Welcome Aboard!
Embark on a journey like no other with our fantastic sailing trips. Dive into the excitement and camaraderie as we set sail on unforgettable charters.
Feel the thrill of the wind in your sails and the warmth of our welcoming community when you join us for a voyage that will make memories to last a lifetime.
With experienced volunteer skippers and first mates to guide us, every trip is a new opportunity for fun, relaxation, and the beauty of the sea. Let's make waves and cherish each moment together.
With forty years of experience to draw on, The Sailing Club has developed a reliable trip planning and execution process. All trips are proposed, planned, and lead by a team of two members, one of whom is a Club-qualified skipper.
A day on the water …
The Sailing Club’s charter trips are designed to provide a balance of sailing and time at anchor and ashore in interesting locations. Most frequently, we sail on the relatively nearby waters of the Chesapeake Bay. This allows us a few days of sailing (usually 3 to 4) with only a few hours drive to and from the boats. In addition, every season usually includes at least one longer trip of 7 to 10 days. These are typically further afield. The club has enjoyed trips to the US west coast, Maine, the Caribbean, Europe, Australia and the fresh waters of Lake Champlain and the Great Lakes.
For those who are new to the Club or new to sailing and who might like to just "try out a trip," we offer two to three days trips on the Chesapeake Bay. This will give you the opportunity to see what it is like to sail on a large boat, to sleep a night or two on board, and to ease into what may be a new experience for you.
Sleeping
We typically charter sloops and sometimes catamarans around 40-feet long. We plan for six crew on a boat this size. Six people can easily share the efforts of sailing and of communal living without anyone feeling overburdened. All boats offer a bunk for each crew member, sometimes in shared cabins and sometimes in the main saloon. Crew are welcome to choose to sleep in the cockpit or even elsewhere on deck if conditions allow. The skipper has sole authority to assign berths and to veto sleeping on deck.
Dining
At least a week before gathering at the marina, you’ll meet with the rest of your crew as well as your skipper and first mate (likely via a video conference). Together you will review the trip itinerary and make a meal plan for your boat. Most trips include one or more dinners, and sometimes other meals, ashore. All the boats we charter have galleys with stoves, refrigerators, and sometimes freezers. Most also have a barbecue grill. (Pre-trip meetings are not held for On Water Training or daysails.)
Sailing
The Sailing Club encourages everyone to take a hand at sailing the boat. Your skipper and first mate, and other crew members, will literally show you the “ropes” (but they’ll call them “lines”) and how to operate the specialized equipment on a sailboat.
Safety
At all times the skipper is focused on the safety of the crew and boat above all else. We do not require that everyone wear a lifejacket, but we absolutely encourage it. The Sailing Club has a spotless safety record and we all want to keep it that way. If your skipper asks you to do something, like put on a lifejacket, or even go below during heavy weather, follow those instructions.
… and at Rest
Most of our trips include a shore-side component, even in places we know well such as the Chesapeake Bay. We recognize that for many people two or three days — or a full week — on a boat can feel confining.
Depending on the location and weather, we plan time for swimming, snorkeling, hiking, shopping, and even special tours ashore.
Dynamics
Sailing is highly weather dependent and no planned itinerary is sacrosanct. When conditions change, so can our plans, and sometimes that means sailing less, or more, and more or less time at anchor or ashore. Our trip leaders and skippers collaborate on decisions about such changes. Our fleet sails, or stays in port, together. Please understand that we make these decisions with the safety and comfort of everyone in mind. Your skipper has sole authority to alter plans both in keeping with the decisions of trip leadership and for your specific boat should special circumstances arise.