosed cockpit. They have hosted a variety of events, including birthdays, promotions, graduations, and anniversaries. The crew of the Pintita strives to make passenger outings as comfortable and entertaining as possible. Reservations for Sail the Pintita can done by phone or online.

Annapolis, MD 21403



SeaAffinity provides two-hour sailing charters in Baltimore. Departing the Canton area, we sail past Fort McHenry and out into the Patapsco River, or toward the inner harbor, past historic Fells Point and Domino Sugar toward Federal Hill and the National Aquarium. We offer both public and private groups for day, sunset, and after dark sailings, including a wine and cheese sunset sail SeaAffinity also provides sailing lessons from novice to advanced, taught by a US Sailing Master Instructor Trainer. Proceeds from sailing charters and lessons fund our outreach programs including middle school STEM education and addiction recovery programs.

2809 Boston Street
Baltimore, MD 21224

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Watermark, located in Baltimore, Maryland, was established in 1972. Since their opening they have maintained the vision of immersing their customers in the culture, history, and fun that resides in the Chesapeake Bay area. Over the years, Watermark’s crew has been the recipient of many awards and accolades. Group Sales Manager Jennifer DeLancey was awarded the 2014 New Professional of the Year, and Tour Guide Mistress Meg Govan was awarded the 2010 Interpreter of the Year by Four Rivers.

Baltimore, MD 21230


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