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 171 108 15

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.

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



HarborSail, located in Baltimore, Maryland, was established in 2001 as a way to share the unique history of Baltimore, while at the same time providing a great sailing experience. They have entertained guests from around the world, and are dedicated to exceeding customer expectations. HarborSail has also hosted many different occasions, including corporate events, engagement parties, family getaways, anniversary celebrations, and birthday celebrations. Cruise booking can be done either by phone or email.

Baltimore, MD 21231


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 Away Catamarans

Sail Away Catamarans, located in Edgewater, Maryland, is owned by Tommy Smith and Amy Michaud. Tom has earned his 100-ton Captain’s license, and is both a charter captain and sailing instructor. Sale Away Catamarans provides a variety of services, including crewed and bareboat charters, sailing instruction courses, and boat sales. They also have nationwide contacts who are capable of performing haul-outs, body work, painting, and window replacement. Services and charters can be scheduled by phone or email.

Edgewater, MD 21037


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


Schooner Woodwind

Schooner Woodwind, located in Annapolis, Maryland, is a touring charter boat that is as entertaining as it is informative. They provide many different sailing experiences, including two-hour public sailing cruises, sunset sails, private cruises, team building events, student groups, and multi-day cruises. Schooner Woodwind has two 74-foot wooden schooners that provide an authentic sailing experience. Since their establishment in 1993, the crews and captains of Schooner Woodwind have been very enthusiastic and engaging in teaching people about the history contained in the Chesapeake Bay area.

Annapolis, MD 21401



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


Yacht Charters on the Bay

Yacht Charters on the Bay, located in Annapolis, Maryland, has a fleet of elegant and luxurious yachts that are perfect for any occasion. Their event planners have arranged events such as corporate outings, employee appreciation events, team building events, off-site meetings and retreats, lunch and dinner cruises, cocktail parties, and Hawaiian Luaus. Yacht Charters on the Bay teams up with some of the most renown caters and entertainers in the area to provide their customers with an experience they will never forget.

Annapolis, MD 21401


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