Sneak Peek at the 2026/27 Sailing Season
Reservations for the 2026/27 sailing season will officially open on March 28. We will have all the details here on that date. But in the meantime, here’s a sneak peek at the dates, destinations, and prices…
May
On Water Training
May 16 - 17 (early board May 15)
Rock Hall, Maryland
$425
Boat systems review, lines and line handling, boat handling under power and sail.
June
Bienvenidos a Mallorca
June 6 - 13
Mallorca, Spain
$1250
A week cruising the northern and eastern coasts of this popular Mediterranean island.
Baltimore 250
June 25 - 29 (early board June 24)
Rock Hall, Maryland to Baltimore, Maryland
$950
Celebrate the 250th Birthday of the United States with Tall Ships, naval vessels, a Blue Angels airshow, Coast Guard rescue demonstrations, and a variety of music festivals in historic Baltimore Harbor. We’re including two quiet nights at anchor bracketing the celebration.
August
Lazy Summer Weekend
August 15 - 17 (early board August 14)
Rock Hall, Maryland to various anchorages
$650
A three-day weekend on the Bay with stops at anchor in two beautiful anchorages. One night we’ll have a fun TSC appetizer dinner. On the other we’ll engage in a trivia contest with prizes for the truly trivial.
September
Classic Chesapeake Cruise
September 17 - 23 (early board September 16)
Rock Hall, Maryland to Oxford Maryland
$1100
Join us for a cruise to several iconic Chesapeake destinations. We’ll moor in Annapolis Harbor - Sail to the Choptank River, taking the fun (and sometimes nail-biting!) shortcut through the Knapps Narrows - And spend a day in Oxford, one of Maryland’s oldest and most charming waterfront towns.
