For optimal vessel availability and scheduling flexibility, we recommend booking your charter at least 4-6 weeks in advance, especially during peak season (May-September).

For special events or peak holiday weekends, up to 6 months advance booking is advisable.

However, we always welcome inquiries for last-minute availability.

DEFIANT can accommodate up to 12 guests for day charters and up to 6 overnight guests across three comfortable staterooms.

DEFIANTone can accommodate up to 6 guests for day charters and up to 4 overnight guests between the master stateroom and cozy forward V-berth cabin.

Guest capacity may vary depending on the nature of the charter experience and applicable U.S. Coast Guard regulations.

Absolutely. Every Chesapeake Charter Experience is tailored to your preferences.

During the booking process, our team will work closely with you to customize your itinerary, catering, beverages, activities, and special requests to create your perfect day on the water.

A reservation deposit is required to confirm all private yacht charters. Day charters and sunset cruises require a 25% initial payment, with the remaining balance due 7 days prior to departure.

Multi-day experiences and special event charters require a 50% initial payment, with final payment due 21 days prior to departure.

Certain peak dates and custom itineraries may require additional advance payment terms.

Your charter experience includes a U.S. Coast Guard licensed captain, professional crew (where applicable), standard local cruising fuel allowance, onboard amenities (bottled water, ice, cooler), safety equipment, and use of the yacht for the reserved charter duration.

Overnight experiences also include fresh linens, bedding, and essential onboard accommodations.

Customized catering, premium provisioning, dockage fees, extended cruising routes, special event services, and curated add-ons may be arranged separately based on your experience preferences.

Yes. Dockage can be arranged at select destinations including Annapolis, St. Michaels, Oxford, Cambridge, and other waterfront towns based on your itinerary and availability.

Dockage arrangements and related marina fees vary by location, season, and duration of stay and may be incorporated into your personalized charter.

Gratuity is not included in the charter fee. While never required, a gratuity of 15-20% of the charter fee is customary for exceptional service and is greatly appreciated by our crew.

For additional questions or to begin planning your Chesapeake Charter Experience, please contact our team at havefun@chesapeakechartersmd.com

We offer charters throughout the Chesapeake Bay region, including Annapolis, Baltimore, St. Michaels, Oxford, Tilghman Island, and numerous other charming destinations.

Our expertise covers both the eastern and western shores, and we're happy to recommend itineraries based on your interests.

We recommend bringing soft-soled shoes, layered clothing (the water can be cooler than land), sunscreen, sunglasses, hats, any personal medications, cameras, and personal toiletries for overnight stays.

We provide towels, linens, basic amenities, and safety equipment.

Yes, we partner with several premier caterers in the Chesapeake region offering cuisine ranging from casual fare to fine dining experiences.

Our team can provide menu options based on your preferences and dietary requirements.

Your safety is our priority. If weather conditions are deemed unsafe by our captain, we will work with you to reschedule your charter at no additional cost.

If rescheduling isn't possible, a full refund will be provided.

For less severe weather that doesn't impact safety but may affect enjoyment, we offer flexible rescheduling options.