Chesapeake Flotillas, LLC

Cruising under sail

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Cruising under sail is one of the most pleasant, relaxing, and peaceful activities that Capt. Rob knows.  Yet, with a sail full of wind and water rushing past the hull, it can also be as exciting as you like!

Capt. Rob frequently cruises on the Chesapeake Bay aboard his sloop, Bay Poet.  She is a beautiful, well-appointed vessel.  Up to four people can sail Bay Poet with Captain Rob and a cook or mate. If you need a different yacht to accomodate 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 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.

Capt. Rob also sails in other venues not on the Chesapeake Bay, including charters internationally.  He has sailed in many parts of the world including Northern Europe, the Caribbean and the Mediterranean.  He prepares methodically and completely for each and every trip...researching destinations, understanding the culture, explaining the gastronomy as well as the navigational issues.  Join him for an adventure of a lifetime.

Capt. Rob will treat your vacation like his own!

The cost of your adventure cruise will depend on the size of the vessel you wish to charter, the adventure you wish to create, and the size of your party (maximum determined by the layout of the yacht selected and the number of hired crew). If your party needs more than one boat, we can handle that too! Contact us to discuss your ideas.  We will plan your experience as if it were our own!

What our clients have to say about Capt. Rob and Chesapeake Flotillas
David Vadovszki, Sr Software Engineer - Oracle/Sun

I've joined Rob on several trips that he has skippered and organized to locations including the Chesapeake Bay, French West Indies, and Croatia (just last year). Each trip has been a memorable experience that he helped facilitate. Despite the fact that I've moved Colorado, I *still* fly out to meet Rob on his latest planned adventure whenever budget and time allow. Trips are highly personalized and I really couldn't ask for more.

His expertise and attention to detail should also be specifically mentioned. It is often the case that boat rental personnel are amazed by the checklist Rob brings to inspections (typically hours before the rest of the crew arrive). Every inch of the boat is inspected to ensure there are no surprises while out on the water, and Rob is happy to teach about the ins and outs of sailing as well as the particulars of the boat at any time during the trip.

Betty Grieve, Nursing Supervisor - Christian Health Care Center

Rob is an excellent communicator who cares about his clients. He delivers an excellent product at a reasonable cost, and is very creative. I have benefitted from his sailing expertise on many occasions. I always learn something from him and no matter what the situation, I know that safety is paramount with Rob. I highly recommend Rob as an instructor and as a captain.

Helene Resky

I became acquainted with Rob in 2011 when I became a student in his Basic Sailing class. Rob's deep knowledge of sailing as well as his infinite patience and enthusiasm make him an excellent instructor. I completed the class feeling that I had a solid foundation in sailing theory.

I have also sailed with him on two occassion for a weekend on his sloop Bay Poet. I had previously sailed with a group in the Seychelles and found the experience intimidating. Rob provides a safe, comfortable, and low-pressure environment in which I was able to put the skills he taught into practice. I trust him as a captain and look forward to another relaxing and entertaining sail with him.

Linda Bobo

My family and I chartered Captain Rob and his boat, Bay Poet, for a long weekend on the Chesapeake Bay.

We found Captain Rob to be a knowledgeable and personable sailor. My husband and I felt we put the safety of our family (3 children) in good hands. We even weathered a storm without incident and were confident that Captain Rob would take good care of us.

We found Captain Rob to be very knowledgeable about his boat and the area in which we sailed. We enjoyed our time on Bay Poet and look forward to future excursions.

We didnít invent adventure but we can put some into your plans!

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

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