Our courses are ideal for people of all levels who want to prepare for anything from weekend trips to long-term cruising.  It is a challenging program… the coast is where all the action is: heavy commercial traffic, tides and currents, variable bathymetry, and shifting weather.

Our courses run in the shoulder season only, when winds are stronger and the sailing is fantastic. On days when the weather doesn’t challenge you, we will “stir the pot” with a few drills and scenarios.  And if dangerous weather is approaching, such as a hurricane or lightning, we will seek a secure anchorage – which will give you the opportunity to stand anchor watch in a crazy storm! If you are planning to cruise long distances, any of these courses are ideal. All our courses for 2019 start and end in the beautiful and historic “sailing capitol of the world”, Annapolis, MD!

To reserve a spot you need to:

(1) fill out the application form
(2) make a $300/person deposit via PayPal

So be sure to do both!

2019 Schedule

Chesapeake Bay Expeditions


Early Season Expeditions

Annapolis, MD
These early season 6-day and 4-day expeditions, pack in a lot of drills, skills, and fun when the spring winds on the bay are still blowing. After a long day of hard work, you’ll be rewarded with a cozy picturesque anchorage. We’ll try to explore the remote Southern Chesapeake, and maybe even get to Tangier Island. Motivated crews may decide to make a stop in St. Michaels for crabs and a visit to the maritime museum.  

Mo(A) 191 • 6-Days • May 5 – May 10 • $2495
Mo(A) 192 • 4-Days • June 2 – June 5 • $1595 Only 2 spots left.
Mo(A) 193 • 6-Days • June 30 – July 5 • $2495
Fill Out Application Pay $300 Deposit

Fall Expeditions

Annapolis, MD
Fall is a great time to be sailing the bay! The winds are stronger and the days are cooler. We’ll take advantage of autumn winds and frequent frontal passages to pack in lessons, navigation, drills, scenarios, and fun. If the winds are favorable we’ll explore the remote Southern Chesapeake, and maybe even get to Tangier Island. We’ll probably have to tuck in a reef or two as we explore the Chesapeake and find some cozy anchorages.

Mo(A) 194 • 6-Days • Sept 22 – Sept 27 • $2495 Only one spot left.
Mo(A) 195 • 6-Days • Oct 20 – Oct 25 • $2495
Fill Out Application Pay $300 Deposit

We also offer customized vacation charters, and sometimes do deliveries. Contact us to find out more.

Rocinante2019 Expedition Schedule