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

Chesapeake Flotillas, LLC

A Sailing Vacation
Marine Services Company

Thomas Point Light




There have been updates to the 2018 calendar.  Take a look to see all that we are doing!

Capt. Rob has found another opportunity to sail!  If you charter from Dream Yacht Charter in Annapolis, ask for Captain Rob as your captain.

Stephen Klueter won the 2017 DHPC Holiday Party Grand Prize!  Congratulations!   Chef Theresa and Captain Rob look forward to welcoming you and your guest aboard S/V Bay Poet in 2018.

You've been wondering...and now I can tell you.  Our 2019 overseas adventure will be exploring the canals and rivers of the Netherlands.  For more information and to make a reservation, please visit the trip information page!

Italy was FANTASTIC!!!  Check out our photos of the Amalfi Coast!

Captain Rob sailed as Watch Captain on the Schooner A.J. Meerwald again for the Great Chesapeake Bay Schooner Race!  It was another good experience.  It was followed by a very successful visit where Capt. Rob and his sister, Judy Williams, presented lectures and re-enactments on African-American Maritime History.

Check out Capt. Rob's article on choosing, launching and recovering a drone from your boat.   Click here to read it.

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 our 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 waters 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 skills.  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: 2/7/2018 10:12:51 AM GMT -4