Enjoy a hands-on experience aboard a 42-foot Catalina sloop with ASA Certified Captain Tony Tommasello. Discover the joy of open water sailing on Maryland’s iconic Chesapeake Bay. Please find out more information below about Captain Tony, excursions, and private lessons.

About Captain Tony

Tony Tommasello is a licensed 50 ton captain, a certified Amerian Sailing Association (ASA) instructor, an experienced sailor and dedicated teacher. He enjoys introducing people to sailing and providing instruction on its finer points to those already engaged in this activity.


The vessel is Equus, a 42 foot Catalina sloop. The Catalina is a stable vessel and can be trimmed to sail close to the wind and make good speed under weigh. After 40 years of sailing Captain Tony wants to introduce others to the excitement of being under sail and moving quietly on the water. Looking ahead while closing in on landmarks and looking astern to see how far one has traveled without the aid of engine power produces a sense of accomplishment that few can experience.

Sailing Excursions

All excursions will last five hours total and begin promptly at noon. The maximum guest count aboard 42-foot Equus is five adults. Complimentary snacks and non-alcoholic refreshments will be served. Enjoy fresh air, sunshine, and hands-on experience; an all-around great time.

Longer cruises are available upon resquest.

Learn more about our ports of departure below

Baltimore Harbor

Have you ever viewed the city skyline of Baltimore by land AND by sea (well, by bay really). It’s incredible. Much of Baltimore’s rich history is tied to the Chesapeake Bay and the Baltimore Harbor -- most notably during the bombardment of Fort McHenry and through the industrial revolution. The Baltimore harbor has been the heart of the city since the port was founded in 1706 and is still a thriving landmark today.

During this excursion, we will depart from Canton marina and enjoy a five-hour day sail past Fort McHenry and below Key Bridge before returning back into Baltimore harbor.

Middle River

Many people are unaware of the hidden gems within middle river. Two of which include Hart and Miller Island and Pooles Island. Hart Miller Island offers a 3,000-foot sandy beach on a completely uninhabited park site, which is only accessible by boat. Here, you can enjoy scenic views teeming with wildlife. Pooles Island welcomes you with it’s signature white lighthouse, which is the oldest lighthouse still standing in Maryland, circa 1825. While landing on the 200-acre island is prohibited, getting a glimpse of its beauty is worthwhile.

During this 5-hour excursion, we will depart from Cutter Marina on Middle River (Old Eastern Avenue by land). We will sail past Hart and Miller Island and make for Pooles Island as we approach the Eastern Shore. Rounding Pooles Island, we will drop anchor for a brief rest or swim before returning to the dock.


The capital of our beautiful state and world-renowned as America's sailing capital, Annapolis is a bustling port town full of quaint shops, eateries, and pubs. Determining our destination from Annapolis depends heavily on the winds. The two options include the Chesapeake Bay Bridge or the Thomas Point Lighthouse (both of which are stunning to see). Thomas Point Lighthouse is the only screw-pile lighthouse in the bay which still stands at its original site today, circa 1875. The Chesapeake Bay bridge is well-known for traffic jams but is so much more pleasant when viewed from the water! Standing almost 200 feet tall and spanning over 4 miles; this bridge is truly a work of art.

During this excursion, we will depart from the Annapolis port and sail to either the Chesapeake Bay bridge or to the Thomas Point Light House (depending on wind). During our 5-hour sail, we will delight in vast open water views and can drop anchor to rest once we reach our destination before returning to port.

Private Lessons

Have you always wanted to experience the joy of sailing but don’t know where to start? Does sailing school seem too rigid for your liking? Well, you’re in the right place. Skip the “classes” and join Captain Tony for hands-on training. With 40 years of experience and ASA certification, Captain Tony can teach you everything you need to know about sailing. Please submit the form below to learn more.

Learn to Sail

Come Sail Away Today

To contact Captain Tony, please fill out the form below.