2017 Event Schedule
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Chesapeake Flotillas offers captained charters, flotillas cruises, and sailing instruction for the northern 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.
When scheduled, the cost of each trip generally includes:
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 2017 Chesapeake sailing opportunities. Don't miss your chance! Contact us now. The calendar will fill quickly!
The featured trip for 2017 is an 7-day cruise along the Amalfi Coast of Italy! This trip is currently fully booked. 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 |
| Volunteer Training for the Schooner A.J. Meerwald | Mar 18 | 0900-1600 hrs | |
| S/V Bay Poet Launched | week of Mar 25 | weather dependent | |
| Volunteer Training for the Schooner A.J. Meerwald | Apr 1 | 1200-1600 hrs | |
| Commissioning Bay Poet | April 8-9 | weather dependent | Crew Only |
| Schooner A.J Meerwald transit to Camden, NJ | April 15 | One-day repositioning cruise | |
| 2017 Spring Sea Trials | April 22-23 | Relocation cruise to return to Harbour Marina. | By Invitation Only |
| Men's Sail | June 9-11 | Old friends doing what we love | |
| Two-hour cruises aboard the Schooner A.J. Meerwald | June 16-18 | Father's Day Weekend. Capt. Rob standing in as captain |
Click here for tickets |
| DHPC Technologies Holiday Party Grand Prize Weekend Cruise |
Aug 5-6 | ||
| Three-day Charter | Aug 25-27 | ||
| Our featured trip for 2017! | Sept 16-23 | Sailing the Amalfi Coast of Italy | Too late! Sold Out - Two full boats |
| Traditional October Trip | Oct 29-30 | Where the winds and whims take us... | Contact us for pricing and availability. |
| Our featured trip for 2018! | Sept 15-22 | Capt. Rob returns to the Dalmatian Coast | Currently sold out. Wait list reservations only. |
*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.
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