Chesapeake Flotillas, LLC

21/10/2024

This past weekend, I sailed my former department head from the Chesapeake Lightship, Chris Krusa (c. 1974), and his girlfriend Julie aboard Bay Poet. It was a very good weekend of memories, catching up, and discussing possibilities. I am grateful for the opportunity.

09/10/2024

This past weekend, we had a father and son charter. It was a good time with some great sailing on Saturday. We toured the remains of the Francis Scott Key Bridge in Baltimore. Saturday night, we were treated to another great meal by Chef Theresa. Sunday, we navigated safely back to Rock Hall in thick fog. The media below is proof a good time was had by all!

23/09/2024

Capt. Rob has another captained charter with Waypoints Yacht Charters out Annapolis. Looking forward to another good sail on the Chesapeake Bay!

14/09/2024

Waiting to get aboard the boat at Tourlos Marina.

Rob Chichester was last located near Latitude 37.464590 Longitude 25.327786 on September 14, 2024

10/09/2024

In 48 hours, we will be eastbound over CT and MA.

Sail Greece in 2020. Travel to the Cyclades Islands in the Aegean Sea with Capt. Rob Chichester. We will see Paros, Ios, Naxos, Mykonos, and other islands.

11/08/2024

Yes, you can arrange a captained charter on S/V Bay Poet but you can also charter any boat and hire Capt. Rob as your captain...just like Ken Randall did.

Capt. Rob was hired to do a captained charter on a DuFour 530 out of Annapolis. The client booked a 5-day charter with Waypoint Charters during which we vis...

05/08/2024

If you charter a yacht from Waypoints Yacht Charters in Annapolis and you need a captain, ask for Capt. Rob. He is now available for captained charters with Waypoints.

The Chesapeake Bay is among the world’s top cruising and sailing destinations. A true American treasure, the Bay delivers a long enjoyable sailing season

07/07/2024

Now you can take home memories in the form of aerial photos and videos when you charter S/V Bay Poet with Captain Rob and Theresa.

Capt. Rob shares the news of getting his Remote Pilot Certifcate and how he will use it to provide added value to his charter clients and students in this tr...

02/07/2024

Making a repair on Bay Poet using tools I inherited from my father.

20/06/2024

Happy Birthday, Theresa Rossi Vollman

17/06/2024

Summer is here and S/V Bay Poet is ready for guests. Come aboard and sail the beautiful Chesapeake Bay for a day or a weekend. There are plenty of options to fit your interests.

Capt. Rob Chichester and Chesapeake Flotillas offers sailing cruises on the Chesapeake Bay. Sail the Chesapeake Bay aboard Capt. Rob's S/V Bay Poet or select a charter yacht in a location of your choice. We will work with you to plan your personalized multiday cruises. The cost of your sailing vacat...

11/06/2024

Passed my FAA Part 107 Exam. I am now a Part 107-compliant Remote (Drone) Pilot. I studied for the test using the Pilot Institute. I am very proud to have scored 95! Time to go fly!

https://pilotinstitute.com/

06/05/2024

How many of us can say we have crewed aboard an actual Lightship? CAPCA member Captain Rob Chichester can say “aye aye” and has stories to tell about his exp...

20/03/2024

S/V Bay Poet will splash in just a few days. We are ready to take reservations. Whether you want a day sail, a weekend, or a long weekend, Chesapeake Flotillas is the right place to experience the Chesapeake Bay! Contact us now.

Capt. Rob Chichester and Chesapeake Flotillas offers sailing cruises on the Chesapeake Bay. Sail the Chesapeake Bay aboard Capt. Rob's S/V Bay Poet or select a charter yacht in a location of your choice. We will work with you to plan your personalized multiday cruises. The cost of your sailing vacat...

21/02/2024

In honor of Black History month...

A brief history of African-American Mariners
Presented aboard S/V AJ Meerwald in Cape Charles Harbor.

The Schooner A.J. Meerwald visited Cape Charles, VA after the 2017 Great Chesapeake Bay Schooner Race. The Meerwald hosted the Cape Charles Yacht Club and t...

11/02/2024

Valentine's Day is here! It is not too early to plan a cruise for you and your honey. Chesapeake Flotillas is offering a 14% discount for all captained day sails or weekened charters booked on February 14, 2024. Available dates are Wednesday through Sunday from May 1 through November 10 for day cruises. Multi-day charters are available on weekends during that same time period. Email [email protected] to start your reservation. Terms and Conditions apply.

https://www.chesapeakeflotillas.com/terms.asp

05/02/2024

Capt. Rob will be presenting the history of the Chesapeake Lightship which is currently on display at the Baltimore Maritime Museum. The Lightship played a significant role in Capt. Rob's Rob's interest in all things maritime. The presentation will be sponsored by the Chesapeake Area Professional Captains' Association. The information on the presentation is below.

How many of us can say we have crewed aboard an actual Lightship? CAPCA member Captain Rob Chichester can say “aye aye” and has stories to tell about his experiences as a crew member on the U.S....

01/02/2024

I spent some time on S/V Bay Poet today. She is less than two months from spring commissioning.

Bay Poet and I will be ready for charter beginning May 1. One to three day charters are available this year. Inquiries are invited.