Luxury Boat Charters Near Severna Park, Maryland — Chesapeake Bay

Stay Tuned is a brand-new 2024 Vision 444 built for blue-water adventures and private multi-day charters. The vessel sleeps six across three cabins and three private heads, combining performance-oriented design with liveaboard comforts: a full galley, air conditioning, large fresh-water capacity, and features intended to simplify life at anchor. The operator supplies snorkeling gear, towels, coolers, and a dinghy—essentials for groups that want to alternate sailing with exploration and swimming.

Operators note practical items for bareboat and crewed charters: captains and crew are available for an additional fee, provisioning is the guest’s responsibility (nearby grocery delivery options are suggested), and fuel is typically refilled on return. For guests seeking an active multi-day itinerary out of Edgewater or nearby marinas, Stay Tuned pairs modern sailing performance with the conveniences of a well-equipped charter.

Williwaw is offered as a Leopard 45 three-cabin, three-head catamaran that comfortably accommodates six in queen staterooms; the salon table can convert for additional guests. The boat is presented as a blend of seaworthiness and interior refinement: air conditioning, a large galley with stove and oven, and electronics including chartplotter and autopilot. Onboard entertainment is provided via a salon TV and a sound system, making this a strong choice for groups that value creature comforts between passages.

As with the other multi-day listings, included items cover towels, a full kitchen stocked with basic supplies, dinghy, and safety gear; captain fees and gratuities are handled separately if you choose a crewed charter. Williwaw suits travelers seeking stylish, comfortable days at sea with the option to stage multi-night itineraries from Edgewater and surrounding Chesapeake marinas.

Sea Wanderer is a Seawind 1160 designed for comfortable short-handed sailing and efficient use of space. The advertised sleeping capacity covers up to seven guests across multiple cabins, and the vessel features two heads with electric flush toilets and a main walk-in shower. Notable onboard systems include twin 40hp Yanmars, a protected saloon connection with a three-way door to the cockpit for sheltered social space, and a functional galley positioned for liveaboard convenience.

Included amenities are basic galley supplies, towels, and a dinghy; the listing reiterates familiar operator notes about captain fees, provisioning, and fuel refueling on return. Sea Wanderer is a practical option for groups that want an award-recognized hull form and protected onboard spaces while exploring Chesapeake anchorages from a base in Edgewater or nearby slips.

The Lady Patty offers a private seven-hour full-day sail from St. Michaels, combining a short harbor cruise with extended time under sail on the Miles River. Operated from Harbour Inn & Marina, the 1935 ketch brings classic sailing character to a private-boat format: the listing highlights scenic waterfront views, open-water sailing, and the option to add a catered lunch or beer and wine tasting to the day.

This experience is organized as a private charter for your group (maximum 13 people), with clear check-in instructions to arrive at the dock 15 minutes before departure. The operator notes that certain add-ons and gratuities are handled separately; for travelers who want a single-day sailing experience with historic character and local catering options, Lady Patty offers an accessible, memorable day on the Chesapeake.

Epiphany is presented as a 44-foot catamaran private-day option that accommodates up to six guests for a seven-hour itinerary departing St. Michaels. The operator positions the boat for scenic harbor time followed by open-water sailing on the Miles River and recommends optional champagne or beer/wine tasting add-ons as well as catered food options from local partners.

The listing clarifies maximum group size and check-in procedures at Harbour Inn & Marina, and it calls out extra charges for tastings and tax/gratuities where applicable. For couples or small groups looking for an elevated day sail with tasting or sunset options, Epiphany provides an intimate platform and the maneuverability of a modern catamaran.

The half-day Lady Patty sail compresses the St. Michaels harbor experience into approximately 4.5 hours, making it suitable for travelers with limited time who still want authentic sailing on a historic ketch. The operator lists weekday and weekend pricing differences and offers beer and wine tasting add-ons for guests 21+, with a maximum group size of 13.

Check-in details mirror the full-day offering—arrive at Harbour Inn & Marina 15 minutes ahead—and the operator reiterates options for pre-ordered catering. If your schedule favors a shorter window on the water without sacrificing the character of a classic sailing vessel, this half-day format provides exactly that: scenic views, a taste of traditional sailing, and the convenience of a compact itinerary.