LAKE SHORE BOAT TOUR FIELD GUIDE
Private Charter aboard the Still Crazy II: A Tailored Cruise on the Chesapeake
A captained, private cruise from Magothy River aboard a 2020 Regal 33 OBX that lets you pick the destination — restaurant hopping, Annapolis, Baltimore, Kent Narrows, or anchoring to swim.
Private Charter aboard the Still Crazy II: A Tailored Cruise on the Chesapeake.
Adventure brief
Private Charter aboard the Still Crazy II: A Tailored Cruise on the Chesapeake
Set out from the Magothy River on Savage Charters' Still Crazy II for a private, captained passage across the Chesapeake Bay. The 2020 Regal 33 OBX is offered for 3-to-8-hour charters that you can shape—tour Annapolis or Baltimore, cruise to Kent Narrows, restaurant-hop, or drop anchor and swim—while the vessel's big hull promises a comfortable, stylish ride.
The Chesapeake Bay, stretching over 200 miles along Maryland and Virginia, offers a prime setting for sailing, cruising, and maritime adventures. Savage Charters' Private Charter on Still Crazy II provides an exceptional way to immerse yourself in this iconic waterway. Whether you're celebrating a special occasion or seeking a relaxing day on the water, this cruise is designed to deliver personalized luxury against a backdrop of scenic beauty. The Still Crazy II yacht combines style and comfort, offering spacious decks perfect for unwinding while taking in views of the bay's shimmering surface. Passengers can customize their itinerary—from restaurant hopping in Annapolis to exploring vibrant Baltimore harbor or simply soaking up the sun with friends. The Chesapeake Bay's marine environment features diverse wildlife including osprey, blue crabs, and the occasional dolphin, making this journey both scenic and lively. The area boasts a rich maritime history, with legends of colonial trades and historic shipwrecks beneath the waves. Savage Charters prides itself on responsible ecotourism, encouraging guests to respect local habitats and minimize environmental impact. This trip stands out in the Chesapeake’s burgeoning boat charter scene thanks to its tailored experience and high-end vessel. The deck setup allows for socializing and privacy alike, while the crew's expertise guarantees a seamless sailing adventure. Perfect for groups seeking exclusivity and comfort, this cruise combines luxury with authentic maritime charm. Prepare for an unforgettable water day in one of the East Coast’s most vibrant and historic waterways, where every turn brings fresh scenic views and possible wildlife sightings. Whether it’s a daytime escape or sunset sail, Savage Charters on Still Crazy II guarantees a memorable voyage on Chesapeake Bay.
Route Schematic
Typical route stops
Select from a handful of common destinations and on-water activities along the Chesapeake.
Annapolis
Sightseeing and onshore stops in Annapolis are offered as a charter option.
Baltimore
You can cruise to and tour Baltimore as part of your private charter itinerary.
Kent Narrows
A cruise to Kent Narrows is listed among the route choices for this charter.
Anchor & Swim
Alternatively, the boat can anchor to allow swimming and relaxing from the vessel.
Capacity and age guidance: the charter accommodates up to 10 passengers and is described as suitable for all ages; organizers should be aware of the stated passenger limit when planning group size.
Highlights
Outing Highlights
A roomy, modern cruiser
The Still Crazy II is a 2020 Regal 33 OBX with a big hull designed to deliver a comfortable ride in style for private charters on the Chesapeake.
Choose your route and pace
Charters are tailored to your group: options include restaurant hopping, sightseeing in Annapolis or Baltimore, or a cruise to Kent Narrows—your itinerary is selectable at booking.
Relax, anchor, swim
Beyond transit and sightseeing, you can opt to anchor, swim and chill from the boat, making this a mixed day of cruising and downtime on the water.
What the day feels like
What the charter feels like
A private charter on the Still Crazy II is straightforward and customizable: a captain handles navigation while your group sets the agenda for a multi-hour jaunt on the Chesapeake—whether that means a moving tour of Annapolis or Baltimore, a leisurely run to Kent Narrows, restaurant stops, or dropping anchor for swimming and sun.
Suitability
Who it's for
Who this charter suits — and who should think twice.
Practical planner
Details to review before reserving
Charters are offered in durations ranging from 3 to 8 hours.
The listed meeting location for departures is Magothy River, Pasadena, MD 21122.
No specific gear requirements are listed in the provided information; the operator provides a captained vessel (Still Crazy II).
Review cancellation policies before reserving.
Frequently asked questions
Planning Your Outing
How long is a private charter?
Charters are offered for 3 to 8 hours.
Where do we meet the boat?
The meeting location is Magothy River, Pasadena, MD 21122.
How many people can come on board?
The charter accommodates up to 10 passengers.
Is the boat captained?
Yes — the experience is described as a captained cruise aboard the Still Crazy II.
What destinations are available?
Options listed include restaurant hopping, touring Annapolis or Baltimore, cruising to Kent Narrows, or anchoring to swim and relax.
What boat will we be on?
The trip uses the Still Crazy II, a 2020 Regal 33 OBX.
How this guide was prepared
This field guide is synthesized using verified supplier specifications, route descriptions, and destination data. Some booking links may generate affiliate revenue for ADV Guides.
- Verified: 2026-11-03T22:24:23.237Z
Some booking links may generate revenue for ADV Guides or The Adventure Collective.
Availability, pricing, schedules and operating details can change.
Trip details and contextual sources were reviewed by ADV Guides Editorial.