Chesapeake Flotillas, LLC

Chesapeake Bay Charters


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The Chesapeake Bay is a large, beautiful, and wondrous body of water.  It is the largest estuary in the United States.  It's role in the history, economy, and recreation of America is well documented.  Sail nearly anywhere along the Bay and you will see the evidence of that in the many cargo vessels, recreational boats, and workboats operated by the famous Chespeake Bay watermen.  The size of the Chesapeake Bay offers its visitors limitless options for streams, gunkholes, and waterside towns.   It is impossible to see all there is on the Chesapeake in one trip or even twenty trips.  You will want to return again and again!

Capt. Rob frequently cruises on the Chesapeake Bay with his sloop, S/V Bay Poet.  She is a beautiful, well-appointed vessel.  Up to four people can sail aboard Bay Poet with Captain Rob and Chef Theresa who sails as cook and mate. If you need a different yacht to accommodate a larger party or to visit a different cruising area, Rob is happy to work with you to find a charter yacht that meets your needs.  Sail the Chesapeake Bay and see the beauty that draws Rob and Theresa back again and again.  Listen to him tell you the history and anecdotes that make the Chesapeake such a unique sailing ground.  Later, at anchor, sing with him as he dispenses poems, songs, and music picked just for the moment.

Theresa is highly skilled at preparing complete and delectable meals aboard.  After conferring with clients to determine if there are any foods to avoid, she will do her thing.  We may not eat steak and lobster on Bay Poet but the food is always fantastic!

Capt. Rob keeps his boat at Haven Harbour Marina in Rock Hall, MD on the Eastern Shore.  Rock Hall is one hour from Annapolis, no more than two hours from Baltimore, Washington, DC and Philadelphia, and about 4 hours from New York City.  Rock Hall at first appears as a small, low-key town but look more carefully and you will find delightful coves, abundant wild life, a full-range of dining experiences and entertainment, and most importantly...easy access to the Chesapeake Bay.   Haven Harbour is a beautiful marina with full services including a bar and grill, swimming pool, master mechanics, and a B&B.

Capt. Rob offers multi-day cruises aboard his boat.   Bay Poet can accommodate up to 4 guests plus her captain and mate.  On a 3 day weekend, it is possible to make it as far as Havre de Grace or ST. Michaels, 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 streams with more activity like Fairlee Creek and the Magothy River.

However, if there are more than four people in your group or if you want to start from a different location, Capt. Rob can help you charter a boat from Havre de Grace, Rock Hall, or Annapolis and then he can skipper that yacht.  There is almost no place along the Chesapeake Bay and most of its tributaries that Captain Rob has not sailed.

Additionally, Capt. Rob will work with you to plan for a special events or themed experiences.  Are you celebrating something? 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 experiences is what we do.   Let Capt. Rob and Chef Theresa help you create something special. (Additional charges may apply.)

A two-day weekend charter on Bay Poet is $1700 and a three-day adventure costs $2150*.  Prices are quoted for the entire trip for up to 4 clients and NOT per person.  Included is the use of the boat, fuel and pump-out, provisions, linens, and of course, the Captain and mate/cook.  All you need to bring are your clothes and whatever personal beverages and items you may wish to have.  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 and Chef Theresa.

Not sure you want to spend more than one day on the water?  Then try a day sail with us for only $400.  We will get underway in the morning and sail for up to 6 hours.  Theresa will serve a light lunch while we are underway.  Alternatively, come aboard the night before and spend a comfortable night in the owner's cabin.  After a full breakfast in the morning, we shove off for your day cruise.  We will return to the slip in the afternoon and you can enjoy dinner at the marina bar and grill as you take in the view of Swan Creek and The Haven.   A night aboard and the cruise cost $650.

Pick a cruise package and let the experience begin.  Capt. Rob and Chef Theresa will treat your vacation like their own!  You will see that Capt. Rob and Chef Theresa are second to none!

Call Capt. Rob at 908.672.3609 to arrange your sailing date. Then you can go online to pay to hold those dates.

Gratuities are always gratefully accepted.

Send Capt. Rob an email now to find out what we can do for you. You may also call Chesapeake Flotillas at 908.672.3609.

* Sailing in the summer can be uncomfortable in high heat conditions.  On days with uncomfortable or dangerously high temperatures, Capt. Rob may return the vessel to the slip or another marina in order to use air conditioning to cool the boat.  When extreme conditions are forecasted, he may even suggest that the charter be rescheduled.


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