About Chesapeake Flotillas, LLC

Chesapeake Flotillas was created as a subsidiary business to a company that was called Custom Float Plans. Custom Float Plans was started by Capt. Dave Steward and Capt. Rob Chichester in the summer of 2003. CFP was launched to offer prepackaged sailing instructions primarily to recreational boaters. Think AAA TripTiks for boaters. They would lay down routes on nautical charts with all the appropriate headings and distance markings. A separate set of sailing instructions that included waypoints, headings, leg distances, total distances, and notes with local knowledge was included in the product. The primary target market at the time was bareboat charter clients on the Chesapeake Bay.

Captain Dave and Rob also offered crewed charter and flotilla charter opportunities. They wanted to keep a distinct identity for that line of business and hence, Chesapeake Flotillas was born. Custom Float Plans ceased operations soon thereafter. Charter clients were not as interested in the route planning product as they had hoped.

In 2009, Capt. Dave relocated to the lower Eastern Shore. Rob received his Master's license in 2010 and continued to operate Chesapeake Flotillas as the sole proprietor by offering trips on the Chesapeake Bay as well as foreign locations. Chesapeake Flotillas was incorporated in New Jersey as an LLC in 2015.

Captain Rob received his Master's license in 2010. He successfully added consulting, training options, public speaking opportunities, and drone photography as company services. In addition to running Chesapeake Flotillas, he is a captain for St. Michaels Sailing Charters and an on-call captain for Chronic Sailing Charters in Annapolis, MD.

Rob has worked as an engineer in the telecommunications, defense, and consumer products industries.  He has been a Lead Engineer and a Manager.  He has retired from Miku, Inc. in Woodbridge, NJ as the Director of Software Engineering. Rob has a BS in Electrical Engineering and Applied Physics from Case Western Reserve University and an MS in Solid State Physics from Stevens Institute of Technology .

Rob has been in love with sailing since his first experiences with the sport back in the mid 70's.  He has been sailing every year now since 1989.  In 1993, Rob joined the Sailing Club, Inc..  He became a club-qualified skipper 2 years later.  He held several posts with the club including Commodore and Training Coordinator.  Rob loves sailing the Chesapeake Bay and will passionately share that love with anyone who will listen.  Other memorable experiences include skippering in two Lucent Regattas in the Netherlands (1999 and 2000) and skippering a 45-foot tugboat for the National Park Service while in high school.

Rob holds a 200-Ton Master's license with Auxiliary Sail and Assistance Towing endorsements.  He also is certified by the American Sailing Association to teach Basic Keelboat Sailing, Basic Coastal Cruising, and Bareboat Chartering.  Rob has been a recurring speaker on several topics at Cruisers' University. He has participated in and is available for yacht deliveries along the Atlantic seaboard from Boston to the the Carolinas. Rob has also planned and executed flotilla cruises all over the Chesapeake Bay, Europe, and the Caribbean.  Rob is the owner and operator of the 41-foot sloop Bay Poet based out of Rock Hall, MD.  He has been added as a Charter Captain by Chronic Sailing Yacht Charters.   Rob worked two seasons as a Relief Captain aboard the 115-foot Schooner A.J. Meerwald, the state tallship of New Jersey.

And...in case you were curious, Capt. Rob is the 12^th one-half cousin, three times removed, of Sir Francis Chichester.

Here is what Rob's clients have said about him:

When it comes to sailing, Rob believes that the journey IS the destination.  He loves planning and executing cruising events for friends and clients.  His essays and poems on sailing have been published in the Sailing Club's newsletter and elsewhere. Capt. Rob also has a blog on various sailing topics. Additionally, he is a contributing author for My Boat Life, a digital magazine. His articles are available at this link.

Email Rob here or call him at +1.908.672.3609

Chef Theresa has been sailing regularly since 2007. She has planned and prepared meals aboard sloops and catamarans from the French West Indies to the Aegean Sea.  Theresa has authored an article on Vegan meal planning for sailing charters. She embraces local ingredients and prepares rich, satisfying meals from them. Theresa is an accomplished sailor in her own right. She is skillful at the wheel and frequently takes the helm for docking and anchoring. She is a gracious hostess who can never do enough for her guests.

Click here to contact Theresa.