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Full Day Sailing Charter on the Chesapeake Bay for up to 6

Rock Hall, Maryland

Full Day Sailing Charter on the Chesapeake Bay for up to 6

Rock Hall, Maryland

Duration: 7 hours

Package: For up to 6 People

Overview

Set sail on a full-day private charter from Rock Hall, Maryland, and explore the scenic beauty of the Chesapeake Bay. Whether it’s a relaxing cruise, a swim stop, or lunch at a waterfront crab house, this sailing experience offers a peaceful escape on one of Maryland’s most iconic waterways.

🛥️ Spend a full day sailing the Chesapeake Bay with a private charter for up to six guests

🥗 Enjoy a picnic on board or stop for lunch at a local waterside restaurant or crab house

🌊 Take a refreshing swim or anchor in a quiet cove for a peaceful break on the water

📸 Soak in stunning views and snap scenic photos of Maryland’s iconic coastline

Spend the day sailing the beautiful waters of the Chesapeake Bay with this full-day private charter departing from Rock Hall, Maryland. This relaxing getaway offers the perfect mix of freedom and fun—pack your own picnic to enjoy on deck or stop for a swim in a quiet cove. Prefer to stay dry? Drop anchor at a local crab house or scenic waterfront spot for a laid-back lunch before cruising back across the bay.

The full-day sailing charter is ideal for small groups looking to disconnect and soak up coastal views without the rush. With space for up to six passengers, this Chesapeake Bay experience lets you chart your own course—whether that means sunbathing on deck, snapping photos of passing boats, or just enjoying the breeze. It’s an easygoing way to explore one of Maryland’s most iconic waterways.

When do I choose a date?

After purchase, you can request your preferred dates and times by following the instructions in the email you receive. If it's a gift, the recipient will also get an email with booking instructions.

Seasonal,
May-October:
Daily 9:00am

When do I choose a date?

After purchase, you can request your preferred dates and times by following the instructions in the email you receive. If it's a gift, the recipient will also get an email with booking instructions.

Seasonal,
May-October:
Daily 9:00am

Any restrictions to participate?

Age: All age groups are welcome
Health limitations: Not suitable for individuals with serious mobility limitations that prevent safe boarding or movement on a vessel
Physical limitations: Must be able to move around a boat with stairs and uneven surfaces
Experience level: All levels are welcome

Who can you accommodate for?

Children: Children are welcome to join
Individuals with disabilities: Not wheelchair accessible; guests must be able to board from a dock and navigate stairs independently
Dietary restrictions: Guests may bring their own food to accommodate personal dietary needs
Pets: Sorry, no pets allowed

What to expect on the day of the experience?

Duration: 6–8 hours
What’s included:
- Private sailing charter aboard a 43-foot Catalina 425 yacht
- Certified captain
- Use of three staterooms, two marine bathrooms (heads), linens, towels, air conditioning and heating
- Cushioned deck lounging space
- Full galley, BBQ grill, and dinghy for water access
- Safety equipment exceeding USCG minimums
Who will be present: A certified captain will be on board at all times; the group may include up to 6 passengers total
Spectators: No spectators are allowed, everyone must have a reservation
Photo/ video: Guests may take personal photos and videos
Specific rules to follow: Smoking is not allowed on board

How to prepare?

Weather dependency: Your captain, at their sole discretion, may cancel or reduce the time on the water on a charter due to inclement weather conditions or circumstances beyond their control. If a charter is cancelled, they will make their best efforts to reschedule the cruise under the same terms and conditions. If the charter cannot be rescheduled, they will issue a 100% credit back to Giftory for your experience. In the event your captain reduces the time on the water, a prorated amount may be calculated for your credit with Giftory.
Arrival: Plan to arrive at least 15 minutes prior to departure time
Parking: Free parking is available at the marina
What to wear: Comfortable layers and soft-soled, non-marking shoes are recommended
What to bring:
- Water, sunscreen, sunglasses, and a hat
- Picnic, snacks, or drinks (alcohol is allowed)
- Phones and small electronics
- Personal items in a soft bag (space is limited)
- Towels and swimwear if planning to swim
- No large, hard-sided coolers or suitcases
Restrooms/ lockers/ changing rooms: Two marine bathrooms (heads) available on board

Anything else I should know before going on this experience?

The itinerary may include anchoring for lunch and swimming, or docking at a waterside restaurant or crab house
All safety protocols and vessel certifications exceed U.S. Coast Guard standards

Any restrictions to participate?

Age: All age groups are welcome
Health limitations: Not suitable for individuals with serious mobility limitations that prevent safe boarding or movement on a vessel
Physical limitations: Must be able to move around a boat with stairs and uneven surfaces
Experience level: All levels are welcome

Who can you accommodate for?

Children: Children are welcome to join
Individuals with disabilities: Not wheelchair accessible; guests must be able to board from a dock and navigate stairs independently
Dietary restrictions: Guests may bring their own food to accommodate personal dietary needs
Pets: Sorry, no pets allowed

What to expect on the day of the experience?

Duration: 6–8 hours
What’s included:
- Private sailing charter aboard a 43-foot Catalina 425 yacht
- Certified captain
- Use of three staterooms, two marine bathrooms (heads), linens, towels, air conditioning and heating
- Cushioned deck lounging space
- Full galley, BBQ grill, and dinghy for water access
- Safety equipment exceeding USCG minimums
Who will be present: A certified captain will be on board at all times; the group may include up to 6 passengers total
Spectators: No spectators are allowed, everyone must have a reservation
Photo/ video: Guests may take personal photos and videos
Specific rules to follow: Smoking is not allowed on board

How to prepare?

Weather dependency: Your captain, at their sole discretion, may cancel or reduce the time on the water on a charter due to inclement weather conditions or circumstances beyond their control. If a charter is cancelled, they will make their best efforts to reschedule the cruise under the same terms and conditions. If the charter cannot be rescheduled, they will issue a 100% credit back to Giftory for your experience. In the event your captain reduces the time on the water, a prorated amount may be calculated for your credit with Giftory.
Arrival: Plan to arrive at least 15 minutes prior to departure time
Parking: Free parking is available at the marina
What to wear: Comfortable layers and soft-soled, non-marking shoes are recommended
What to bring:
- Water, sunscreen, sunglasses, and a hat
- Picnic, snacks, or drinks (alcohol is allowed)
- Phones and small electronics
- Personal items in a soft bag (space is limited)
- Towels and swimwear if planning to swim
- No large, hard-sided coolers or suitcases
Restrooms/ lockers/ changing rooms: Two marine bathrooms (heads) available on board

Anything else I should know before going on this experience?

The itinerary may include anchoring for lunch and swimming, or docking at a waterside restaurant or crab house
All safety protocols and vessel certifications exceed U.S. Coast Guard standards

Unused Experience Vouchers can be returned within 15 days for a full refund to the original purchaser, no questions asked.

If you have any unused Experience Vouchers, you can exchange them for anything else in our marketplace, no matter when. If you choose an experience that's more expensive, you'll need to pay the difference, but if you choose one that costs less, you'll receive a credit towards your next booking.

No refunds are allowed once the experience is booked. If you need to cancel your sail, the sailing provider reserves the right to charge the full price of the charter; rescheduling the charter will be at the sole discretion of the operator. For any changes to your reservation, please contact the experience provider directly.

Unused Experience Vouchers can be returned within 15 days for a full refund to the original purchaser, no questions asked.

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