Planning the perfect day on a Chesapeake Bay Cruise in the Annapolis region requires choosing between two distinct options: private versus public yacht charters (as well as whether your prefer a sailboat versus powerboat experience (Link)). Your choice will significantly impact which of the Bay’s offerings you can experience

Best decide up front whether you’re imagining a relaxed half-day cruise, a magical sunset experience, a full day of exploration and activities, an over-night adventure, or just a short excursion. Consider also whether you are cruising to celebrate a special occasion, such as a birthday, graduation, an anniversary, or even a bachelorette party, and whether the Fourth of July, or Blue Angels display, or the Memorial Day start of summer in being celebrated too. Also, you want to prioritize the journey, have a specific activity or destination in mind?
Both options let you witness the Chesapeake’s stunning scenery, spot local wildlife like ospreys and herons, and experience the thrill of being on a boat. However, they differ dramatically in activity options, destinations, as well as privacy and control over your time at anchor for swimming and water activities. Let’s explore how private and public charters compare in delivering your ideal mix of adventure and relaxation on the Chesapeake’s historic waters.

Private Charter Advantages
- Your own floating sanctuary on a private charter offers substantial freedom and opportunity. Private charters can be of much longer duration than public outings, and can extent from short, half-day, full and even overnight experiences. Generally, public charters are of limited duration, rarely more than two hours.
- Boats on private charters tend to be smaller and have much greater accessibility to secluded coves that are inaccessible to larger vessels because of their deeper draft. There are very few private public charters that offer anchor time and water sport activities too; you have to do those separately.
- Compared to public chargers, you get to enjoy intimate family time without strangers or noisy cruisers aboard. The crew becomes your personal guides – offering sailing lessons, sharing local knowledge, and tailoring the experience to your interests.
- Private charters can offer a stay overnight in a peaceful cove or marina with family amenities to catch both sunrise and sunset? The choice is yours.
Private Charter Disadvantages
- This premium experience comes with a price tag ranging from $350 for 2 h booking, to $1800 when including an overnight stay (usually at anchor or in a distant marina).
- Because the charters are longer, there’s more organization required with respect to food and beverages. Enjoying water toys also requires bringing swimsuits and towels.
Public Charter Advantages
- Simplicity and affordability define public charters. At $45-125 per person, you get a professionally managed experience with basic amenities included.
- No need to worry about planning routes or making weather calls – the crew handles everything while you relax and enjoy the bay.
- Private Time.
Public Charter Disadvantages
- The structure that makes public charters simple also limits your experience. Fixed departure times, preset 2 – 4 hour routes, and sharing space with 20 – 40+ other passengers means less flexibility and privacy. You’ll use shared facilities, follow standard itineraries, and might not even sit together as a group.

So, making the Right Choice: Consider your priorities. If you value freedom, privacy, and creating unique memories, a private charter offers unmatched possibilities – from personal sailing instruction to overnight anchoring. The higher cost often feels worthwhile when split among six people. If you’re seeking a straightforward introduction to bay life without planning complexities or premium pricing, public charters deliver a pleasant, structured experience. Basically: you’re trading control and privacy for simplicity and savings. Your ideal choice depends on what matters most: the freedom to create your perfect day on the water, or a preset experience that lets you simply show up and enjoy the ride.