Chesapeake Flotillas, LLC - 2022 Event Schedule

Chesapeake Flotillas offers captained charters, flotillas cruises, and sailing instruction on the middle and northen portion of the Chesapeake Bay. International charters are offered in conjunction with a charter partner such as Sunsail, LateSail, Kiriacoulis, LeBoat, and others. Custom cruise planning is also available. Call Capt. Rob for more information at 908.672.3609.

Chesapeake Flotillas offers flotilla cruises and crewed yacht charters which start from Rock Hall, MD. They are two or three-day trips which run Saturday through Sunday with boarding Friday evening or Friday through Sunday boarding Thursday evening. If you would like to make it a flotilla cruise, reserve a whole boat and assemble your own crew or possibly sign up to join an existing crew. Sailors interested in being Skippers for a flotilla will be required to demonstrate their abilities at the time of reservation by submitting a sailing resume at a minimum. More information may be requested depending on the extent of the resume.

Do you have an idea for a special or themed cruise you might like to take? Capt. Rob and Chef Theresa will create an experience for you as if it were their very own! Contact Chesapeake Flotillas at 909.672.3609 or by email. The journey begins with YOU...

Chesapeake Flotillas is now taking reservations for 2022 Chesapeake sailing opportunities. Don't miss your chance! Contact us now. The calendar will fill quickly!

The featured trip for 2021 was a 7-day cruise of Southern Croatia! The featured trip for 2022 will be a weeklong cruise along the Shannon River in Ireland. WE are currently full and accepting wait-list reservations only.

Send us an email now to find out how to create your sailing vacation. You may also call Chesapeake Flotillas at 908.672.3609.

Event*	Dates	Notes	Cost
S/V Bay Poet Launched	week of Mar 20
Spring Commissioning S/V Bay Poet	Mar 25-27	Crew Only
Spring Sea Trials for S/V Bay Poet.	April 8-10	Crew only
Our featured trip for 2022!	Sept 17-24	Cruising the Shannon River of Ireland	SOLD OUT! Accepting wait-list reservations only.
Traditional October Trip	Oct 27-30	Wherever the winds and whims take us...
Featured Trip for 2023	Sept 16-23, 2023	To be announched January 2022

*Not all events and dates may be shown in this table. Please call or email Capt. Rob to see if the dates you want are available.

Do you need some help with your boat handling technique? Or perhaps all you need is a little refresher course to start your season off. Check out the training opportunities.