Chesapeake Flotillas, LLC - 2024 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.

A guided flotilla cruise is simply a fleet of cruising yachts, chartered or otherwise, sailing to a common destination each day. The flotilla is supported by trip leaders who will sail on a lead boat. In some cases, it may be possible to put experienced crew aboard your yacht to assist with sailing and navigating the vessel. Participants get the benefits of a bareboat chartering experience and experienced guides to help you find and enter lesser known anchorages and towns in the cruising area.

Chesapeake Flotillas offers cruises 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 2024 Chesapeake sailing opportunities. Don't miss your chance! Contact us now. The calendar will fill quickly!

The featured trip for 2024 is a 7-day cruise of the Cyclades Islands in Greece! The Croatia cruise goes on sale January 15.

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 Apr 1
Spring Commissioning S/V Bay Poet	Apr 6-7		Crew Only
2024 Spring Sea Trials for S/V Bay Poet.	April 20-21		Cancelled due to Covid-19
Our featured trip for 2024! Our last overseas charter!	Sep 14-21	Exploring the Cyclades Islands	Going on sale soon!
Traditional October Trip	Oct 28-31	Wherever the winds and whims take us...	Contact us for pricing and availability.

*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.