Luxury Sailing & Coastal Courses Around Edgewood, Maryland

Stay Tuned is a 2024 Vision 444, a 44'4" lightweight performance catamaran marketed for blue‑water cruising. Operator notes list three cabins and three heads with sleeping capacity for six, plus a full kitchen, air conditioning and significant fresh water and fuel capacity—220 and 200 gallons respectively. The specification emphasizes cruisability and comfort for multi‑day passages and island hopping across the Chesapeake and adjacent waters.

The charter includes a dinghy, snorkeling gear, coolers and towels; guests can expect picnic‑style provisioning and onboard barbecue options. Operators call out standard exclusions—crew fees if you hire a captain, fuel refill on return, and provisioning costs—so plan to provision locally or arrange delivery. For travelers who want private space and overnight capability, this boat balances sailing performance with live‑aboard comforts.

Lily Rose is listed as a 2025 Seawind 1170 multi‑day charter operating from the Edgewater area. The Seawind 1170 is a contemporary cruising catamaran platform well suited to shallow Chesapeake anchorages and comfortable coastal passages. The experience listing identifies the boat and charter format; for specifics on guest capacity, included gear and exact itineraries consult the operator page.

For travelers seeking a recent‑model catamaran for multi‑night coastal cruising, this listing indicates a turnkey private charter option. Confirm provisioning, captain availability and the intended anchorages with the operator before booking to match the vessel’s layout to your group’s needs.

This six‑hour private charter is designed as a luxury half‑day on the Chesapeake Bay. The fleet description specifies capacity for up to 12 guests and a flexible program—snorkeling, sailing, or simply relaxing—with included snorkeling gear, pool noodles, coolers, a sound system, full kitchen and barbecue grill. The package is ideal for families or groups seeking an elevated day afloat without overnight commitments.

Practical notes from the listing: the primary charterer must be at least 21 years old, and guests should bring food, beverages, ice, swimwear and non‑spray sunscreen. The operator emphasizes customization—pick the balance of sailing versus anchored leisure when you book—to suit snorkeling stops, calm anchorages or a scenic sail along the Bay.

This five‑day live‑aboard ASA 103/104 course runs from BaySail and immerses students in coastal cruising aboard a 30–45' sloop. The listing describes four nights at anchor or in local marinas, focused classroom and on‑deck training in sail trim, docking, anchoring, heavy weather handling, electronic navigation and meteorology. Successful completion qualifies participants to act as skipper of a 30–45' boat in coastal waters and is recognized internationally.

The course fee and capacity details are included in the operator listing; the program notes a minimum age of 16 and a prerequisite of ASA 101 or equivalent experience. Classes are live‑aboard with limited enrollment, so check prerequisites and the operator’s minimum-student policy before reserving a spot.

This four‑day, three‑night live‑aboard cruise departs from Maryland Marina in Middle River. The course covers advanced sail trim, coastal navigation, anchoring, docking and emergency procedures and includes two textbooks, ASA 103 and 104 certifications and the ASA International Proficiency Certificate (IPC). The operator notes provision costs (approx. $200) and that fuel, pump‑outs and docking fees are included in the course package.

Itineraries often include stops or overnights in Rock Hall, Annapolis, Baltimore or Kent Island, offering practical experience in varied Chesapeake anchorages. The program is aimed at adult students (18+) with a prerequisite of ASA 101, so it’s a direct path for sailors intending to charter in Europe or other international waters where the IPC is required.

This 3.5‑day live‑aboard program departs from Maryland Marina in Middle River and concentrates on ASA 104-level skills with the ASA IPC included. The course work emphasizes coastal navigation, advanced sail trim, auxiliary engines, provisioning and emergency operations during a short multi‑night cruise. Included materials and fuel/docking fees are noted; students should expect additional provisioning costs around $200.

Prerequisites are stricter than entry courses—ASA 103 is required—so this offering suits sailors who have completed prior coastal cruising training and want a compact path to ASA 104 and international proficiency certification. The live‑aboard rhythm places students into real‑world skipper and crew scenarios across Chesapeake anchorages.