Chesapeake Bay Captained Sailing Charter Cruises

Chesapeake Bay Sailing Charters

Experience sailing on the Chesapeake Bay with a professional yacht captain offering charter sailboat cruises

boat gear shop

The Chesapeake Bay is an amazing body of water to explore. The largest estuary in America, the Chesapeake Bay is approximately 200 miles long from its northern headwaters in the Susquehanna River in Maryland to its outlet in the Atlantic Ocean at Virginia. And of course the best way to experience all that the Chesapeake Bay has to offer is by boat.

Chartering a boat, either bareboat (by yourself) or captained (with a licensed boat captain) is a great way to spend a day or more on the bay.

If you are looking for a sailing experience on the bay, but lack the knowledge to sail a bareboat charter, then a charter cruise with a professional yacht captain may be the ideal way to get out and enjoy the Chesapeake. And smaller group private charters will allow you to have a truly unique experience to remember.

Trending Now: Custom Boat Life Gear

Chesapeake Flotillas Sailing Charters

Chesapeake FlotillasChesapeake Flotillas is a great option for a personal sailing experience complete with a professional captain. Owner/operator Capt. Rob Chichester hails out of Rock Hall on the Eastern Shore of Maryland and offers a variety of charter opportunities on board a 41 foot sloop Bay Poet.

Centrally located on the Chesapeake Bay, the home port of Haven Harbor Marina in Rock Hall provides easy access to the bay and is conveniently located one hour from Annapolis, two hours from Philadelphia, and about 4 hours from New York City. The small waterside town offers dining with some of the best Maryland crabs on the bay, and the beautiful full service marina offers a bar and grill, swimming pool and a B&B.

Captain and Crew

Bay Poet CrewAll captained charters are hosted by Capt. Rob – a USCG Licensed Master who has planned and executed flotilla cruises all over the Chesapeake Bay, Europe, and the Caribbean. Capt. 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.

Also on board is Chef Theresa, who has planned and prepared meals aboard sloops and catamarans from the French West Indies to the Adriatic Sea. 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.

Charter Options

Cheaspeake FlotillasYour sailing experience with Chesapeake Flotillas can be a one day or multi-day cruise.

For multi-day cruises, Bay Poet can accomodate up to 4 guests plus the captain and, if desired, a cook or mate. On a 3 day weekend, it is possible to make it as far as Havre de Grace or Oxford, MD. For a two day weekend, all of the most popular destinations are easily within reach. If you want to stop in a town, Annapolis, Baltimore, and Galesville are all within a day of Rock Hall…or less. If you prefer the quiet and solitude of an isolated anchorage, we can visit the Corsica River, Harness Creek, or the Rhode River. There are also creeks with more activity like Fairlee Creek and the Magothy River.

However, if you have a larger party or you want to start from a different location, Capt. Rob can help you charter one or more boats from Havre de Grace, Rock Hall, or Annapolis. For those looking to go even farther afield, charter yachts are also available in Solomons, MD and Deltaville, VA. There is almost no place along the Chesapeake Bay and most of its tributaries that Captain Rob has not sailed.

Watch some sample video of a cruise on the Chesapeake Bay:

sailing chesapeake baySpecial Events

Capt. Rob can also work with you to plan special events or themed experiences. Are you celebrating a special event? Looking for open air music? Maybe you would like to have a wine tasting.

Celebrations on the water are special because they are unique and intimate. Planning is what we do. Let Capt. Rob and Chef Theresa help you create something special.

“If anyone ever wants to tour/sail the Chesapeake I would highly recommend Capt Rob. A more knowlegeable, skilled, and personable skipper you’ll never find.” – Wayne B.

Pricing and Accommodations

Contact Capt. Rob for pricing on two- or three-day weekend cruises. Prices are quoted for the entire trip with up to 4 clients and NOT per person. Included is the use of the boat, fuel and pump-out, provisions, bed linens, and of course, the Captain and a cook. All you need to bring are your clothes, towels, pillows, and whatever personal beverages you may wish. Weekend cruises on charter yachts in other locations will be priced based on the vessel you wish to charter, the adventure you wish to create, and the size of your party (maximum number determined by the layout of the yacht selected and the number of hired crew). We are sure that you will be pleasantly surprised at the cost AND the quality of the experience you will have with Captain Rob.

To learn more, visit or contact Capt. Rob directly via email or phone at 908.672.3609.

Trending Now: Must-Have Boat Gear for Your Boat Life

Trending Now: Custom Nautical Decor for Your Boat Life

Disclosure: This site may contain links affiliated with companies where we receive compensation. Also, as an Amazon Associate we may earn from qualifying purchases we refer but it does not impact the price you pay. Full disclosure policy.

Sponsored Post

View posts by Sponsored Post
My Boat Life offers sponsored content opportunities for businesses with relevant marine products or services. Build your brand while offering valuable content to boaters. Learn More
Scroll to top