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.
Sailing- Catered to you
No two charters are the same. Whether you prefer active sailing and learning the ropes, relaxed cruising with long swims, or a culinary-focused journey exploring coastal restaurants, we design each trip around your vision.
Who Are Multi-Day Charters For?
Couples seeking a romantic escape
Families wanting a unique vacation
Groups of friends celebrating special events
Adventure travelers
Anyone ready to disconnect and reconnect with nature
You don’t need prior sailing experience — just a love for the sea!
Start Your Sailing Adventure
A multi-day sailing charter with Shardana Sailing is more than a vacation — it’s a journey shaped by wind, water, and unforgettable moments.
Ready to plan your escape?
Contact us today to create your personalized multi-day sailing experience.