Luxury Boat Rentals near Prince Frederick, MD — Private Charters & Lessons

Williwaw is presented as a Leopard 45 configured to sleep six across three staterooms, each with a queen bed and private bathroom. The operator-supplied description emphasizes interior comfort alongside sailing performance: salon seating, a full kitchen with a 4-burner stove, oven, microwave and refrigeration, air conditioning, and a sound system. Technical notes in the listing include twin 45hp Yanmar diesel engines, chartplotter/GPS with autopilot, and significant fresh water and fuel capacity. Guests should note what’s included—towels, coolers, dinghy—and what isn’t: provisions, fuel refills at the end of charter, and crew service fees or gratuities if a captain or crew are hired.

For travelers seeking multi-day private time on the water, Williwaw’s layout and amenities make it a clear offering: three private cabins with ensuite heads, convertible salon sleeping for extra guests, and the convenience of a fully equipped galley. The operator also lists practical Know-Before-You-Go points: the primary charterer must be at least 21, and bareboat renters receive a checkout sail prior to departure. Full booking details and availability are on the operator’s booking page.

Lily Rose is listed as a 2025 Seawind 1170 offered for multi-day charter out of Edgewater. The operator-supplied headline identifies the vessel and its role as a multi-day charter platform; detailed specifications and availability are provided on the booking page. For travelers seeking a compact, modern multihull for a private sailing itinerary, the Seawind 1170 platform frequently appeals for its balance of livability and performance.

Because the public listing for Lily Rose emphasizes the charter format without a long structured description in the supplied dataset, prospective bookers should consult the operator booking page for cabin layout, included amenities, crewing options and provisioning guidance. The booking page preserves the operator’s current availability and any rental prerequisites.

The Bentley Pontoon listing is framed as a short private rental designed for small groups who prefer a casual self-operated outing. The headline notes a three-hour rental duration; within the dataset the provider description also references capacity for up to 10 people. This type of rental is suited to families or groups of friends who want a comfortable deck platform for sightseeing and short cruises without the structure of a captained charter.

Operators typically list these pontoon rentals as offered without a captain, so be sure that at least one member of your party is comfortable operating the vessel and understands local rules. The booking page linked with this listing contains the operator’s specific check-in details, safety requirements and availability windows. Confirm passenger limits, life jacket provisions and any local launch instructions directly with the provider before departure.

The ASA 104 Bareboat Cruising course aboard Epiphany is presented in the operator’s structured description as a multi-day certification designed to prepare sailors to skipper and crew a cruising sailboat on multi-day coastal voyages. The listing details course learning objectives including voyage planning, docking and maneuvering, sail handling, anchoring techniques, weather awareness, safety procedures and onboard systems. The operator explicitly notes that completing ASA 104 aboard a catamaran provides practical multihull experience, including twin-engine maneuvering and specific catamaran handling characteristics.

Practical course details are supplied: the program runs three days, pricing brackets are listed by student count (for example, 1 Student: $2395; other tiers are supplied in the operator description), and the course departs from Harbour Inn & Marina in St. Michaels with a request to arrive at the dock 15 minutes before scheduled departure. Prerequisites for enrollment include ASA 101 and ASA 103. Prospective students should confirm the exact lodging and cabin arrangements and any guest policies on the booking page.

The Floating Lounge listing positions a 45’ Luxury Water Lounge as a turnkey private-venue option for celebrations and corporate gatherings. The operator-supplied description highlights climate-controlled comfort with both heating and air conditioning, turning the vessel into a seasonally reliable event platform. The listing calls out common use cases—birthdays, bridal showers, corporate events—framing the lounge as an adaptable private space on the water for groups seeking an elevated event setting.

Because the public listing is focused on the event nature of the offering, operators generally manage setup, capacity and timing through the booking page. The dataset preserves a two-hour private rental duration in the headline; for custom event lengths, menu and service options and exact capacity, consult the linked booking page to confirm availability and any special requirements.

The Full Day Luxury Private Charter is offered as an eight-hour catamaran experience with capacity for up to 12 guests. The operator-supplied description highlights features such as a full kitchen, barbecue, sound system and pool noodles—amenities intended to support a varied day of stops and activities. The listing frames the charter as appropriate for groups wanting to visit multiple anchorages within a single day.

Operators note basic Know-Before-You-Go guidance in the supplied description: the primary charterer must be at least 21 years old and guests should bring food, drinks and non-spray sunscreen. For groups that require a captain or crew, check the operator booking page for crewing options, fuel arrangements and any additional service fees prior to booking.