Multi-Day and Overnight Sailing Charters
Multi-Day Sailing Trips
Welcome aboard! Experience the freedom of life at sea with Shardana Sailing’s multi-day sailing charters. From romantic overnight escapes to a week of exploration and adventure, and everything in between, Shardana Sailing Charters has it all. Our multi-day escapes are completely customizable to your group, so you enjoy every second. Plan a quick weekend of sailing and outdoor activities or a 2-4 day trip during the week for your perfect getaway on the Chesapeake Bay.
Why Choose a Multi-Day Charter?
A single day on the water is unforgettable — but multiple days allow you to truly disconnect, explore further, and immerse yourself in the rhythm of the sea.
Wake up in secluded anchorages
Swim in crystal-clear waters before breakfast
Explore charming coastal villages
Enjoy sunset dinners on deck
Sail at a relaxed, unhurried pace
Each itinerary is customized based on weather conditions, your preferences, and the spirit of adventure you bring aboard.
Choose Your Sailing Adventure
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Weekend Sailing Charters (2–3 Days)
Perfect for a quick escape without taking extended time off.
A weekend charter gives you enough time to:
Sail beyond the typical day-trip routes
Anchor in quiet bays overnight
Experience sunset and sunrise at sea
Dine under the stars
Learn hands-on sailing if you wish
Ideal for couples, families, or small groups of friends looking to recharge and reconnect.
Popular for:
Romantic getaways, birthday celebrations, anniversary surprises, or spontaneous adventures. -
Overnight Sailing Charters
Spend one magical night at anchor and experience the sea in its most peaceful form.
Your overnight charter includes:
Afternoon sailing and swimming stops
Sunset aperitivo on deck
Dinner in a coastal village or onboard
A tranquil night at anchor
Morning swim and breakfast with a view
There is nothing like falling asleep to the gentle motion of the boat and waking up surrounded by open water.
Perfect for:
Couples, special occasions, or first-time multi-day guests who want a taste of extended sailing. -
Weekly Sailing Charters (5–7 Days)
For those who want the full sailing experience, a weekly charter unlocks the true magic of coastal exploration.
Over the course of a week, you can:
Discover multiple islands and remote anchorages
Visit historic harbors and seaside towns
Snorkel, paddleboard, and swim in hidden coves
Experience a mix of lively ports and peaceful nature
Fully unwind from daily routines
Longer charters allow flexibility in route planning, giving us the ability to follow the best weather conditions and discover less crowded destinations.
Best for:
Families, groups of friends, milestone celebrations, and travelers seeking an immersive Mediterranean sailing holiday.
Activities — Make Your Day What You Want
We know that everyone has different ideas of fun or relaxation. On a full day sailing charter with Shardana, you’re free to choose your experience:
Sailing & sailing-lessons — if you’re curious, you’re welcome to help raise sails, steer the boat, and learn sailing basics under the guidance of your licensed captain.
Swimming — bring your swimsuit, and when we anchor in a calm spot, take a dip in peaceful Bay waters (clear and refreshing).
Sunbathing, relaxing & reading — soak up the sunshine on deck, breathe the salt air, enjoy a book, or simply watch the horizon — peaceful solitude and seascapes create the perfect escape.
Picnic or BYO food & drinks — you’re welcome to bring food, snacks, and drinks on board. Many guests pack a picnic and enjoy a meal while anchored or drifting.
Wildlife & nature viewing — keep an eye out for birds, waterfowl, and the natural beauty along the coast. The Bay’s shorelines and waters are home to abundant wildlife.
Photography & memories — the Bay offers stunning skies, water reflections, and changing light — perfect for capturing photos or simply savouring the moment.
What to Bring — Packing for a Perfect Sail
To make the most of your full day sailing charter, here’s a suggested packing list:
Sunscreen (ideally non-aerosol)
Sunglasses, sun hat, and light clothing (breezy, comfortable attire)
Bathing suit and towel (for swimming)
Non-slip, non-marking shoes or boat-friendly sandals
Light jacket or windbreaker (it can get breezy on open water)
Drinking water, snacks or a full picnic — bring whatever you like to eat or drink (BYOB is permitted).
Camera or phone (for photos), but be cautious around water
Why Choose Shardana for Your Full Day Sailing Charter
At Shardana, we believe sailing should be personal, flexible, and memorable. Here’s what sets us apart:
Private & personalized charters — with a maximum of six passengers, your group gets exclusive access to the boat and a day tailored to you.
Flexible itineraries over calm waters or open Bay — we adapt based on weather and your wishes.
Comfortable sailing vessel — our 43-foot sloop (Catalina 425) is designed for cruising, comfort, and a true sailing experience.
Experienced, licensed captain & attentive service — ensuring safety, smooth sailing, and a day focused on your enjoyment.
Ideal for multiple occasions — romantic getaways, family outings, small group fun, coastal exploration, or just a day off from the ordinary.
Booking & Departure Information
Departure port: Osprey Point Marina, Rock Hall, MD (20786 Rock Hall Ave)
Reservations required: We schedule full day charters in advance. A deposit and written confirmation are required.
BYOB friendly: Bring your own snacks, meals, drinks — we provide water, ice, and soft drinks.
If you're ready for a day on the water — where the wind, the waves, and your imagination set the course — your “full day sailing trip” aboard Shardana awaits.
Want to Customize Your Day?
We’re happy to tailor your trip. Want to anchor and swim, or sail out into the open Bay? Prefer relaxation or activity? Just tell us. Whether you’re dreaming of a peaceful escape or a Bay adventure, we’ll build a plan that fits your vision.
Get in touch with us today to ask about availability or to start planning your private full day charter on the Chesapeake Bay.