Full Day Sailing Trips
Shardana’s Most popular Trip
Welcome aboard! Our full day sailing trips give you the perfect opportunity to truly experience the beauty and freedom of the Chesapeake Bay. Whether you’re planning a relaxing getaway, a family outing, or a day with friends — a private sailing charter with Shardana offers you a customized, carefree day on the water without the rush of a sunset sail or half-day trip.
What to Expect on a Full-Day Charter
On a full-day Shardana Sailing charter, you’ll enjoy light breezes, open water, calm coves — and all the time you need to relax, explore, and make the day yours. Departing from our home port in Rock Hall, Maryland (Osprey Point Marina), Shardana — our 43-foot sloop (a 2017 Catalina 425) — will take you to some of the most scenic and peaceful corners of the Bay.
Your day on the water will be private: no crowds, just your group (maximum six passengers) and your licensed captain to explore all of the beauty that Chesapeake Bay has to offer.
The itinerary for your full day may include:
Sailing under full sail on the open Chesapeake Bay, feeling the wind and watching the coastline change.
Cruising through scenic waterways, inlets, and channels near Rock Hall and the surrounding areas.
Anchoring in secluded coves for swimming, paddle-boarding, or simply relaxing on deck.
Exploring waterfront views, shoreline vistas, and local wildlife.
Where We Sail: Bay & Beyond
On a full day trip aboard Shardana, here are some of the destinations or water-side experiences we often recommend or reach when conditions allow:
Eastern Shore & Rock Hall environs — calm waterways, scenic views, and easy access from Osprey Point Marina.
Scenic routes across the Chesapeake Bay — open-water sailing with full sails, salt breezes, and expansive views.
Secluded anchorages & coves — ideal for relaxing, swimming, or paddle-boarding. We can chart a course to quieter waters depending on your group’s comfort and preferences.
Waterways, channels, and bays near Rock Hall and the upper Chesapeake region — for those who prefer a more sheltered, calm-sailing experience on the Bay’s eastern shore.
Because we operate a private charter, we tailor each trip to the day’s weather, your group’s preferences, and your desired pace — whether that’s calm and relaxed or adventurous and active.
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 & paddle-boarding — bring your swimsuit, and when we anchor in a calm spot, take a dip or paddle 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 reef-safe)
Sunglasses, sun hat, and light clothing (breezy, comfortable attire)
Bathing suit and towel (for swimming or paddle-boarding)
Secure, 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.