Luxury Boat Tours & Private Charters near Grasonville, Maryland

Stay Tuned is the newest platform in this collection, a 2024 Vision 444 built for comfortable long-distance cruising. The vessel sleeps six across three cabins and three heads, and is designed by Vision Yachts with features that favor livability at sea: a full, well-equipped kitchen, large fresh water capacity and air conditioning. The advertised inventory includes snorkeling gear, towels, coolers and a dinghy—essentials for extended days at anchor and shore excursions.

Practical details matter when you’re planning days or a week aboard: this Vision is powered by 38 HP Nanni diesel engines and carries substantial fuel and water stores (200 gallons fuel, 220 gallons fresh). Operators offer the choice of bareboat or captained charters; note that crew fees and provisioning are listed separately. For a small group wanting modern systems, private cabins and a performance-minded hull, Stay Tuned is a strong choice for multi-day Chesapeake itineraries.

Williwaw is presented as a Leopard 45 configured for comfort and seaworthiness, with three queen staterooms each paired to private bathrooms, a convertible salon berth and a full suite of galley appliances. The layout is aimed at groups who expect generous interior space: a dedicated lounge, multiple dining areas and a 32” flat-screen lounge TV are listed alongside chart plotter/GPS and autopilot systems.

Underpinning that comfort is capable propulsion: two 45hp Yanmar diesels and a high-capacity fresh water and fuel system allow longer passages without constant refueling. Included inventory covers basic provisioning tools—towels, sound system and a dinghy—while crew fees, fuel and provisioning are handled separately by the operator. Choose Williwaw if you want roomy guest cabins paired with a catamaran built for comfortable, efficient cruising.

The Seawind 1160 is noted for an efficient layout and short-handed sailing performance, making it a smart pick for families or groups that want a balance of interior protection and deck space. Listed capacity accommodates seven comfortably with two queen cabins and an additional full berth; the saloon can host up to eight. The design emphasizes a protected three-way door between cockpit and saloon, which creates a comfortable living space in varied weather.

Mechanical specs include twin 40hp Yanmar diesels and substantial fresh water capacity. The inventory focuses on self-sufficiency—galley facilities, a dinghy, towels and basic supplies—while operators allow either bareboat or captained options. For travelers prioritizing sheltered onboard time, efficient handling and the ability to cruise several days without shore support, Sea Wanderer represents a practical, award-recognized choice.

Lady Patty is a restored 1935 ketch used for private seven-hour day sails out of St. Michaels. The experience begins with a harbor cruise, then opens into sailing on the Miles River—an itinerary built for scenic cruising, relaxed sailing and on-deck social time. The operator partners with local businesses to offer pre-ordered food options, and an optional beer and wine tasting add-on is available for guests 21 and older.

This charter is designed as a private outing for groups up to 13; the operator lists a private charter rate and notes that taxes and crew gratuity are added separately. Travelers seeking a character-rich vessel, wide views of waterfront towns and a full-day on the water with catering options will find Lady Patty delivers a distinct, nostalgia-tinged luxury sail.

Epiphany is a 44‑foot catamaran positioned for private full-day experiences with a small, intimate guest list—advertised for up to six guests on private day charters. The trip pattern mirrors other St. Michaels departures: an initial harbor cruise followed by open-water sailing on the Miles River. The operator lists optional tasting add-ons and the ability to pre-order catered meals to enhance the onboard experience.

Because Epiphany is sized for a smaller party, the day feels personal and flexible—ideal for special occasions, small friend groups or couples traveling together. Operators note that amusement tax and crew gratuity are additional; check-in details indicate the Harbour Inn & Marina as the departure point and recommend arriving 15 minutes early. For guests prioritizing privacy and a modern day-sail platform, Epiphany is an efficient and elegant option.

This 4.5-hour private option aboard Lady Patty condenses the classic full-day itinerary into a refined half-day: a quick harbor tour, followed by raised sails on the Miles River. The operator publishes weekday and weekend charter rates and offers a beer and wine tasting add-on for guests 21 and older. For groups seeking a shorter but full-service luxury sail—an afternoon outing or a sunset cruise—this format delivers the same characterful vessel with a briefer time commitment.

Logistics are straightforward: Lady Patty departs from Harbour Inn & Marina in St. Michaels and the operator asks that guests arrive 15 minutes before departure. With a historic deck, experienced crew and curated food and beverage options available by pre-order, the half-day is an excellent way to sample Chesapeake sailing without committing to a full day on the water.