Join us on a sailing adventure in 2026
Welcome to the 2026-2027 Sailing Club Season
Welcome to the 2025-2026 Sailing Club season, our 44th year as The Sailing Club. We welcome back our veteran members and extend a warm welcome to our new members and those considering membership.
On the Water Training
This two-day training session provides an opportunity to practice boat handling and sailing skills. On the Water Training (OWT) provides new sailors with experience in steering the boat and performing various roles during anchoring, reefing, rescuing, and sailing. Experienced sailors can practice maneuvers and refresh their less-used skills.
Bienvenidos a Mallorca
Sun-drenched beaches, secluded coves with crystal-clear water, ancient olive groves, and vibrant historic towns await you in Spain’s Balaeric Islands. Sample tapas and cava while listening to local musicians. Swim in crystal clear water over a white-sand bottom. Trim the sails for a fast reach to explore another beautiful bay.
We’ll spend seven days absorbing the sunshine, food, and culture of this vacation island. Plan your visit to begin ahead of the sailing trip or stay on a few days after. There’s plenty to do in the Balearic Islands and nearby northeastern Spain.
Lazy Summer Weekend
Summer in the Chesapeake has a bad reputation, but in recent years we’ve proved that it can be a delightful experience. We will likely have sunshine and some swimmable water in brackish creeks where the stinging fish varieties are less common.
Classic Chesapeake Cruise
Join us for a cruise to several iconic Chesapeake destinations. We’ll moor in Annapolis Harbor. We’ll sail to the Choptank River, taking the shortcut through Knapps Narrows, and we’ll spend a day in Oxford, one of Maryland’s oldest and most charming waterfront towns.