Around the Bay or around the world... This is

Chesapeake Flotillas, LLC

A Sailing Vacation
Marine Services Company

Thomas Point Light




See what's happening on the 2017 Events page.

I am taking reservations for 2017 for 2 and 3 days crewed charters on my beautiful S/V Bay Poet!  Click here for full information.   Dates are going fast! Two bookings in the last week alone!

My article on charter destinations on the Chesapeake Bay is available online. Click here to read it.

Read my articles about winter maintenance and bottom painting. You will find them all here.

It is time to start getting ready for Italy.  I am looking forward to it as well as to be working with Capt. Lemart Presley. The pre-trip meeting will be June 24, 2017.  Check out what you are missing!

Chesapeake Flotillas will return to Croatia in 2018! The trip is currently sold out but check back check back often in case a vacancy opens.  OR make a wait-list reservation now...just in case!

Captain Rob is looking forward to completing training and practice as Relief Captain on the Schooner A.J. Meerwald, New Jersey's Tallship!   The 2017 schedule has been posted.

Capt. Rob is writing articles for My Boat Life online magazine.  You will find all of his articles at this link.

Be sure to like my Facebook Page for Chesapeake Flotillas.  Click here to do that now.

Cruising Vacations

Training and Instruction

Vessel Delivery and
Professional Services

Whether your interest is in domestic sailing opportunities or exploring foreign venues by water, Chesapeake Flotillas offers all-inclusive vacation packages at excellent values.  From the Chesapeake Bay to the warm waters of the Caribbean and to the deep blue water of the Mediterranean Sea, we deliver excellent travel experiences to our clients.  Click the links below to learn more about what we offer.

Chesapeake Bay Sailing

International Cruising Vacations

Chesapeake Flotillas offers two- or three-day training opportunities on several topics.  Do you need some additional training in Boat Handling or Coastal Navigation?  Some courses are designed especially for women sailors.  Gather up your friends and come learn with Capt. Rob and Chef Theresa.

Click here for more details on our training and course offerings.

Captain Rob Chichester is a USCG licensed Master.  He is available to relocate your vessel along the East Coast or within the Chesapeake Bay region.  Captain Rob is also prepared to speak about or present seminars on a variety of topics from Cruising the Chesapeake Bay to steps to getting a Captain's license.

For more information on Captain Rob's background and qualifications and that of his available crew, click this link.

Chesapeake Flotillas accepts payment by credit or debit card as well as cash, check, or money order.  Call Capt. Rob for information on the most convenient way to pay for your next sailing experience.

The Journey IS the Destination!

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Last modified on: 4/25/2017 11:18:50 AM GMT -4